- Red-emitting fluorescent probe for detecting hypochlorite acid in vitro and in vivo
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Due to the importance of hypochlorous acid (HClO) in biological and industrial, development of fluorescent probes for HClO has been an active research area. Here, a new red-emitting ratiometric fluorescent probe (P) was synthesized and well defined characterization via NMR, HR-MS, and fluorescence spectrum, which serves as a selective and sensitive probe for ClO? group. The probe showed a ratiometric fluorescent response to hypochlorite at the emission intensities ratio (I480/I612) increasing from 0.28 to 27.46. The emission intensities ratio (I480/I612) was linearly enhanced (I480/I612 = 0.064 X + 0.096) with the ClO? concentration range from 1 to 30 μM. The detection limitation for ClO? in aqueous solution is 0.47 μM. Moreover, this biocompatible red-emitting ratiometric fluorescent probe was utilized to the fluorescence imaging of ClO? in living cells and Zebrafish.
- Chen, Hong,Sun, Tao,Qiao, Xiao-Guang,Tang, Qian-Oian,Zhao, Shan-Chao,Zhou, Zhan
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- Facile Synthesis of Some 3-(Benzimidazol-2-yl)-And 3,6-Di(Benzimidazol-2-yl)-9-ethyl-9H-carbazoles
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A simple and efficient synthesis of novel 3-(benzimidazol-2-yl)-And 3,6-di(benzimidazol-2-yl)-9-ethyl-9H-carbazoles is described. The synthetic approach for the preparation of 2-substituted benzimidazoles 4-8 and bis-benzimidazoles 9-12 was achieved by the condensation of carbazole-3-carbaldehyde 2 and carbazole-3,6-dicarbaldehyde 3 with o-phenyldiamines in dimethylformamide or dimethylsulfoxide in moderate to excellent yield. The identities of synthesized compounds were confirmed using 1H NMR, 13C NMR, infrared (IR), and high-resolution mass spectrometry (HRMS).
- Kandemir, Hakan,Sengul, Ibrahim F.
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- Carbazole–azine based fluorescence ‘off–on’ sensor for selective detection of Cu2+ and its live cell imaging
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A new carbazole–azine based fluorescent sensor was synthesized and characterized. The selectivity of the sensor for Cu2+ over other counter ions in a dimethyl sulfoxide/H2O mixture was shown through enhancement in fluorescence – an off to on transformation. The specificity of the probe towards Cu2+ was evident in ultraviolet/visible, fluorescence, Fourier transform infrared and mass studies. Application of the probe in the cell imaging and cytotoxicity of living cells is illustrated.
- Christopher Leslee, Denzil Britto,Karuppannan, Sekar,Vengaian, Karmegam Muthu,Gandhi, Sivaraman,Subramanian, Singaravadivel
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- Fast detecting hypochlorous acid based on electron-withdrawing group promoted oxidation and its biological applications in cells and root tips of plants
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Hypochlorous acid, a type of reactive oxygen species, has been shown to play an important role in organisms. Nowadays, there are many kinds of fluorescence detecting mechanisms to detect hypochlorous acid in vivo. Due to the high selectivity, the mechanism of using the strong oxidation of hypochlorous acid to break carbon?carbon double bonds has been favored by many scientists. However, the reported probes of breaking carbon?carbon double bonds still had drawback such as slow response. Based on this, we introduced electron-withdrawing group malonitrile to accelerate the oxidation of hypochlorous acid, resulting in reaction time less than 150 s. Meanwhile, the probe exhibited excellent selectivity, optical stability, high sensitivity and the detection limit as low as 0.19 μM. More importantly, we also successfully proved the potential application of the probe for the detection of intracellular ClO? living cells and Arabidopsis root tip by fluorescence imaging.
- Li, Ming,Chao, Jianbin,Liu, Yaoming,Xu, Miao,Zhang, Yongbin,Huo, Fangjun,Wang, Juanjuan,Yin, Caixia
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- Microwave assisted one-pot synthesis, photophysical and physicochemical studies of novel biologically active heterocyclic Donor (D)-π-Acceptor (A) chromophore
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A donor-π-acceptor (D-π-A) chromophore, 2-amino-4-(9-ethyl-9H-carbazol-3-yl)-8-methoxy-5,6-dihydrobenzo[h]quinoline-3-carbonitrile (AEDQ) was synthesized from the condensation of 6-methoxy-3,4-dihydronaphthalen-1(2H)-one, 9-ethyl-9H-carbazole-3-carbaldehyde, malononitrile and NH4OAc in ethanol. Spectroscopic techniques and elemental analysis were employed to establish the structure of AEDQ. Photophysical parameters and fluorescence quantum yield were calculated in the different polarity solvents to evaluate the interactions of the solvent with AEDQ chromophore. Further, the interaction of the AEDQ with cationic and anionic surfactants (CTAB, SDS) were also evaluated by using fluorescence spectroscopy techniques. The intensity of the fluorescence spectrum increased as the concentration of surfactants increased, suggesting that strong interaction occurs between AEDQ with surfactants, and this interaction arises from electrostatic forces. As a result, the AEDQ chromophore could be used to determine the CMC of surfactants. The disc diffusion and minimal inhibitory concentration (MIC) technique were used to test in-vitro antibacterial activity against Gram +ve and Gram ?ve bacteria, and the results are compared with the standard drug, tetracycline. AEDQ also showed good ADMET, pharmacokinetics and drug-likeness properties, which are desirable for a good drug candidate. The molecule also fits well in the DNA gyrase A active pocket site with the binding free energy of ?17.92 kcal/mol, which testifies its good antibacterial activity.
- Khan, Salman A.,Ullah, Qasim,Syed, Salahuddin,Alimuddin,Almalki, Abdulraheem S.A.,Kumar, Sanjay,Obaid, Rami J.,Alsharif, Meshari A.,Alfaifi,Parveen, Humaira
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- Rational Development of a New Reaction-Based Ratiometric Fluorescent Probe with a Large Stokes Shift for Selective Detection of Bisulfite in Tap Water, Real Food Samples, Onion Tissues, and Zebrafish
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Bisulfite (HSO3-) is usually widely added to tap water and food because it has antibacterial, bleaching, and antioxidant effects. However, its abnormal addition would cause a series of serious diseases related to it. Therefore, development of an effective method for HSO3- detection was of great significance to human health. In this work, a new reaction-based ratiometric fluorescent probe KQ-SO2 was rationally designed, which could be used for the highly selective detection of HSO3- in tap water, real food samples, onion tissues, and zebrafish. Specifically, a positively charged benzo[e]indolium moiety and a carbazole group through a condensation reaction resulted in KQ-SO2, which displayed two well-resolved emission bands separated by 225 nm, fast response (1 min), and high selectivity and sensitivity toward HSO3- upon undergoing the Michael addition reaction, as well as low cytotoxicity in vitro. In addition, KQ-SO2 has been successfully applied for the detection of HSO3- in tap water, real food samples, onion tissues, and zebrafish with satisfactory results. We predict that KQ-SO2 could be used as a powerful tool to reveal the relationship between HSO3- and the human health.
- Yuan, Gangqiang,Zhou, Liyi,Yang, Qiaomei,Ding, Haiyuan,Tan, Libin,Peng, Longpeng
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- Properties, theoretical study and crystal structure of 3-benzothiazole-9-ethyl carbazole
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The title compound of 3-benzothiazole-9-ethyl carbazole was synthesized by the reaction of 3-aldehyde-9-ethyl carbazole and 2-aminothiophenol. The compound was characterized by 1H nuclear magnetic resonance (NMR) and mass spectrometry (MS). Its crystal structure was obtained and determined by single crystal X-ray diffraction. The results showed that the crystal belongs to the orthorhombic crystal system and the cell parameters of space group P2(1)2(1)2(1) were a?=?5.6626 (12) ?, b?=?12.606 (3) ?, c?=?22.639 (5) ?, α?=?90°, β?=?90°, γ?=?90°, V?=?1616.0 (6) ?3, Z?=?4, Dc?=?1.350?mg/m3. The UV–vis and fluorescence spectra were also studied preliminarily. The fluorescence spectra of the title compound with bovine serum albumin (BSA) showed that BSA could be marked with the compound and the stability constant between them was 0.82?×?107?M?1. Meanwhile, the crystal and molecule were theoretically surveyed by density functional tight-binding (DFTB). The results showed that there was an orbital overlap for lowest unoccupied molecular orbital (LUMO) between the neighbouring molecules for the crystal, which is different from the molecule structure. It was also showed that the crystal structure is a non-conductor. Copyright
- Gu, Yingchun,Fei, Xuening,Wang, Cuihong,Li, Ling,Zhou, Jianguo,Tang, Yalin,Lin, Dayong
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- Spectra, stability and labeling of a novel carbazole derivative as a fluorescent turn-on DNA probe
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A novel fluorescent dye, 1-(6-carboxyhexyl)-4-(2-(9-ethyl-carbazole-3-yl) vinyl) quinolizinium bromide, was synthesized, and its structure was characterized by 1H NMR, 13C-NMR, IR and HRMS. The spectra properties of this dye in different solvents and under different pH value were invest'igated preliminarily, and the results showed that its fluorescent properties was affected by the polarity and the dipole moment of the solvent. The photostability and thermostability test results showed that its photoreduction rate constant was 1.64×10-5 mol/Min and its fluorescent intensity decreased little after heating at 80 °C for 6 h, suggesting the dye was quite stable. In the labeling experiment of BSA and DNA with the dye, the fluorescent all intensity increased with the addition of BSA and DNA. Specially, the dye showed an excellent turn-on effect upon binding with ctDNA.
- Fei, Xuening,Li, Ran,Lin, Dayong,Gu, Yingchun,Yu, Lu
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- Carbazole-Linked Near-Infrared Aza-BODIPY Dyes as Triplet Sensitizers and Photoacoustic Contrast Agents for Deep-Tissue Imaging
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Four new N-ethylcarbazole-linked aza-boron-dipyrromethene (aza-BODIPY) dyes (8 a,b and 9 a,b) were synthesized and characterized. The presence of the N-ethylcarbazole moiety shifts their absorption and fluorescence spectra to the near-infrared region, λ≈650–730 nm, of the electromagnetic spectrum. These dyes possess strong molar absorptivity in the range of 3–4×104 m?1 cm?1 with low fluorescence quantum yields. The triplet excited state and singlet oxygen generation of these dyes were enhanced upon iodination at the core position. The core-iodinated dyes 9 a,b showed excellent triplet quantum yields of about 90 and 75 %, with singlet oxygen generation efficiency of about 70 and 60 % relative to that of the parent dyes. Derivatives 8 a,b showed dual absorption profiles, in contrast to dyes 9 a,b, which had the characteristic absorption band of aza-BODIPY dyes. DFT calculations revealed that the electron density was spread over the iodine and dipyrromethene plane of 9 a,b, whereas in 8 a,b the electron density was distributed on the carbazole group and dipyrromethene plane of aza-BODIPY. The uniqueness of these aza-BODIPY systems is that they exhibit efficient triplet-state quantum yields, high singlet oxygen generation yields, and good photostability. Furthermore, the photoacoustic (PA) characteristics of these aza-BODIPY dyes was explored, and efficient PA signals for 8 a were observed relative to blood serum with in vitro deep-tissue imaging, thereby confirming its use as a promising PA contrast agent.
- Gawale, Yogesh,Adarsh, Nagappanpillai,Kalva, Sandeep Kumar,Joseph, Joshy,Pramanik, Manojit,Ramaiah, Danaboyina,Sekar, Nagaiyan
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- A large stokes-shifted fluorescent dye synthesized as a new probe for the determination of protein
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A novel fluorescent dye, 1-(2-hydroxyethyl)-4-((E)-2-(3-benzothiazol-2yl-9-ethyl-carbazole-3yl)vinyl) pyridinium bromide, was synthesized for determination of protein and its structure was characterized by 1H NMR. Photophysics of the new probe in different solvents has been delineated in this paper, the new fluorescent molecular dye exhibited a large stokes-shifted and fluorescence quantum yields in organic solvent. The photostability and thermostability of the new dye were also studied and the results suggested the stable was excellent. The interactions of the dye with bovine serum albumin (BSA) , Human serumal bumin (HSA) and calf thymus deoxyribonucleic acid (ctDNA) were studied by fluorescence and absorption spectroscopy. The binding constant for BSA, HSA and DNA were calculated to be 8.91?×?107, 1.86?×?106 and 2.9?×?104, respectively. The experimental results indicated a potential value of the new dye for biomarker.
- Lin, Dayong,Fei, Xuening,Li, Ran,Gu, Yingchun,Tang, Yalin,Zhou, Jianguo,Zhang, Baolian
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- Microstructure elucidation of poly(9-ethyl-3-hydroxymethylcarbazolyl methacrylate) using two-dimensional NMR spectroscopy
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The configurational assignments of poly(9-ethyl-3-hydroxymethylcarbazolyl methacrylate) prepared by solution polymerization with 2,2′- azobisisobutyronitrile (AIBN) as free radical initiator were studied by combination of one- and two-dimensional NMR spec
- Brar, Ajaib Singh,Gandhi, Sonia,Markanday, Meghna
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- Design and synthesis of a fluorescent probe with a large stokes shift for detecting thiophenols and its application in water samples and living cells
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A turn-on florescent probe (probe-KCP) was developed for highly selective detection of thiophenols based on a donor-excited photo-induced electron transfer mechanism. Herein, the synthesis of the probe, a chalcone derivative, through a simple straightforward combination of a carbazole-chalcone fluorophore with a 2,4-dinitrophenyl functional group. In a kinetic study of the probe-KCP for thiophenols, the probe displayed a short response time (~30 min) and significant fluorescence enhancement. In selection and competition experiments, the probe-KCP exhibited excellent selectivity for thiophenols over glutathione (GSH), cysteine (Cys), sodium hydrosulfide (NaSH), and ethanethiol (C2H5SH) in addition to common anions and metal ions. Using the designed probe, we successfully monitored and quantified thiophenols, which are highly toxic. This turn-on fluorescence probe features a remarkably large Stokes shift (130 nm) and a short response time (30 min), and it is highly selective and sensitive (~160-fold) in the detection of thiophenols, with marked fluorescence in the presence of thiophenols. probe-KCP responds to thiophenols with a good range of linearity (0–15 μM) and a detection limit of 28 nM (R2 = 0.9946) over other tested species mentioned including aliphatic thiols, thiophenol analogues, common anions, and metal ions. The potential applications of this carbazole-chalcone fluorescent probe was successfully used to determine of thiophenols in real water samples and living cells with good performance and low cytotoxicity. Therefore, this probe has great potential application in environment and biological samples.
- Liu, Hua,Guo, Chuanlong,Guo, Shuju,Wang, Lijun,Shi, Dayong
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- Carbazole substituted BODIPY dyes: Synthesis, photophysical properties and antitumor activity
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Abstract In this study, two different BODIPYs containing carbazole groups at the meso position were designed and synthesized. All compounds were fully characterized by elemental analysis, FT-IR, matrix-assisted laser desorption/ionization time-of-flight m
- Sengul, Ibrahim F.,Okutan, Elif,Kandemir, Hakan,Astarci, Erhan,?o?ut, Bünyemin
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- Carbazole-hydrazinobenzothiazole a selective turn-on fluorescent sensor for Hg2+ions – Its protein binding and electrochemical application studies
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The sensor 2-(benzothiazol-2-yl)-1-((9-ethyl-9H-carbazol-6-yl)methylene)hydrazine (CBT-1) is successfully synthesized. The sensor CBT-1 showed selective detection of Hg2+ ions in pool of different metal ions through colorimetric and fluorimetric color changes. The sensing mechanism involves Intramolecular charge transfer process between carbazole unit and benzothiazole moiety on interaction with Hg2+ ions. The binding nature of CBT-1 and Hg2+ ion is understood with help of varied analytical techniques such as UV–vis, fluorescence, Mass IR spectral analysis and computational studies. The protein binding studies of CBT-1 and CBT-1+Hg2+ ensemble with protein (Bovine Serum Albumin, BSA) is carried out through one- and three-dimensional fluorescence spectral studies. The cyclic voltammetric analysis of the sensor CBT-1 with distinct metal ions has also been carried out to investigate its potential ability in electrochemical sensing of Hg2+ ions.
- Christopher Leslee, Denzil Britto,Karuppannan, Sekar,Kothottil, Mahendra Mohan
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- Synthesis, one and two-photon optical properties of two asymmetrical and symmetrical carbazole derivatives containing quinoline ring
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The carbazole derivatives are suitable for two-photon absorption optical storage and photoluminescence material. Two carbazole derivatives, asymmetrical and symmetrical type molecules containing quinoline rings as electron acceptors and an N-ethylcarbazole group as electron donor, 9-ethyl-3-(2-quinolin)viny- carbazole (4) and 9-ethyl-3,6-bis(2-(quinolin)vinyl)-carbazole (5), had been synthesized by the Vilsmeier reaction of formylation and Knoevenagel condensation. The one-photon properties including absorption, fluorescence emission spectra, fluorescence quantum yields and fluorescence decay behaviors were investigated in N,N-dimethylformamide. Meanwhile, these compounds were theoretically surveyed by the density functional theory (DFT) and the time-dependent functional theory (TD-DFT). The two-photon excited fluorescence and two-photon absorption cross-sections were measured for the compounds by 120 fs pulse at 800 nm Ti: sapphire laser operating at 1 kHz repetition rate. The results showed that both of the two compounds 4 and 5 had higher fluorescence quantum yield (Φ) of 0.77 and 0.81 comparing with carbazole. Compounds 5 with symmetric π conjugated structure possessed longer fluorescence lifetime (τ) of 21.4 ns and larger two-photon absorption cross-sections (δTPA) of 364 × 10-50 cm4 s/photon than those of compounds 4 with asymmetric π conjugated structure (τ = 10.03 ns and δTPA = 81 × 10-50 cm4 s/photon). It was indicated that the one and two-photon optical properties of carbazole derivatives are influenced strongly by the symmetry and length of π conjugated structure.
- Li, Liang,Wang, Ping,Zhang, Yichi,Wu, Yiqun,Chen, Zhimin,He, Chunying
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- Ratiometric detection of viscosity using a two-photon fluorescent sensor
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In the thick of it: A carbazole-based cyanine derivative has been used as a ratiometric fluorescent sensor to detect mitochondrial viscosities over the range 1-950 cP within live cells and living tissues by using two-photon microscopy. Its success is based on the fast- and low-barrier rotation around its methine bond (see figure) and the huge increase of the fluorescence quantum yield (QY) from the loss of mobility in viscous media. Copyright
- Liu, Fei,Wu, Tong,Cao, Jianfang,Cui, Shuang,Yang, Zhigang,Qiang, Xinxin,Sun, Shiguo,Song, Fengling,Fan, Jiangli,Wang, Jingyun,Peng, Xiaojun
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- Ferrocenes conjugated with thiophene, carbazole, and pyrimidine fragments: Synthesis and properties
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Ferrocenyl-containing chalcones containing π-excessive heterocyclic fragments capable of electrochemical polymerization (carbazole, thiophene, 2,4-ethylenedioxythiophene) were prepared by the Claisen-Schmidt reaction. 2,4,6-Trisubstituted pyrimidines deri
- Abashev,Antuf'eva,Bushueva,Kudryavtsev,Osorgina,Syutkin,Shklyaeva
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- A general strategy to increase emission shift of two-photon ratiometric pH probes using a reversible intramolecular reaction of spiro-oxazolidine
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Fluorescent pH probes have been served as powerful tools in biological and pathological studies in recent years due to the important roles of pH values in various physiological processes. Although plenty of pH probes have been delivered, development of two-photon ratiometric pH probes with large emission shift for detecting the variation of intracellular pH values is still a greatly challenging task. To address this concern, in this work, we have discovered a general strategy designing pH probes by means of a pH-dependent reversible intramolecular reaction of spiro-oxazolidine which can efficiently change their conjugation length and the electronic effect concurrently. To display the generality of the strategy, we have synthesized six pH probes, and all these probes exhibit short emission in basic conditions and dramatically red-shifted emission in acid environments. The emission shift of the six probes is more than 150 nm and even up to 210 nm, much larger than shift of all commercial and reported pH probes. The chemical sensing mechanism of intramolecular ring opening/closing reaction of spiro-oxazolidine has been confirmed with 1H NMR spectra and density functional theory (DFT) calculations. Finally, we have used one of six with one- and two-photon properties to successfully image lysosomal pH changes under confocal and two-photon microscopes in a ratiometric manner. We believed that this spiro-oxazolidine strategy can serve as a general and powerful platform for the design of ideal pH probes.
- He, Xiuquan,Tian, Minggang,Yang, Rui,Yu, Xiaoqiang,Zhang, Huamiao
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- Carbazole-based π-conjugated 2,2′-Bipyridines, a new class of organic chromophores: Photophysical, ultrafast nonlinear optical and computational studies
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The developmen of donor-acceptor (D-A) architecture based organic chromophores with large two-photon absorption (2 PA) cross-sections are essential for myriad of applications, ranging from nonlinear microscopy to biomedical imaging. Here, we present the results from a comprehensive study of 2 PA cross-sections of a new series of carbazole mono substituted-π-conjugated-2,2′-bipyridine derivatives with D-π-A architecture, possessing carbazole as the donor moiety and bipyridine core as an acceptor. Further, we have extended the π-conjugation by introducing the phenyl and butoxy substituted phenyl linkers. The fluorescence properties of these D-A chromophores are highly sensitive to solvent polarity and alteration of electron donor functionalities. The relevant computation studies support our experimental results, e.g., a shift in emission maxima and band gaps of the molecules. The third-order nonlinear optical (NLO) properties of the title donor-acceptor (D-A) chromophores demonstrated that 2 PA cross-section values are in the range of 6–39 GM, obtained using ~50 fs (fs) laser pulses at a wavelength of 800 nm. Further, the nonlinear refractive indices (n2) of these chromophores were found to be ~10?14 cm2/W, rendering them potential optical switching candidates since the coefficients were obtained with kHz, fs pulses extracting pure electronic nonlinearities. Based on our experimental findings and theoretical calculations presented in this study, we believe that carbazole-based π-conjugated 2,2′-bipyridines, demonstrated in this work, would be potential ligands to obtain a series of transition metal coordination complexes of interesting physical properties (for example, superior NLO behaviour).
- Bodapati, Ramakrishna,Das, Samar K.,Dey, Gaurav Ranjan,Jose, K. V. Jovan,Krishnakanth, Katturi Naga,Ramteke, Gunjan R.,Rao, S. Venugopal
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- Multi-Step Synthesis, Physicochemical investigation and optical properties of pyrazoline derivative: A Donor-π-Acceptor chromophore
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The new extended π-bond pyrazoline derivative (ENTD) was prepared from heterocyclic chalcone with 2-hydrazinylbenzo[d] thiazole. The spectroscopic methods established the structure of the ENTD, and the elemental analysis established the purity of the ENTD. In ten different solvents, physicochemical ENTD parameters such as the molar absorption coefficient, transition dipole moments, Stokes shift, oscillator intensity and fluorescence quantum yield were determined to see the effect of the solvent with pyrazoline derivative (ENTD) on the basis of different polarity. In addition, the interaction of ENTD chromophore with the cationic and anionic surfactants have been studied. The intensity of fluorescence spectrum of the ENTD was found to increase with an increase in the surfactant concentration. This indicates that there is a strong interaction between ENTD and surfactants. The ENTD chromophore can therefore be used as a probe to define the surfactants' CMC.
- Alfaifi, S. Y.,Alimuddin,Almalki, Abdulraheem S. A.,Alsharif, Meshari A.,Khan, Salman A.,Kumar, Sanjay,Obaid, Rami J.,Syed, Salauddin,Ullah, Qasim
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- Design, synthesis and evaluation of carbazole derivatives as potential antimicrobial agents
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Five series of novel carbazole derivatives containing an aminoguanidine, dihydrotriazine, thiosemicarbazide, semicarbazide or isonicotinic moiety were designed, synthesised and evaluated for their antimicrobial activities. Most of the compounds exhibited potent inhibitory activities towards different bacterial strains (including one multidrug-resistant clinical isolate) and one fungal strain with minimum inhibitory concentrations (MICs) between 0.5 and 16 μg/ml. Compounds 8f and 9d showed the most potent inhibitory activities (MICs of 0.5–2 μg/ml). Furthermore, compounds 8b, 8d, 8f, 8k, 9b and 9e with antimicrobial activities were not cytotoxic to human gastric cancer cell lines (SGC-7901 and AGS) or a normal human liver cell line (L-02). Structure–activity relationship analyses and docking studies implicated the dihydrotriazine group in increasing the antimicrobial potency and reducing the toxicity of the carbazole compounds. In vitro enzyme activity assays suggested that compound 8f binding to dihydrofolate reductase might account for the antimicrobial effect.
- Xue, Yi-Jie,Li, Ming-Yue,Jin, Xue-Jun,Zheng, Chang-Ji,Piao, Hu-Ri
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p. 295 - 306
(2021/01/13)
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- Carbazole-based semicarbazones and hydrazones as multifunctional anti-Alzheimer agents
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With the aim to combat a multi-faceted neurodegenerative Alzheimer’s disease (AD), a series of carbazole-based semicarbazide and hydrazide derivatives were designed, synthesized and assessed for their cholinesterase (ChE) inhibitory, antioxidant and biometal chelating activity. Among them, (E)-2-((9-ethyl-9H-carbazol-3-yl)methylene)-N-(pyridin-2-yl)hydrazinecarbothioamide (62) and (E)-2-((9-ethyl-9H-carbazol-3-yl)methylene)-N-(5-chloropyridin-2-yl)hydrazinecarbothioamide (63) emerged as the premier candidates with good ChE inhibitory activities (IC50 values of 1.37 μM and 1.18 μM for hAChE, IC50 values of 2.69 μM and 3.31 μM for EqBuChE, respectively). All the test compounds displayed excellent antioxidant activity (reduction percentage of DPPH values for compounds (62) and (63) were 85.67% and 84.49%, respectively at 100 μM concentration). Compounds (62) and (63) conferred specific copper ion chelating property in metal chelation study. Molecular docking studies of compounds (62) and (63) indicate strong interactions within the active sites of both the ChE enzymes. Besides that, these compounds also exhibited significant in silico drug-like pharmacokinetic properties. Thus, taken together, they can serve as a starting point in the designing of multifunctional ligands in pursuit of potential anti-AD agents that might further prevent the progression of ADs. Communicated by Ramaswamy H. Sarma.
- Chaudhary, Bharat N.,Gandhi, Bhumi,Kanhed, Ashish M.,Patel, Dushyant V.,Patel, Kirti V.,Patel, Kishan B.,Patel, Nirav R.,Prajapati, Navnit K.,Shah, Bhavik S.,Teli, Divya M.,Yadav, Mange Ram
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- Multi-step Synthesis, Characterization and Photophysical Investigation of Novel Biologically Active Heterocyclic Chalcone (AECO)
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Novel alkylated heterocyclic chalcone (E)-1-(2-(allyloxy)phenyl)-3-(9-ethyl-9H-carbazol-3-yl)prop-2-en-1-one (AECO) with extended π-bond was prepared by the multi-steps synthesis. The structure of the AECO was established by the spectroscopic technics and purity of the compound was confirmed by the elemental analysis. Physicochemical parameters of the AECO such as molar absorption coefficient, transition dipole moments, stokes shift, oscillator strength and fluorescence quantum yield were calculated in ten various solvents on the basis of polarity of the solvents to see the effect of the solvent with AECO. Interaction of the AECO chromophore with cationic CTAB and anionic SDS surfactants were determined by using the fluorescence spectroscopy techniques. The intensity of the florescence spectrum increase with increasing the concentrations of surfactants. This suggests that strong interaction occurs between AECO with surfactants and this interaction arise from electrostatic forces. So, AECO chromophore could be used as analysis to define the Critical Micelle Concentration (CMC) of the surfactants. In addition the in-vitro antibacterial active of novel heterocyclic chalcone agents four bacteria’s strain were evaluated and result showed AECO is beater antibacterial agent against Gram-Negative Bacteria (E. coli and S. flexneri) as compare to the Gram Negative Bacteria with respected to the standard drug Tetracycline.
- Zayed, Mohie E. M.,Alzahrani, Khalid Ahmed,Khan, Salman A.
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p. 1823 - 1831
(2021/09/18)
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- Dicarbazole oxime ester type photoinitiator as well as preparation method and application thereof
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The invention relates to the technical field of new material organic chemicals, discloses a dicarbazole oxime ester type photoinitiator as well as a preparation method and application thereof, and in particular relates to a novel dicarbazole oxime ester type photoinitiator as shown in a formula (I), a chemical preparation process technology thereof, application of the novel dicarbazole oxime ester type photoinitiator as a radiation curing photoinitiator, and application of the novel dicarbazole oxime ester type photoinitiator various occasions such as radiation curing formula products, particularly UV-Vis-LED excitable photocuring coatings or printing ink .
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Paragraph 0043-0047; 0054-0056
(2021/06/21)
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- RNA fluorescent probe for quickly distinguishing cancer from normal tissues by utilizing morphological changes of nucleolus
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The invention discloses an RNA fluorescent probe for quickly distinguishing cancer from normal tissues by utilizing morphological changes of nucleolus, wherein the probe is (E)-1-(3-aminopropyl)-4-(2-(9-ethyl-carbazole-3-alkenyl)vinyl)pyridine dibromide, called CAPY-AP for short; the RNA fluorescent probe can display RNA and nucleolus distribution in living cells and normal tissues or cancer tissues at the same time, and the judgment index for quickly distinguishing the cancer from the normal tissues by utilizing the morphological changes of the nucleolus is that only single unobvious nucleolus exists in the normal tissues, but polynucleolus and large nucleolus exist in the cancer tissues; compared with other existing RNA probes, the probe provided by the invention has high RNA affinity and ultrahigh permeability, and can easily image RNA and nucleolus in a tissue slice. In addition, the probe disclosed by the invention has the characteristics of good membrane permeability, strong color development and strong light stability, and is expected to be deeply applied to preparation of a rapid pathological diagnosis reagent in tumor surgery.
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Paragraph 0040; 0041; 0044
(2021/01/29)
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- PHENANTHROLINE, CARBAZOLE AND FLAVYLIUM BASED CYANINES AND COMPOSITIONS AND METHODS OF MAKING AND USING THE SAME
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The present disclosure is in the field of pharmaceutical and chemical sciences, including the synthesis of theranostic agents and processes for preparing such agents. In particular, the disclosure relates to important phenanthroline, carbazole and flavylium based cyanine group containing chemical compounds, method of preparing such molecules and compositions thereof, and the use of such molecules and compositions as a probe and diagnostic agent in the diagnosis and treatment of diseases including cancer.
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Page/Page column 80-81
(2021/09/11)
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- New green phosphorescent Ir(III) complex with carbazolylbenzimidazole ligand for solution-processed organic light-emitting diode
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We developed a new green phosphorescent iridium (III) complex, bis[2-(9-ethyl-9H-carbazol-3-yl)-1-methyl-1H-benzo[d]imidazole]iridium(III) acetylacetonate [(Bic)2Ir(acac)], which functions as a solution-processable dopant for organic light-emitting diodes (OLEDs). 2-(9-Ethyl-9H-carbazol-3-yl)-1-methyl-1H-benzo[d]imidazole was incorporated as the main ligand, while acetylacetone was introduced as an ancillary ligand in the heteroleptic iridium (III) complex. The molecular structure of the synthesized (Bic)2Ir(acac) was characterized by 1H- and 13C-NMR. In addition, it was well soluble in common organic solvents, suitable for solution processible dopant material. The Ir (III) complex exhibited a green emission in solution state (dichloromethane) with an emission maximum at 503 nm. The solution-processed OLED device using (Bic)2Ir(acac) as a green dopant achieved an external quantum efficiency of 6.85%, with a power efficiency of 14.96 lm/W, a maximum luminous efficiency of 23.00 cd/A, and Commission Internationale de Eclairage coordinates of (0.30, 0.61) at 7?wt% doping concentration.
- Hwang, Do-Hoon,Jadhav, Amol Maruti,Jang, Jae-Ho,Kwak, Seon Lee,Park, Hea Jung,Park, Jeong Yong
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supporting information
(2021/11/17)
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- Lu(iii) bis-phthalocyanines containing carbazole moieties: Synthesis, characterization, electrochemical properties and sensor applications
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A new range of sandwich type tetra and octa bis-phthalocyanines (Car-Pc2-1 and Car-Pc2-2) starting from commercially available N-ethylcarbazole were successfully prepared whereby two phthalocyanine moieties are connected with a lutetium ion. Structural characterization of Lu(iii) bis phthalocyanines (Lu(iii)bisPc) was performed by 1H NMR, 13C NMR, infrared (IR), UV-vis-NIR, and MALDI-TOF spectroscopic techniques. The electrochemical properties of bis-phthalocyanines were characterized using cyclic voltammetry (CV) and square wave voltammetry (SWV). Lu(iii)bisPcs were then electropolymerized on glassy carbon electrodes (GCE). Furthermore, new modified electrodes with the electropolymerization of Lu(iii) bisPc by doping with graphane were developed in order to detect low concentrations of ascorbic acid (AA), dopamine (DA) and uric acid (UA). The surface morphologies of the hybrid electrodes were investigated using SEM/EDX, UV-Vis, IR and Raman spectroscopies. The sensing behavior of the modified electrodes was also tested to detect AA, DA and UA analytes. The Grp/Car-Pc2-1/GCE electrode selectively detected AA with a limit of detection (LOD) of 1.56 μM, while LOD values of Ply(Car-Pc2-2)/GCE and Grp/Ply(Car-Pc2-2)/GCE were determined to be 0.16 μM and 1.07 μM for DA and UA, respectively, by voltammetric analyses. Moreover, the modified electrodes were also applied to detect AA, DA and UA in tap water samples using the standard addition method with satisfactory results. This journal is
- Gürek, Ay?e Gül,Sario?ullari, Hidayet,Sengul, Ibrahim F.
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p. 22714 - 22731
(2021/12/24)
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- Butterfly-Shaped Thiophene-Pyridine Hybrids: Green Electroluminescence and Large Third-Order Optical Nonlinearities
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A set of four symmetric, butterfly-shaped 4-(4-(decyloxy)phenyl)-2,6-di(thiophen-2-yl)pyridine (TPY) derivatives 2TPA-TPY (TPY center and triphenylamine end groups), 2CBZ-TPY (TPY center and N-ethyl carbazole end groups), 2TPY-TPA (triphenylamine center and TPY at the periphery) and 2TPY-CBZ (N-ethyl carbazole center and TPY at the periphery) was synthesized. The molecules show reverse saturable absorption (RSA) which is consistent with two-photon absorption (2PA) associated with excited-state absorption (ESA) when excited using a 532 nm laser beam. The molecules 2TPA-TPY and 2TPY-TPA possess extremely low limiting thresholds of 1.73 and 2.68 J cm?2, respectively. An organic light-emitting diode (OLED) fabricated from 2TPA-TPY exhibits green emission with a maximum luminance of 207 cd m?2, a current efficiency (ηCE) of 1.51cd A?1, a maximum power efficiency (ηPmax) of 0.46 lm W?1 and an external quantum efficiency (ηEQE) of 0.48 % at 100 cd m?2.
- Chandrasekharan, Keloth,Dalimba, Udaya Kumar,Darshan, Vibhu,Gangadharappa, Sathish Chatnahalli,Kakekochi, Viprabha,Narayanan Unni, K. N.,Nikhil, P. P.
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p. 1762 - 1777
(2020/09/02)
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- The aggregation induced fluorescence effect enhanced by a reasonable length of carbon chain
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Six different barbituric acid derivatives using ethyl, propyl, butyl, pentyl, hexyl and heptyl groups as hydrophobic substituents were prepared. Molecular dynamics simulation was carried out to study the effect of different carbon chain lengths on the aggregation-induced emission process. Among the compounds, the CB-5 containing a hexyl substituent exhibited the strongest Aggregation induced emission (AIE) effect, not the CB-6 with longest carbon chain. The aggregates of CB-5 was used to detect the 2, 4, 6-trinitrotoluene (TNT) in aqueous media, exhibiting a maximum quenching constant of 3.1 × 105 M? 1. The paper sensor based on CB-5 showed a superior sensitivity toward TNT both in vapor and solution. This provided a clear strategy for designing compounds that utilize the hydrophobic interaction of long-chain alkyl chains to enhance the AIE effect.
- Zhang, Hanjun,Tao, Furong,Cui, Yuezhi,Xu, Zhen
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- Carbazolyl compounds alkylated in 9 position in position, as well as preparation method and application of carbazole compound (by machine translation)
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The invention provides a carbazole compound capable 9 of being alkylated in a-position manner, a preparation, method of the carbazole compound and a chemical structural formula of the carbazole compound as shown in the specification. The carbazolyl, R compounds C2-C9 of the present disclosure which have a straight-chain alkyl. group according to one AIE of, the above TNT-mentioned aspect of the. present disclosure not only have a higher index of refraction, but also have a sensitivity higher than the sensitivity of the detection. (by machine translation)
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- Novel carbazole-stilbene hybrids as multifunctional anti-Alzheimer agents
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Molecules capable of engaging with multiple targets associated with pathological condition of Alzheimer's disease have proved to be potential anti-Alzheimer's agents. In our goal to develop multitarget-directed ligands for the treatment of Alzheimer's disease, a novel series of carbazole-based stilbene derivatives were designed by the fusion of carbazole ring with stilbene scaffold. The designed compounds were synthesized and evaluated for their anti-AD activities including cholinesterase inhibition, Aβ aggregation inhibition, antioxidant and metal chelation properties. Amongst them, (E)-1-(4-(2-(9-ethyl-9H-carbazol-3-yl)vinyl)phenyl)-3-(2-(pyrrolidin-1-yl)ethyl)thiourea (50) appeared to be the best candidate with good inhibitory activities against AChE (IC50 value of 2.64 μM) and BuChE (IC50 value of 1.29 μM), and significant inhibition of self-mediated Aβ1–42 aggregation (51.29% at 25 μM concentration). The metal chelation study showed that compound (50) possessed specific copper ion chelating property. Additionally, compound (50) exhibited moderate antioxidant activity. To understand the binding mode of 50, molecular docking studies were performed, and the results indicated strong non-covalent interactions of 50 with the enzymes in the active sites of AChE, BuChE as well as of the Aβ1-42 peptide. Additionally, it showed promising in silico ADMET properties. Putting together, these findings evidently showed compound (50) as a potential multitarget-directed ligand in the course of developing novel anti-AD drugs.
- Chaudhary, Bharat N.,Gandhi, Pallav M.,Joshi, Prashant D.,Kanhed, Ashish M.,Patel, Dushyant V.,Patel, Kirti V.,Patel, Kishan B.,Patel, Nirav R.,Patel, Sagar P.,Prajapati, Navnit K.,Teli, Divya M.,Yadav, Mange Ram
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- Design and synthesis of carbazole fluorescence derivatization reagent and application of carbazole fluorescence derivatization reagent in fipronil and fipronil metabolite detection
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The invention relates to the field of food and agricultural safety detection, in particular to design and synthesis of a carbazole fluorescence derivatization reagent with a novel structure and application of the carbazole fluorescence derivatization reagent in fipronil and fipronil metabolite detection. Tests prove that the carbazole fluorescence derivatization reagent designed and synthesized bythe invention has very high fluorescence intensity, an HPLC-FLD (High Performance Liquid Chromatography-Fluorescence Detection) method for determining fipronil and metabolite fipronil sulfoxide thereof by pre-column derivatization established on the basis of the derivatization reagent is high in sensitivity, low in detection limit and quantification limit, good in stability and reproducibility and high in sensitivity, when the method is applied to detection of residual fipronil and metabolite fipronil sulfoxide thereof in eggs, the results are accurate and reliable, and the method is superiorto HPLC-MS/MS and GC-MS methods reported at present. The carbazole fluorescence derivatization reagent designed and synthesized by the invention has excellent performance, and the fipronil and metabolite pre-column derivatization detection method established based on the carbazole fluorescence derivatization reagent is sensitive, reliable and accurate, and has a good application prospect.
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Paragraph 0013; 0034-0036
(2020/09/09)
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- Synthesis, electronic structure, linear and nonlinear photophysical properties of novel asymmetric branched compounds
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A series of novel asymmetric branched compounds that utilize a 1,3,5-triazine core and feature D-π-A-(π-D′-π-A′)0-2 configurations (D = donor, A = acceptor, π = conjugated bridge) were designed, successfully synthesized, and fully characterized by 1H NMR, 13C NMR, FT-IR, and HRMS. Their photophysical properties including linear absorption, one-photon excited fluorescence, two-photon absorption, and frequency up-converted fluorescence, were systematically investigated in different solvents. With a rise in the polarity of solvents, the peak positions of the one-photon excited fluorescence are red-shifted and the Stokes shifts increase, while the linear absorption wavelengths change slightly. In addition, the target compounds except CZ show the positive solvatokinetic effect. With a rise in the number of branches, the red shifts of the absorption and emission maxima, the hyperchromicity of the molar absorption coefficients, and the decrease of the Stokes shifts are observed. The peripheral electron donors (carbazole, phenothiazine) and acceptors (pyridine, benzimidazole) also exert an important influence on the photophysical properties. Under excitation of 690–930 nm fs laser pulses, all the target compounds emit frequency up-converted fluorescence with the maximal peaks at 471–575 nm, and the two-photon absorption cross-sections in THF are 132 (PTZ), 182 (CZ), 453 (CZ-Py1), 844 (CZ-Py2), 1244 (CZ-BI1), and 2072 (CZ-BI2) GM, respectively. Their two-photon response is found to be nearly additive with respect to the number of branches. The time-dependent density functional theory calculations were conducted to gain an insight into their electronic structures and to better understand the structure-photophysical property relationships. The results clearly indicate the importance of appropriate structural units on the enhancement of two-photon absorption properties.
- Cai, Zhi-Bin,Chen, Li-Jun,Li, Sheng-Li,Ye, Qing,Tian, Yu-Peng
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- Ratio type fluorescent probe for detecting sulfur dioxide and application of ratio type fluorescent probe
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The invention provides a ratio type fluorescent probe for detecting sulfur dioxide. The chemical structure formula of the ratio type fluorescent probe is shown in the specification. The probe is capable of detecting existence of sulfate radicals hydrogen sulfite radicals in solutions, cells or living bodies, is very rapid in recognition speed, and is capable of meeting a balance state within a short time. In addition, the probe is successfully applied to cell imaging, is also applied to mouse imaging, and has great superiority in living body analysis and detection.
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- MODIFIED CARBAZOLES AS THERAPEUTIC AGENTS
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This disclosure relates to compounds that target microtubules, pharmaceutical compositions comprising them, and methods of using the compounds and compositions for treating diseases. More particularly, this disclosure relates to modified carbazole compounds and pharmaceutical compositions thereof, methods of targeting microtubules with these compounds, and methods of treating diseases affected by microtubule disruption.
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- Copper(II)-Catalyzed Iodinations of Carbazoles: Access to Functionalized Carbazoles
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A copper-catalyzed iodination of carbazoles has been developed. Barluenga's reagent IPy2BF4 is used to generate a soft electrophilic halonium species for the iodination of the carbazoles. This report represents the first concept of copper-catalyst-promoted electrophilic halogenation of carbazoles. We demonstrated numerous applications of this methodology synthesizing diverse carbazole derivatives, i.e., both electron-rich and electron-deficient systems.
- Przypis, Lukasz,Walczak, Krzysztof Zdzislaw
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- Comparison of Carbazole and Fluorene Donating Effects on the Two-Photon Absorption and Nitric Oxide Photorelease Capabilities of a Ruthenium–Nitrosyl Complex
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A ruthenium–nitrosyl derivative of formula [RuII(CzT)(bipy)(NO)](PF6)3 [CzT = 4′-(N-ethylcarbazol-3-yl)-2,2′:6′,2′′-terpyridine, bipy = 2,2′-bipyridine] has been synthesized and fully characterized, and compared with the previously reported [RuII(FT)(bipy)(NO)](PF6)3 complex [FT = 4′-(9,9-dihexyl-9H-fluoren-2-yl)-2,2′:6′,2′′-terpyridine]. Additionally, the X-ray crystal structure of [RuII(CzT)(bipy)(NO2)](PF6), the precursor of [RuII(CzT)(bipy)(NO)](PF6)3, is reported. The presence of a tertiary amine in the carbazole unit leads to redshifted charge-transfer transitions towards the electron-withdrawing Ru–NO fragment and hence enhanced two-photon absorption (TPA) properties. In contrast, the quantum yield of the NO· photorelease process is lower for the carbazole-containing complex. The issue of optimization of the TPA versus NO·-release capabilities is addressed.
- Enriquez-Cabrera, Alejandro,Lacroix, Pascal G.,Sasaki, Isabelle,Mallet-Ladeira, Sonia,Farfán, Norberto,Barba-Barba, Rodrigo M.,Ramos-Ortiz, Gabriel,Malfant, Isabelle
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p. 531 - 543
(2017/12/07)
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- Pseudohalide assisted aerobic oxidation of alcohols in the presence of visible-light
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Pseudohalides are well known to do similar chemistry like halides. Thiocyanate, a pseudohalide acts like halides in many ways. Thiocyanate radicals ([rad]SCN) are generated from readily available thiocyanate salts using Rose Bengal through single electron transfer (SET) in the presence of visible light. Thiocyanate radicals abstract hydrogen like other halide radicals, so this aspect of chemistry was used for the oxidation of alcohols to their corresponding aldehydes using oxygen as the terminal oxidant. This method shows a broad scope and well tolerance towards various functional groups.
- Sheriff Shah, Sk,Pradeep Singh
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supporting information
p. 247 - 251
(2018/01/03)
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- Modified carbazoles destabilize microtubules and kill glioblastoma multiform cells
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Small molecules that target microtubules (MTs) represent promising therapeutics to treat certain types of cancer, including glioblastoma multiform (GBM). We synthesized modified carbazoles and evaluated their antitumor activity in GBM cells in culture. Modified carbazoles with an ethyl moiety linked to the nitrogen of the carbazole and a carbonyl moiety linked to distinct biaromatic rings exhibited remarkably different killing activities in human GBM cell lines and patient-derived GBM cells, with IC50 values from 67 to >10,000 nM. Measures of the activity of modified carbazoles with tubulin and microtubules coupled to molecular docking studies show that these compounds bind to the colchicine site of tubulin in a unique low interaction space that inhibits tubulin assembly. The modified carbazoles reported here represent novel chemical tools to better understand how small molecules disrupt MT functions and kill devastating cancers such as GBM.
- Diaz, Philippe,Horne, Eric,Xu, Cong,Hamel, Ernest,Wagenbach, Michael,Petrov, Ravil R.,Uhlenbruck, Benjamin,Haas, Brian,Hothi, Parvinder,Wordeman, Linda,Gussio, Rick,Stella, Nephi
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- Preferential intermolecular interactions lead to chiral recognition: Enantioselective gel formation and collapse
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Interesting self-assembly of an amino acid based molecular material into a hydrogel in the presence of selective enantiomeric chiral amines leading to chiral recognition has been demonstrated. Moreover, collapse of a metallogel formed from the same material in the presence of selective enantiomers validated its enantioselective affinity. Importantly, in addition to relevant experimental techniques, DFT studies have been successfully explored to establish chiral recognition through enantioselective gelation.
- Gambhir, Diksha,Kumar, Sunil,Dey, Gourab,Krishnan, Venkata,Koner, Rik Rani
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p. 11407 - 11410
(2018/10/20)
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- Synthesis of carbazole derivatives containing chalcone analogs as non-intercalative topoisomerase II catalytic inhibitors and apoptosis inducers
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Novel topoisomerase II (Topo II) inhibitors have gained considerable interest for the development of anticancer agents. In this study, a series of carbazole derivatives containing chalcone analogs (CDCAs) were synthesized and investigated for their Topo II inhibition and cytotoxic activities. The results from Topo II mediated DNA relaxation assay showed that CDCAs could significantly inhibit the activity of Topo II, and the structure-activity relationship indicated the halogen substituent in phenyl ring play an important role in the activity. Further mechanism studies revealed that CDCAs function as non-intercalative Topo II catalytic inhibitors. Moreover, some CDCAs showed micromolar cytotoxic activities. The most potent compound 3h exhibited notable growth inhibition against four human cancer cell lines. Flow cytometric analysis revealed that compounds 3d and 3h arrested the HL-60 cells in sub G1 phase by induction of apoptosis. It was further confirmed by Annexin-V-FITC binding assay. Western blot analysis revealed that compound 3h induces apoptosis likely through the activation of caspase proteins.
- Li, Peng-Hui,Jiang, Hong,Zhang, Wen-Jin,Li, Yong-Lian,Zhao, Min-Cong,Zhou, Wei,Zhang, Lan-Yue,Tang, Ya-Dong,Dong, Chang-Zhi,Huang, Zhi-Shu,Chen, Hui-Xiong,Du, Zhi-Yun
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p. 498 - 510
(2018/01/17)
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- p-TsOH-mediated, Versatile, and Efficient Approach for the Synthesis of Triazolyl-Carbazoles from Nitrovinylcarbazoles and Azide via 1, 3-Dipolar Cycloaddition
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An efficient method for the synthesis of N-alkylated 3-(1-benzyl-1H-1,2,3-triazole-4-yl)-9H-carbazoles (5, 6, 7, 8, 9, 10) and 9-ethyl-3,6-di(1H-1,2,3-triazole-4-yl)-9H-carbazole (13) has been developed from nitroolefines. The effects of catalyst and solvent on these reactions have been investigated. p-TsOH-THF was found to be the best system for this reaction. Various triazolyl-carbazoles were prepared in good to excellent yields.
- Avula, Vijay Kumar Reddy,Vallela, Swetha,Anireddy, Jaya Shree,Chamarthi, Naga Raju
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p. 1361 - 1368
(2017/03/27)
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- Novel alkyl chain-based fluorescent probes with large Stokes shifts used for imaging the cell membrane and mitochondria in different living cell lines
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Fluorescent dyes with large Stokes shifts play a key role in developing multi-purpose fluorescent probes for a wide variety of targets. In this study, we developed two novel alkyl chain-based fluorescent probes (CA-C12 and CA-C2) with large Stokes shifts. The alkyl chain length of the probes affect the membrane permeability, and hence both probes can be successfully applied for sensing the cell membrane and mitochondria in different living cell lines. Furthermore, the probes CA-C12 and CA-C2 exhibited large Stokes shifts and excellent photostability in the different cell lines. The fluorescent dyes with large Stokes shifts were expected to have broader applications for developing various fluorescent probes with excellent optical properties.
- Meng, Fangfang,Liu, Yong,Niu, Jie,Lin, Weiying
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p. 16087 - 16091
(2017/03/22)
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- Discovery of novel nitroimidazole enols as Pseudomonas aeruginosa DNA cleavage agents
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A series of nitroimidazole enols as new bacterial DNA-targeting agents were for the first time designed, synthesized and characterized by NMR, IR and HRMS spectra. The antimicrobial screening revealed that 2-methoxyphenyl nitroimidazole enol 3i possessed stronger anti-P. aeruginosa efficacy (MIC = 0.10 μmol/mL) than reference drugs Norfloxacin and Metronidazole. Time-kill kinetic assay manifested that the active molecule 3i could rapidly kill the tested strains. Molecular docking indicated that the interactions between compound 3i and topoisomerase II were driven by hydrogen bonds. Quantum chemical study was also performed on 3i to understand the structural features essential for activity. Further research found that compound 3i was not able to effectively intercalate into bacterial DNA but could cleave DNA isolated from the standard P. aeruginosa strain, which might block DNA replication to exert the efficient bioactivities, and this active molecule was also able to be stored and carried by human serum albumin via hydrophobic interactions and hydrogen bonds.
- Li, Zhen-Zhen,Gopala, Lavanya,Tangadanchu, Vijai Kumar Reddy,Gao, Wei-Wei,Zhou, Cheng-He
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p. 6511 - 6522
(2017/11/03)
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- Synthesis, antimicrobial and antimalarial activities of some carbazole derivatives
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A series of novel carbazole-tethered pyrazolines and chromone derivatives was synthesized from 9-ethyl-9H-carbazole-3-carbaldehyde. The structures of newly synthesized compounds were confirmed by their infrared, nuclear magnetic resonance and mass spectral data. All the synthesized compounds were screened for their in vitro antibacterial, antifungal, and antimalarial activity. Some of the synthesized compounds showed comparable or even better antibacterial, antifungal, and antimalarial activities than the reference drugs ampicillin, griseofulvin, and quinine, respectively.
- Kadnor, Vijay A.,Shirole, Gopinath D.,Mhaske, Ganesh R.,Shelke, Sharad N.
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- Synthesis of carbazole-derived ligands and their metal complexes: characterization, thermal, catalytic, and electrochemical features
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Abstract: Heading from N-ethylcarbazole, two novel carbazole-derived imine compounds and their copper, cobalt, and nickel complexes have been synthesized. Their open structures have been proposed on the basis of various spectroscopic analyses. All the synthesized compounds have also been examined for their catalytic, thermal, and electronic features. Good or moderate results have been obtained for the catalytic activities of the synthesized complexes. Thermal features showed that the coordination compounds can be used in many organic reactions like oxidation reactions depending on high temperatures. Electronic features of these newly synthesized compounds have also been reported for the first time with this paper. Graphical abstract: [Figure not available: see fulltext.]
- Bal, Selma,K?ytepe, Süleyman,Connolly, Joseph D.
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p. 2061 - 2071
(2016/11/17)
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- Substituted Carbazoles-A New Class of Anthelmintic Agent
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A series of novel carbazoles were synthesized based on structural modifications to lead carbazole 1 (EC100≤2.5M against Haemonchus contortus in vitro), which was revealed in a small molecule screening program as a potentially promising platform for the development of new anthelmintic drugs. Subsequently, analogues 19, 21, 41, 42 (EC100≤ 1.25M, all), and 39 (EC100≤0.625M) were demonstrated to exhibit enhanced in vitro anthelmintic activity over the lead structure, with compound 39 also being shown to be active in vivo against Heligmosomoides polygyrus.
- Rennison, David,Gueret, Stephanie M.,Laita, Olivia,Bland, Ross J.,Sutherland, Ian A.,Boddy, Ian K.,Brimble, Margaret A.
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p. 1268 - 1276
(2016/11/25)
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- A dual-site two-photon fluorescent probe for visualizing mitochondrial aminothiols in living cells and mouse liver tissues
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Thiol-containing amino acids (RSH) play a key role in maintaining the redox environment. In this work, we developed a novel dual-site two-photon (TP) fluorescent RSH probe (CA-TPP) for imaging mitochondrial RSH in living cells and mouse liver tissues. This probe exhibited rapid response and high TP photostability towards mitochondrial RSH. In particular, probe CA-TPP was capable of using TP fluorescence to track mitochondrial RSH over a long period.
- Meng, Fangfang,Liu, Yong,Yu, Xiaoqiang,Lin, Weiying
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p. 7399 - 7406
(2016/09/12)
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- Synthesis of Novel Pyrrolo[3,2- c ]carbazole and Dipyrrolo[3,2- c:2′,3′- g ]carbazole Derivatives
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Pyrrolocarbazole and dipyrrolocarbazoles have been synthesized via the Hemetsberger indole synthesis, starting from 9-ethyl carbazole-3-carbaldehyde and 9-ethylcarbazole-3,6-dicarbaldeyde, respectively. The pyrrolocarbazole structures were confirmed through 1H NMR, 13C NMR, IR, mass spectrometry and single crystal X-ray diffraction techniques. The targeted compounds showed potent in vitro cytotoxicity against human colon cancer HT29 cells.
- Sengul, Ibrahim Fazil,Astarci, Erhan,Kandemir, Hakan
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p. 1277 - 1281
(2016/05/10)
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- A new series of two-photon blue/violet fluorescent trans-alkenes: Green synthesis and optical properties
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A new series of trans-alkenes (3a-3e) containing different electron-donating groups were synthesized by the solvent-free Horner-Wadsworth-Emmons reaction, and characterized by infrared, hydrogen nuclear magnetic resonance, mass spectrometry and elemental analysis. Their UV-visible absorption, one-photon excited fluorescence, two-photon absorption, and two-photon excited fluorescence were systematically investigated in different solvents. Experimental results show different trends in linear and nonlinear optical properties with different donor units. 3a with triphenylamine donor exhibits the best optical properties. It emits strong blue up-converted fluorescence, and the two-photon absorption cross-section can be as large as 218 GM in DCM.
- Huang, Jiu-Qiang,Cai, Zhi-Bin,Jin, Fan,Li, Sheng-Li,Tian, Yu-Peng
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p. 164 - 170
(2015/11/16)
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- Synthesis, optical characterization, and solvatochromism study of new two-photon absorption compounds
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The new donor-π-acceptor/acceptor-π-acceptor compounds (FQQ, KZQ, JYQ, and LVQ) were facilely synthesized and characterized by infrared, proton nuclear magnetic resonance, mass spectrometry, and elemental analysis. Their UV-visible absorption, one-photon excited fluorescence, two-photon absorption, and two-photon excited fluorescence were systematically investigated in different solvents. The experiment results indicate that all these compounds exhibit relatively strong up-converted fluorescence and obvious solvatochromic effects. KZQ shows the largest σ value of 707 GM in THF upon 830 nm excitation. Its excellent optical properties provide a promising alternative as a polarity-sensitive two-photon fluorescent probe. Aided with the quantum chemical density functional theory calculations, the relationships between the structures and the properties were studied.
- Zhou, Yan-Tao,Cai, Zhi-Bin,Pan, Yu-Lu,Bai, Li,Zheng, Guo-Chuang,Li, Sheng-Li,Tian, Yu-Peng
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p. 2271 - 2279
(2016/04/19)
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- Synthesis, structures, and DNA and protein binding of ruthenium(ii)-p-cymene complexes of substituted pyridylimidazo[1,5-a]pyridine: enhanced cytotoxicity of complexes of ligands appended with a carbazole moiety
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A series of organometallic Ru(ii)-arene complexes of the type [(η6-p-cymene)Ru(L)Cl](BF4) 1-6, where L is 3-phenyl-1-pyridin-2-yl-imidazo[1,5-a]pyridine (L1), dimethyl-[4-(1-pyridin-2-yl-imidazo[1,5-a]pyridin-3-yl)phenyl]-amine (L2), diphenyl-[4-(1-pyridin-2-yl-imidazo[1,5-a]pyridin-3-yl)phenyl]amine (L3), 9-[4-(1-pyridin-2-yl-imidazo-[1,5-a]pyridin-3-yl)-phenyl]-9H-carbazole (L4), 9-ethyl-3-(1-pyridin-2-yl-imidazo-[1,5-a]pyridin-3-yl)-9H-carbazole (L5), and 10-ethyl-3-(1-pyridin-2-yl-imidazo[1,5-a]pyridin-3-yl)-10H-phenothiazine (L6), has been isolated and characterised by elemental analysis, ESI-MS, NMR and cyclic voltammetry. The photophysical properties of the complexes have been studied by electronic absorption and emission spectral techniques. All the ligands exhibit tuneable photoluminescence behaviour with the emission maximum spanning through the visible region (475-670 nm) in dichloromethane while all the complexes are emissive in acetonitrile. The single crystal X-ray structures of 2, 3 and 4 reveal that the complexes have a “piano stool” coordination geometry, comprising one π-bonded arene centroid, two σ-bonded nitrogen atoms from the chelating ligand and one Cl- ion. From DNA induced EthBr emission quenching experiments the apparent DNA binding constants of the complexes (Kapp) have been evaluated, which follows the order, 2 (1.3) 5 M-1). This trend reveals the role of ligand hydrophobicity on the DNA binding ability of complexes, the non-planar phenothiazine ring (6) and the specific interactions the planar carbazole chromophore (4, 5) make with DNA. The value of Ksv obtained as the slope of the linear plot of F0/F vs. [complex] follows the order 1 (3.1) -1), which supports the inferences from DNA binding experiments. All the complexes, except, 1 and 2 (>100 μM), exhibit in vitro cytotoxicity against A549 small lung cancer cell lines higher than cisplatin (~69 μM), as revealed by both MTT (11.8-18.1 μM) and crystal violet staining (12.7-23.5 μM) assays, which is in agreement with their DNA and BSA binding affinity. Also, the complexes 3-6 cause higher cell death mainly through the apoptotic mode, as revealed by the observation of a higher percentage of apoptotic cells in AO/EB (36-43%) and Annexin V-Cy3 (36-45%) stained cancer cells.
- Khamrang, Themmila,Kartikeyan, Radhakrishnan,Velusamy, Marappan,Rajendiran, Venugopal,Dhivya, Rajakumar,Perumalsamy, Balaji,Akbarsha, Mohammad Abdulkadher,Palaniandavar, Mallayan
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p. 114143 - 114158
(2016/12/24)
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- Synthesis, characterization and antitumor activity of 9H-carbazol-3-imidazo [4,5-f][1,10]phenanthrolin derivatives
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A series of 9H-carbazol-3-imidazo[4,5-f][1,10]phenanthrolin derivatives (1-6) have been synthesized and characterized by IR, NMR and MS. The cytotoxicity of compounds 1-6 against HL-60, BGC-823, Bel-7402, and KB cell lines have been tested by MTT assays. The results indicate that compound 1 exhibits potent anticancer activity better than cisplatin with IC50 values of 0.41, 0.99, 1.19, and 0.49 μM against BGC-823, Bel-7402 and KB cell lines. The side chains have an important influence on the cytotoxicity of the compounds. The cytotoxicity of compounds 1-6 decreases with the increasing length of side chains.
- Fang, Zhang Fang,Pei, Feng Wei,Chao, Zhang Jin,Hui, Li Sheng,Ying, Qin Xin,Xiang, Wang Shu
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p. 713 - 717
(2017/01/18)
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- Novel pyrromethene dyes with N-ethyl carbazole at the meso position: a comprehensive photophysical, lasing, photostability and TD-DFT study
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Two novel BODIPY (pyrromethene, PM) dyes containing N-ethyl carbazole at the meso position are synthesized and their photophysical properties in different solvents and the photochemical stabilities and laser performances in n-heptane are investigated. The n-heptane solution of the dyes was used as a gain medium in a constructed narrow band dye laser, pumped by a Q-switched (10 Hz) frequency-doubled (532 nm) Nd:YAG laser and the results gave enhanced photo stabilities and similar peak efficiencies of the synthesized dyes as compared to parent dye PM567. When substituted at the meso position with N-alkyl carbazole, photostability is found to be increased in comparison to PM567, and also when substituted at 2- and 6-positions with a benzyl group instead of an ethyl group along with N-ethyl carbazole at the meso position, the photo stability is further increased in n-heptane. A comprehensive study on structural, photophysical and electronic properties of dyes by means of DFT and TD-DFT in the solvents of various polarities has revealed remarkable characteristics of the BODIPY chromophore.
- Thorat, Kishor G.,Kamble, Priyadarshani,Ray, Alok K.,Sekar, Nagaiyan
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p. 17221 - 17236
(2015/07/02)
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