- Direct Olefination of Fluorinated Quinoxalines via Cross- Dehydrogenative Coupling Reactions: A New Near-Infrared Probe for Mitochondria
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A large library of 5,8-distyrylquinoxaline fluorophores was synthesized in good-to-excellent yields via a palladium-catalyzed oxidative C–H/C–H cross-coupling of electron-deficient fluorinated quinoxalines with electron-rich styrenes. The resulting quinoxaline fluorophores (Qu-Fluors) exhibited tunable color emissions with the quantum yields of up to 83% and large Stokes shifts of up to 6236 cm?1 in dichloromethane. The bioimaging performance of the Qu-Fluors was shown to have potential as near-infrared fluorescent probes for mitochondria. (Figure presented.).
- Zhang, Zeyuan,Zheng, Yiwen,Sun, Zuobang,Dai, Zhen,Tang, Ziqiang,Ma, Jiangshan,Ma, Chen
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- Enhancing the coplanarity of the donor moiety in a donor-acceptor molecule to improve the efficiency of switching phenomenon for flash memory devices
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Two conjugated small molecules were synthesized by Heck coupling reaction, wherein 1,8-naphthalimide acted as an electron acceptor, while either carbazole or triphenylamine, which contributed the different coplanarity, acted as electron donors, respectively. The devices based on both materials show non-volatile flash memory characteristics, and the effect of molecular coplanarity of the donor groups on the device performance was precisely studied. The results indicated that the reproducibility of the switching phenomenon for the memory device based on the carbazole containing naphthalimide derivative was much better than that based on the triphenylamino based naphthalimide due to the rigid carbazole moiety which improved the surface morphology as revealed by atomic force microscopy measurement. Therefore, the significance of the coplanarity of the donor moiety on improving reproducibility of switching phenomenon for memory device applications was revealed.
- Ren, Wusheng,Zhuang, Hao,Bao, Qing,Miao, Shifeng,Li, Hua,Lu, Jianmei,Wang, Lihua
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- High-efficiency deep blue fluorescent emitters based on phenanthro[9,10-d]imidazole substituted carbazole and their applications in organic light emitting diodes
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A series of highly efficient deep blue emitters comprising of carbazole and phenanthro[9,10-d]imidazole moieties are designed and synthesized. These compounds present deep blue emission, narrow FWHM, high quantum yields, high thermal and morphological stabilities. Among them, the design strategy of 2:1 ratio of phenanthro[9,10-d]imidazole and carbazole unit affords M2 with more balanced carrier injection and transporting properties. OLEDs using M2 as emitting layer is observed to deliver a truly deep blue CIE of y 3is attained with a maximum current efficiency of 33.35 cd A-1, a power efficiency of 22.99 lm W-1and a maximum external quantum efficiency of 9.47%. When doped with an orange fluorescent material, upon careful tuning the doping proportion, the two-emitting-component white OLED is successfully fabricated with a maximum current efficiency of 5.53 cd A-1and CIE coordinates of (0.313, 0.305). Both the non-doped and doped devices exhibited high operational stability with negligible efficiency roll-off over the broad current density range.
- Gao, Zhao,Wang, Zhiming,Shan, Tong,Liu, Yulong,Shen, Fangzhong,Pan, Yuyu,Zhang, Huanhuan,He, Xin,Lu, Ping,Yang, Bing,Ma, Yuguang
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- Exploration of high-performance light-conversion agents based on cyanostilbene and phenanthrenecarbonitrile backbones:E/Zand position isomerism, high-contrast Michael addition reaction activity and intramolecular photocyclization
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As light-conversion agents, traditional organic fluorescent dyes easily suffer from solid-state fluorescence quenching and photooxidation, leading to the deterioration of their application performance. To enhance the fluorescence emission and photostability of light-conversion agents in a doped film, in this paper, some luminogens with a cyanostilbene or a phenanthrenecarbonitrile backbone were designed and synthesized based on aggregation-induced emission (AIE) theory,E/Zisomerization and our previous research results, and were characterizedviaNMR, HR-MS and single-crystal X-ray diffraction. The experimental results indicate that bothZ-oCaandZ-pCaexhibit high-contrast Michael addition reaction activity and intramolecular photocyclization, as well as fluorescence quantum yields in the doped film, but similarE/Zphotoisomerization and AIE activity. Besides,E-oCashows stable configuration in solution, but not forZ-pCa, meanwhile,E-oCaandZ-oCadisplay different AIE activities. More importantly,C-Cawith a twisted molecular configuration succeeded in avoiding fluorescence quenching induced by intramolecular photocyclization, emitting strong fluorescence in the solid state and the PABT-doped film (PLQY = 0.65). After an intensified UV radiation of 20 h, 94% of the initial intensity is reserved, and emission peaks exhibit tiny shifts. Based on matching excitation and emission maxima (374 nm and 433 nm), high PLQY, excellent photostability and light-conversion quality in the doped film,C-Cais a potential high-performance light-conversion agent. Finally, light-conversion properties and the intrinsic mechanism are discussed in detail using the UV-vis absorption spectra, fluorescence emission spectra, crystal analysis, the photosynthetic photon flux density, the percentages of different wavelength bands, theoretical calculations and XRD patterns. This work is the first report on a highly efficient light-conversion agent with the phenanthrenecarbonitrile backbone; meanwhile, it contributes considerably to the molecular design of photostable luminogens and basic photochemistry.
- Wang, Yongtao,Qian, Zhean,Li, Xueming,Qin, Anjun,Guo, Yanjun,Tang, Benzhong
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- Development of a carbazole-based fluorescence probe for G-quadruplex DNA: The importance of side-group effect on binding specificity
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G-quadruplex DNAs are highly prevalent in the human genome and involved in many important biological processes. However, many aspects of their biological mechanism and significance still need to be elucidated. Therefore, the development of fluorescent probes for G-quadruplex detection is important for the basic research. We report here on the development of small molecular dyes designed on the basis of carbazole scaffold by introducing styrene-like substituents at its 9-position, for the purpose of G-quadruplex recognition. Results revealed that the side group on the carbazole scaffold was very important for their ability to selectively recognize G-quadruplex DNA structures. 1a with the pyridine side group displayed excellent fluorescence signal turn-on property for the specific discrimination of G-quadruplex DNAs against other nucleic acids. The characteristics of 1a were further investigated with UV–vis spectrophotometry, fluorescence, circular dichroism, FID assay and molecular docking to validate the selectivity, sensitivity and detailed binding mode toward G-quadruplex DNAs.
- Wang, Ming-Qi,Ren, Gui-Ying,Zhao, Shuang,Lian, Guang-Chang,Chen, Ting-Ting,Ci, Yang,Li, Hong-Yao
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- meso-borneol- andmeso-carbazole-substituted porphyrins: multifunctional chromophores with tunable electronic structures and antitumor activities
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Herein, a series of fiveC2symmetric H2porphyrins withmeso-borneol andmeso-carbazole units have been synthesized and isolated. An analysis of the electronic structures was carried out by spectroscopic investigations and electrochemica
- Fu, Bo,Dong, Xinyi,Yu, Xiaoxiao,Zhang, Zhen,Sun, Lei,Zhu, Weihua,Liang, Xu,Xu, Haijun
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- Luminescence switching of a persistent room-temperature phosphorescent pure organic molecule in response to external stimuli
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4-(Carbazol-9-yl)benzaldehyde could emit yellow RTP, which could last for 3 s because of efficient intersystem crossing. Moreover, multicolor luminescent switches could be realized by simply applying a mechanical force stimulus.
- Xue, Pengchong,Sun, Jiabao,Chen, Peng,Wang, Panpan,Yao, Boqi,Gong, Peng,Zhang, Zhenqi,Lu, Ran
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- Synthesis, crystal structure and photoluminescence of phosphorescent copper (I) complexes containing hole-transporting carbazoly moiety
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Two new mononuclear Cu(I) complexes based on 2-(2′-pyridyl) benzimidazolyl derivative ligand containing hole-transporting carbazole (L), [Cu(L)(DPEphos)](BF4) and [Cu(L)(PPh3)2] (BF4), where L = (4-(9H-carbazol-
- Yu, Tianzhi,Chai, Haifang,Zhao, Yuling,Zhang, Chengcheng,Liu, Peng,Fan, Duowang
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- Carbazole-containing push-pull chromophore with viscosity and polarity sensitive emissions: Synthesis and photophysical properties
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Carbazole based D-π-A extended styryl dyes with intramolecular charge transfer characteristics were synthesized. The intramolecular charge transfers of these D-π-A extended styryls have been examined with the study of photophysical properties like absorption, emission and quantum yield in various solvents of different polarities. All the dyes demonstrated positive solvatochromism. They showed largely improved photophysical properties and large Stokes shifts due to twist geometry. Oscillator strengths and transition state dipole moments have been studied to understand charge transfer within the molecules. The fluorescence molecular rotors properties of the series of extended styryls have been evaluated. The dyes having good charge transfer characteristics showed better FMR properties. Sensitivity of the fluorescence emission towards solvent polarity and viscosity has been investigated using fluorescence emission spectra.
- Telore, Rahul D.,Sekar, Nagaiyan
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- Carbazole-based sensitizers for potential application to dye sensitized solar cells
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Two push-pull molecules employing carbazole and alkyl thiophene (CAR-THIOHX) or carbazole and triphenylamine (CAR-TPA) as donor moieties, with the cyanoacrylic group as the acceptor, have been designed and synthesized by simple organic transformations. Photophysical and electrochemical studies revealed the potential of these two systems in dye sensitized solar cells (DSSC). Under standard irradiation conditions, CAR-TPA and CAR-THIOHX exhibited 2.12 and 1.83% of overall power conversion efficiencies respectively. The moderate photovoltaic efficiency of the sensitizers has been attributed to the poor light absorption of the sensitizers in the visible region. Density functional theory (DFT) calculations have shown a strong intramolecular charge transfer character, with the HOMOs of both the sensitizers exclusively localized on the corresponding donor moieties and LUMOs on the cyanoacrylic acid acceptor. On the other hand, the calculated high dihedral angle between the carbazole donor and the phenyl bridge for these sensitizers impedes the conjugation along the dyes backbone, and thus leads to less extended and intense absorption spectra in the visible region. [Figure not available: see fulltext.]
- Duvva, Naresh,Kanaparthi, Ravi Kumar,Kandhadi, Jaipal,Marotta, Gabriele,Salvatori, Paolo,De Angelis, Filippo,Giribabu, Lingamallu
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- Nonvolatile bistable resistive switching in a new polyimide bearing 9-phenyl-9H-carbazole pendant
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A new polyimide bearing the functional pendant 9-phenyl-9H-carbazole moieties, poly[2,2-(4,4′-di(N-benzyloxycarbazole)-3,3′-biphenylene) propane-hexafluoroisopropylidenediphthalimide] (6F-BAHP-PC PI), has been designed as a functional material for resista
- Hu, Benlin,Zhuge, Fei,Zhu, Xiaojian,Peng, Shanshan,Chen, Xinxin,Pan, Liang,Yan, Qing,Li, Run-Wei
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- Highly efficient organic photosensitizer with aggregation-induced emission for imaging-guided photodynamic ablation of cancer cells
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We design an organic photosensitizer with a donor-π-acceptor configuration. The photosensitizer exhibits aggregation-induced emission characteristics and efficient singlet oxygen production in the aggregated state. It is then enveloped into the water-soluble micelle to afford a nanoprobe. The water-soluble nanoprobe keeps the photosensitizer in the aggregation state and is used for imaging-guided photodynamic ablation of cancer cells.
- Li, Yipeng,Yu, Qi,Gao, Pengli,Yang, Huiran,Huang, Tianci,Liu, Shujuan,Zhao, Qiang
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- Self-Stabilized Amorphous Organic Materials with Room-Temperature Phosphorescence
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The stability of pure organic room-temperature phosphorescent (RTP) materials in air has been a research hotspot in recent years. Without crystallization or encapsulation, a new strategy was proposed to obtain self-stabilized organic RTP materials, based
- Xu, Wei,Yu, Yaguo,Ji, Xiaonan,Zhao, Huarui,Chen, Jinming,Fu, Yanyan,Cao, Huimin,He, Qingguo,Cheng, Jiangong
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- Synthesis of high-triplet-energy host polymer for blue and white electrophosphorescent light-emitting diodes
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A high-triplet-energy host polymer consisting of 9-(4-(bis(9-(2-ethylhexyl)-9H-carbazol-3-yl)methyl)phenyl)-9H-carbazole and tetraphenylsilane units was designed and synthesized. The triplet energy (2.67 eV) is one of the highest values reported for conju
- Xu, Fei,Kim, Ji-Hoon,Kim, Hee Un,Jang, Jae-Ho,Yook, Kyoung Soo,Lee, Jun Yeob,Hwang, Do-Hoon
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- Synthesis of Linear and V-Shaped Carbazolyl-Substituted Pyridine-3,5-dicarbonitriles Exhibiting Efficient Bipolar Charge Transport and E-Type Fluorescence
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With the aim of developing all-organic bipolar semiconductors with high charge mobility and efficient E-type fluorescence (so-called TADF) as environmentally friendly light-emitting materials for optoelectronic applications, four noble metals-free dyes with linear and V-shapes were designed using accepting pyridine-3,5-dicarbonitrile and donating carbazole units. By exploiting a donor-acceptor design strategy and using moieties with different donating and accepting abilities, TADF emitters with a wide variety of molecular weights were synthesized to achieve the optimum combination of charge-transporting and fluorescent properties in one TADF molecule. Depending on molecule structures, different TADF emitters capable of emitting in the range from 453 to 550 nm with photoluminescence quantum yields up to 98 % for the solutions in oxygen-free toluene were obtained. All compounds showed bipolar charge-transport. Hole mobility of 2.8×10?3 cm2/Vs at 7×105 V cm?1 was observed for the compound containing two di-tert-butyl-substituted carbazole moieties. The compounds were tested in both non-doped and doped organic light-emitting diodes using different hosts. It was shown that the developed TADF emitters are suitable for different color devices with electroluminescence ranging from blue to yellow and with brightness, maximum current and external quantum efficiencies exceeding 10 000 cd m?2, 15 cd/A, and 7 %, respectively.
- Vigante, Brigita,Leitonas, Karolis,Volyniuk, Dmytro,Andruleviciene, Viktorija,Simokaitiene, Jurate,Ivanova, Anna,Bucinskas, Audrius,Grazulevicius, Juozas V.,Arsenyan, Pavel
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- Simply Structured Near-Infrared Emitters with a Multicyano Linear Acceptor for Solution-Processed Organic Light-Emitting Diodes
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Near-infrared (NIR) organic light-emitting diodes (OLEDs) show great potential in a variety of applications including sensors, night vision, and information security. Despite the superiority of thermally activated delayed fluorescence (TADF) in 100 % exci
- Zhao, Bingjie,Xie, Guohua,Wang, Huiqin,Han, Chunmiao,Xu, Hui
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- Multifunctional phosphorescent iridium (III) complexes based on 2-phenylbenzothiazole derivative for highly efficient organic light-emitting diodes
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Phosphorescent robust heteroleptic iridium (III) [Ir(III)] complexes based on 2-(4-(9H-carbazol-9-yl)phenyl)benzothiazole integrated with three auxiliary ligand were designed, synthesized and used to fabricate organic light-emitting diodes (OLEDs). The Ir(III) complexes emitted intense phosphorescence with yellow or orange color at room temperature with high quantum efficiencies and relatively short lifetimes. The auxiliary ligand greatly influenced the electronic and photophysical properties of their corresponding heteroleptic Ir(III) complexes. The complexes showed reversible redox characteristics. Hole-only single-carrier devices indicated that three complexes all possessed excellent hole-transporting ability. The phosphorescent OLEDs using three Ir(III) complexes as dopants exhibited turn-on voltages of ca. 4 V, maximum current efficiencies of 22.3-44.2 cd A-1 and maximum power efficiencies of 18.3-23.3 lm W-1, which were superior to the (bt)2Ir(acac)-based device (19.1 cd A-1, 9.3 lm W -1) under the same condition. The elevated devices' performances based on the new Ir(III) complexes as emitters were probably attributed to the hole-transporting rigid carbazole moiety resulting in more balanced electron and hole transportation and recombination in emissive layer.
- Li, Xiao,Zang, Tie-Nan,Chi, Hai-Jun,Dong, Yan,Xiao, Guo-Yong,Zhang, Dong-Yu
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- Hypercrosslinked porous polycarbazoles from carbazolyl-bearing aldehydes or ketones
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Hypercrosslinked polymers have drawn increasing interest due to their porous structure, large specific surface area, and excellent chemical and thermal stability. Using the carbonyl bearing carbazole monomers Cz-22~27, a series of hypercrosslinked porous polycarbazoles CPOP-22~27 have been synthesized through oxidative coupling polymerization and Friedel–Crafts reaction in one-step promoted by FeCl3. The Brunauer–Emmett–Teller specific surface areas of CPOP-22~27 are between 440 and 760 m2 g?1. Their dominant pore sizes vary from 0.99 to 1.06 nm, which indicating that the polymers are predominantly microporous. This work provides a new method to synthesis of hypercrosslinked porous polycarbazoles from carbonyl functionalized carbazoles. It is also found that parts of aldehyde groups can not react through the Friedel–Crafts alkylation when increasing the number of carbazole groups. The residual aldehyde groups in the polymer can even react with Tollens’ reagent solution to form Ag nanoparticles composite.
- Zhang, Rong-Rong,Yin, Qing,Liang, Hai-Peng,Chen, Qi,Luo, Wei-Hua,Han, Bao-Hang
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- Photoinduced energy transfer in carbazole-BODIPY dyads
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A series of carbazole (CBZ)-boron dipyrromethene (BODIPY) based donor-acceptor dyads, CB1, CB2, and CB3, with CBZ as an energy donor, tethered together with spacers of varied sizes i.e., phenyl bridge, biphenyl bridge and diphenylethyne bridge, respectively, are reported. The newly synthesized dyads were characterized by various spectroscopic techniques. A comparison of the absorption and electrochemical data of the dyads with their reference compounds (i.e., 9-phenyl-9H-carbazole (C0) and N,N′-difluoroboryl-1,3,7,9-tetramethyl-5-phenyldipyrrin (B0)) revealed minimal ground-state interactions between the chromophores. Selective excitation of CBZ in the dyads at 290 nm resulted in the quenching of the CBZ emission followed by the appearance of BODIPY emission, revealing efficient energy transfer from singlet excited CBZ (1CBZ?) to BODIPY. The photoinduced energy transfer phenomenon was studied in three different solvents of varying polarity. The driving forces for energy transfer (ΔGEN) for all the dyads were found to be exothermic. The rate constants for energy transfer, kENT, measured by the femtosecond transient absorption technique in toluene were found to be in the range of 0.8-2.0 × 1010 s-1, depending on the type of spacer between the CBZ and BODIPY entities, and were in close agreement with the theoretically estimated rates according to the F?rster energy transfer model. In contrast, selective excitation of BODIPY in these dyads at 485 nm resulted in small quenching of the BODIPY emission, suggesting a lack of major photochemical events originating from 1BODIPY?.
- Reddy, Govind,Duvva, Naresh,Seetharaman, Sairaman,D'Souza, Francis,Giribabu, Lingamallu
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- Pyridine derivatives; New efficient additives in bromide/tribromide electrolyte for dye sensitized solar cells
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In this work, two new inexpensive pyridine derivatives, propyl isonicotinate (PIN) and isopropyl isonicotinate (IPIN), have been synthesized through a simple and low cost method and for the first time, they have been applied as effective additives in bromide/tribromide electrolyte in dye sensitized solar cells (DSSCs). Although the iodide/triiodide redox shuttle shows remarkable performance in DSSCs, but bromide/tribromide couple has a more positive redox potential in comparison to this couple. Therefore, it is good idea to design dyes whose HOMO and LUMO levels match with the redox potential of bromide/tribromide and the conduction band (CB) of TiO2, respectively. We have synthesized 3-(4-carbazole-9-yl-phenyl)-2-cyano-acrylic acid (TC301) and 2-cyano-3-(4-(3,6-di-tert-butyl-9H-carbazole-9-yl)phenyl) acrylic acid (TC302) as two carbazole dyes and applied them with modified electrolyte in DSSCs. The influence of PIN and IPIN additives in bromide/tribromide redox electrolyte on the DSSC performances is investigated. In comparison to electrolyte without additive, adding 0.5 M of these additives to the electrolyte solution leads to an increase in the open circuit voltage (Voc) and short current density (Jsc), consequently the energy conversion efficiency (η) improves. Electrochemical impedance spectroscopy show that the enhancement in Voc is due to increasing electron density in the CB of TiO2 so that a shift in the Fermi level (EF) occurs. It leads to a suppression in electron recombination that has beneficial effect on the Voc. Furthermore, cyclic voltammetry results reveal that PIN and IPIN has similar effect mechanisms to 4-tert-butylpyridine (TBP) additive in the DSSCs. Our findings show that TBP can be replaced with PIN and IPIN in the DSSCs.
- Bagheri, Omid,Dehghani, Hossein,Afrooz, Malihe
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- Synthesis and the effect of a peripheral N-arylcarbazole moiety on the acid-base and DNA binding properties of a novel RuII complex
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A novel RuII complex of [Ru(bpy)2(cpipH)](ClO 4)2 (where bpy = 2,2′-bipyridine, cpipH = 2-[4-(9H-carbazol-9-yl)phenyl]-1H-imidazol[4,5-f][1,10]phenanthroline) was synthesized. The binding of the complex to calf thymus DNA was investigated with UV/Vis absorption and luminescence titrations, steady-state emission quenching by [Fe(CN)6]4-, DNA competitive binding with ethidium bromide, and thermal denaturation. The pH effects on the UV/Vis absorption and emission spectra of the complex were also studied, and the ground- and excited-state ionization constants were derived. The results indicated that the complex intercalatively bound to the DNA, with an intrinsic binding constant of (8.2 ± 0.8) × 105 M-1 in buffered 50 mM NaCl, is stronger than the parent complex, [Ru(bpy)2(pip)]2+ (pip = 2-phenylimidazo[4,5-f][1,10]phenanthroline), and its excited states are 0.7-0.8 pKa units more basic than those of the ground states. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
- Lue, Yuan-Yuan,Gao, Li-Hua,Han, Mei-Jiao,Wang, Ke-Zhi
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- Engineering a double-rotor-based fluorescent molecule to sensitively track mitochondrial viscosity in living cells and zebrafish with high signal-to-background ratio (S/B)
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An innovative design strategy has been proposed to construct viscosity-sensitive fluorescent probes with superior sensitivity and high signal-to-background ratio (S/B) based on double-rotor molecular platform. As a proof-of-concept, a double-rotor-based f
- He, Longwei,Lin, Weiying,Yang, Yunzhen
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- Two stimulus-responsive carbazole-substituted D–π–A pyrone compounds exhibiting mechanochromism and solvatochromism
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Two D–A compounds were designed and synthesized from 2,6-dimethyl-4-pyrone and carbazole compounds. Both of them exhibited unique fluorescence properties in the aggregated state. Red shifts of the spectrum of 102?nm and 130?nm were observed for BCSP and C
- Liu, Dongqi,Cao, Yuqi,Yan, Xilong,Wang, Bowei
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- Novel benzothiadiazine 1,1-dioxide based bipolar host materials for efficient red phosphorescent organic light emitting diodes
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In this work, three novel bipolar host materials TPA-SA, 3CBZ-SA and 4CBZ-SA have been designed and synthesized by incorporating triphenyl amine and carbazole as donor and benzothiadiazine 1,1-dioxide as an acceptor. These molecules exhibit moderately high triplet energies and bipolar carrier transport characteristics (ambipolarity) which is useful for the exothermic energy transfer to the dopants and also for the balanced carrier injection/transport in the emissive layers. These materials exhibited good performances in PhOLEDs and furnished external quantum efficiency in the range of 10.0–15.0%. Notably, a red phosphorescent device using TPA-SA as the host doped with Ir(pq)2(acac) exhibited a maximum EQE, power efficiency and current efficiency of 15.0%, 16.0 lm/W, and 25.3 cd A?1, respectively.
- Lade, Jatin,Lee, Nian-Yun,Patil, Bhausaheb,Deshpande, Yogita Y.,Pownthurai,Hsieh, Chung-An,Pingale, Subhash S.,Chen, Li-Yin,Chaskar, Atul
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- Synthesis, photophysical and electrochemical properties of novel D-π-D and D-π-a triphenylamino-chalcones and β-arylchalcones
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A series of triphenylamino (TPA)-chalcones and triphenylamino-β-arylchalcones, displaying either D-π-D or D-π-A architecture, were synthesized through aldol condensations and Heck reactions. The chalcone derivatives display intense absorption bands rangin
- Da Costa, Rafaela G.M.,Farias, Francisco R.L.,Maqueira, Luis,Neto, Carlos Castanho,Carneiro, Leonardo S.A.,Almeida, Joseany M.S.,Buarque, Camilla D.,Aucélio, Ricardo Q.,Limberger, Jones
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- Synthesis, crystal structures, and photoluminescent properties of bis(pyrazol-1-yl)methane derivative and Zn(II) halide complexes (ZnLX2, X=Cl, Br, I)
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A novel bis(pyrazol-1-yl)methane derivative 9-(4-(di(1H-pyrazol-1-yl) -methyl) phenyl)-9H-carbazole (L) and its zinc halide complexes (ZnLX2, X = Cl (1), Br (2), and I (3)) were prepared and fully characterized. The structures of the ligand (L) and complexes 2 and 3 were also characterized by single-crystal X-ray diffraction analysis. The results reveal that the central zinc(II) atom in the complexes is coordinated by two nitrogen atoms from ligands (L) and two halide anion forming a distorted tetrahedron coordination geometry. And then the hydrogen bonding interactions between the molecules from 1D to 3D supramolecular structures were investigated. Furthermore, the photophysical properties of the complexes 1-3 and L were investigated both experimentally and theoretically. The experimental results are consistent with that of the theoretical calculation.
- Wang, Shi-Chao,Zhang, Yan-Can,Jin, Feng,Liu, Wan-Ding,Zhou, Hong-Ping,Wu, Jie-Ying,Tian, Yu-Peng
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- Synthesis and characterisation of RuII polypyridyl complexes: DNA-binding, photocleavage, and topoisomerase i and II inhibitory activity
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Two mixed-ligand ruthenium(ii) complexes [Ru(phen)2(cptcp)]2+ (Ru1; phen≤1,10-phenanthroline, cptcp≤2-(4-carbazol-9-yl-phenyl)-1H-1,3,7,8- tetraaza-cyclopenta-[l]-phenanthrene) and [Ru(phen)2(btcpc)]2+ (Ru2; btcpc≤9-butyl-6-(1H-1,3,7,8-tetraaza-cyclo-cyclopenta-[l]-phenanthren-2-yl) -9H-carbazole-3-carbaldehyde) have been synthesised and characterised. The DNA-binding behaviours of the two complexes have been investigated by using spectroscopic and viscosity measurements. Results suggest that the two complexes bind to DNA by intercalation. The photocleavage of plasmid pBR322 DNA indicates that Ru1 exhibits more effective DNA cleavage activity in comparison to that exhibited by Ru2 under the same conditions, and different cleavage mechanisms are determined. Topoisomerase inhibition and DNA strand passage assay confirm that Ru1 may act as an efficient dual inhibitor of topoisomerases I and II, whereas Ru2 may only act as a single inhibitor of topoisomerases II. CSIRO 2013.
- He, Xiaojun,Yang, Guang,Sun, Xiaonan,Xie, Lingjun,Tan, Lifeng
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- Synthesis and photophysical properties of [60]fullerene adducts carrying oligocarbazole dendrons
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[60]Fullerene adducts carrying oligocarbazole moieties were successfully prepared by the Bingel reactions. Their fluorescence spectra and transient absorption spectra suggested the intramolecular electron transfer from the oligocarbazole moiety to the ful
- Nakamura, Yosuke,Konno, Takashi,Watanabe, Satoru,Suzuki, Masato,Yoshihara, Toshitada,Tobita, Seiji,Nishimura, Jun
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- Carbazole/triphenylamine-cyanobenzimidazole hybrid bipolar host materials for green phosphorescent organic light-emitting diodes
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With a view to attain balanced charge flux for higher device performance of PhOLEDs, we have used carbazole/triphenyl amine as hole transporting moiety and cyano along with benzimidazole as electron transporting core in 3-Cbz-ImdCN, 4-Cbz-ImdCN and TPA-Im
- Patil, Bhausaheb,Lade, Jatin,Chiou, Shian-Sung,Cheng, Yen-Chia,Jadhav, Yogesh,Chetti, Prabhakar,Chang, Chih-Hao,Chaskar, Atul
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- Photophysical properties of 3-[2-(N-phenylcarbazolyl)benzoxazol-5-yl] alanine derivatives-experimental and theoretical studies
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Solvatochromic probes are often used in biophysical studies to obtain information about polarity of the microenvironment. As there is not much natural fluorophores with such properties, there is still need for new synthetic compounds such as 3-(2-benzoxaz
- Guzow, Katarzyna,Czerwinska, Marlena,Ceszlak, Agnieszka,Kozarzewska, Marta,Szabelski, Mariusz,Czaplewski, Cezary,Lukaszewicz, Anna,Kubicki, Aleksander A.,Wiczk, Wieslaw
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- Multi-response quinoxaline-based fluorophores: Solvatochromism, mechanochromism, and water sensoring
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Three new D-π-A type quinoxaline-cored fluorophores were elaborately designed and synthesized. It was found that P-1, P-2, and P-3 (Ps) all presented bathochromic-shifted mechanochromic (MFC) nature upon grinding, accompanied with 30 nm, 8 nm, and 37 nm r
- Yu, Jia,Liu, Zhifang,Wang, Bowei,Cao, Yuqi,Liu, Dongqi,Wang, Yixian,Yan, Xilong
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- Study of the influences of molecular planarity and aluminum evaporation rate on the performances of electrical memory devices
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In this paper, two conjugated small molecules (CZ-BT and TPA-BT) were designed and successfully synthesized to investigate the influence of different electron donor moieties on thin-film morphology and their electrical memory device properties. Current-vo
- Liu, Hongzhang,Bo, Rongcheng,Liu, Haifeng,Li, Najun,Xu, Qingfeng,Li, Hua,Lu, Jianmei,Wang, Lihua
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- Sensitive and selective Cu2+ sensor based on 4-(3-(thiophen-2-yl)-9H-carbazol-9-yl)benzaldehyde (TPCBZ) conjugated copper-complex
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4-(3-(thiophen-2-yl)-9H-carbazol-9-yl)benzaldehyde (TPCBZ) was synthesized under microwave irradiation with auto generated pressure (at 130.0 °C) and characterized by 1H NMR, 13C NMR, Mass and FTIR spectroscopy, thin-layer chromatogr
- Rahman, Mohammed M.,Alamry, Khalid A.,Saleh, Tamer S.,Asiri, Abdullah M.
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Read Online
- Experimental and theoretical study of three new benzothiazole-fused carbazole derivatives
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Three new D-π-A type compounds, each containing one benzothiazole ring as an electron acceptor and one N-ethylcarbazole group as electron donor, were synthesized and characterized by elemental analysis, NMR, MS and thermogravimetric analysis. The absorption and emission spectra of three compounds were experimentally determined in several solvents and were simultaneously computed using density functional theory (DFT) and time-dependent density functional theory (TDDFT). The calculated reorganization energy for hole and electron indicates that three compounds are in favor of hole transport than electron transport. The calculated absorption and emission wavelengths are well coincident with the measured data. The calculated lowest-lying absorption spectra can be mainly attributed to intramolecular charge transfer (ICT). And the calculated fluorescence spectra can be mainly described as originating from an excited state with intramolecular charge transfer (ICT) character. The results show that three compounds exhibited excellent thermal stability and high fluorescence quantum yields, indicating their potential applications as excellent optoelectronic material in optical field.
- Shi, He-Ping,Xu, Lei,Cheng, Ying,He, Jing-Yuan,Dai, Jian-Xin,Xing, Li-Wen,Chen, Bai-Quan,Fang, Li
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Read Online
- Photophysical and Electrochemical Properties of Highly π-Conjugated Bipolar Carbazole-1,3,4-Oxadiazole-based D-π-A Type of Efficient Deep Blue Fluorescent Dye
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In this contribution, we have designed and synthesized a novel carbazole-1,3,4-oxadiazole based bipolar fluorophore (E)-2-(4-(4-(9H-carbazol-9-yl)styryl)phenyl)-5-(4-(tertbutyl) phenyl)-1,3,4-oxadiazole (CBZ-OXA-IV). Wittig reaction is utilised for the synthesis of the designed bipolar target compound CBZ-OXA-IV.1H NMR, 13C NMR, FT-IR and ESI–MS results confirmed the designed chemical structure of the fluorophore CBZ-OXA-IV. The photophysical properties have been investigated in detail using UV–Vis absorption, photoluminescence spectroscopy. Also, the photoluminescence studies on solid state samples (as thin films) were carried out. The CBZ-OXA-IV dye emits intense deep blue fluorescence with observed absorption and emission maxima occurring are at 353?nm and 470?nm, respectively. Fluorophore CBZ-OXA-IV has shown high Stokes shift of 7052?cm?1. The experimentally measured optical band gap (Egopt) value is found to be 3.01?eV and the fluorescence quantum yields (Φf) is 0.40. The intramolecular charge transfer property of CBZ-OXA-IV dye was examined by using photophysical properties such as absorption, emission in different solvents of different varying polarities. In addition, Density Functional Theory computations are studied in detail including the MEP surface plots and natural bond orbital analysis. The electrochemical properties have been investigated in detail by using cyclic voltammetry measurements. Thermal gravimetric analysis (TGA) and differential scanning calorimetry (DSC) measurement results display a high thermal stability with decomposition temperature (Td5%) 387?°C and a large glass transition temperature (Tg) of 98?°C. The obtained results demonstrated that the novel bipolar fluorophore CBZ-OXA-IV could play an important role in organic optoelectronics and possibly can be utilized as bipolar transport materials for electroluminescence applications in optoelectronic devices/OLEDs. Graphical abstract: [Figure not available: see fulltext.]
- Najare, Mahesh Sadashivappa,Patil, Mallikarjun Kalagouda,Tilakraj, Tarimakki Shankar,Yaseen, Mohammed,Nadaf, AfraQuasar A,Mantur, Shivaraj,Inamdar, Sanjeev Ramchandra,Khazi, Imtiyaz Ahmed M
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Read Online
- Benzimidazole blue-light-emitting material as well as preparation method and application thereof
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The invention discloses a benzimidazole blue-light-emitting material as well as a preparation method and application thereof. The benzimidazole blue-light-emitting material is prepared from the following compounds: 9-(4-(5, 6-difluoro-1-methyl-1H-benzo [d] imidazole-2-yl) phenyl)-9H-carbazole, 4-(5, 6-difluoro-1-methyl-1H-benzo [d] imidazole-2-yl)-N, N-diphenylamine, 2-(4-(9H-carbazole-9-yl) phenyl)-1-(4-cyanophenyl)-5-cyano-1H-benzo [d] imidazole, 1-(4-cyanophenyl)-2-(4-(diphenylamino) phenyl)-5-cyano-1H-benzo [d] imidazole, or 2-(2-(9H-carbazole-9-yl) phenyl)-1-(4-cyanophenyl)-5-cyano-1H-benzo [d] imidazole. The benzimidazole blue-light-emitting material has good thermal stability and relatively high color purity and luminous efficiency, and is an excellent electroluminescent material.
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Paragraph 0111-0115
(2021/09/26)
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- A long persistent phosphorescent metal-organic framework for multi-level sensing of oxygen
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A novel metal-organic framework (MOF) with long persistent luminescence (LPL) for multilevel oxygen detection is proposed, for which, the phosphorescence intensity, phosphorescence lifetime and LPL performance were applied to detect oxygen levels in 300-100 mbar, 0-150 mbar and 8 mbar, respectively. Uniquely, the new idea of LPL detection makes the monitoring of ultra-low oxygen content possible with visualization.
- Fan, Ya-Nan,Mo, Jun-Ting,Pan, Mei,Wang, Zheng,Zhu, Cheng-Yi
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supporting information
p. 9916 - 9922
(2020/08/21)
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- A class of asymmetric V-shaped organic dye sensitizers, preparation method and applications thereof
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The invention discloses a class of asymmetric V-shaped organic dye sensitizers, wherein the molecules adopt triphenylamine and phenothiazine as electron donating groups, a long carbon chain is introduced into the N atom of the phenothiazine, benzothiazole
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Paragraph 0042-0045; 0056-0059
(2020/03/09)
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- Thermochromic material and preparation method and application thereof
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The invention discloses a piezochromic material, a preparation method and applications thereof. The preparation method comprises the following steps: adding 3 grams of carbazole, 3.3 grams of p-bromobenzaldehyde, 3.7 grams of potassium carbonate, 0.33 gra
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Paragraph 0007; 0009
(2020/04/02)
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- COMPOUND FOR ORGANIC OPTOELECTRONIC DEVICE, COMPOSITION FOR ORGANIC OPTOELECTRONIC DEVICE AND ORGANIC OPTOELECTRONIC DEVICE AND DISPLAY DEVICE
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The present invention relates to: a compound for an organic optoelectronic device, which is represented by chemical formula 1; a composition for an organic optoelectronic device; and an organic optoelectronic device and a display device to which the compound and composition are applied. The details of the chemical formula 1 are as defined in the specification. One embodiment provides the compound for the organic optoelectronic device, which can realize the organic optoelectronic device having high efficiency and long lifetime.
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Paragraph 0263-0265
(2020/09/12)
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- Ligand compound and functionalized metal-organic framework compound prepared from ligand compound, and preparation methods and applications thereof
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The invention discloses a ligand compound and a functionalized metal-organic framework compound prepared from the ligand compound, and preparation methods and applications thereof. The structure of the ligand compound is represented by formula (I), the li
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Paragraph 0063; 0067-0068
(2020/06/16)
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- Light induced intramolecular energy and electron transfer events in carbazole-corrole and phenothiazine-corrole dyads
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We report two corrole based donor-acceptor (D-A) dyads, Cbz-Cor and Ptz-Cor to understand the energy/electron transfer reactions. In these D-A systems, the donor, either carbazole (Cbz) or phenothiazine (Ptz), is covalently connected at the meso-phenyl po
- Shivaprasadachary,Ramya,Reddy, Govind,Giribabu
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p. 693 - 704
(2019/09/17)
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- OPTICAL DATA COMMUNICATION SYSTEM COMPRISING PARA-PHENYLENEVINYLENES AND SPECIFIC PARA-PHENYLENEVINYLENES
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An optical data communication system comprising para-phenylenevinylenes, a receiver for an optical data communication system comprising para-phenylenevinylenes, a transmitter for an optical data communication system comprising para-phenylenevinylenes, the use of para- phenylenevinylenes in an optical data communication system, specific para-phenylenevinylenes and their preparation.
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Page/Page column 49-50
(2020/01/08)
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- Long-life room-temperature phosphorescent material and preparation method and application thereof
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The invention discloses a long-life room-temperature phosphorescent material and a preparation method and application thereof. Phenolic hydroxyl is introduced into an organic aromatic ring structure,a complex formed by phenol anions and amine cations is p
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Paragraph 0073-0076
(2019/11/20)
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- Novel carbazole fluorescent thiol marking reagent as well as synthesis method and application thereof
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The invention provides a novel carbazole fluorescent thiol marking reagent as well as a synthesis method and application thereof. The florescent marking reagent adopts carbazole as a fluorescent basering and activated C=C double bonds as reaction activity
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Paragraph 0028; 0029; 0030
(2018/09/21)
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- Double-photon fluorescent probe used for temperature detection and derived from carbazole and preparation method of double-photon fluorescent probe
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The invention relates to the technical field of temperature probes, in particular to a double-photon fluorescent probe used for temperature detection and derived from carbazole and a preparation method of the double-photon fluorescent probe. The structural formula of the double-photon fluorescent probe is shown in the description. The fluorescence quantum yield of the probe is high, the detectionrange is wide, the application range of the double-photon fluorescent probe is greatly widened, and the detection reliability is improved.
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Paragraph 0026
(2018/04/03)
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- Bipolar 9-linked carbazole-π-dimesitylborane fluorophores for nondoped blue OLEDs and red phosphorescent OLEDs
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Three dimesitylborane-containing fluorophores with various π-conjugated systems attached at the 9th position of carbazole, namely, 9-(4′-bromobiphenyl-4-yl)-9H-carbazole (Cz9Ph2B), 9-(4-(5-(dimesitylboryl)thiophen-2-yl)phenyl)-9H-carbazole (Cz9ThPhB), and 9-(4-(4-(dimesitylboryl)styryl)phenyl)-9H-carbazole (Cz9SB) were synthesized and their photophysical and electroluminescent properties were investigated for application in nondoped blue OLEDs as well as red phosphorescent OLEDs (PhOLEDs). The electron-accepting dimesitylboryl group and various π-conjugated segments appended to the electron-donating carbazole moiety impart the three fluorophores with bipolar transporting ability, and their energy levels are matched with those of the adjacent carrier-transporting layers. These bulky fluorophores are thermally stable with glass transition temperatures and degradation temperatures reaching up to 105 and 383 °C, respectively. In addition, efficient nondoped Cz9PhThB- and Cz9SB-based blue OLEDs with maximum currents of 1.51 and 4.03 cd A?1 and external quantum efficiencies (EQE) of 2.30 and 4.72% were achieved, respectively. Notably, the Cz9Ph2B-based red PhOLEDs exhibits a relatively low turn-on voltage (3.3 V) and high electroluminescence efficiencies (maximum current = 23.12 cd A?1 and EQE = 14.10%). Their performance is superior to that of the corresponding device using conventional 4,4′-N,N′-dicarbazolbiphenyl as the host material. Moreover, a maximum brightness of 39700 cd m?2 was also achieved.
- Liu, Chi-Kan,Chen, Ying-Hsiao,Long, Yi-Jun,Sah, Pai-Tao,Chang, Wei-Che,Chan, Li-Hsin,Wu, Jhao-Lin,Jeng, Ru-Jong,Yeh, Shih-Chieh,Chen, Chin-Ti
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p. 101 - 108
(2018/05/04)
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- Tuning the solid-state emission of small push-pull dipolar dyes to the far-red through variation of the electron-acceptor group
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Series of solid-state emitters based on the D-π-A dipolar structure and featuring various electron-donor and electron-acceptor groups were designed, and their spectroscopic properties studied. From weak emission in dilute solutions, intense emissions in aggregated state (AIE) and in the crystalline state were obtained. Analysis in light of crystal structures obtained by X-ray diffraction revealed specific crystal packing and presence of long chain of emitting aggregates. This simple molecular engineering around the D-π-A dipolar structure provides easy access to a wide range of effective solid-state emitters allowing modulation of emission wavelengths up to the near infrared (λem reaching 735 and 768 nm for compound 2f and 3f bearing the strongest electron-withdrawing group).
- Redon, Sébastien,Eucat, Gwena?lle,Ipuy, Martin,Jeanneau, Erwann,Gautier-Luneau, Isabelle,Ibanez, Alain,Andraud, Chantal,Bretonnière, Yann
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p. 116 - 132
(2018/04/16)
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- Mitochondrion-targeted viscosity determination fluorescent probe as well as preparation method and application thereof
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The invention synthesizes a mitochondrion-targeted viscosity fluorescent probe which takes carbazole as a fluorophore and a positive nitrogen ion as a mitochondrion positioning group by virtue of molecular design. The invention also provides a simple prep
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Paragraph 0020; 0022
(2017/09/26)
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- Molecular Engineering of UV/Vis Light-Emitting Diode (LED)-Sensitive Donor–π–Acceptor-Type Sulfonium Salt Photoacid Generators: Design, Synthesis, and Study of Photochemical and Photophysical Properties
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A series of donor–π–acceptor-type sulfonium salt photoacid generators (PAGs) were designed and synthesized by systematically changing electron-donating groups, π-conjugated systems, electron-withdrawing groups, and the number of branches through molecular engineering. These PAGs can effectively decompose under UV/Vis irradiation from a light-emitting diode (LED) light source because of the matching absorption and emitting spectra of the LEDs. The absorption and acid-generation properties of these sulfonium salts were elucidated by UV/Vis spectroscopy and so forth. Results indicated that the PAG performance benefited from the introduction of strong electron-donating groups, specific π-conjugated structures, certain electron-withdrawing groups, or two-branched structures. Most sulfonium salts showed potential as photoinitiators under irradiation by a wide variety of UV and visible LEDs.
- Wu, Xingyu,Jin, Ming,Xie, Jianchao,Malval, Jean-Pierre,Wan, Decheng
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supporting information
p. 15783 - 15789
(2017/10/20)
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- Facile fabrication of AIE/AIEE-active fluorescent nanoparticles based on barbituric for cell imaging applications
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Four barbituric derivatives (1-4), were synthesized with obvious aggregation induced emission (AIE) or aggregation induced emission enhancement (AIEE) behaviors. The optical properties in different states and the mechanisms of the enhanced emission of 1-4 were investigated. We found that there were a large number of globular or blocky nanoparticles with average diameters from 229 to 394 nm in tetrahydrofuran (THF)/water solutions when the water fraction (fw) was 90%. The single crystal data of 2 and 4 reveal that multiple intermolecular interactions restrict the intramolecular motions, and promote the formation of a herringbone arrangement (4), thus permitting intense emission in the aggregate state. In addition, the frontier molecular orbital energy and band gap calculated by density functional theory (DFT) are consistent with the experimental results. Compound 4 is cell-permeable: upon entering the live cells, the dye molecules can accumulate in the lysosomes and turn on the fluorescence.
- Li, Kai,Zhang, Yang,Qiao, Bing,Tao, Furong,Li, Tianduo,Ding, Yunqiao,Raymo, Fran?isco M.,Cui, Yuezhi
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p. 30229 - 30241
(2017/07/07)
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- Intermolecular interactions boost aggregation induced emission in carbazole Schiff base derivatives
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Six D-π-A model compounds (compounds 1-6) were conveniently synthesized and characterized by 1H NMR, 13C NMR, MS and single crystal X-ray diffraction. One photon absorption and emission properties were studied by using a series of UV-visible and fluorescence spectra and theoretical calculations were applied to investigate the structure-property relationships, which showed that all six compounds possessed an obvious intramolecular charge transfer process which could be attributed to their optical properties. We simultaneously investigated their fluorescence emission performance in water/acetonitrile mixtures and found that they all have outstanding aggregation induced emission properties. Scanning electron microscopy testing illustrated that orderly aggregation was the main reason for their aggregation induced emission properties. Cytotoxicity tests indicated that all these compounds had good biocompatibility for living cells, and bio-imaging studies highlighted the potential application of the six compounds in one-photon fluorescence microscopy imaging domains.
- Gan, Xiaoping,Liu, Guangjin,Chu, Mingjie,Xi, Wengang,Ren, Zili,Zhang, Xiuli,Tian, Yupeng,Zhou, Hongping
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p. 256 - 264
(2016/12/27)
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- Triarylpyridine derivatives containing carbazole frameworks and preparation method and application thereof
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The invention relates to triarylpyridine derivatives containing carbazole frameworks and a preparation method and application thereof. Through Witting-Horner and Suzuki coupling reaction, six D-pi-A molecules based on carbazole and 2, 4, 6-triarylpyridine
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Paragraph 0020; 0021; 0022
(2017/08/28)
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- COMPOSITIONS CONTAINING BENZOCYCLOBUTENE SUBSTITUTED CARBAZOLES, AND ELECTRONIC DEVICES CONTAINING THE SAME
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The invention provides compositions comprising crosslinkable BCB-functionalized materials for use in OLEDs applications. The inventive compositions can be used to form hole-transporting materials for use in electroluminescent devices. In particular, the invention provides a composition comprising at least one compound selected from Structure A, as described herein.
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Page/Page column 24
(2016/03/13)
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- Styrene-acrylic acid compound and its preparation and use in medicine
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The invention discloses a novel benzene propanoic acid compound represented by formula I, an optical isomer and a raceme thereof as well as physiologically acceptable salts, a solvate and a crystallizing form thereof. The invention further discloses a preparation method of the compound, a medicine preparation containing the compound and a clinical application of the compound for treating diseases related to insulin resistance.
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Paragraph 0207; 0208
(2016/10/08)
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- 5,15-di-(4-(3,6-dibromo-9-carbazole)phenyl)-10,20-di-(4-bornyl formate phenyl)porphyrin and preparation method of 5,15-di-(4-(3,6-dibromo-9-carbazole)phenyl)-10,20-di-(4-bornyl formate phenyl)porphyrin
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The invention provides 5,15-di-(4-(3,6-dibromo-9-carbazole)phenyl)-10,20-di-(4-bornyl formate phenyl)porphyrin with the molecular formula of C90H72Br4N6O4. The molecular structural formula (I) is shown as in the specification. A preparation method of the 5,15-di-(4-(3,6-dibromo-9-carbazole)phenyl)-10,20-di-(4-bornyl formate phenyl)porphyrin comprises the following steps: synthesizing 9-(4-formylphenyl)carbazole by carbazole and p-fluorobenzaldehyde and brominating the 9-(4-formylphenyl)carbazole by Br2 to obtain 3,6-dibromo-9-(4-formylphenyl)carbazole; synthesizing 5-(4-(3,6-dibromo-9-carbazole)phenyl)dipyrromethane by taking the 3,6-dibromo-9-(4-formylphenyl)carbazole and pyrrole as raw materials under the catalytic effect of trifluoroacetic acid; finally, taking the 5-(4-(3,6-dibromo-9-carbazole)phenyl)dipyrromethane and p-bornyl formate benzaldehyde to react to prepare the 5,15-di-(4-(3,6-dibromo-9-carbazole)phenyl)-10,20-di-(4-bornyl formate phenyl)porphyrin. The compound provided by the invention has relatively good solubility in organic solvents including dichloromethane, chloroform, N,N-dimethylformamide and the like, and has a potential application prospect in the fields of biomedicine, photoelectric functional materials and the like.
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Paragraph 0014; 0028; 0029
(2016/10/24)
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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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- Rigid triarylamine donor-π-acceptor porphyrin dyes and their application in dye-sensitized solar cells
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Three donor-π-acceptor porphyrin dyes bearing a variety of rigid triarylamine donor groups were synthesized for application as photosensitizers in TiO2 based dye-sensitized solar cells (DSSCs). Compared with the "naked" porphyrin ZnP, i.e. havi
- Zhou, Yongzhu,Lee, Nicholas A.,Ngo, Ken T.,Peng, Xiao,Feng, Yaqing,Rochford, Jonathan
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p. 41193 - 41202
(2015/05/20)
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- Carbazole-functionalized organic photosensitizer for dye-sensitized solar cells
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We designed and synthesized the photosensitive ?? -conjugated organic dyes (CB-1, CB-2 and CB-3) with the carbazole substituted triphenylamine moiety as an electron donor unit and the cyanoacetic acid moiety as an acceptor for the application as a photosensitizer of dye-sensitized solar cells. The dyes with two carbazole units connected to triphenylamine moiety (CB-2 and CB-3) showed enhanced electron donating property than the one with one carbazole moiety as an electron donor unit (CB-1), which resulted in longer absorption maximum wavelength, higher overall photon to current conversion efficiency and IPCE values. In particular, CB-3 showed an absorption maximum wavelength at 428 nm and overall solar-to-energy conversion efficiency of 7.58% at AM 1.5 illumination (100 mW.cm-2) without mask.
- Lee, Jeonghun,Im, Hunbae,Kim, Sukwon,Kim, Chulhee
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p. 1434 - 1442
(2015/02/19)
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- A novel stilbene-based organic dye with trans-cis isomer, polymorphism and aggregation-induced emission behavior
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Cis-trans isomer and polymorphism of 9-(4-(4-nitrostyryl)phenyl)-9H-carbzole (Dye 1) were obtained unexpectedly. Each isomer has two polymorphs, which was characterized by X-ray single crystal diffraction. Polymorphs T1 and T2 are trans-configuration and both crystallize in monoclinic space group P21/c. Polymorphs C1 and C2 are cis-configuration and crystallize in triclinic space group P-1 and monoclinic space group P21/c, respectively. Trans-isomer shows better stability and higher density than that of cis-isomer, but cis-isomer displays better solubility than that of trans-isomer. The molecular structures and packing arrangements of the four kinds of crystals show different features. The twisted conformation of cis-isomer effectively avoids π-π interactions and close packing. Both the trans and cis isomers show remarkable aggregation-induced emission effect in the acetonitrile/water mixture. In addition, fluorescence cell imaging experiment proves the potential application of the two isomers of dye 1.
- Xi, Wengang,Zhang, Yubin,Chen, Boyu,Gan, Xiaoping,Fang, Min,Zheng, Jun,Wu, Jieying,Tian, Yupeng,Hao, Fuying,Zhou, Hongping
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- Promising ZnO-based DSSC performance using HMP molecular dyes of high extinction coefficients
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Employing newly synthesized di-substituted tri-phenyl amine (HMP-9) and carbazole (HMP-11) dyes (with limited acidic carboxyl anchor groups), a power conversion efficiency as high as 7.03% in ZnO nanocrystallite (NC)-based dye-sensitized solar cells (DSSCs) is achieved. The specific molecular designs of HMP-09 and HMP-11 consisting of with and without hexyloxy spacer groups, and added tri-phenyl amine or 9-phenyl-9H-carbazole donor groups, respectively, attached on the ancillary ligands are advantageous, evidenced from electrochemical impedance spectroscopy measurements, for ZnO NC-based DSSCs. This journal is the Partner Organisations 2014.
- Ganesh,Nguyen, Hong-Minh,Mane, Rajaram S.,Kim, Nakjoong,Shinde, Dipak V.,Bhande, Sambhaji S.,Naushad, Mu.,Hui,Han, Sung Hwan
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supporting information
p. 11305 - 11308
(2014/07/21)
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