- New copper complex derivatives including bis-dipyrrinato ligand for color filter pigments
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Four red compounds for color filter (CF) pigments in which phenyl, 4-chloro-phenyl, 4-fluoro-phenyl and pentafluorophenyl groups are substituted to 5-position of dipyrrinato group based on bis-dipyrrinato ligand were synthesized, and physical properties f
- Park, Jongwook,Park, Junghyo,Shin, Hawnkyu,Park, Youngil,Shin, Yunseop,Kim, Seungho
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- Synthesis of porphyrins bearing trans-thiols
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(matrix presented) A route to porphyrins bearing frans-thiols is described using a thioacetyl-containing aldehyde or a thioacetyl-containing dipyrromethane in the presence of catalytic BF3·OEt2 followed by oxidation. Metal complexation and ammonium hydroxide induced acetyl removal provides a route to these important molecular systems for future electronics experiments in which the thiols would serve as the adhesion points to gold probes.
- Jagessar, Raymond C.,Tour, James M.
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- Synthesis, structure, photophysical, electrochemical properties and antibacterial activity of brominated BODIPYs
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A series of mono- and di-brominated BODIPYs (1-5) was synthesized and characterized with a view to study the performance of dyes towards antibacterial activity. Regioselective bromination at the 2- and 2,6-positions of the BODIPY core was achieved with quantitative yield. The bromination of meso-(4-hydroxyphenyl) BODIPY (5) yielded an unexpected dibromo derivative, where the bromine groups were installed at the 3,5-positions of the phenyl ring rather than the 2,6-positions of the BODIPY core, which is confirmed and supported by UV-visible, fluorescence, and 1H NMR spectroscopic analyses, electrochemical studies, and also by single crystal X-ray crystallography. We observed a red shift of ~16 nm in the absorption and 20-29 nm in the emission spectra in CH2Cl2 for the installation of each bromine group at the BODIPY core. The small difference between the first reduction potentials of the parent and dibromo derivative (5 and 5b) reveal that dibromination does not occur on the pyrrolic moiety. The intermolecular interactions involving C?H, F?H, H?H, and Br?H are the key factors in stabilizing the molecular crystal packing. The antibacterial properties of these dyes were investigated and the brominated derivatives showed better antibacterial effects than their corresponding parent BODIPYs, particularly the unusual dibromo derivative, 5b.
- Prasannan, Dijo,Raghav, Darpan,Sujatha, Subramaniam,Hareendrakrishna Kumar, Haritha,Rathinasamy, Krishnan,Arunkumar, Chellaiah
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- Green Chemistry for Preparation of Oligopyrrole Macrocycles Precursors: Novel Methodology for Dipyrromethanes and Tripyrromethanes Synthesis in Water
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A novel methodology for preparation of linear oligopyrroles is presented. Synthetic protocol uses water as a solvent for acid catalysed condensation of an aldehyde or ketone with unsubstituted pyrrole. While the most procedures for the above-mentioned com
- Karl, Vladimir,Vasek, Petr,Dolensky, Bohumil
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- Meso- and axially-modified IrIIItriarylcorroles with tunable electrocatalytic properties
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The synthesis of three A2B type Ir(III)triarylcorroles with meso-aryl substituents that provide electron donating (push) and withdrawing (pull) properties and three A3 type IrIIItriphenylcorroles with differing pyridine axial ligands is reported, along with their structural characterization. An analysis of the structure-property relationships in the optical and redox properties has been carried out by comparing their optical spectroscopy and electrochemistry to trends predicted in DFT and TD-DFT calculations. The results demonstrate that A2B type IrIIItriarylcorroles are highly efficient electrocatalyzed oxygen reduction reactions (ORRs) and that their reactivity can be modulated by modulating the electronic structure by changing the nature of the meso-substituent at the B-positions, and even axial pyridine ligands.
- Zhang, Xifeng,Wang, Yu,Zhu, Weihua,Mack, John,Soy, Rodah C.,Nyokong, Tebello,Liang, Xu
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- Single azopyridine-substituted porphyrin molecules for configurational and electronic switching
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A new azopyridine functionalized Ni-porphyrin was synthesized as a model compound for deposition and switch on surfaces. Two geometrically and electronically different states of single molecules on Au(111) were found by scanning tunneling microscopy/spectroscopy and analyzed with density functional calculations.
- Matino, Francesca,Schull, Guillaume,Jana, Umasish,Koehler, Felix,Berndt, Richard,Herges, Rainer
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- Poly (ethylene oxide) tethered trans-porphyrin: Synthesis, self-assembly with fullerene (C60) and DNA binding studies
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trans-Porphyrin containing phenyl group at both ends was synthesized via corresponding dipyrromethanes (DPM) in the presence of TFA and DDQ. The polyethyleneglycole (PEG) chains were attached at the trans positions of ABA type porphyrinic moiety. The prep
- Akhtar, Muhammad Asim,Riaz, Sara,Hayat, Akhtar,Nasir, Muhammad,Muhammad, Nawshad,Rahim, Abdur,Nawaz, Mian Hasnain
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- Synthesis of dipyrromethanes in aqueous media using boric acid
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Boric acid acts as an efficient and green catalyst for the condensation reaction of pyrrole and aldehydes in aqueous medium to produce parallel library of dipyrromethanes including new compound analogue, meso-acetyldipyrromethane in moderate to good yield. The use of boric acid as catalyst and selective reactivity of aldehydes over ketones in its presence, and water as reaction medium are important attributes in the present protocol.
- Singhal, Anchal,Singh, Snigdha,Chauhan, Shive M. S.
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- Expanded dipyrrins with electron-withdrawing substituents: Broad range of absorption in the visible region
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Reaction of meso-aryl-substituted dipyrromethanes with tetracyanoethylene led to generation of a mono-tricyanovinyl-substituted species as well as an expanded dipyrrin analogue bearing both a dicyanomethylene and a tricyanovinyl substituent at the α-posit
- Liang, Xu,Shimizu, Soji,Kobayashi, Nagao
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- Enforced effects of side group substitution position on luminescence properties; Synthesis of bis(dipyrrinato)zinc complex derivatives
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New yellow-green emitting materials using bis(dipyrrinato)zinc complex moiety were synthesized by substituting phenyl group and 1- or 2-positioned naphthalene group. Bis[5-(1-naphthalenyl)-dipyrrinato]zinc complex (Zn(1-NaPN)2) substituted at p
- Lee, Sola,Seok, Chang-Hun,Park, Youngil,Lee, Areum,Jung, Dong Hyun,Choi, Seung-Hoon,Park, Jongwook
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- New Zn complex derivatives for red OLEDs host materials
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New two metal complexes, di-(Phenyl dipyrrylmethene)zinc (Zn(PPM)2) and di-(Pentafluorophenyl dipyrrylmethene)zinc (Zn(PFPPM)2) as a host material instead of Alq3 were synthesized. To evaluate electroluminescent properties, multi-layered organic light-emi
- Hyun, Ae-Ran,Kim, Soo-Kang,Kang, In-Nam,Park, Jong-Wook,Shin, Ji-Young,Song, Ok-Keun
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- Gold(III) corroles for high performance organic solar cells
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While the use of molecular materials having long-lived triplet excited state(s) for harvesting solar energy could be an effective approach to boost up the power conversion efficiency (PCE) of organic solar cells (OSCs), the performances of this kind of OSCs as reported in the literature are low ( 2.9% PCE attained for the vacuum-deposited OSCs). Herein is described the realization of high performance OSCs by using gold(III) 5,10,15-triphenylcorrole (Au-C1), gold(III) 10-(p-trifluoromethylphenyl)-5,15-diphenylcorrole (Au-C2), and gold(III) 10-(pentafluorophenyl)-5,15-diphenyl-corrole (Au-C3), as electron-donors. These gold(III) corroles display excited state lifetimes of ≥ 25 μs and low emission quantum yields of 0.15%. With the complexes Au-C1, Au-C2, and Au-C3, vacuum-deposited OSCs, which give PCEs of 2.7%, 3.0%, and 1.8%, respectively, are fabricated. The PCE can be further boosted up to 4.0% after thermal treatment of the OSC devices. Meanwhile, a solution-processed OSC based on Au-C2 with a high PCE of 6.0% is fabricated. These PCE values are among the best reported for both types of vacuum-deposited and solution-processed OSCs fabricated with metal-organic complexes having long-lived excited states as electron-donor material. The underlying mechanism for the inferior performance of the reported OSCs is discussed.
- Lai, Shiu-Lun,Wang, Lin,Yang, Chen,Chan, Mei-Yee,Guan, Xiangguo,Kwok, Chi-Chung,Che, Chi-Ming
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- An easily accessible and recyclable copper nanoparticle catalyst for the solvent-free synthesis of dipyrromethanes and aromatic amines
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A facile method to prepare a reusable copper nanocatalyst is reported. Transmission electron microscopy shows that the CuNPs are spherical in nature and reside in the nanoscopic template of the capping agent, guar gum. Powder X-ray diffraction studies confirm the crystalline nature of the CuNPs. The catalytic efficiency and recyclability of the synthesized CuNPs were demonstrated through the synthesis of dipyrromethanes (DPMs) and aromatic amines. Various DPMs are obtained in very good yields under solvent-free conditions and nitroarenes are converted to the corresponding amino compounds within 10 min, as evidenced by the kinetic study.
- Megarajan, Sengan,Ayaz Ahmed, Khan Behlol,Rajmohan, Rajamani,Vairaprakash, Pothiappan,Anbazhagan, Veerappan
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p. 103065 - 103071
(2016)
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- Green synthesis of dipyrromethanes in aqueous media catalyzed by SO3H-functionalized ionic liquid
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A mild, efficient and metal-free method was described for the green synthesis of dipyrromethanes from aldehydes and unsubstituted pyrrole catalyzed by SO3H-functionalized ionic liquids (SO3H-ILs) in aqueous media at room temperature. Notably, SO3H-ILs, 1-butylsulfonic-3-methylimidazolium hydrogen sulfate ([bsmim][HSO4]) was the most efficient catalyst for moderate to good yields of the corresponding desired products.
- Senapak,Saeeng,Jaratjaroonphong,Kasemsuk,Sirion
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- Activating the Fe(I) State of Iron Porphyrinoid with Second-Sphere Proton Transfer Residues for Selective Reduction of CO2to HCOOH via Fe(III/II)-COOH Intermediate(s)
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The ability to tune the selectivity of CO2 reduction by first-row transition metal-based complexes via the inclusion of second-sphere effects heralds exciting and sought-after possibilities. On the basis of the mechanistic understanding of CO2 reduction by iron porphyrins developed by trapping and characterizing the intermediates involved (J. Am. Chem. Soc. 2015, 137, 11214), a porphyrinoid ligand is envisaged to switch the selectivity of the iron porphyrins by reducing CO2 from CO to HCOOH as well as lower the overpotential to the process. The results show that the iron porphyrinoid designed can catalyze the reduction of CO2 to HCOOH using water as the proton source with 97% yield with no detectable H2 or CO. The iron porphyrinoid can activate CO2 in its Fe(I) state resulting in very low overpotential for CO2 reduction in contrast to all reported iron porphyrins, which can reduce CO2 in their Fe(0) state. Intermediates involved in CO2 reduction, Fe(III)-COOH and a Fe(II)-COOH, are identified with in situ FTIR-SEC and subsequently chemically generated and characterized using FTIR, resonance Raman, and M?ssbauer spectroscopy. The mechanism of the reaction helps elucidate a key role played by a closely placed proton transfer residue in aiding CO2 binding to Fe(I), stabilizing the intermediates, and determining the fate of a rate-determining Fe(II)-COOH intermediate.
- Amanullah, Sk,Saha, Paramita,Dey, Abhishek
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- Enhancing the Viscosity-Sensitive Range of a BODIPY Molecular Rotor by Two Orders of Magnitude
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Molecular rotors are a class of fluorophores that enable convenient imaging of viscosity inside microscopic samples such as lipid vesicles or live cells. Currently, rotor compounds containing a boron-dipyrromethene (BODIPY) group are among the most promis
- Toliautas, Stepas,Dodonova, Jelena,?virblis, Audrius,?iplys, Ignas,Polita, Artūras,Devi?is, Andrius,Tumkevi?ius, Sigitas,?ulskus, Juozas,Vy?niauskas, Aurimas
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- One-step synthesis of dipyrromethanes in water
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In this communication we describe the first results of an efficient synthesis of β-free-dipyrromethanes in water. This new method affords very pure products in moderate to high yields, using a cheap, non-toxic, environment friendly solvent, in a one-step procedure from pyrrole and carbonyl compounds, needing little or no work up procedures.
- Sobral, Abílio J.F.N.,Rebanda, Nuno G.C.L.,Da Silva, Melo,Lampreia, Sandra H.,Ramos Silva,Matos Beja,Paix?o,Rocha Gonsalves, Anto?nio M. D'A.
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- Physicochemical and computational insight of 19F NMR and emission properties of: Meso -(o -aryl)-BODIPYs
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A series of electronic and physicochemical parameters were explored to determine their effect on experimental spectroscopic and photophysical data. Through a systematic obtention of a series of meso-(o-aryl)-BODIPYs, 19F NMR spectra were analyzed and thei
- Farfán-Paredes, Mónica,González-Antonio, Oscar,Tahuilan-Anguiano, Diana E.,Peón, Jorge,Ariza, Armando,Lacroix, Pascal G.,Santillan, Rosa,Farfán, Norberto
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- Triarylcorroles by oxidative coupling of triaryltetrapyrranes
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A general two-step, one-pot synthesis of meso-triphenylcorrole from 5-phenyldipyrrane is presented. A number of p-phenyl-substituted 5-phenyldipyrranes were condensed with substituted benzaldehydes under acid catalyzed conditions to produce a mixture high
- Bri?as,Brückner
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- Synthesis and luminescent properties of lanthanide-cored supramolecular complexes based on porphyrins for optical amplification
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We have investigated the development of lanthanide-cored supramolecular complexes containing porphyrins to circumvent the solubility problem and maximize the optical amplification properties. Their chemical structures were identified by FT-IR, 1/sup
- Paik, Kyung Lim,Kim, Hwan Kyu
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- Sulfonated graphenes catalyzed synthesis of expanded porphyrins and their supramolecular interactions with pristine graphene
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A newer synthesis of sulfonic acid functionalized graphenes have been developed, which have been characterized, examined as heterogeneous solid acid carbocatalyst in the synthesis of selected expanded porphyrins in different reaction conditions. This envi
- Mishra, Sweta,Arora, Smriti,Nagpal, Ritika,Chauhan, Shive Murat Singh
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- One-flask synthesis of meso-substituted dipyrromethanes and their application of the synthesis of trans-substituted porphyrin building blocks
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The reaction at room temperature of an aldehyde with excess pyrrole in the absence of solvent affords the meso-substituted dipyrromethane. The reaction is catalyzed with trifluoroacetic acid or with BF3·O(Et)2. The dipyrromethane is purified by crystallization or by flash chromatography on silica with eluants containing 1% triethylamine. The reaction is compatible with aliphatic or aromatic aldehydes, including 2,6-disubstituted benzaldehydes. Nine dipyrromethanes have been prepared in this manner in yields of 47-86%, indicating the broad scope of the reaction. The dipyrromethanes are stable in the purified form in the absence of light and air. Similar reaction with terephthalaldehyde and pyrrole affords the corresponding bis-dipyrromethane. The reaction of a meso-substituted dipyrromethane with an aldehyde under the conditions of the two-step one-flask porphyrin synthesis affords a direct route to trans-substituted meso-porphyrins. Acidolysis of the dipyrromethane is negligible under the conditions of the porphyrin-forming reaction. Four porphyrins bearing peripheral functional groups and facially-encumbering groups have been prepared which serve as key building blocks in the synthesis of linear porphyrin arrays.
- Lee,Lindsey
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- Facile synthesis of meso-substituted dipyrromethanes and porphyrins using cation exchange resins
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The macroporosity and acidity of cation exchange resins play a crucial role in the synthesis of dipyrromethanes and porphyrins; for the first time, cation exchange resins have been used as heterogeneous solid acid catalysts to produce dipyrromethanes and porphyrins in good yields. The reaction, at room temperature, of substituted aromatic aldehydes with pyrrole catalysed by cation exchange resin afforded the corresponding meso-substituted dipyrromethane in yields ranging from 70 to 80%, indicating the broad scope of the reaction. Further, the condensation of meso-substituted dipyrromethane with similar or different substituted aromatic aldehydes, using cation exchange resins furnished meso-tetrakis-symmetrical and mixed porphyrins, respectively. One-pot synthesis of porphyrins can also be carried out directly from the aldehydes and pyrrole under the above conditions. Acidolysis of the dipyrromethane is negligible under the conditions of the porphyrin-forming reaction.
- Naik, Rajan,Joshi, Padmakar,Kaiwar, Sharada P.,Deshpande, Rajesh K.
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- A novel method for the synthesis of dipyrromethanes by metal triflate catalysis
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5-Substituted dipyrromethanes were synthesized by the reaction of N-tosyl imines with excess pyrrole in the presence of metal triflates. Tripyrromethane and other oligomeric side products were not observed. High yields of 5-substituted dipyrromethanes wer
- Temelli, Baris,Unaleroglu, Canan
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- 5,10-Diphenyltripyrrane, a useful building block for the synthesis of meso-phenyl substituted expanded macrocycles
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Pyrrole and benzaldehyde were condensed under acidic conditions to produce a mixture of 5-phenyldipyrromethane and 5,10-diphenyltripyrrane; the tripyrrane was utilized in syntheses of meso-phenylsapphyrins, meso-diphenylpentaphyrin and meso-hexapnenylhexa
- Brückner, Christian,Sternberg, Ethan D.,Boyle, Ross W.,Dolphin, David
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- A Scalable Synthesis of Meso-Substituted Dipyrromethanes
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A one-flask synthesis of meso-substituted dipyrromethanes has been refined. The procedure entails reaction of an aldehyde in 100 equiv of pyrrole as the solvent containing a mild Lewis acid (e.g., InCl3) at room temperature. Following removal and recovery of excess pyrrole, the dipyrromethane is obtained by crystallization. The procedure generates minimal waste and does not require aqueous/organic extraction, chromatography, or distillation. The procedure has been scaled linearly to obtain >100 g of 5-phenyldipyrromethane. The utility of various analytical methods for characterizing dipyrromethanes has been investigated.
- Laha, Joydev K.,Dhanalekshmi, Savithri,Taniguchi, Masahiko,Ambroise, Arounaguiry,Lindsey, Jonathan S.
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- Synthesis of dipyroromethanes in water and investigation of electronic and steric effects in efficiency of olefin epoxidation by sodium periodate catalyzed by manganese tetraaryl and trans disubstituted porphyrin complexes
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Condensation of pyrrole with various aldehydes in the presence of BF3?etherate as an acid catalyst in water provides good yield of some dipyrromethanes. Prolongation of the reaction time with aldehydes substituted by electron-donating (mesityl) or electron-withdrawing (2,6-dichlorophenyl) groups on the ortho positions of the phenyl did not lead to decomposition or scrambling. Manganese trans disubstituted porphyrin complexes which derive from various dipyrromethanes and manganese tetraaryl porphyrin complexes including various substituents with different steric and electronic properties show good catalytic activity in epoxidation of alkenes by NaIO4 in the presence of imidazole (ImH). The study of steric and electronic effects of the catalysts on the epoxidation of olefins shows that Mn-porphyrin complexes with more bulky and electron-releasing groups on meso phenyls could increase the epoxidation yield of most alkenes.
- Bagherzadeh, Mojtaba,Jonaghani, Mohammad Adineh,Amini, Mojtaba,Mortazavi-Manesh, Anahita
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- Synthesis of novel porphyrin-based biscalix[4]arenes
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A novel method for the preparation of porphyrin-based biscalix[4]arenes has been developed, starting from appropriate aryldipyrrolyhnethane and calix[4]arene monoaldehyde. The condensation reaction in the presence of BF3 · Et2O leads
- Dudic, Miroslav,Lhotak, Pavel,Kral, Vladimir,Lang, Kamil,Stibor, Ivan
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- One-Pot Synthetic Approach toward Porphyrinatozinc and Heavy-Atom Involved Zr-NMOF and Its Application in Photodynamic Therapy
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Herein, we report an iodine-attached Zn(II)-porphyrinic dicarboxylic building block (ZnDTPP-I2-2H, 1) that can be introduced into UiO-66 NMOF via one-pot synthetic approach to generate a new ZnDTPP-I2 doped UiO-66 type nano metal-organic framework (NMOF) of ZnDTPP-I2?UiO-66 (2). Compared to its homologous iodine-free NMOF of ZnDTPP?UiO-66 (4), ZnDTPP-I2?UiO-66 (2) with heavy iodine atoms is a more effective nanosized photosensitizer for singlet oxygen generation under physiological conditions. As expected, 2 displayed a high photodynamic therapy efficacy for treatment of liver cancer cells in vitro.
- Zhou, Le-Le,Guan, Qun,Li, Yan-An,Zhou, Yang,Xin, Yu-Bin,Dong, Yu-Bin
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- Short-Chained Anthracene Strapped Porphyrins and their Endoperoxides
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The syntheses of short-chained anthracene-strapped porphyrins and their Zn(II)complexes are reported. The key synthetic step is a [2+2] condensation between a dipyrromethane and an anthracene bisaldehyde, 2,2'-((anthracene-9,10-diylbis(methylene))bis(oxy))dibenzaldehyde. Following exposure to white light, self-sensitized singlet oxygen and the anthracene moieties underwent [4+2] cycloaddition reactions to yield the corresponding endoperoxides. 1H NMR studies demonstrate that the endoperoxide readily formed in [D]chloroform and decayed at 85 °C. X-ray crystallography and absorption spectroscopy were used to confirm macrocyclic distortion in the parent strapped porphyrins and endoperoxides. Additionally, X-ray crystallography indicated that endoperoxide formation occurred exclusively on the outside face of the anthracene moiety.
- Callaghan, Susan,Flanagan, Keith J.,O'Brien, John E.,Senge, Mathias O.
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- Direct synthesis of aryldipyrromethanes
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The synthesis of aryldipyrromethanes from the direct condensation of pyrroles with aromatic aldehydes is described. Yields are improved with strong electronegative substituents on the aromatic aldehyde.
- Vigmond, Stephen J.,Chang, Martin C.,Kallury, Krishna M. R.,Thompson, Michael
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- Chiral porphyrin imine manganese complex as catalyst for asymmetric epoxidation of styrene derivatives
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New chiral porphyrin imine was synthesized from (S)-3-benzyl-2-methyl-4-phenylbutanal according to dipyrromethane method using trifluoroacetic acid, BF3 etherate, and p-chloranil. Manganese complex of this chiral porphyrin imine ligand was used as catalyst in the asymmetric epoxidation of styrene derivatives possessing different substituents. Styrene derivatives possessing electron withdrawing groups gave the corresponding chiral epoxides in high yield up to 98% and ee up to 99%. The mechanism for the catalytic asymmetric epoxidation was also discussed based on transfer of oxygen.
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- Selective detection of D-lactulose by a porphyrin-based diboronic acid
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Cis-5,15-bis[2-(dihydroxyboronyl)phenyl]-10,20-diphenylporphine (cis-DBPP) bearing two boronic acid groups in a 9 A distance has been synthesized. The absorption, fluorescence, and CD spectral changes were induced only by D-lactulose among 10 disaccharide
- Kijima, Hideomi,Takeuchi, Masayuki,Shinkai, Seiji
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- Intermolecular Hydroalkoxylation of Terminal Alkynes Catalyzed by a Dipyrrinato Rhodium(I) Complex with Unusual Selectivity
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An operationally simple and atom-economical method for the E-selective preparation of enol ethers is described. A novel dicarbonyl(5-phenyldipyrrinato)rhodium complex, 2, was prepared in four synthetic steps, characterized by X-ray crystallography and NMR
- Lam, Raphael H.,Walker, D. Barney,Tucker, Matthew H.,Gatus, Mark R. D.,Bhadbhade, Mohan,Messerle, Barbara A.
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- Synthesis and characterization of two novel red-shifted isothiocyanate BODIPYs and their application in protein conjugation
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Fluorescent organic small molecules are very important tools for researchers in the fields of biochemistry and biotechnology, and boron-dipyrromethene (BODIPY) class of organic fluorophores gained much attention in recent years due to their remarkable pho
- Amorim, Fernanda G.,Amorim, Vanessa G.,Coitinho, Juliana B.,Coutinho, Paulo Arthur,Emery, Flavio S.,Leite, Ruan F.,Melo, Shaiani M. G.,Pires, Rita G. W.,Rezende, Lucas C. D.,Silva, André R.,da Silva, Sarah M. P.
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- Wavelength dependent photochemistry of BODIPY-phenols and their applications in the fluorescent labeling of proteins
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A series of BODIPY dyes were synthesized, that were at the 3, or 3 and 5 positions, substituted by photochemically reactive quinone methide (QM) precursor moieties. Fluorescence properties of the molecules were investigated and we demonstrated that the molecules undergo wavelength dependent photochemistry. Photodeamination to deliver QMs takes place only upon excitation to higher excited singlet states, showing unusual anti-Kasha photochemical reactivity. The findings were corroborated by TD-DFT computations. Laser flash photolysis experiments could not reveal QMs due to the low efficiency of their formation, but enabled the detection of phenoxyl radicals. The applicability of the molecules for the fluorescent labeling of bovine serum albumin as a model protein upon photoexcitation at 350 nm was demonstrated.
- Antol, Ivana,Basari?, Nikola,Cindri?, Matej,Kralj, Marijeta,Mihaljevi?, Branka,Uzelac, Lidija,Zlati?, Katarina
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- A glycyl-substituted porphyrin as a starting compound for the synthesis of a π-π-stacked porphyrin-fullerene dyad with a frozen geometry
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A synthetic route for obtaining a porphyrin-fullerene dyad with a constrained geometry forcing the [60]fullerene sphere to lie on the porphyrin plane is reported, revealing a strong interaction in the ground state between the two chromophores. The Royal S
- Lembo, Angelo,Tagliatesta, Pietro,Cicero, Daniel,Leoni, Alessandro,Salvatori, Alisa
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- Dicationic pyridium porphyrins appending different peripheral substituents: Synthesis and studies for their interactions with DNA
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Twelve trans-dicationic pyridium porphyrins appending different peripheral substituents were synthesized and their abilities to bind and cleave DNA under irradiation have been investigated. Their binding modes to DNA were studied by UV-vis spectroscopy, circular dichroism. The apparent constants were measured by EB competitive fluorescence method and most of them were in the range of 104-105 M-1. We found that both the position of positive charges and steric hindrance could greatly influence their binding affinities and modes to DNA, and then affect their photocleaving abilities to DNA.
- Wu, Song,Li, Zheng,Ren, Lige,Chen, Bo,Liang, Feng,Zhou, Xiang,Jia, Tao,Cao, Xiaoping
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- Electroreduction of 8-(thiophen-2-yl)- and 8-(phenyl)- dipyrrometheneboron difluorides. A mechanistic study by cyclic voltammetric digital simulation
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The electrochemical reduction of two meso-substituted dipyrrometheneboron difluorides, BODIPYs, 8-(thiophen-2-yl)-dipyrrometheneboron difluoride and 8-(phenyl)-dipyrrometheneboron difluoride, was studied in acetonitrile. Both compounds underwent two conse
- Rivera-González, Enrique,Galván-Miranda, Elizabeth K.,Aguilar-Martínez, Martha,Farfán, Norberto,Xochitiotzi-Flores, Elba,Macías Ruvalcaba, Norma A.
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- Porphyrin-based Pt/Pd-containing metallopolymers: Synthesis, characterization, optical property and potential application in bioimaging
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In this work, we report two metallopolymers (Pt-P and Pd-P) through coupling of PtII or PdII porphyrin with fluorene derivatives. The structure and photophysical properties of these two metallpolymers were fully characterized, which
- Bian, Wanli,Lian, Hong,Zhang, Yixia,Tai, Feifei,Wang, Hua,Dong, Qingchen,Yu, Baofeng,Wei, Xuehong,Zhao, Qiang
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- Novel synthesis of hybrid calixphyrin macrocycles
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(matrix presented) The reaction of benzaldehyde with excess pyrrole at room temperature in the absence of solvent affords a mixture of meso-substituted polypyrranes species. After separation by column chromatography, these may be used to prepare a range of calix[4]phyrin macrocycles by condensation with acetone under conditions of acid catalysis.
- Bucher, Christophe,Seidel, Daniel,Lynch, Vincent,Kral, Vladimir,Sessler, Jonathan L.
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- Efficient synthesis of meso-substituted corroles in a H2O-MeOH mixture
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New and efficient conditions for the synthesis of meso-substituted corroles were developed. The first step, involving the reaction of aldehydes with pyrrole, was carried out in a water-methanol mixture in the presence of HCl. A relatively narrow distribut
- Koszarna, Beata,Gryko, Daniel T.
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- Colorimetric and fluorometric ph sensor based on bis(methoxycarbonyl)ethenyl functionalized Bodipy
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We report a difluoroboradiaza-s-indacene (BODIPY) dye substituted with bis(methoxycarbonyl)ethenyl at 3 and 5 positions as a near-IR colorimetric and fluorometric "on-off" pH sensor. The sensor absorbs and emits light at ca. 600 nm with high absorbance an
- Teknikel, Efdal,Unaleroglu, Canan
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Read Online
- Improved synthesis of meso substituted 21-Oxa and 2l-Thia tetra phenyl porphyrins
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An efficient method for the exclusive formation of 21-Oxa and 21-Thia tetra phenyl porphyrins in high yields by condensation of dipyrromethane and furan or thiophene diols is described.
- Srinivasan, Alagar,Sridevi, Bashyam,Reddy, Mereddy Venkat Ram,Narayanan, Seenichamy Jeyaprakash,Chandrashekar, Tavarekere K.
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Read Online
- Synthesis, characterization and application of trans-D-B-A-porphyrin based dyes in dye-sensitized solar cells
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A series of metal-free trans-D-B-A porphyrin dyes have been synthesized and characterized as photo-sensitizers for dye-sensitized solar cells (DSSCs). These dye molecules contain a porphyrin unit as a π-bridge, a substituted phenyl group as an electron do
- Pasunooti, Kalyan Kumar,Song, Jun-Ling,Chai, Hua,Amaladass, Pitchamuthu,Deng, Wei-Qiao,Liu, Xue-Wei
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Read Online
- Selective synthesis of meso-naphthylporphyrins
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A series of novel meso-(8-substituted naphth-1-yl)porphyrins has been synthesized creating derivatives with a tight recognition environment above the porphyrin plane. The selective synthesis of single atropisomers is discussed. Condensation of bisnaphthaldehyde 12 with phenyldipyrromethane unexpectedly led to selective synthesis of the α,α-5,10-bridged isomer 14. A mechanism is proposed for this unusual scrambling, and alternative syntheses of α,α-5,15-bisnaphthylporphyrins are described. Synthesis of 5,15-analogues can be achieved by employing (pentafluorophenyl)-dipyrromethane or via presynthesis of a bis(dipyrromethane) derivative 22 (from bisnaphthaldehyde 12) and subsequent condensation with benzaldehyde.
- Cammidge, Andrew N.,Oeztuerk, Orhan
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Read Online
- New Synthetic Receptors Derived from Porphyrins
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A new porphyryn-based molecular cleft has been synthesized: it shows high affinity for appropriate guests.
- Shipps, Gerald Jr.,Rebek, Julius Jr.
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Read Online
- A novel “turn-on” dipyrrin-type fluorescent detector of Zn2+ based on tetraphenylethene
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A tetraphenylethene-containing dipyrrin (TPEpy) has been synthesized and its photophysical properties and metal detecting properties have been investigated. TPEpy displays a high selectivity and sensitivity with a detection limit of 8.96?×?10?8
- Dong, Yu-Jie,Meng, Zhengong,Ho, Cheuk-Lam,Wong, Wai-Yeung
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Read Online
- Structural modification of RhIIItriarylcorroles for enhanced electrocatalyzed hydrogen evolution reactions
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A series of A3 type RhIIItriarylcorroles 2a-c with different meso-substituents with differing electron-donating and withdrawing properties and two A2B type RhIIItriarylcorroles 4a-b with meso-methylthiophenyls at the B position have been prepared and characterized. An analysis of structure-property relationships of 2a-c and 4a-b has been carried out by comparing the optical spectroscopy and electrochemistry of the dyes to trends predicted in DFT and TD-DFT calculations. Rational structural modification strategies that enhance the suitability of 2a-c for use as highly efficient catalysts for hydrogen evolution reactions on glassy carbon electrodes coated with 2a-c/reduced graphene oxide composites and of 4a-b in surface-modified Au electrodes are explored.
- Dingiswayo, Somila,Li, Lihua,Liang, Xu,Mack, John,Nyokong, Tebello,Wang, Yu,Zhu, Weihua
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- New phosphorescent iridium(iii) dipyrrinato complexes: synthesis, emission properties and their deep red to near-infrared OLEDs
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A series of heteroleptic Ir(iii) complexes composed of two cyclometalated C^N ligands and one dipyrrinato ligand used as an ancillary ligand are synthesized and characterized. With the introduction of a fluorine atom, phenyl ring or diphenylamino group into both C^N ligands and by keeping the ancillary ligand unchanged, these Ir(iii) dipyrrinato phosphors do not show an obvious shift in their emission bands. They exhibit emissions extending well into the near-infrared region with an intense band located at around 685 nm in both photo- and electroluminescence spectra, and the deep red to near-infrared organic light emitting diodes (OLEDs) based on them afforded a maximum external quantum efficiency of 2.8%. Density functional theory (DFT) calculations show that both the electronic contributions on the lowest unoccupied molecular orbitals (LUMOs) and the highest energy semi-occupied molecular orbitals (HSOMOs) are mainly localized on the dipyrrinato ligand, indicating that the ancillary ligand, which remains unchanged in this series, exhibits a lower triplet state energy in the iridium phosphors than those involving the C^N ligands. Therefore a switch from “(C^N)2Ir” to dipyrrinato ligand-based emission is observed in these iridium(iii) complexes.
- Chen, Shuming,Chen, Zhao,Harvey, Pierre D.,Schlachter, Adrien,Tanner, Kevin,Wang, Haitao,Wong, Wai-Yeung,Zhang, Hongyang
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p. 10629 - 10639
(2021/08/09)
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- Ligand Non-innocence and Single Molecular Spintronic Properties of AgII Dibenzocorrole Radical on Ag(111)
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A facile method for the quantitative preparation of silver dibenzo-fused corrole Ag-1 is described. In contrast to the saddle conformation resolved by single-crystal X-ray analysis for Ag-1, it adopts an unprecedented domed geometry, with up and down orientations, when adsorbed on an Ag(111) surface. Sharp Kondo resonances near Fermi level, both at the corrole ligand and the silver center were observed by cryogenic STM, with relatively high Kondo temperature (172 K), providing evidence for a non-innocent AgII-corrole.2? species. Further investigation validates that benzene ring fusion and molecule-substrate interactions play pivotal roles in enhancing Ag(4d(x2?y2))–corrole (π) orbital interactions, thereby stabilizing the open-shell singlet AgII-corrole.2? on Ag(111) surface. Moreover, this strategy used for constructing metal-free benzene-ring fused corrole ligand gives rise to inspiration of designing novel metal–corrole compound for multichannel molecular spintronics devices.
- Xu, Jialiang,Zhu, Li,Gao, Hu,Li, Chenhong,Zhu, Meng-Jiao,Jia, Zhen-Yu,Zhu, Xin-Yang,Zhao, Yue,Li, Shao-Chun,Wu, Fan,Shen, Zhen
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supporting information
p. 11702 - 11706
(2021/04/29)
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- Graphene oxide modified H4L-ion imprinting electrochemical sensor for the detection of uranyl ions
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The rapid development of the nuclear industry has gradually aroused people′s attention to the problem of nuclear pollution. Due to the biological toxicity of uranium and its aqueous solution, simple and rapid detection of uranium in the water environment is quite important. An ion imprinted carbon nanomaterial (graphene oxide) electrochemical sensor for the detection of trace uranyl ions was prepared by using the synthesized bipolar tetradentate macrocyclic uranyl ligand cyclo-bis-phenylenediamine-bis-(phenylmethyl-diphyrrolecarbaldehyde) (H4L) as functional monomer. The sol-gel polymer was prepared by hydrolysis and polymerization of H4L ligand, 3-aminopropyltrimethoxysilane and tetraethoxysilane. H4L-ion imprinted polymer (U-IIP) was prepared by adding 1 mM uranyl ion as template ions. Then the polymer was bonded to graphene oxide modified carbon paste electrode, and the template ions were eluted to obtain H4L-ion imprinted-graphene oxide modified carbon paste electrode (U-IIP/GO/CPE). Differential pulse voltammetry was used to detect trace uranyl ions. The results showed that the U-IIP/GO/CPE sensor system can detect uranyl ions with high sensitivity and specificity, and the peak current appeared around ?0.26v. In the range of 0.01 μM~3.0 μM, the detection current had a good linear relationship with the molar concentration of uranyl ions, and the method detection limit was 1.32 nM (S/N=3). Through the detection of actual samples, it had a good acceptable recovery rate (95.45 %~106.25 %), and the relative standard deviation was less than 3.25 %.
- Li, Yujie,Wang, Zhimei,Liu, Chen,Zhang, Di,Liao, Lifu,Xiao, Xilin
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supporting information
p. 1914 - 1920
(2021/08/30)
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- K2S2O8mediated synthesis of 5-Aryldipyrromethanes and meso-substituted A4-Tetraarylporphyrins
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The synthesis of dipyrromethanes from pyrrole and arylglyoxylic acids in the presence of K2S2O8at 90 C is reported affording dipyrromethanes in very good yields. Unlike an excess pyrrole traditionally used in dipyrromethane synthesis, the current method uses a stoichiometric amount of pyrrole avoiding any use of Br?nsted or Lewis acid. A gram scale synthesis of 5-phenyldipyrromethane is also achieved demonstrating potential scale up of dipyrromethanes using this method feasible. Subsequently, dipyrromethanes were converted to A4tetraarylporphyrins also in the presence of K2S2O8at 90C. A direct synthesis of A4-tetraphenylporphyrin from excess pyrrole and phenylglyoxylic acid in the presence of K2S2O8 at 90C is also reported.
- Laha, Joydev K.,Hunjan, Mandeep Kaur
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p. 664 - 673
(2021/06/03)
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- K2S2O8activation by glucose at room temperature for the synthesis and functionalization of heterocycles in water
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While persulfate activation at room temperature using glucose has primarily been focused on kinetic studies of the sulfate radical anion, the utilization of this protocol in organic synthesis is rarely demonstrated. We reinvestigated selected K2S2O8-mediated known organic reactions that invariably require higher temperatures and an organic solvent. A diverse, mild functionalization and synthesis of heterocycles using the inexpensive oxidant K2S2O8 in water at room temperature is reported, demonstrating the sustainability and broad scope of the method. Unlike traditional methods used for persulfate activation, the current method uses naturally abundant glucose as a K2S2O8 activator, avoiding the use of higher temperature, UV light, transition metals or bases.
- Laha, Joydev K.,Hunjan, Mandeep Kaur
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p. 8437 - 8440
(2021/09/02)
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- Ultraviolet-responsive metalloporphyrin complex Preparation method of polycarbonate and preparation method of polycarbonate (by machine translation)
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The invention provides an ultraviolet light responsive metalloporphyrin complex with a formula (I) or formula (II). The metalloporphyrin complex comprises an anthracene substituted group with ultraviolet light responsiveness. By using the [4 π + 4 π] dimerization and depolymerization reaction of anthracene under different wavelength ultraviolet light, the number of active centers in a single catalyst molecule is changed, and a reversible preparation of a double-center or multi-center metalloporphyrin complex is realized. Under the action of the metal porphyrin complex serving as a main catalyst and a co-catalyst, carbon dioxide and epoxide perform ultraviolet light responsive copolymerization reaction, so that the ON-OFF control of the polymerization reaction is realized. High activity, high selectivity for the preparation of polycarbonates, especially at low catalyst concentrations, are achieved. The method has important significance on research of activity reduction and even inactivation of the catalyst at low concentration. (by machine translation)
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Paragraph 0174-0175
(2020/12/30)
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- The role of porphyrin peripheral substituents in determining the reactivities of ferrous nitrosyl species
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Ferrous nitrosyl {FeNO}7 species is an intermediate common to the catalytic cycles of Cd1NiR and CcNiR, two heme-based nitrite reductases (NiR), and its reactivity varies dramatically in these enzymes. The former reduces NO2- to NO in the denitrification pathway while the latter reduces NO2- to NH4+ in a dissimilatory nitrite reduction. With very similar electron transfer partners and heme based active sites, the origin of this difference in reactivity has remained unexplained. Differences in the structure of the heme d1 (Cd1NiR), which bears electron-withdrawing groups and has saturated pyrroles, relative to heme c (CcNiR) are often invoked to explain these reactivities. A series of iron porphyrinoids, designed to model the electron-withdrawing peripheral substitution as well as the saturation present in heme d1 in Cd1NiR, and their NO adducts were synthesized and their properties were investigated. The data clearly show that the presence of electron-withdrawing groups (EWGs) and saturated pyrroles together in a synthetic porphyrinoid (FeDEsC) weakens the Fe-NO bond in {FeNO}7 adducts along with decreasing the bond dissociation free energies (BDFENH) of the {FeHNO}8 species. The EWG raises the E° of the {FeNO}7/8 process, making the electron transfer (ET) facile, but decreases the pKa of {FeNO}8 species, making protonation (PT) difficult, while saturation has the opposite effect. The weakening of the Fe-NO bonding biases the {FeNO}7 species of FeDEsC for NO dissociation, as in Cd1NiR, which is otherwise set-up for a proton-coupled electron transfer (PCET) to form an {FeHNO}8 species eventually leading to its further reduction to NH4+.
- Amanullah, Sk,Dey, Abhishek
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p. 5909 - 5921
(2020/07/13)
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- Fluorescent probe for rapidly detecting hydrogen sulfide as well as preparation method and application thereof
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The invention discloses a fluorescent probe for rapidly detecting hydrogen sulfide as well as a preparation method and an application of the fluorescent probe, the name of the fluorescent probe is 5,15-bis (4-2 ', 4'-dinitrobenzenesulfonyloxy phenyl)-10, 20-diphenyl porphyrin, which is called TPP-DDNBS for short, and the structural formula of the fluorescent probe is shown in the specification. The preparation method is completed through four steps and is used for detecting hydrogen sulfide in water. The fluorescent probe provided by the invention can quickly identify hydrogen sulfide and shorten the response time; the fluorescent probe provided by the invention has high sensitivity, good selectivity and anti-interference performance, can realize real-time and effective detection of hydrogen sulfide, is simple in preparation process, and has wide value in the fields of environmental detection and biomedicine. The fluorescent probe is suitable for the technical field of analytical chemistry.
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Paragraph 0041-0045; 0050; 0052-0057
(2020/06/20)
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- Fluorescence probe for detecting cyanide ions and preparation method and application of fluorescence probe
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The invention relates to a fluorescence probe for detecting cyanide ions and a preparation method and application of the fluorescence probe. The fluorescence probe is a cyanide ion fluorescence probetaking boron dipyrromethene (BODIPY) as a fluorescence s
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Paragraph 0010; 0053; 0056-0059
(2019/10/01)
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- Synthesis of dipyrrolo-diazepine derivatives via intramolecular alkyne cyclization
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A regioselective approach was developed for the synthesis of dipyrrolo-diazepine derivatives. The synthetic route to dipyrrolo-diazepines first involves the synthesis of dipyrromethanes, followed by reaction of propargyl bromide in the presence of NaH to attach one alkyne functionality to the pyrrole nitrogen atom. Intramolecular heterocyclization with NaH in DMF between the alkyne functionality and pyrrole nitrogen atom gave the desired structures in good yields.
- Bask?n, D?lge?,?etinkaya, Yasin,Balci, Metin
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p. 4062 - 4070
(2018/06/14)
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- Photoinduced Dynamics of Bis-dipyrrinato-palladium(II) and Porphodimethenato-palladium(II) Complexes: Governing Near Infrared Phosphorescence by Structural Restriction
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Although superficially similar, the bis-dipyrrinato-palladium(II) complex 1 and the bridged porphodimethenato-palladium(II) complex 2 possess dramatically different structures in the ground state (proved by X-ray structure analysis) and in the singlet and
- Riese, Stefan,Holzapfel, Marco,Schmiedel, Alexander,Gert, Ingo,Schmidt, David,Würthner, Frank,Lambert, Christoph
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supporting information
p. 12480 - 12488
(2018/10/25)
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- Synthesis, characterization and electrochemistry of dipyrrinato nickel(II) complexes with different aromatic rings to meso-position
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Three kinds of dipyrrinato nickel(II) complexes with different aromatic substituted groups on meso-carbon position have been synthesized while their properties have been studied. The aromatic substituents of investigated compounds are phenyl (2a), 2-napht
- Xue, Zhaoli,Dong, Yuan,Ma, Jurui,wang, Yemei,Zhu, Weihua
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p. 287 - 292
(2017/03/16)
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- QUINONE-METHIDE PRECURSORS WITH BODIPY CHROMOPHORE, METHOD OF PREPARATION, BIOLOGICAL ACTIVITY AND APPLICATION IN FLUORESCENT LABELLING
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The invention relates to BODIPY derivatives of Formula (I) that bear one or more functional groups which in the photochemical reaction upon irradiation with visible light undergo deamination and deliver quinone methides. Furthermore, the invention relates
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Page/Page column 22; 28-29
(2017/12/15)
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- Fluorescent amino acid based on BODIPY as well as synthetic method and application thereof
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The invention discloses fluorescent amino acid based on BODIPY as well as a synthetic method and an application thereof. A general structural formula of the fluorescent amino acid based on BODIPY is shown in the formula (I) in the specification. The fluorescent amino acid based on BODIPY can be directly applied to polypeptide synthesis and preparation of fluorescence-labelled polypeptide after being prepared and also can structurally induce the polypeptide to form a stable secondary structure, so that the obtained fluorescent polypeptide has certain biological activity, can be directly applied to study of protein-protein interaction as a probe and has a great practical application prospect.
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Paragraph 0078
(2016/10/08)
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- Compound for verifying amino acid capability of inducing polypeptide to form beta-sheet secondary structure and preparation method thereof
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The invention discloses a compound used for verifying amino acid capability of inducing polypeptide to form a beta-sheet secondary structure. The compound is characterized in that its structure is as shown in the formula. By testing whether amino-hydrogen and ketonic oxygen in a compound 2 can form an intramolecular hydrogen bond, whether a compound 1 can induce linked polypeptides to form a stable beta-sheet secondary structure is determined, which is of great guiding significance for determining whether synthesized fluorescent amino acid can be applied in fields of fluorescence kit development, research and development of drugs and the like.
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Paragraph 0056; 0057
(2016/11/21)
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- METALPORPHYRIN COMPLEX, PREPARATION METHOD THEREFOR AND METHOD FOR PREPARING POLYCARBONATE
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The present invention provides a metalporphyrin complex having structure represented by formula (I), wherein R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are independently selected from one of hydrogen, halogen, aliphatic group, substituted heteroaliphatic group, aryl and substituted heteroaryl; n is 1-6; L is quaternary ammonium functional group or quaternary phosphonium functional group; M is a metal element; and X is one of halogen, —NO3, BF4—, —CN, p-methyl benzoate, o-nitrophenol oxygen anion, 2,4-dinitrophenol oxygen anion, 2,4,6-trinitrophenol oxygen anion, 3,5-dichlorophenol oxygen anion and pentafluorophenol oxygen anion. The metalporphyrin complex provided in the present invention has two quaternary ammonium functional groups or two quaternary phosphonium functional groups, and compared with the prior art, the metalporphyrin complex shows higher catalytic activity in catalyzing polymerization reaction of carbon dioxide and an epoxide.
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Paragraph 0121-0123
(2016/08/07)
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- Preparation method of porphyrin aluminum complex and preparation method of polycarbonate
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The invention provides a porphyrin aluminum complex with a structure as shown in a formula (I) or a formula (II), a preparation method of the porphyrin aluminum complex, and a preparation method of polycarbonate. Under the catalysis of a main catalyst and
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Paragraph 0151; 0152; 0153
(2017/01/02)
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- Porphyrin-based metallopolymers: Synthesis, characterization and pyrolytic study for the generation of magnetic metal nanoparticles
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Metallopolymers with different metal centers, pendant groups and linkages exhibit diverse structures and properties, thus giving rise to versatile applications, e.g., as emissive and photovoltaic materials, optical limiters, materials for nano-electronics
- Dong, Qingchen,Qu, Wenshan,Liang, Wenqing,Tai, Feifei,Guo, Kunpeng,Leung, Chi-Wah,Lo, Yih Hsing,Wong, Wai-Yeung
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p. 5010 - 5018
(2016/06/15)
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- Boron dipyrromethene compound containing alpha,beta-unsaturated ketone, and application of same in detection of sulfite
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The invention relates to a boron dipyrromethene compound containing alpha,beta-unsaturated ketone, and application of same in detection of sulfite. A novel fluorescent probe utilizes the characteristic that C-C double bonds on the alpha,beta-unsaturated k
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Paragraph 0042; 0043
(2016/12/01)
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- Selective Synthesis of Tripyrranes, Tetrapyrranes, and Corroles
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A new, catalytic, and general methodology was developed for the direct synthesis of unsymmetrical AB-type tripyrranes by reaction of dipyrromethanesulfonamides with pyrrole. Key structure dipyrromethanesulfonamides were synthesized by the addition of meso
- Aydin, Gokcen,Temelli, Baris,Unaleroglu, Canan
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p. 7583 - 7593
(2016/01/25)
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- BODIPY-based colorimetric/ratiometric fluorescence probes for sulfite in aqueous solution and in living cells
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Two colorimetric/ratiometric fluorescence probes (BSP1 and BSP2) for sulfite utilizing the Michael-addition mechanism were designed and synthesized by incorporating a substituted pyridinium/methyl pyridinium to a BODIPY fluorophore linked with an α,β-unsa
- Liu, Shanshan,Song, Lun,Sun, Qian,Chen, Zhaoyang,Ge, Yu,Zhang, Weibing,Qian, Junhong
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p. 91863 - 91868
(2015/11/11)
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- PHOTOVOLTAIC CONVERSION ELEMENT AND PHOTOVOLTAIC CELL
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Described herein are organic photovoltaic (OPV) cells using gold complex(es) with as chemical structure of Structure (I) as active material wherein R1‐R15 are independently hydrogen, halogen, hydroxyl, an unsubstituted alkyl, a subst
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Page/Page column 12
(2015/04/15)
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- 5-Phenyl-dipyrromethane and 5-(4-pyridyl)-dipyrromethane as modular building blocks for bio-inspired conductive molecularly imprinted polymer (cMIP). An electrochemical and piezoelectric investigation
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5-Phenyl-dipyrromethane (5-ph-DP) and 5-(4-pyridyl)dipyrromethane (5-py-DP) are proposed, for the first time, as electroactive building blocks for the preparation of sensors based on molecularly imprinted conductive polymers (cMIP). This paper reports the
- Susmel,Comuzzi
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p. 78379 - 78388
(2015/09/28)
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- SubPc-ZnPorphyrin conjugates - Synthesis, characterization and properties
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A set of SubPc-Porphyrin dyads and triads have been synthesized by the nucleophilic substitution reaction of hydroxyl-containing meso-substituted porphyrins and a good electron acceptor, dodecafluorosubphthalocyanine. Acid-catalyzed condensation of p-hydr
- Kasi Viswanath, Lakshmi C.,Shirtcliff, Laura D.,Krishnan, Sadagopan,Darrell Berlin
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p. 283 - 289
(2014/11/08)
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- DYE COMPRISING PYRROMETHENE BORON COMPLEX COMPOUND
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The present invention relates to a dye comprising a pyrromethene boron complex compound. The dye comprising a pyrromethene boron complex according to the present invention does not have fluorescence, and absorbs light of a specific wavelength, thereby being used as a display dye.COPYRIGHT KIPO 2016
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Paragraph 0106
(2016/11/17)
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- Synthesis and catalytic properties of trans-A2B2-type metalloporphyrins in cyclohexane oxidation
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A new efficient and mild protocol for synthesizing a series of trans-A 2B2-porphyrins through a TFA-catalyzed condensation reaction between various aldehydes and dipyrromethanes has been developed. Several trans-A2B2-metalloporphyrins (cobalt, nickel) were synthesized and used to catalyze cyclohexane oxidation C-H bonds with dioxygen in the absence of additives and solvents. The results show that the catalytic activities were relative to the nature of the substituted groups and the central metal ions of trans-A2B2-metalloporphyrin. Cobalt metalloporphyrin presents better catalytic performance in the conversion of cyclohexane than the nickel metalloporphyrin under the same reaction conditions.
- Xie, Yujia,Zhang, Fengyong,Liu, Pingle,Hao, Fang,Luo, He'An
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- Synthesis of novel (phenothiazinyl)dipyrrolylmethanes
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An optimized experimental protocol for the preparation of novel (hetero/aryl)dipyrrolylmethane derivatives is described and validated by the synthesis of a series of (phenothiazinyl)dipyrromethanes containing alkyl substituents of increasing bulk (methyl-
- Brem, Balazs,Gal, Emese,Gaina, Luiza,Cristea, Castelia,Silaghi-Dumitrescu, Lumini?a
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p. 947 - 952
(2015/07/15)
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- Green synthesis and anti-inflammatory studies of a series of 1,1-bis(heteroaryl)alkane derivatives
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Molecular iodine has been used as an efficient catalyst for a double Friedel-Crafts reaction of various heteroarenes, i.e. 2-methylfuran, 2-ethylfuran, 2-methylthiophene, pyrrole, N-methylpyrrole and indole, using aldehydes as alkylating agents under "open-flask" conditions with toluene or water as the reaction media. In the presence of 10 mol% iodine in toluene at room temperature, both aliphatic and aromatic aldehydes reacted smoothly to give the corresponding bis(heteroaryl)alkanes in good to excellent yields. Interestingly, with water as the solvent, the bis(heteroaryl)alkane adducts were obtained in moderate to good yields. The use of mild reaction conditions, low catalyst loadings, and eco-friendly reagents in a single step synthesis are the advantages of the present procedure. In an effort to discover novel non-steroidal anti-inflammatory agents, the synthesized bis(heteroaryl)alkanes were evaluated for the anti-inflammatory activity in the lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophage model. These compounds (50 μM) significantly inhibited NO production and did not exhibit significant cytotoxic effects on macrophage cells. Among them, bis[(5-methyl)2-furyl](4- nitrophenyl) methane exhibited the most potent inhibition of NO with IC 50 value of 42.4 ± 1.9, which is similar to that of the positive control, aminoguanidine (43.3 ± 2.5 μM). Thus, the bis[(5-methyl)2-furyl](4-nitrophenyl) methane could be considered a lead compound for the development of novel anti-inflammatory agents.
- Jaratjaroonphong, Jaray,Tuengpanya, Surisa,Saeeng, Rungnapha,Udompong, Sarinporn,Srisook, Klaokwan
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supporting information
p. 561 - 568
(2014/07/21)
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