107798-98-1Relevant articles and documents
New copper complex derivatives including bis-dipyrrinato ligand for color filter pigments
Park, Jongwook,Park, Junghyo,Shin, Hawnkyu,Park, Youngil,Shin, Yunseop,Kim, Seungho
, p. 43 - 49 (2012)
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
Synthesis, structure, photophysical, electrochemical properties and antibacterial activity of brominated BODIPYs
Prasannan, Dijo,Raghav, Darpan,Sujatha, Subramaniam,Hareendrakrishna Kumar, Haritha,Rathinasamy, Krishnan,Arunkumar, Chellaiah
, p. 80808 - 80824 (2016)
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.
Meso- and axially-modified IrIIItriarylcorroles with tunable electrocatalytic properties
Zhang, Xifeng,Wang, Yu,Zhu, Weihua,Mack, John,Soy, Rodah C.,Nyokong, Tebello,Liang, Xu
, (2020)
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.
Poly (ethylene oxide) tethered trans-porphyrin: Synthesis, self-assembly with fullerene (C60) and DNA binding studies
Akhtar, Muhammad Asim,Riaz, Sara,Hayat, Akhtar,Nasir, Muhammad,Muhammad, Nawshad,Rahim, Abdur,Nawaz, Mian Hasnain
, p. 235 - 239 (2017)
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
Expanded dipyrrins with electron-withdrawing substituents: Broad range of absorption in the visible region
Liang, Xu,Shimizu, Soji,Kobayashi, Nagao
, p. 256 - 258 (2014)
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
New Zn complex derivatives for red OLEDs host materials
Hyun, Ae-Ran,Kim, Soo-Kang,Kang, In-Nam,Park, Jong-Wook,Shin, Ji-Young,Song, Ok-Keun
, p. 33 - 39 (2007)
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
An easily accessible and recyclable copper nanoparticle catalyst for the solvent-free synthesis of dipyrromethanes and aromatic amines
Megarajan, Sengan,Ayaz Ahmed, Khan Behlol,Rajmohan, Rajamani,Vairaprakash, Pothiappan,Anbazhagan, Veerappan
, p. 103065 - 103071 (2016)
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.
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)
Amanullah, Sk,Saha, Paramita,Dey, Abhishek
, p. 13579 - 13592 (2021)
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.
One-step synthesis of dipyrromethanes in water
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.
, p. 3971 - 3973 (2003)
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.
Triarylcorroles by oxidative coupling of triaryltetrapyrranes
Bri?as,Brückner
, p. 442 - 444 (2001)
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
Sulfonated graphenes catalyzed synthesis of expanded porphyrins and their supramolecular interactions with pristine graphene
Mishra, Sweta,Arora, Smriti,Nagpal, Ritika,Chauhan, Shive Murat Singh
, p. 1729 - 1736 (2014)
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
Facile synthesis of meso-substituted dipyrromethanes and porphyrins using cation exchange resins
Naik, Rajan,Joshi, Padmakar,Kaiwar, Sharada P.,Deshpande, Rajesh K.
, p. 2207 - 2213 (2003)
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.
5,10-Diphenyltripyrrane, a useful building block for the synthesis of meso-phenyl substituted expanded macrocycles
Brückner, Christian,Sternberg, Ethan D.,Boyle, Ross W.,Dolphin, David
, p. 1689 - 1690 (1997)
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
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
Bagherzadeh, Mojtaba,Jonaghani, Mohammad Adineh,Amini, Mojtaba,Mortazavi-Manesh, Anahita
, p. 671 - 678 (2019)
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.
One-Pot Synthetic Approach toward Porphyrinatozinc and Heavy-Atom Involved Zr-NMOF and Its Application in Photodynamic Therapy
Zhou, Le-Le,Guan, Qun,Li, Yan-An,Zhou, Yang,Xin, Yu-Bin,Dong, Yu-Bin
, p. 3169 - 3176 (2018)
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.
Direct synthesis of aryldipyrromethanes
Vigmond, Stephen J.,Chang, Martin C.,Kallury, Krishna M. R.,Thompson, Michael
, p. 2455 - 2458 (1994)
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.
Selective detection of D-lactulose by a porphyrin-based diboronic acid
Kijima, Hideomi,Takeuchi, Masayuki,Shinkai, Seiji
, p. 781 - 782 (1998)
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
Synthesis and characterization of two novel red-shifted isothiocyanate BODIPYs and their application in protein conjugation
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.
, (2020)
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
A glycyl-substituted porphyrin as a starting compound for the synthesis of a π-π-stacked porphyrin-fullerene dyad with a frozen geometry
Lembo, Angelo,Tagliatesta, Pietro,Cicero, Daniel,Leoni, Alessandro,Salvatori, Alisa
, p. 1093 - 1096 (2009)
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
Electroreduction of 8-(thiophen-2-yl)- and 8-(phenyl)- dipyrrometheneboron difluorides. A mechanistic study by cyclic voltammetric digital simulation
Rivera-González, Enrique,Galván-Miranda, Elizabeth K.,Aguilar-Martínez, Martha,Farfán, Norberto,Xochitiotzi-Flores, Elba,Macías Ruvalcaba, Norma A.
, p. 375 - 383 (2019)
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
Novel synthesis of hybrid calixphyrin macrocycles
Bucher, Christophe,Seidel, Daniel,Lynch, Vincent,Kral, Vladimir,Sessler, Jonathan L.
, p. 3103 - 3106 (2000)
(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.
Colorimetric and fluorometric ph sensor based on bis(methoxycarbonyl)ethenyl functionalized Bodipy
Teknikel, Efdal,Unaleroglu, Canan
, p. 239 - 244 (2015)
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
Synthesis, characterization and application of trans-D-B-A-porphyrin based dyes in dye-sensitized solar cells
Pasunooti, Kalyan Kumar,Song, Jun-Ling,Chai, Hua,Amaladass, Pitchamuthu,Deng, Wei-Qiao,Liu, Xue-Wei
, p. 219 - 225 (2011)
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
New Synthetic Receptors Derived from Porphyrins
Shipps, Gerald Jr.,Rebek, Julius Jr.
, p. 6823 - 6826 (1994)
A new porphyryn-based molecular cleft has been synthesized: it shows high affinity for appropriate guests.
Structural modification of RhIIItriarylcorroles for enhanced electrocatalyzed hydrogen evolution reactions
Dingiswayo, Somila,Li, Lihua,Liang, Xu,Mack, John,Nyokong, Tebello,Wang, Yu,Zhu, Weihua
, (2022/01/03)
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.
Ligand Non-innocence and Single Molecular Spintronic Properties of AgII Dibenzocorrole Radical on Ag(111)
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
supporting information, p. 11702 - 11706 (2021/04/29)
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.
