20998-75-8Relevant articles and documents
Physical basis of self-assembly. Part 2. A theoretical and experimental study of the self-assembly of a zinc meso-pyridyl porphyrin
Ercolani,Ioele,Monti
, p. 783 - 789 (2001)
A previously reported theoretical treatment for self-assembly macrocyclisations occurring under thermodynamic control has been tested experimentally. The fundamental quantities on which the treatment is based are the effective molarity (EM) of the self-assembling cyclic n-mer and the equilibrium constant for the intermolecular model reaction between monofunctional reactants (Kinter). Provided that estimates of EM and Kinter are available, this treatment can be used to predict not only whether the self-assembly process is more or less favoured, but also the distribution of all the species present in solution. Since Kinter values are approximately known from the literature, we have proposed a method, based on molecular modelling techniques, to estimate the EM. The method has been applied to the self-assembly of Zn(PyP3P), where PyP3P is 5-(4-pyridyl)-10,15,20-triphenylporphyrinato dianion. An EM greater than 0.1 mol L-1 has been estimated for its cyclotetramerisation by PM3 calculations, suggesting that self-assembly should be favoured in solvents like toluene and chloroform. Self-assembly of Zn(PyP3P) has been studied in these solvents by UV/visible spectroscopy. The data are consistent with the formation of the cyclotetramer, and at variance with the model of linear polymerisation. The experimental values of the EM were little affected by the nature of the solvent (EM values were 20 mol L-1 in toluene and 15 mol L-1 in chloroform), indicating that the solvent affects the process of self-assembly mainly through the value of Kinter.
Synthesis of meso-substituted corroles and porphyrins using iodine as a catalyst
Chauhan, Shive M S,Dandia, Anshu
, (2020)
Abstract: Different types of corroles and porphyrins are synthesized from substituted aldehydes and pyrrole. The current synthetic method involves iodine as catalyst and proceeds at room temperature itself. By varying the amounts of reactants (i.e., pyrrole and aldehydes), the corrole and porphyrins were obtained in good to excellent yields. These products were characterized by 1H-NMR, UV-visible, and HRMS techniques. The reaction approach utilizes the readily available pyrrole and substituted aldehydes as starting materials and makes this reaction highly attractive in diversity-oriented synthesis. Graphic abstract: Different types of porphyrins and corroles are synthesized from substituted aldehydes and pyrrole using iodine as a catalyst and the reaction proceeds at room temperature itself. By varying the amount of reactants (i.e. pyrrole and aldehydes), the porphyrins and corroles are obtained in good to excellent yields.[Figure not available: see fulltext.]
Porphyrin architectures bearing functionalized xanthene spacers
Chang, Christopher J.,Yeh, Chen-Yu,Nocera, Daniel G.
, p. 1403 - 1406 (2002)
A modular synthetic strategy for the construction of cofacial porphyrin architectures bearing hydrogen-bond synthons on a xanthene platform is presented. The convergent approach is based on a xanthene aldehyde-ester building block that is easily obtainable on a multigram scale with minimal purification. Treatment of this xanthene derivative with a variety of aryl aldehydes and pyrrole under standard Lindsey conditions affords a family of meso-substituted porphyrins bearing a single functionalized xanthene spacer. Direct modification of the hydrogen-bond synthon after macrocyclization proceeds smoothly to furnish porphyrin systems with a variety of cofacial functionalities (e.g., carboxylic acid, ester, amide). Porphyrins bearing two trans-functionalized xanthene spacers are prepared by the MacDonald [2 + 2] condensation of the xanthene aldehyde-ester with readily available 5-aryl-substituted dipyrromethanes such as 5-mesityldipyrromethane to afford the pure α,α- and α,β-porphyrin atropisomers after chromatographic separation. The versatility of this synthetic method offers intriguing opportunities for the use of these and related templates for the study of proton-coupled activation of small molecules.
Control of Porphyrin Planarity and Aggregation by Covalent Capping: Bissilyloxy Porphyrin Silanes
Adler, Marc J.,Bismillah, Aisha N.,Hussein, Burhan A.,Mcgonigal, Paul R.,Pia, Julia E.,Pilkington, Melanie,Shakeel, Zainab,Turley, Andrew T.,Wolfstadt, Kody M.
, p. 13533 - 13541 (2020)
Porphyrins are cornerstone functional materials that are useful in a wide variety of settings, ranging from molecular electronics to biology and medicine. Their applications are often hindered, however, by poor solubilities that result from their extended
"N-confused porphyrin": A new isomer of tetraphenylporphyrin
Furuta, Hiroyuki,Asano, Tsutomu,Ogawa, Takuji
, p. 767 - 768 (1994)
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Poly(L-Glutamic Acid)-Drug Conjugates for Chemo- and Photodynamic Combination Therapy
Yu, Haiyang,Bao, Yanli,Xu, Caina,Chen, Li,Tang, Zhaohui
, (2021)
Despite the polymeric vascular disrupting agent (poly(L-glutamic acid)-graft-methoxy poly(ethylene glycol)/combretastatin A4) nanoparticles can efficiently inhibit cancer growth, their further application is still a challenge owing to the tumor
Selective synthesis of 5-aryl-10-(nitromethyl) substituted 15-azatripyrrane, 15-oxatripyrrane and 15-thiatripyrrane: Access to nitromethyl functionalized A3B-porphyrins
Seyitdanlioglu, Pinar,Altundal, Gulberil,Cinar, Seda,Unaleroglu, Canan
, p. 14163 - 14169 (2018)
A chemical strategy toward the selective synthesis of unsymmetrical tripyrranes was developed for the formation of meso-aryl and -nitromethyl substituted A3B porphyrins. The iodine catalyzed addition of meso-substituted dipyrromethanes to nitrovinylarenes to generate unsymmetrical 5-aryl-10-(nitromethyl) substituted 15-azatripyrranes, 15-oxatripyrranes and 15-thiatripyrrane under mild conditions has been investigated. The multicomponent reactions of 15-azatripyrranes provided the construction of meso-aryl and -nitromethyl substituted A3B-porphyrins. To the best of our knowledge, the first examples of 5-aryl-10-(nitromethyl) substituted 15-azatripyrranes, 15-oxatripyrranes and 15-thiatripyrrane, and 5-(nitromethyl)-10,15,20-tris(aryl)porphyrins are introduced in this study.
Synthesis, electrochemistry and spectroelectrochemistry of a porphyrin- viologen donor-acceptor diad
Barton, Matthew T.,Rowley, Natalie M.,Ashton, Peter R.,Jones, Christopher J.,Spencer, Neil,Tolley, Malcolm S.,Yellowlees, Lesley J.
, p. 555 - 560 (2000)
A new donor-acceptor (D-A) molecule, 5,10,15,20-[N-benzyl-N'-(4-benzyl- 4,4'-bipyridinium-4-pyridyl)]triphenylporphyrin tris(hexafluorophosphate), 4, has been synthesised. The diad, 4, and its precursors, have been fully characterised by 1H and 13C NMR spectroscopy, mass spectrometry, UV/Visible spectroscopy and cyclic voltammetry. In-situ UV/Visible and EPR measurements show that the site of the first electrochemical reduction is the benzylviologen component of the molecule. The second reduction wave from cyclic voltammetry was shown by in-situ EPR to comprise two unresolved one- electron processes, and this was confirmed by chronocoulometry. The first of these two reduction processes rendered the diad diamagnetic, as was shown by the disappearance of the signal due to the benzylviologen radical. The second gave rise to the appearance of a new EPR signal, which was found to correspond to the porphyrin radical. We believe this to be the first reported resolved spectrum of a monoreduced porphyrin radical.
SOD activity and DNA binding properties of a new symmetric porphyrin Schiff base ligand and its metal complexes
?ay, Sevim,K?se, Muhammet,Tümer, Ferhan,G?lcü, Ay?egül,Tümer, Mehmet
, p. 821 - 838 (2015)
4-Methoxy-2,6-bis(hydroxymethyl)phenol (1) was prepared from the reaction of 4-methoxyphenol and formaldehyde. The compound (1) was then oxidized to the 4-methoxy-2,6-diformylphenol (2) compound. Molecular structure of compound (2) was determined by X-ray
Synthesis of meso-TPP revisited: Its "green-oriented" optimization under controlled microwave heating
Mikus, Agnieszka,Bielinska, Marta E.,Lipinska, Teodozja,Ostrowski, Stanislaw
, p. 3703 - 3713 (2011)
A practical and proecological improvement for synthesis of meso-tetraphenylporphyrin (meso-TPP) under microwave irradiation is described. A cyclocondensation reaction of benzaldehyde and pyrrole followed by oxidation of the porphyrinogen formed as an inte
New insights into the influence of weak and strong acids on the oxidative stability and photocatalytic activity of porphyrins
Zakavi, Saeed,Hoseini, Saiedeh,Mojarrad, Aida G.
, p. 11053 - 11059 (2017)
A series of electron-rich and electron-demanding meso-tetra(aryl)porphyrins (aryl = phenyl, 4-methoxyphenyl, 4-methylphenyl, 4-chlorophenyl, 2-methylphenyl and 2-chlorophenyl) and their dications with weak and strong acids (CF3COOH, CHCl2
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Adler et al.
, p. 476 (1967)
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Tabushi et al.
, p. 1821 (1978)
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Stereoretentive Ligand Exchange Reactions of N-Fused Porphyrin Ruthenium(II) Complexes
Matsuo, Hideaki,Toganoh, Motoki,Ishida, Masatoshi,Mori, Shigeki,Furuta, Hiroyuki
, p. 13842 - 13851 (2017)
The ligand exchange reactions of the ruthenium(II) complex of N-fused tetraphenylporphyrin, Ru(NFp)(CO)2Cl (2), with various anions were investigated. The chloride ligand of the isomers 2a-c was stereoretentively exchanged with bromide (Br-), iodide (I-), and acetate (AcO-) anions in toluene at 100 °C, structures of which were confirmed by 1H NMR as well as single crystal X-ray diffraction analysis. The silver (AgOAc, AgOTf) and boron (NaBPh4) reagents also afforded the corresponding stereoretentive products. On the other hand, the reaction with NaBH4 afforded the hydride complex Ru(NFp)(CO)2H (7) with low stereospecificity, showing a higher reactivity of 2c than other isomers. The ligand dissociation mechanism was proposed with the help of theoretical calculations on the plausible five-coordinated intermediates.
Electrochemical determination of antioxidant properties of a series of tetraphenylporphyrin derivatives and their zinc complexes
Tesakova, Mariya V.,Semeikin, Aleksandr S.,Parfenyuk, Vladimir I.
, p. 1032 - 1038 (2015)
Zinc complexes of a series of substituted tetraphenylporphyrins containing OH-groups in the phenyl rings were synthesized. Their antioxidant capacity was estimated in reaction of the porphyrins with 2,2′-diphenyl-1-picrylhydrazyl (DPPH) by cyclic voltamme
Reversible sequestering of CO2 on a multiporous crystalline framework of 2-quinolyl-porphyrin
Silva, Joana De A. E,Domingos, Valdemar F.,Marto, Daniela,Costa, Leticia D.,Marcos, Mariana,Silva, Manuela R.,Gil, Jo?o M.,Sobral, Abilio J.F.N.
, p. 2449 - 2451 (2013)
In this Letter we describe the synthesis and characterization of a new multiporous crystalline framework based on meso-tetra-(2-quinolyl)-porphyrin, that presents crystal channels adequate for CO2 reversible sequestering, from 1 to 5 bar of CO2 pressures. This behaviour is very different from the parent meso-tetraphenyl-porphyrin, which points to an important favourable interaction of CO2 with meso-substituted nitrogen aromatic porphyrin free bases.
A facile and rapid iodine-catalyzed meso-tetraphenylporphyrin synthesis using microwave activation
Lucas, Romain,Vergnaud, Julien,Teste, Karine,Zerrouki, Rachida,Sol, Vincent,Krausz, Pierre
, p. 5537 - 5539 (2008)
This Letter describes a rapid, easy and efficient one-pot procedure for tetraphenylporphyrin synthesis using iodine-catalysis and microwave activation. Commercial pyrrole, benzaldehyde and dichloromethane were being used as such, without prior distillatio
Tetraphenylporphyrin tethered chitosan based carriers for photochemical transfection
Gaware, Vivek S.,Haì?kerud, Monika,Leósson, Kristján,Jónsdóttir, Sigrídur,H?gset, Anders,Berg, Kristian,Másson, Már
, p. 807 - 819 (2013)
Water-soluble amphiphilic chitosan nanocarriers tethered with the photosensitizer meso-tetraphenylporphyrin were synthesized in a seven-step procedure, starting from 3,6-di-O-tert-butyldimethylsilyl-chitosan and 5-(p-aminophenyl)-10,15,20-triphenylporphyr
Levanon, Haim,Neta, P.
, p. 100 - 103 (1980)
The effect of functional substitution on thermal stability of pyridinylporphyrins under argon atmosphere
Berezina,Minh, Do Ngoc,Tikhonova, Yu. I.,Tumanova,Guseinov,Bazanov,Berezin,Glazunov,Semeikin
, p. 835 - 839 (2016)
The data on thermal stability under argon atmosphere of a series of porphyrin ligands containing meso- and β-positioned electron-donor (Me, Et, or Ph) groups as well as electron-acceptor pyridinyl substituents differing in the heteroatom location are presented. Thermogravimetric analysis and electron absorption spectroscopy studies have shown that pyridinylporphyrins are thermally stable at heating to 360–500°С depending on the functional substitution in the molecule.
Synthesis of glycoporphyrin derivatives and their antiviral activity against herpes simplex virus types 1 and 2
Tome, Joao P.C.,Neves, Maria G.P.M.S.,Tome, Augusto C.,Cavaleiro, Jose A.S.,Mendonca, Ana F.,Pegado, Ines N.,Duarte, Ricardo,Valdeira, Maria L.
, p. 3878 - 3888 (2005)
Studies on the synthesis, structural elucidation, and antiviral evaluation of several carbohydrate-substituted meso-tetraarylporphyrins against herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) are described. The potential of those photosensitizers, and of their precursors, on the photoinactivation of HSV-1 and HSV-2 was examined in Vero cells. Their virucidal and viral replication effects were assessed under white light, at their maximum noncytotoxic concentrations. The highest inhibitory effects on viral replication, for both viruses, were obtained with the glycoporphyrins where the sugar moiety bears unprotected hydroxyl groups. Strong inhibition of virus yield was observed even at concentrations much lower than their maximum noncytotoxic concentrations. These compounds can be postulated to be useful as potential drugs for the treatment of herpes simplex viruses infections.
Synthesis and structural characterization of nonplanar tetraphenylporphyrins with graded degree of β-ethyl substitution
Kalisch, Werner W.,Senge, Mathias O.
, p. 1183 - 1186 (1996)
Tetraphenylporphyrins bearing two, four, and six β-ethyl groups have been synthesized by mixed condensation of benzaldehyde with diethylpyrrole and pyrrole. Investigation of all isomers by spectroscopy and X-ray crystallography shows a series of porphyrins with graded degree of nonplanarity depending on number and position of the ethyl substituents.
Synthesis and pharmacological evaluation of chlorin derivatives for photodynamic therapy of cholangiocarcinoma
Gao, Ying-Hua,Li, Man-Yi,Sajjad, Faiza,Wang, Jin-Hai,Meharban, Faiza,Gadoora, Malaz Abdelazeem,Yan, Yi-Jia,Nyokong, Tebello,Chen, Zhi-Long
, (2020)
Photodynamic therapy (PDT) has been developed as a promising therapeutic method in cancer treatment. The discovery of effective photosensitizer, which is the key factor of PDT, is highly desired. This paper reports the synthesis of novel chlorin derivativ
Synthesis and functionalization of meso-aryl-substituted corroles
Paolesse,Nardis,Sagone,Khoury
, p. 550 - 556 (2001)
The Rothemund condensation reaction of pyrrole and aldehydes is an extensively used route to meso-tetraarylporphyrins, but simple modifications of the reaction conditions allow the formation of different macrocycles other than the expected porphyrin. In the presence of an excess of pyrrole, this modified Rothemund approach leads to the synthesis of meso-triaryl-substituted corroles. This methodology allows the preparation of a wide range of substituted corroles starting from commercially available products. Higher yields have been obtained in the case of benzaldehydes bearing electron-withdrawing substituents, while the reaction fails in the presence of 2,6-disubstituted benzaldehydes. Although if not isolated, some experimental evidences indicate that the linear 5,10,15-triphenylbilane 4 is the precursor of the final corrole ring. Reaction of 5,10,15-triphenylcorrole 2 with an excess of NBS leads to the complete bromination of the macrocycle. Spectroscopic characterization seems to indicate the formation of the porphodimethene-like structure 5, where the macrocyclic aromatic conjugation is interrupted at the 10 position. Metalation of this compound with cobalt acetate and PPh3 affords the corresponding complex. The X-ray crystal structure of triphenylphosphine [2,3,7,8,12,13,17,18-octabromo-5,10,15-tris(4-nitropheriyl)corrolato]-cobalt( III) 8 confirms the ability of corrole ring to retain an almost planar conformation when fully substituted at the peripheral positions.
One-pot direct synthesis of fluorescent polyaniline-porphyrin macrospheres from porphyrin
Ajit, Singh,Palaniappan, Srinivasan,Kumar, Putcha Uday,Madhusudhanachary, Perikati
, p. 884 - 889 (2012)
Porphyrins are very important chromophores as sensitizer in solar cell. Hole and electron transport layers are being used as an important layer to move the electrons and holes away from the sensitizer molecule to electrodes. In this work, a simple process
Physicochemical Basis for the Creation of Liquid-Phase Sensor Materials Based on Tetraaryldithiaporphyrins
Ivanova, Yu. B.,Kiselev, A. N.,Pukhovskaya, S. G.,Syrbu, S. A.
, p. 231 - 240 (2022/03/18)
Abstract: Basic properties of 5,10,15,20-tetraaryl-21-thia- and 5,10,15,20-tetraaryl-21,23-dithiaporphyrins in acetonitrile were examined spectrophotometrically. The geometry of the heteroporphyrins was optimized in the DFT approximation (hybrid functiona
K2S2O8mediated synthesis of 5-Aryldipyrromethanes and meso-substituted A4-Tetraarylporphyrins
Laha, Joydev K.,Hunjan, Mandeep Kaur
, p. 664 - 673 (2021/06/03)
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.
Tetraphenylporphyrin covalent functionalized titanium disulfide nonlinear nanometer hybrid material and preparation thereof
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Paragraph 0041-0044, (2021/12/07)
The invention relates to a tetraphenylporphyrin covalent functionalized titanium disulfide nonlinear nanometer hybrid material and a preparation method thereof, wherein the hybrid material is prepared from tetraphenylporphyrin diazonium salt TPP-N. 2
