Supramolecular Regioselectivity of meso-Phenylporphyrin Sulfonation. Synthesis of 5,10,15-Tris(4’-sulfophenyl)porphine

Sheinin, V. B.; Ivanov, Dmitriy A.; Койфман, О. И.

doi:10.6060/mhc170833s

Cited by 3 publications

(1 citation statement)

References 14 publications

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“…[3][4][5][6][7][8][9][10][11] III. ) 2 c гидросульфат-анионами, которые активируют протонированный порфирин к электро-фильному замещению в пара-положения фенильных колец (супрамолекулярный контроль региоселективности [12] [13,14] выступающего в качестве мономера самосборки порфириновых нанотрубок (ПНТ). Движущей силой самосборки [H 4 P 2+ (PhNH 3…”

Section: синтез аш-конъюгата и промежуточных соединенийunclassified

Diazotization of 5-(4`-Aminophenyl)-10,15,20-tris(4`-sulfophenyl)porphine in Water. Synthesis of Conjugate with H-Acid

Ivanov¹,

Sheinin²,

Lyubimtsev³

et al. 2019

MHC

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15,porphine was obtained by three-stage synthesis from tetraphenylporphyrin under conditions of supramolecular control of regioselectivity of nitration and sulfonation reactions. In acidic medium (pH ≈ 2) the trianion H 2 P(PhNH 2 )(PhSO 3 -) 3 is protonated at the porphyrin platform and the amino group to form the aqua complex of the zwitterion [H 4 P 2+ (PhNH 3 )(PhSO 3 H)(PhSO 3 -) 2 ](H 2 O) 2 , which is self-assembled into porphyrin nanotubes (PNTs), the outer surface of which is covered with positively charged groups -PhNH 3 + , and the inner surface with electroneutral groups -PhSO 3 H. By the action of nitrous acid, stable diazotized PNTs were obtained. Supramolecular self-assembly inhibits the azo coupling reaction of H 4 P 2+ (PhN 2 + )(PhSO 3 H) (PhSO 3 -) 2 tectons with H-acid in an acidic medium. H-Conjugate was obtained by azo coupling in an alkaline medium (pH ≈ 10), where diazotized PNTs are destroyed with formation of the diazocompound H 2 P(PhN 2

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Section: синтез аш-конъюгата и промежуточных соединенийunclassified

Diazotization of 5-(4`-Aminophenyl)-10,15,20-tris(4`-sulfophenyl)porphine in Water. Synthesis of Conjugate with H-Acid

Ivanov¹,

Sheinin²,

Lyubimtsev³

et al. 2019

MHC

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pH-controlled solubilization of photosensitizer tetraphenylporphyrin

Sheinin

Kulikova

2021

Dyes and Pigments

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Interface chemistry and displacement of porphyrin macrocycles on semiconductor quantum dot surface

Zenkevich¹,

Sheinin²,

Kulikova³

et al. 2023

J. Porphyrins Phthalocyanines

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Here, we present comparative experimental data and results of quantum chemical calculations (method MM+) describing electrostatic interactions of positively charged 5,10,15,20-(tetra-N-methyl-4-pyridyl)porphyrin molecules with negatively charged glutathione stabilized core/shell semiconductor quantum dots (QD) AgInS/ZnS leading to the formation of stable QD-porphyrin nanoassemblies in water (pH 7.5) at ambient temperature. Based on steady-state absorption/ photoluminescence, time-resolved experiments (TCSPC), and Raman spectroscopy, interface phenomena and changes in spectral properties for interacting subunits in nanoassemblies are analyzed. Using an elaborated size-consistent quantum chemical atomistic 3D model for glutathione stabilized AgInS/ZnS QD, we propose a detailed physico-chemical mechanism for the interaction of the porphyrin molecule with the QD surface. It includes electrostatic interactions of the positively charged porphyrin free base molecule with negatively charged capping ligand (glutathione), followed by a very fast metalation of porphyrin free base (formation of ligated Zn-porphyrin complex) which is directly fixed on the QD surface. These results highlight the complexity of interface processes in “QDs – porphyrin” nanoassemblies and provide valuable strategies for the detailed analysis of the excitation energy relaxation in the systems under study.

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Supramolecular Regioselectivity of meso-Phenylporphyrin Sulfonation. Synthesis of 5,10,15-Tris(4’-sulfophenyl)porphine

Abstract: The results of the prognostic computer synthesis of meso-phenylporphyrins Н 2 Р(Ph) n

Cited by 3 publications

References 14 publications

Diazotization of 5-(4`-Aminophenyl)-10,15,20-tris(4`-sulfophenyl)porphine in Water. Synthesis of Conjugate with H-Acid

Diazotization of 5-(4`-Aminophenyl)-10,15,20-tris(4`-sulfophenyl)porphine in Water. Synthesis of Conjugate with H-Acid

pH-controlled solubilization of photosensitizer tetraphenylporphyrin

Interface chemistry and displacement of porphyrin macrocycles on semiconductor quantum dot surface

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