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Current Organic Chemistry

Current Organic Chemistry

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ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

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Research Article

Synthesis and State of Hydroxy-substituted Porphyrins in Premicellar and Micellar Solutions of SDS

Author(s): Natalia Lebedevaorcid of author, Elena Yurinaorcid of author, Sabir Guseinovorcid of author, Irina Skorobogatkinaorcid of author, Yana Kibirevaorcid of author and Sergey Syrbu*

Volume 29, Issue 20, 2025

Published on: 20 May, 2025

Page: [1536 - 1546] Pages: 11

DOI: 10.2174/0113852728378651250507075627

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Abstract

The use of micelles enables the resolution of a number of problems associated with the aggregation and reduction in photocatalytic activity of porphyrins. The formation of transport systems is impossible without information on the localization of porphyrins containing hydrophilic and hydrophobic parts in highly organized systems, such as liposomes or model systems–micelles. To solve the above issues, 5,10,15,20-tetra(3ʹ,4ʹ- dihydroxyphenyl)porphin (Por(OH)8), 5-(3ʹ,4ʹ-dihydroxyphenyl)-10,15,20-triphenylporphin (Por(OH)2), and 5-(3ʹ,4ʹ-dihydroxyphenyl)-10,15,20-tri(pyridinium-3ʹ-yl)porphine (PorN (OH)2) were synthesized, and their state was studied in aqueous media in the presence of an anionic surfactant in the premicellar region. It was found that the porphyrins are sedimentation- stable in the premicellar region, while in the micellar region, Por(OH)2 and PorN(OH)2 are localized inside SDS micelles. However, the peripheral substituents of PorN(OH)2 are oriented toward the "head" of the surfactant. Por(OH)8 is the worst isolated from water molecules of all the studied porphyrins, and can be located both on the surface and inside the micelle, orienting the OH groups toward the surface of the micelle, or the channels inside it. The results obtained can be used to design transport systems for the delivery of hydroxy-substituted porphyrin photosensitizers.

Keywords: Porphyrins, SDS, micelles, localization, fluorescence, premicellar region.

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Graphical Abstract

Graphical abstract illustrating key findings of the study

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