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Monomeric and Dimeric Boron (III) Subphthalocyanines Functionalized with 4-Hydroxy-Benzoic Acid as Potential Photosensitizers and Photocatalysts in Sulfoxidation.

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Title: Monomeric and Dimeric Boron (III) Subphthalocyanines Functionalized with 4-Hydroxy-Benzoic Acid as Potential Photosensitizers and Photocatalysts in Sulfoxidation.
Authors: Skvortsov IA; Organic Chemistry Department, Research Institute of Macroheterocycles, Ivanovo State University of Chemistry and Technology (ISUCT), Sheremetievskiy Av 7, Ivanovo, 153000, Russia., Filatova EO; Institute of Fine Chemical Technologies, MIREA-Russian Technological University, Vernadsky Av. 86, Moscow, 119571, Russia., Birin KP; Frumkin Institute of Physical Chemistry and Electrochemistry RAS, Leninskii pr. 31, Moscow, 119991, Russia., Kalyagin AA; G.A. Krestov Institute of Solution Chemistry RAS, Akademicheskaya st. 1, Ivanovo, 153045, Russia., Chufarin AE; Organic Chemistry Department, Research Institute of Macroheterocycles, Ivanovo State University of Chemistry and Technology (ISUCT), Sheremetievskiy Av 7, Ivanovo, 153000, Russia., Lapshina DA; Organic Chemistry Department, Research Institute of Macroheterocycles, Ivanovo State University of Chemistry and Technology (ISUCT), Sheremetievskiy Av 7, Ivanovo, 153000, Russia., Shagalov EV; Organic Chemistry Department, Research Institute of Macroheterocycles, Ivanovo State University of Chemistry and Technology (ISUCT), Sheremetievskiy Av 7, Ivanovo, 153000, Russia., Stuzhin PA; Organic Chemistry Department, Research Institute of Macroheterocycles, Ivanovo State University of Chemistry and Technology (ISUCT), Sheremetievskiy Av 7, Ivanovo, 153000, Russia.
Source: ChemPlusChem [Chempluschem] 2024 Oct; Vol. 89 (10), pp. e202400319. Date of Electronic Publication: 2024 Aug 13.
Publication Type: Journal Article
Language: English
Journal Info: Publisher: Wiley-VCH Country of Publication: Germany NLM ID: 101580948 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 2192-6506 (Electronic) Linking ISSN: 21926506 NLM ISO Abbreviation: Chempluschem Subsets: MEDLINE; PubMed not MEDLINE
Imprint Name(s): Original Publication: Weinheim, Germany : Wiley-VCH, [c2012]-
Abstract: Axial modification of boron (III) subphthalocyanine bromides with 4-hydroxy-benzoic acid successfully led to the formation of the macrocycles with anchored 4-carboxyphenoxy group [RsPcPHBA] (R=tBu, H) in the axial position and to a new dimer [sPcPHBAsPc] as minor product. Tri-tert-butyl and unsubstituted subphthalocyanines bearing benzoate ([tBusPcBA], [sPcBA]), phenoxy-group ([tBusPcOPh], [sPcOPh])) in the axial position, have been also investigated as well as control sPcs. All compounds were characterized by NMR, IR, UV-Vis and mass spectrometry. The electrochemical properties were studied using cyclic voltammetry (CV) and square wave voltammetry (SWV). Singlet oxygen generation was systematically measured for all synthesized [RsPcX] by kinetic method of chemical trap decomposition (DPBF) and by determination of phosphorescence of singlet oxygen (at 1270 nm). Axially modified subphthalocyanines exhibit high quantum yields of singlet oxygen (1O2) generation (0.47-0.62). The observed exceptional photostability in oxygen-saturated ethanol or toluene solutions and high 1O2 quantum yields allows to use [tBusPcPHBA] as photocatalysts of selective oxidative transformations of organic sulfides to sulfoxides. Loading the catalyst to 9.7 ⋅ 10-2 mol % made it possible to achieve complete conversion of the substrate (TON up to 1700).
(© 2024 Wiley-VCH GmbH.)
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Grant Information: 23-73-01234 Russian Science Foundation; 122 011 300052-1 Ministry of Science and Higher Education of the Russian Federation; 075-15-2021-671 Ministry of Science and Higher Education of Russia
Contributed Indexing: Keywords: Axial modification; Photocatalysis; Singlet oxygen; Subphthalocyanines; Sulfide photooxidation
Entry Date(s): Date Created: 20240629 Latest Revision: 20241015
Update Code: 20260130
DOI: 10.1002/cplu.202400319
PMID: 38943622
Database: MEDLINE
Description
ISSN:2192-6506
DOI:10.1002/cplu.202400319