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Type: Artigo de periódico
Title: Synthesis of [60]fullerene derivatives bearing five-membered heterocyclic wings and an investigation of their photophysical kinetic properties
Author: Santos, LJ
Goncalves, ASP
Krambrock, K
Pinheiro, MVB
Eberlin, MN
Vaz, BG
de Freitas, RP
Alves, RB
Abstract: The preparation, characterization and photophysical properties of six new stable [6,6]-closed fullerene cycloadducts bearing five-membered heterocycles are described. The modified [60]fullerenes are obtained by a simple and rapid synthesis via a Bingel-type reaction with tetrazole and oxadiazole malonate derivatives. The photophysical kinetics of these new fullerene derivatives in toluene solution under ultraviolet illumination (375 nm, UVA) are studied by electron paramagnetic resonance and free-radical spin-trapping using alpha-phenyl-N-tert-butyl nitrone as a spin-trap. The results are compared with pure [60]fullerene and [6,6]-phenyl C-61 butyric acid methyl ester (C-60-PCBM). It is concluded that for all six new compounds as well as pure [60]fullerene and PCBM both superoxide and singlet oxygen are produced in the first stages of UVA illumination following the type I and II mechanisms, respectively. In all cases singlet oxygen is produced as the primary dominant species; however, the type I mechanism always occurs in parallel with type II. In the end, the superoxide is self-dismuted into hydroxyl radicals, thus yielding PBN-OH center dot spin adducts (g = 2.007 and a(hf) (N-14) = 1.54 mT). The kinetic reaction constants and their efficiencies in the production of reactive oxygen species at 375 nm and per mW of absorbed power are determined. The experimental results are consistent with an autocatalytic reaction model in which the system evolutes under UVA illumination, with superoxide catalyzing the conversion of singlet oxygen into more superoxide. (C) 2010 Elsevier B.V. All rights reserved.
Subject: Fullerene C-60 derivatives
Electron paramagnetic resonance
Reactive oxygen species
Country: Suíça
Editor: Elsevier Science Sa
Citation: Journal Of Photochemistry And Photobiology A-chemistry. Elsevier Science Sa, v. 217, n. 1, n. 184, n. 190, 2011.
Rights: fechado
Identifier DOI: 10.1016/j.jphotochem.2010.10.007
Date Issue: 2011
Appears in Collections:Unicamp - Artigos e Outros Documentos

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