Synthesis and antioxidant activity of [60]fullerene-BHT conjugates

Chemistry : a European Journal
Roger F EnesLuca Valgimigli

Abstract

Fullerene derivatives incorporating one or two 3,5-di-tert-butyl-4-hydroxyphenyl groups were synthesized by 1,3-dipolar cycloaddition of azomethine ylides to C(60). The O-H bond dissociation enthalpies (BDEs) of these compounds were estimated by studying, by means of EPR spectroscopy, the equilibration of each of these phenols and 2,6-di-tert-butyl-4-methylphenol (BHT) with the corresponding phenoxyl radicals. The antioxidant activity of the investigated phenols was also determined by measuring the rate constants for their reaction with peroxyl radicals in controlled autoxidation experiments and compared to that recorded under identical experimental settings for [60]fullerene itself and unlinked BHT. The results indicate that linking of the BHT structure to C(60) does not substantially alter the thermochemistry and kinetics of its reaction with peroxyl radicals, but such adducts may behave as interesting bimodal radical scavengers. The inherent rate constant for trapping of peroxyl radicals by C(60) per se (k(inh)=3.1+/-1.1 x 10(2) m(-1) s(-1)) indicates that, contrary to previous reports, [60]fullerene is an extremely weak chain-breaking antioxidant.

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Citations

Dec 8, 2006·Bioscience, Biotechnology, and Biochemistry·Hiroya TakadaTakumi Oshima
Jan 11, 2012·Bioscience, Biotechnology, and Biochemistry·Akio KadowakiRyo Yamauchi
Dec 25, 2013·Beilstein Journal of Organic Chemistry·Luca ValgimigliDerek A Pratt
Apr 14, 2018·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Luca ValgimigliRiccardo Amorati
Sep 2, 2020·Free Radical Biology & Medicine·Jacek GrebowskiGrzegorz Litwinienko
Aug 28, 2010·Organic Letters·Riccardo AmoratiChryssostomos Chatgilialoglu
Jun 3, 2021·International Journal of Molecular Sciences·Ivan V MikheevMikhail A Proskurnin
Jul 14, 2012·The Journal of Organic Chemistry·Jason J HanthornDerek A Pratt
Feb 16, 2013·Langmuir : the ACS Journal of Surfaces and Colloids·Bo CuiLi-Jun Wan
Apr 11, 2013·Chemical Reviews·Manolis D Tzirakis, Michael Orfanopoulos

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