Abstract
Chalcone, flavone, and arylideneflavanone derivatives bearing one or two 3,5-di-
tert-butyl-4-hydroxyphenyl groups were synthesized from 2′,4′-dihydroxyacetophenone and 3,5-di-
tert-butyl-4-hydroxybenzaldehyde. These flavonoids were converted into the corresponding malonates and then reacted with C
60 to yield the title compounds. The O–H bond dissociation enthalpies (BDE) and the chain-breaking antioxidant activity of the flavonoid derivatives and the corresponding C
60 conjugates were evaluated. These results are consistent with the phenolic moiety being the main responsible for the reaction with peroxyl radicals, while the C
60 part of the molecule acts synergically by trapping alkyl radicals under reduced O
2 partial pressure. These novel C
60–flavonoid conjugates are therefore promising leads for broad-spectrum radical scavengers.
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