Synthesis, spectroscopic and electrochemical properties of axially symmetric fullerene-porphyrin dyad with a rigid pyrrolo[3,4-c]pyrrole spacer

A.S. Konev, A.F. Khlebnikov, T.G. Nikiforova, A.A. Virtsev, H. Frauendorf

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20 Citations (Scopus)

Abstract

A new approach to porphyrinofullerene donor-acceptor dyads, based on consecutive 1,3-dipolar cycloaddition of azomethine ylides, generated from bis-aziridinedicarboxylate, to C60 and to porphyrin with a maleimidophenyl substituent, was developed. A synthesis of the axially symmetric porphyrin-fullerene-C60 ensemble 5 with a novel rigid pyrrolo[3,4-c]pyrrolic linker was realized. Theoretical, electrochemical, and spectroscopic studies of compound 5 showed that it is capable of forming a charge-separated state. © 2013 American Chemical Society.
Original languageEnglish
Pages (from-to)2542-2552
JournalJournal of Organic Chemistry
Volume78
Issue number6
DOIs
Publication statusPublished - 2013

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