INTRAMOLECULAR ELECTRON-TRANSFER OF C60-OLIGOANILINE LEUCOEMERALDINE CONJUGATES UPON PHOTOACTIVATION

Abstract

ABSTRACT Conductive starburst C60-derived macromolecules were synthesized using C60(NO2)6 as a precursor intermediate for linking π-conjugate oligomers, such as tetraaniline and hexadecaaniline, directly onto the fullerene cage. Subsequent phenylhydrazine reduction of the resulting hexa(tetraanilino)[60]fullerene and hexa(hexadecaanilino)[60]fullerene emeraldines produced the corresponding leucoemeraldine donors. Photoexcitation of these hexa(oligoanilino)[60]fullerene leucoemeraldines under N2 induced intramolecular electron-transfer from benzenoid moieties of oligoaniline arms to the C60 cage, that regenerated the emeraldine structure in oligoaniline arms. Proceeding on the number of electrons transferred was followed and estimated by in situ chemical trapping method on the reaction of electrophiles with fullerenic anions generated. That substantiated the capability of the fullerene cage to accept multiple electrons during the irradiation process.