Double Molecular Antenna Pyrene – Bridge - Fullerene C60

Abstract

The synthesis of the target compds. [C60-fullerene-pyrene-anthracene-vinylene triads] was achieved in good yield by an alkylation reaction of pyrene-anthracene alkyl chloride and a fullerene-phenol [4,4'-(cyclopropa[1,9][5,6]fullerene)bis[phenol]] and NMR data indicate the formation of only the trans isomers. The presence of lateral butoxy chains imparts good soly. Subsequent UV-vis spectra show the pyrene electronic transition with an absorption band extending from 400-800 nm due to a combination of the π-π electronic transition of the anthrylvinylene moiety and the C60 band, regardless the extension of the anthrylvinylene moiety. However, the emission is almost mirror-like with respect to the absorption bands of pyrene, suggesting that the HOMO and LUMO are more localized on this substituent. The resulting products were confirmed by 1H-NMR, 13C-NMR, FT-IR, UV-Vis, fluorescence spectroscopy, MALDI-TOF, electrospray or FAB-MS and elemental anal. [on SciFinder(R)]