Double Molecular Antenna Pyrene – Bridge - Fullerene C60

C 60 pyrene anthrylvinylene triads were synthesized with good yields by an O-alkylation reaction of pyrene anthracene chloride derivatives and functionalized fullerene C 60 . The presence of lateral butoxy chains imparts good solubility. The NMR data indicate the formation of only the trans isomers. After C 60 cyclopropanation, the UV-Vis spectra show the pyrene electronic transition with an absorption band extending from 400 to 800 nm due to the combination of the electronic transition of the antrylvinylene moiety and the C 60 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. All the obtained compounds were characterized by 1 H and 13 C NMR, FTIR, UV-Vis, fluorescence spectroscopy, MALDI-TOF, Electrospray or FAB+ mass spectrometry, and elemental analysis.