The Open Organic Chemistry Journal

2010, 4 : 15-23
Published online 2010 October 29. DOI: 10.2174/1874095201004010015
Publisher ID: TOOCJ-4-15

Double Molecular Antenna Pyrene – Bridge - Fullerene C

Jorge G. Domínguez-Chávez , Sandra Cortez-Maya , Ivana Moggio , Eduardo Arias-Marín , Tatiana Klimova , Irina Lijanova and Marcos Martínez-García
Instituto de Química, Universidad Nacional Autónoma de México, Cd. Universitaria, Circuito Exterior, Coyoacán, C.P. 04510, México D.F., México.

ABSTRACT

C60 pyrene anthrylvinylene triads were synthesized with good yields by an O-alkylation reaction of pyrene anthracene chloride derivatives and functionalized fullerene C60. The presence of lateral butoxy chains imparts good solubility. The NMR data indicate the formation of only the trans isomers. After C60 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 π-π electronic transition of the antrylvinylene 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. All the obtained compounds were characterized by 1H and 13C NMR, FTIR, UV-Vis, fluorescence spectroscopy, MALDI-TOF, Electrospray or FAB+ mass spectrometry, and elemental analysis.

Keywords:

Molecular antennas, molecular rods, pyrene.