Theoretical and Experimental Study of Bis-adducted trans-1 and e isomers of Bis(4-methoxyphenyl)methano[60]fullerene

Tatsuo TOIDA*, Kozue SOYA, Katsumi Uchida, Tadahiro ISHII and Hirofumi YAJIMA

Department of Applied Chemistry, Faculty of Science, Tokyo University of Science
Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan

(Received: October 11, 2005; Accepted for publication: November 31, 2005; Published on Web: May 1, 2006)

In this study, we report the synthesis of bis(4-methoxyphenyl)methano[60]fullerene and the separation of trans-1 and e isomers. The number of adducts was determined by FAB MS, while the MALDI-TOF MS spectrum reveals a 'ghost peak' one adduct larger by mass (Figure 7). The observed and calculated (ZINDO/S) absorption spectra of the separated isomers were similar in the 300-400nm range. The difference between isomers is appearing in the 500-550nm range, where a broad band for e isomer is observed and calculated (Figure 9). It appears that the nature of this addend did not affect the transitions. The qualitative yields of bis-adduct isomers were predicted by LUMO of the mono-adduct and confirmed by experimental results. In the same way, the qualitative yields of tri-adduct were predicted and we found that the common tri-adduct derivatives of trans-1 and e isomers are scarce. Additionally, we report a new program tool to create the structure file of any multi-adduct coordinates (Figure 2).

Keywords: Fullerene, Bis-adduct, Absorption spectrum, ZINDO

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