Synfacts 2007(5): 0487-0487  
DOI: 10.1055/s-2007-968415
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Fullerene Complex with Tetrathiafulvalene-Type Donors

Contributor(s): Timothy M. Swager, Wei Zhang
E. M. Pérez, M. Sierra, L. Sánchez, M. R. Torres, R. Viruela, P. M. Viruela, E. Ortí*, N. Martín*
Universitat de València, Paterna and Universidad Complutense de Madrid, Spain
Further Information

Publication History

Publication Date:
24 April 2007 (online)


A threefold Wittig-Horner olefination reaction of truxenone 1 with the carbanion generated in situ from the corresponding phosphonate esters 2-4 in the presence of n-BuLi provided truxene-tetrathiafulvalene (TTF) compounds 5-7 in 42-67% yields. X-ray crystallography study of 5 showed that the concave bowl-shaped configuration adopted by the truxene core perfectly mirrors the convex surface of fullerenes. The association of 5 and fullerenes in solution was investigated by 1H NMR titrations of 5 as host with C60 and C70 as guests, which afforded binding constants of (1.2 0.3) 103 M-1 and (8.0 1.5) 103 M-1 for C60 and C70, respectively. Theoretical calculations also indicate that C70 interacts with 5 more effectively than C60, leading to slightly more stable complexes.