Click chemistry for the efficient preparation of functionalized [60]fullerene hexakis-adducts

摘要

A T_h-symmetrical C_(60) hexakis-adduct bearing 12 peripheral azide groups has been prepared and used to produce functionalized derivatives by the copper mediated Huisgen 1,3-dipolar cycloaddition of azides and alkynes. Fullerene hexakis-adducts with a T_h-symmetrical octahedral addition pattern have received increasing attention in the past few years. Apart from their aesthetically appealing chemical structure resulting from their high symmetry, fullerene hexa-adducts are also unique three-dimensional molecules for the preparation of new materials such as liquid crystals. On the other hand, hexakis-adducts with interesting photophysical properties have also been reported. As far as the synthesis of fullerene hexakis-adducts is concerned, most of them have been prepared by the one-pot reaction of C_(60) with malonates under the conditions initially developed by Hirsch and further improved by Sun.