Synthesis and Water Solubility of Novel Fullerene Bisadduct Derivatives

Abstract

The synthesis of four classes of bisadduct derivatives of C60 is reported. The solubility of the new compounds in aqueous solvents is enhanced and is among the highest ever reported for fullerene derivatives. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

Synthesis and Orthogonal Functionalization of [60]Fullerene e,e,e‐Trisadducts with Two Spherically Defined Addend Zones

“…[33] This outcome correlates well with the generalized observation that at least three ionic charges with an appropriate arrangement at the fullerene surface or some combination of net charging and other polar moieties is required for sufficient water solubility. [33,[45][46][47][48][49] Selective functionalization of the polar addend zone: For the selective functionalization of the polar addend zone, the focal benzene moiety has to be removed first. In principle, this removal could be achieved through suitable disconnection reactions that cleave the ether or ester bonds in 13-15.…”

Anti-HIV properties of cationic fullerene derivatives

“…9 For this reason in the last decade many efforts have been made to overcome this problem, obtaining promising results. 10,11 Exploration of anti-HIV properties of fullerene derivatives has been performed by different research groups, [12][13][14][15][16] and up to now, the best result has been that of dendrofullerene 1 (Fig. 1), prepared by Brettreich and Hirsch, 10 which has an EC 50 of 0.22 lM in human lymphocytes acutely infected by HIV-1 LAI .…”

1H NMR Spectroscopic Studies of the Conformational Isomers of Pyrrolidinofullerenes

“…Although there have been studies of fullerene bis-adducts with two different substituents, only a few reports describe mixed bis-adducts bearing a cyclopropane and a pyrrolidine addend. [25,26] If the addends are different, but symmetrical, all of the regioisomers except for trans-1, e' and e'' will be produced as racemic mixtures.…”