Reversible Template-Directed Activation of Equatorial Double Bonds of the Fullerene Framework: Regioselective Direct Synthesis, Crystal Structure, and Aromatic Properties ofTh-C66(COOEt)12

Abstract

Activation by a template is the key to the very simple, high‐yield synthesis of the stable, Th‐symmetric C60 hexaadduct 1 (R = COOEt) from fullerene. The data from a crystal structure analysis of 1 shows an enhanced aromaticity in the remaining benzoid π‐electron system relative to C60.

Photophysics and Photochemistry of a Water-Soluble C60 Dendrimer: Fluorescence Quenching by Halides and Photoinduced Oxidation of I-

“…[15][16][17][18] C 60 (>99%) was obtained from Stefan Kaesdorf (Munich, Germany). Toluene (spectroscopic grade, Merck) and ethanol (spectroscopic grade, Aldrich) were used as supplied.…”

Basic hydrolysis of fullerene-based esters: a tiny step away from nucleophilic addition to fullerene

“…18 We have used C 60 (99.5+ % purity), supplied by MER Corporation (USA), 9,10-dimethylanthracene (99%, Aldrich), 1,8-diazabicyclo [5,4,0]undec-7-ene (98%, Aldrich), and diethyl bromomalonate (95%, Merck). Reaction product was purified by column chromatography using SiO 2 as a stationary phase (Kieselgel 60, 0.043-0.060 mm), and toluene/ethyl acetate mobile phase (95:5 v/v at the beginning, and 88:12 v/v at the end of the chromatographic separation).…”

“…Identity and purity of the isolated T h -C 66 (COOEt) 12 was confirmed by thin layer chromatography on SiO 2 stationary phase (mobile phase: toluene/ethyl acetate 95:5 v/v; R f = 0.24) and by 1 H and 13 C NMR spectra. 18 Hydrolysis of T h -C 66 (COOEt) 12 with KOH in acetone (Procedure 1). 19.8 mg of T h -C 66 (COOEt) 12 was dissolved in 70 mL of acetone at room temperature to give clear bright yellow solution.…”

Synthesis of giant globular multivalent glycofullerenes as potent inhibitors in a model of Ebola virus infection

“…In particular, hexakis-adducts of [60]fullerene with a Th-symmetrical octahedral addition pattern have a unique three-dimensional structure which allows the introduction of six one-type or mixed-types addends. 10,11 Such derivatives can be obtained in one synthetic step by the addition of malonates to C60, but it has been somehow limited by the low yields resulting with bigger malonates, as the reaction is very sensitive to steric effects. 12 We have recently developed a procedure based on a click-chemistry approach which provides hexakis-adducts with twelve alkyne or azide terminal groups in high yields from simple malonates.…”