Synthesis of a propargyl alcohol having a C60 cage, its transformation into C60 derivatives with polar functional groups, and the solubility measurements

The reactions of fullerene C-60 With lithium acetylide derived from silylated propargyl alcohol and quenching either with trifluoroacetic acid or iodomethane afforded the corresponding adduct at the 6-6 bond of C-60, i. e., the 1-(3-siloxy-1-propynyl)-1,2-dihydro[60]fullerene (3) or the 1-(3-siloxy-1-propynyl)2-methyl-1, ,2-dihydro[60]fullerene (4), both in 56% yield. In order to obtain C-60 derivatives having solubility in water or in other polar organic solvents, the propargyl alcohol derived from 4 was allowed to react with succinic anhydride and with diglycolic anhydride to give the corresponding carboxylic acids 6 and 7 having ester groups. In the same manner, the reaction of C-60 With tetraethylene glycol derivative of propargyl alcohol afforded the corresponding tetraethylene glycol monoether derivative of C-60 (10). The solubility of the newly obtained C-60 derivatives in common organic solvents and in aqueous organic solvents was determined. (C) 1998 Elsevier Science Ltd. All rights reserved.