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

✍ Scribed by Koichi Fujiwara; Yasujiro Murata; Terence S.M. Wan; Koichi Komatsu

• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 739 KB
• Volume: 54
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(97)10415-x

✦ Synopsis

The reactions of fullerene C,, 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,,, i. e., the I-(3-siloxy-I-propynyl)-l,2-dihydro[6O]fullerene (3) or the I-(3-siloxy-lpropynyl)-2-methyl-I ,2-dihydro[60]fullerene (4). both in 56% yield. In order to obtain C, 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,, with tetraethylene glycol derivative of propargyl alcohol afforded the corresponding tetraethylene glycol monoether derivative of Cc,, (10). The solubility of the newly obtained C,, derivatives in common organic solvents and in aqueous organic solvents was determined.