aM.V. Lomonosov State University of Fine Chemical Technologies, 119571 Moscow, Russian Federation
bN.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation
KEYWORDS: chlorin-p6, cycloimides, fullerenes, donor-acceptor systems, synthesis
Macroheterocycles, 2014, v. 7, pp. 196-198
The synthesis of chlorin-fullerene conjugate, in which fullerene C60 is attached to chlorin p6 13,15-N-hydroxycycloimide through benzoylisoxazoline spacer moiety was carried out. The conjugate was obtained by the convenient method of 1,3-dipolar cycloaddition to the double bond of the fullerene nitrile oxide, produced from hydroxyiminomethyl substituted chlorin and diacetoxyiodobenzene, at mild conditions. Chlorin p6 N-hydroxycycloimide was condensed with 4-carboxybenzaldehyde in the presence of 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ) and the formyl-containing chlorin obtained was converted into corresponding hydroxyiminomethyl derivative. The latter reacted with diacetoxyiodobenzene and C60 in toluene at room temperature to form chlorin-fullerene with 53% yield.