SYNTHESIS OF CHLORIN-FULLERENE CONJUGATE

F.M. Karmovaa, V.S. Lebedevaa, Ph.V. Toukachb, A.F. Mironova

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

DOI: 10.6060/mhc140495l


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.


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