SYNTHESIS OF CHLORIN-FULLERENE CONJUGATE

F.M. Karmova^a, V.S. Lebedeva^a, Ph.V. Toukach^b, A.F. Mironov^a

^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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