N-methyl-2-(4-styrylphenyl)-3,4-fulleropyrrolidine synthesis and structure

Abstract

New stilbene fulleropyrrolidine has been synthesized by С60 fullerene triple-component condensation with sarcosine and trans-4-stilbene carboxaldehyde in Prato reaction conditions. It was demonstrated that primary factor having influence on this reaction final product yield is the homogeneity of the reaction medium. The highest yield of N-methyl-2-(4-styrylphenyl)-3,4-fulleropyrrolidine is observed when reaction performed in xylene and reactive medium is heated. Synthesized compound structure has been studied by IR-, UV-, NMR 1Н and 13С spectroscopy as well as by two-dimensional COSY (1H-1H) and HMQC (1H-13C) spectra data. The purity and individuality of obtained fulleropyrrolidine have been evaluated using HPLC analysis. N-methyl-2-(4- styrylphenyl)-3,4-fulleropyrrolidine synthesis proceeds by the 1,3-dipolar addition to fullerene С60 mechanism through formation of active azomethinilides. N-methyl-2-(4-styrylphenyl)-3,4-fulleropyrrolidine and poly-Nvinylpyrrolidone water-soluble complex has been obtained in dichloromethane. It was shown that complex formation is outcome of fulleropyrrolidine solubilization by PVP chains and lactamic group physical interaction with the fullerene sphere.