New pyrrolidine and pyrroline derivatives of fullerenes: from the synthesis to the use in light-converting systems |
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Authors: | P A Troshin A S Peregudov S I Troyanov R N Lyubovskaya |
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Institution: | (1) Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 prosp. Akad. Semenova, 142432 Chernogolovka, Moscow Region, Russian Federation;(2) A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991 Moscow, Russian Federation;(3) Department of Chemistry, M. V. Lomonosov Moscow State University, 1 Leninskie Gory, 119991 Moscow, Russian Federation |
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Abstract: | The results of the authors’ studies on the 2+3] cycloaddition of azomethine and nitrile ylides generated from picolylamine
and benzylamine derivatives to fullerenes are systematized and new experimental data are considered. Catalysts and microwave
radiation promoting the formation of ylides and their addition to fullerenes were successfully used for the first time. A
large series of new pyrrolidine and pyrroline derivatives of fullerenes C60 and C70 were synthesized and characterized. The proposed procedures afford the reaction products in yields twice as high (80–85%)
as those attained by the classical Prato reaction. The reactions proceed with virtually complete regio- (in the case of C70) and stereoselectivity to afford only cis-2′,5′-disubstituted and trans-1′,2′,5′-trisubstituted pyrrolidinofullerenes. Pyridyl-substituted pyrrolidinofullerenes react with metalloporphyrins and
phthalocyanines to form self-ordered coordination complexes. The latter are analogs of natural photosynthetic antenna systems
due to photoinduced charge separation that occurs in these complexes upon exposure to light.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 873–898, May, 2008. |
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Keywords: | fullerenes azomethine ylides nitrile ylides 1 3-dipoles [2+3] cycloaddition light conversion photoinduced charge separation solar cells |
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