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The Effect of Spin Multiplicity On the Photochemical Reaction of a 2-Vinylnaphthalene-Dichloromaleic Anhydride System

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image of Research on Chemical Intermediates

The photochemical reaction of a 2-vinylnaphthalene - dichloromaleic anhydride system has been studied in order to elucidate the correlation between the spin multiplicity of an excited-state molecule and reaction pathways in electron donor - acceptor systems. Direct irradiation of the system resulted mostly in the recovery of the starting materials. By contrast, the triplet-sensitized reaction using benzophenone as a sensitizer produced a copolymer and two stereoisomeric cycloadducts of 2-vinylnaphthalene with dichloromaleic anhydride. It is suggested that electron transfer takes place both in the electronically excited singlet and triplet states, although a triplet-state reaction also proceeds simultaneously in the benzophenone-sensitized reaction, and that the reaction pathway of the radical-ion pair generated in the excited singlet state is greatly different from that generated in the excited triplet state.

Affiliations: 1: Department of Applied Chemistry, Faculty of Engineering, Osaka University, Yamadaoka, Suita, Osaka 565, Japan


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