Abstract
AbstractThe rate of intramolecular photoinduced electron transfer (PET) between a naphthacene electron donor (D) and a sulfonium electron acceptor (A) was found to be dependent on the thermodynamics for PET and distance between D and A. The slopes of In kET vs through‐bond and through‐space distance plots was found to be −0·60 and −0·91 Å−1, respectively. The product distribution obtained from the photolysis of regioisomeric naphthacenyl sulfonium salt derivatives was found to be independent of distance. Photolysis of three regioisomeric naphthacenyl phenylmethyl‐p‐cyanobenzylsulfonium salts produced unsubstituted thiomethylphenylnaphthacene and mono‐, di‐ and tri‐p‐cyanobenzyl‐substituted thiomethylphenylnaphthacene. The appearance of the out‐of‐cage di‐ and trisubstituted photoproducts suggests that secondary photochemistry and intermolecular electron transfer bond‐cleavage reactions are occurring when the concentration of the sulfonium salt in acetonitrile is 10−2 and 10−3 M and the degree of conversion is high. The primary photoproduct is the mono‐substituted naphthacene derivative.
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