Co-Authors:
Green, B.S., Department of Structural Chemistry, Weizmann Institute of Science, Rehovot, Israel
Rejtö, M., Department of Structural Chemistry, Weizmann Institute of Science, Rehovot, Israel
Johnson, D.E., Department of Chemistry, Northwestern University, Evanston, IL 60201, United States
Hoyle, C.E., Department of Chemistry, Northwestern University, Evanston, IL 60201, United States
Simpson, J.T., Department of Chemistry, Northwestern University, Evanston, IL 60201, United States
Correa, P.E., Department of Chemistry, Northwestern University, Evanston, IL 60201, United States
Ho, T.-I., Department of Chemistry, Northwestern University, Evanston, IL 60201, United States
McCoy, F., Department of Chemistry, Northwestern University, Evanston, IL 60201, United States
Lewis, F.D., Department of Chemistry, Northwestern University, Evanston, IL 60201, United States
Abstract:
The fluorescence of trans-stilbene is quenched by several electron-poor alkenes. Quenching by dimethyl fumarate and fumaronitrile is accompanied by the appearance of exciplex fluorescence in nonpolar solvents. Quenching constants increase with increasing alkene electron affinity, indicating that singlet stilbene acts as an electron donor in exciplex formation. The stilbene-dimethyl fumarate exciplex forms a single cycloadduct, dimethyl μ-truxinate, at low conversions. Evidence is also presented for inefficient addition of cis-stilbene and dimethyl fumarate to form selectively dimethyl neotruxinate. Excitation of the weak ground-state complexes of trans-stilbene with dimethyl fumarate and fumaronitrile results in the same chemical reactions and fluorescence which are observed upon diffusive encounter of singlet trans-stilbene and ground-state alkene. Quenching of stilbene excimer by dimethyl fumarate results in the formation of an oxetane cycloadduct and not the cyclobutane formed from singlet stilbene (monomer) with dimethyl fumarate. © 1979 American Chemical Society.
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