Article
Photochemistry and Photophysics of Halogen-Substituted Dibenzothiophene Oxides1
The Journal of Organic Chemistry
Document Type
Article
Disciplines
Publication Version
Published Version
Publication Date
10-26-2004
DOI
10.1021/jo0490346
Abstract
Dibenzothiophene-5-oxide (DBTO) cleanly produces dibenzothiophene (DBT) on direct photolysis, but with very low quantum yield. A proposed mechanism involves scission of the S−O bond which is coupled to an intersystem crossing step, thus producing the sulfide and O(3P) via a unimolecular pathway. To test this hypothesis, heavy atom substituted DBTOs were prepared and photolyzed. Iodo-, bromo-, and chloro-substituted DBTOs show higher quantum yields for deoxygenation than does the parent molecule, in the order consistent with an intersystem crossing-related heavy atom effect. 2-Iododibenzothiophene also undergoes photochemical deiodination. Phosphorescence data are consistent with heavy-atom assisted intersystem crossing.
Rights
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Copyright Owner
American Chemical Society
Copyright Date
2004
Language
en
File Format
application/pdf
Citation Information
Mrinmoy Nag and William S. Jenks. "Photochemistry and Photophysics of Halogen-Substituted Dibenzothiophene Oxides1" The Journal of Organic Chemistry Vol. 69 Iss. 24 (2004) p. 8177 - 8182 Available at: http://works.bepress.com/william_jenks/24/
Reprinted (adapted) with permission from The Journal of Organic Chemistry, 2004 69(24); 8177-8182. DOI: 10.1021/jo0490346. Copyright 2004 American Chemical Society.