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Photochemistry and Photophysics of Halogen-Substituted Dibenzothiophene Oxides1
The Journal of Organic Chemistry
  • Mrinmoy Nag, Iowa State University
  • William S. Jenks, Iowa State University
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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.

Reprinted (adapted) with permission from The Journal of Organic Chemistry, 2004 69(24); 8177-8182. DOI: 10.1021/jo0490346. Copyright 2004 American Chemical Society.

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American Chemical Society
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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
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