Issue 5, 2015

Efficient halogen photoelimination from dibromo, dichloro and difluoro tellurophenes

Abstract

We present the reactivity and photochemistry of 2,5-diphenyltellurophene. A change in oxidation state from Te(II) to Te(IV) occurs by oxidative addition of bromine, chlorine, and fluorine from appropriate halogen sources. Photoreductive halogen elimination is demonstrated using optical absorption spectroscopy and NMR spectroscopy. The photodebromination reaction occurs with 16.9% quantum yield, the highest value for any Te compound. Photoreductive elimination of chlorine and fluorine occurs with quantum yields of 1.6% and 2.3%, respectively, albeit with less efficient halogen trapping when an organic trap is used. Improved fluorine trapping was achieved using water, allowing for much cleaner photodefluorination. This is the first example of photodefluorination from a tellurium compound.

Graphical abstract: Efficient halogen photoelimination from dibromo, dichloro and difluoro tellurophenes

Supplementary files

Article information

Article type
Paper
Submitted
12 Jun 2014
Accepted
19 Aug 2014
First published
19 Aug 2014
This article is Open Access
Creative Commons BY license

Dalton Trans., 2015,44, 2092-2096

Author version available

Efficient halogen photoelimination from dibromo, dichloro and difluoro tellurophenes

E. I. Carrera and D. S. Seferos, Dalton Trans., 2015, 44, 2092 DOI: 10.1039/C4DT01751J

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