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Issue 5, 2015
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Efficient halogen photoelimination from dibromo, dichloro and difluoro tellurophenes

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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

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Publication details

The article was received on 12 Jun 2014, accepted on 19 Aug 2014 and first published on 19 Aug 2014


Article type: Paper
DOI: 10.1039/C4DT01751J
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Dalton Trans., 2015,44, 2092-2096
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    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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