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Triphenylsulfonium topophotochemistry

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Abstract

The products from the 193 nm irradiation of triphenylsulfonium nonaflate (TPS) embedded in a poly(methyl methacrylate) (PMMA) film have been characterized. The analysis of the photoproduct formation was performed using chromatographic techniques including HPLC, GPC and GC-MS as well as UV-vis and NMR spectroscopic methods. Two previously unreported TPS photoproducts, triphenylene and dibenzothiophene, were detected; additionally, GPC and DOSY-NMR spectroscopic analyses after irradiation suggested that TPS fragments had been incorporated into the polymer film. The irradiation of acetonitrile solutions containing 10% w/v PMMA and 1% w/v TPS in a 1 cm-path-length cuvette showed only a trace amount of triphenylene or dibenzothiophene, indicating that topochemical factors were important for the formation of these molecules. The accumulated evidence indicates that both products were formed by in-cage, secondary photochemical reactions: 2-(phenylthio)biphenyl to triphenylene, and diphenylsulfide to dibenzothiophene.

Graphical abstract: Triphenylsulfonium topophotochemistry

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Publication details

The article was received on 25 Aug 2017, accepted on 03 Nov 2017 and first published on 03 Nov 2017


Article type: Paper
DOI: 10.1039/C7PP00324B
Citation: Photochem. Photobiol. Sci., 2018, Advance Article
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    Triphenylsulfonium topophotochemistry

    E. Despagnet-Ayoub, W. W. Kramer, W. Sattler, A. Sattler, P. J. LaBeaume, J. W. Thackeray, J. F. Cameron, T. Cardolaccia, A. A. Rachford, J. R. Winkler and H. B. Gray, Photochem. Photobiol. Sci., 2018, Advance Article , DOI: 10.1039/C7PP00324B

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