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Triphenylsulfonium Topophotochemistry

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, H B Gray

Photochem Photobiol Sci. 2018 Jan 17;17(1):27-34.

PMID: 29143029

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP144317442	Triphenylsulfonium perfluoro-1-butanesufonate		144317-44-2	Price

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