Related Experiment Video
Updated: Feb 18, 2026
![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
Published on: May 21, 2019
Triphenylsulfonium topophotochemistry
E Despagnet-Ayoub1, W W Kramer, W Sattler
1Beckman Institute, California Institute of Technology, Pasadena, California 91125, USA. despagne@caltech.edu.
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.
More Related Videos
Related Concept Videos
Preparation and Reactions of Thiols
Preparation and Reactions of Sulfides
Electrophilic Aromatic Substitution: Sulfonation of Benzene
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

