115205-70-4Relevant academic research and scientific papers
Competitive Singlet-Singlet Energy Transfer and Electron Transfer Activation of Aryl Azides: Application to Photo-Cross-Linking Experiments
Shields, Charles J.,Falvey, Daniel E.,Schuster, Gary B.,Buchardt, Ole,Nielsen, Peter E.
, p. 3501 - 3507 (2007/10/02)
Direct irradiation of 4-phenyl azide (DAA) in an inert solvent with UV light causes ring expansion to an inermediate dehydroazepine and eventual isolation of 4,4'-azobisbenzene> (AZB).The dehydroazepine can be trapped with nucleophilic reagents to give substituted 3H-azepines.The photochemistry of DAA takes a different course when it is sensitized by pyrene, 1-acetamidopyrene (5), or 9-acetamidoacridine (2).Under these conditions, single-electron transfer occurs in competition with energy transfer as evidenced by detection of radical ions in laser transient absorption spectroscopy and by formation of 4-aniline (DAH) as a major product.Energy transfer and electron transfer compete also when the sensitizer and the aryl azide are linked together by a flexible chain of methylene groups.These results have particular significance for the application of such compounds to phtolabeling experiments.
