Photo-Fries rearrangements of 4-dodecylphenyl phenylacetate have been investigated in polyethylene films with 0–71% crystallinity and in hexane over a range of temperatures. The results are compared to those reported previously from phenyl phenylacetate and 1-naphthyl tetradecanoate to assess the influence of a long alkyl chain on the in-cage motions of the intermediate singlet radical pairs. It is demonstrated that the reactivity and selectivity of intimate singlet radical pairs can be tuned by judicious placement of long-chain substituents and selection of a specific polyethylene type as the reaction matrix.
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1 January 2006
Comparisons of Photo-Fries Rearrangements of 4-Dodecylphenyl Phenylacetate and Two Structurally Related Esters in Hexane and Polyethylene Cages. How Important Are Anchoring Chains?
Chuping Luo,
Philippe Passin,
Richard G. Weiss
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Photochemistry and Photobiology
Vol. 82 • No. 1
January 2006
Vol. 82 • No. 1
January 2006