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Photofragmentation of a benzophenone derivative having benzylic C–O bond studied by laser flash photolysis in solution

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Abstract

Photochemical profiles of p-(4-phenylphenoxy)methylbenzophenone (PPMeBP) in solution were investigated by means of emission and transient absorption measurements. PPMeBP showed that fluorescence originating from the corresponding p-phenylphenoxy (PP) moiety at 295 K, and dual phosphorescence originating from the corresponding p-benzoylbenzyl (BB) and PP moieties at 77 K was observed. These observations indicated that the BB and PP moieties of PPMeBP have very little electronic conjugation. 266- and 308-nm laser flash photolyses of PPMeBP showed the formation of the p-phenylphenoxy radical, indicating that photoexcited PPMeBP undergoes C–O bond cleavage. Upon 355-nm laser photolysis of PPMeBP, the C–O bond did not dissociate, and formation of the triplet state of the PP moiety was observed. The apparent quantum yields of fragmentation of PPMeBP were found to depend on the excitation wavelength. Triplet sensitization of PPMeBP using benzophenone revealed that the C–O bond does not cleave in the triplet state of the PP moiety. Based on the schematic energy diagram for excited PPMeBP, the mechanism of the C–O bond was discussed.

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Acknowledgments

This work was partially supported by KAKENHI (a Grant-in-Aid for Scientific Research (C); no. 19550005) from the Japan Society for the Promotion of Science (JSPS). Technical assistance with preparing the PPMeBP from Michiyo Ogasawara of Gunma University is gratefully acknowledged.

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  1. Department of Chemistry and Chemical Biology, Graduate School of Engineering, Gunma University, Kiryu, Gunma, 376-8515, Japan

    Minoru Yamaji

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  1. Minoru Yamaji
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Correspondence to Minoru Yamaji.

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Yamaji, M. Photofragmentation of a benzophenone derivative having benzylic C–O bond studied by laser flash photolysis in solution. Res Chem Intermed 35, 175–186 (2009). https://doi.org/10.1007/s11164-008-0020-6

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