Porphycene-mediated photooxidation of benzylamines by visible light
- 27 August 2010
- journal article
- research article
- Published by Springer Science and Business Media LLC in Photochemical & Photobiological Sciences
- Vol. 9 (10), 1359-1366
- https://doi.org/10.1039/c0pp00192a
Abstract
A variety of primary and secondary benzylic amines were oxidized efficiently to N-benzylidenebenzylamines and imines, respectively, using 2,7,12,17-tetrapropylporphycene (H2TPrPc) photocatalyst and blue light emitting diodes (LEDs). The photooxidation of 4-methoxybenzylamine in the presence of H2TPrPc and its tin(IV) complex Sn(TPrPc)Cl2 was studied in detail in order to show that operating mechanisms can be different depending on the photosensitizer type. Two experiments involving solvent deuterium isotope effect and competitive quenching with DABCO provide evidence for the singlet oxygen mechanism as the major pathway in the H2TPrPc-catalyzed reaction and the predominance of the direct electron transfer from the photoexcited dye to the amine when the Sn(TPrPc)Cl2 complex was used as a photocatalyst.This publication has 71 references indexed in Scilit:
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