Issue 2, 2004
From the journal:

Photochemical & Photobiological Sciences

Photoreduction of oxoisoaporphines. Another example of a formal hydride-transfer mechanism

Julio R. De la Fuente,*a   Carolina Jullian,a   Claudio Saitz,a   Eduardo Sobarzo-Sánchez,a   Verónica Neira,a   Claudio González,a   Rodrigo Lópeza  and  Hernán Pessoa-Mahanaa  

* Corresponding authors

a Departamento de Química Orgánica y Fisicoquímica, Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Casilla 233, Santiago, Chile
E-mail: jrfuente@ciq.uchile.cl

Abstract

Photoreduction of 5,6-dimethoxy-, 5-methoxy- and 2,3-dihydro-7H-dibenzo[de,h]quinolin-7-one (A) by tertiary amines in oxygen-free solutions generates long-lived semi-reduced metastable photoproducts, A–NH−, via a stepwise electron–proton–electron transfer mechanism with a limit quantum yield of about 0.1 at high TEA concentrations. These metastable photoproducts revert thermally to the initial oxoisoaporphine nearly quantitatively in the presence or absence of oxygen. We present spectrophotometric, NMR and UV-vis data for the metastable photoproducts. The spectrophotometric results and PM3 and ZINDO/S calculations support the proposed mechanism for the photoreduction of the oxoisoaporphines.

Graphical abstract: Photoreduction of oxoisoaporphines. Another example of a formal hydride-transfer mechanism

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Article information

DOI
https://doi.org/10.1039/B310696A
Article type
Paper
Submitted
03 Sep 2003
Accepted
02 Oct 2003
First published
21 Oct 2003

Photochem. Photobiol. Sci., 2004,3, 194-199

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Photoreduction of oxoisoaporphines. Another example of a formal hydride-transfer mechanism

J. R. De la Fuente, C. Jullian, C. Saitz, E. Sobarzo-Sánchez, V. Neira, C. González, R. López and H. Pessoa-Mahana, Photochem. Photobiol. Sci., 2004, 3, 194 DOI: 10.1039/B310696A

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