Photoinduced One‐Electron Oxidation of Estrone Derivatives: A Combined Steady‐State and Time‐Resolved Spectroscopy Investigation

Author:

Quindt Matías I.12,Protti Stefano3,Merli Daniele4,Bonesi Sergio M.123ORCID

Affiliation:

1. Universidad de Buenos Aires Facultad de Ciencias Exactas y Naturales, Departamento de Química Orgánica Buenos Aires C1428EGA Argentina

2. CONICET – Universidad de Buenos Aires Centro de Investigaciones en Hidratos de Carbono (CIHIDECAR) Buenos Aires C1428EGA Argentina

3. PhotoGreen Lab, Department of Chemistry University of Pavia V.le Taramelli 12 27100 Pavia Italy

4. Department of Chemistry University of Pavia V.le Taramelli 12 27100 Pavia Italy

Abstract

AbstractA detailed investigation of the photophysics and of the redox properties of a set of selected estrone carboxylate and sulfonate esters was carried out by means of steady‐state and time‐resolved spectroscopies. The observed dual fluorescence was assigned to an efficient intramolecular energy transfer from the aromatic moiety to the carbonyl group. On the other hand, the photoinduced monoelectronic oxidation of R−OX in the presence of persulphate anion is followed by mesolytic fragmentation of the so generated radical cation into the corresponding phenoxyl radical with rate constant values (kfrag) of 104–105 s−1, that depend on the X−O bond dissociation energy values.

Funder

Università degli Studi di Pavia

Publisher

Wiley

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Analytical Chemistry

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