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The Photochemical Reduction of 2,1,3-Benzothiadiazole-4,7-dicarbonitrile in the Presence of Cationic Micelles, and Onward Electron-transfer Reactions

DOI: 10.1039/f19898503385

Source and publish data:

Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases p. 3385 - 3394 (1989)

Update date:2022-08-17

Topics:

Authors:

Robinson, Julian N.Robinson, Julian N.

Cole-Hamilton, David J.Cole-Hamilton, David J.

Camilleri, PatrickCamilleri, Patrick

Dainty, ChristineDainty, Christine

Maxwell, VirginiaMaxwell, Virginia

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Article abstract of DOI:10.1039/f19898503385

Photolysis of solutions containing 2,1,3-benzothiadiazole-4,7-dicarbonitrile (BTDN) ethylenediaminetetra-acetic acid disodium salt (EDTA) and cetyltrimethylammonium bromide (CTAB) micelles at pH 5.5 produces the radical anion, BTDN.-, with BTDN acting both as an electron acceptor and as a chromophore.Variations in the efficiency of this reaction with pH, and are interpreted in terms of the formation of a complex between EDTA and BTDN which is broken down by the micelles.Net electron transfer does not occur within the complex.Alternative electron donors such as triethanolamine (TEOA) or 4-morpholine-ethanesulphonic acid (MES) can be employed, but not ascorbic acid or sulphite ion.The use of BTDN.- to reduce anthraquinones in stoichiometric or catalytic (with continuous photolysis) reactions is described.This allows an estimate of the redox potential of BTDN/BTDN.- when incorporated into micelles.

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