Issue 11, 2000


The novel annelated monomer thieno[3′,4′:5,6][1,4]dithiino[2,3-b]quinoxaline 1 has been electropolymerised on a variety of electrodes, resulting in films which are electroactive in non-aqueous and aqueous solution. The polymer films exhibit a transformation in voltammetric response corresponding to a positive shift in redox potential in the presence of silver cation, the maximum shift being ca. 150 mV in acetonitrile and ca. 400 mV in aqueous LiClO4 solution. Mercury dication demonstrates a similar, but smaller (ca. 130 mV) shift in aqueous solution. Theoretical calculations clearly show the potential of poly(1) as a metal complexation agent. The Ag+ ion coordinates with 1 in two ways: (i) an apical conformation involving the two dithiine sulfurs and (ii) a lateral σ-complex with a contribution from the quinoxaline nitrogens. The Hg2+ ion prefers to coordinate with the sulfur atoms. The calculations performed for the trimer illustrate that the metal ions can be coordinated simultaneously by two repeat units in the polymer chain.

Article information

Article type
16 May 2000
21 Jul 2000
First published
22 Sep 2000

J. Mater. Chem., 2000,10, 2458-2465

Electrochemical molecular recognition of silver cation by electropolymerised thieno[3′,4′:5,6][1,4]dithiino[2,3-b]quinoxaline: a joint experimental and theoretical study

L. M. Goldenberg, P. J. Skabara, D. M. Roberts, R. Berridge, E. Ortí, P. M. Viruela and R. Pou-Amérigo, J. Mater. Chem., 2000, 10, 2458 DOI: 10.1039/B003914O

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