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, R. Pou-Amerigo

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

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 epsilon 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 sigma -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.
LanguageEnglish
Pages2458-2465
Number of pages7
JournalJournal of Materials Chemistry
Volume10
Issue number11
DOIs
Publication statusPublished - 2000

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Quinoxalines
Molecular recognition
Silver
Cations
Positive ions
Sulfur
Ions
Complexation
Acetonitrile
Mercury
Polymer films
Metal ions
Conformations
Polymers
Nitrogen
Monomers
Metals
Atoms
Electrodes

Keywords

  • molecular recognition
  • electropolymerisation
  • quinoxaline derivative

Cite this

Goldenberg, L.M. ; Skabara, P.J. ; Roberts, D.M. ; Berridge, R. ; Ortí, E. ; Viruela, P.M. ; Pou-Amerigo, R. / 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. In: Journal of Materials Chemistry. 2000 ; Vol. 10, No. 11. pp. 2458-2465.
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abstract = "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 epsilon 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 sigma -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.",
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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. / Goldenberg, L.M.; Skabara, P.J.; Roberts, D.M.; Berridge, R.; Ortí, E.; Viruela, P.M.; Pou-Amerigo, R.

In: Journal of Materials Chemistry, Vol. 10, No. 11, 2000, p. 2458-2465.

Research output: Contribution to journalArticle

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T1 - 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

AU - Goldenberg, L.M.

AU - Skabara, P.J.

AU - Roberts, D.M.

AU - Berridge, R.

AU - Ortí, E.

AU - Viruela, P.M.

AU - Pou-Amerigo, R.

PY - 2000

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N2 - 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 epsilon 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 sigma -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.

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