Electrochemical, spectroelectrochemical, and comparative studies of novel organic conjugated monomers and polymers featuring the redox-active unit tetrathianaphthalene

J.C. Forgie, A.L. Kanibolotsky, P.J. Skabara, S.J. Coles, M.B. Hursthouse, R.W. Harrington, W. Clegg

Research output: Contribution to journalArticle

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Abstract

A series of monomers has been synthesized and characterized on the basis of the incorporation of tetrathianaphthalene (1) and its saturated (2) and open cyclic (3) forms as fused side groups onto polythiophene chains. The X-ray crystal structures of compounds 1 and 2 are reported. Tetrathianaphthalene (TTN) is an isomer of tetrathiafulvalene (TTF) however, monomer and polymer versions of 1 do not show any similarity to TTF in cyclic voltammetry (CV) or spectroelectrochemical measurements. CV experiments have shown that 1 and 3 are easier to oxidize than 2, whereas 1 also has an additional reduction peak, giving it a smaller HOMO-LUMO gap than the other two monomers. All three polymers of 1-3 have nearly the same oxidation and reduction potentials as well as band gaps; small variations can be attributed to the differences in the side groups. Spectroelectrochemical measurements revealed that the polymers showed electrochromic behavior; switching times and colorimetry 0 measurements are reported. From this data, all three polymers have a color change of red to yellow with poly(3) having the best color contrast and percentage change in absorbance from various switching times
Original languageEnglish
Pages (from-to)2570-2580
Number of pages10
JournalMacromolecules
Volume42
Issue number7
DOIs
Publication statusPublished - 14 Apr 2009

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Polymers
Monomers
Cyclic voltammetry
Color
Colorimetry
Isomers
Energy gap
Crystal structure
X rays
Oxidation
Oxidation-Reduction
Experiments
tetrathiafulvalene

Keywords

  • manganese(ii) dialkyls
  • crystal-structure
  • polymerization
  • adducts
  • bridges

Cite this

Forgie, J. C., Kanibolotsky, A. L., Skabara, P. J., Coles, S. J., Hursthouse, M. B., Harrington, R. W., & Clegg, W. (2009). Electrochemical, spectroelectrochemical, and comparative studies of novel organic conjugated monomers and polymers featuring the redox-active unit tetrathianaphthalene. Macromolecules, 42(7), 2570-2580. https://doi.org/10.1021/ma900010n
Forgie, J.C. ; Kanibolotsky, A.L. ; Skabara, P.J. ; Coles, S.J. ; Hursthouse, M.B. ; Harrington, R.W. ; Clegg, W. / Electrochemical, spectroelectrochemical, and comparative studies of novel organic conjugated monomers and polymers featuring the redox-active unit tetrathianaphthalene. In: Macromolecules. 2009 ; Vol. 42, No. 7. pp. 2570-2580.
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Electrochemical, spectroelectrochemical, and comparative studies of novel organic conjugated monomers and polymers featuring the redox-active unit tetrathianaphthalene. / Forgie, J.C.; Kanibolotsky, A.L.; Skabara, P.J.; Coles, S.J.; Hursthouse, M.B.; Harrington, R.W.; Clegg, W.

In: Macromolecules, Vol. 42, No. 7, 14.04.2009, p. 2570-2580.

Research output: Contribution to journalArticle

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T1 - Electrochemical, spectroelectrochemical, and comparative studies of novel organic conjugated monomers and polymers featuring the redox-active unit tetrathianaphthalene

AU - Forgie, J.C.

AU - Kanibolotsky, A.L.

AU - Skabara, P.J.

AU - Coles, S.J.

AU - Hursthouse, M.B.

AU - Harrington, R.W.

AU - Clegg, W.

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N2 - A series of monomers has been synthesized and characterized on the basis of the incorporation of tetrathianaphthalene (1) and its saturated (2) and open cyclic (3) forms as fused side groups onto polythiophene chains. The X-ray crystal structures of compounds 1 and 2 are reported. Tetrathianaphthalene (TTN) is an isomer of tetrathiafulvalene (TTF) however, monomer and polymer versions of 1 do not show any similarity to TTF in cyclic voltammetry (CV) or spectroelectrochemical measurements. CV experiments have shown that 1 and 3 are easier to oxidize than 2, whereas 1 also has an additional reduction peak, giving it a smaller HOMO-LUMO gap than the other two monomers. All three polymers of 1-3 have nearly the same oxidation and reduction potentials as well as band gaps; small variations can be attributed to the differences in the side groups. Spectroelectrochemical measurements revealed that the polymers showed electrochromic behavior; switching times and colorimetry 0 measurements are reported. From this data, all three polymers have a color change of red to yellow with poly(3) having the best color contrast and percentage change in absorbance from various switching times

AB - A series of monomers has been synthesized and characterized on the basis of the incorporation of tetrathianaphthalene (1) and its saturated (2) and open cyclic (3) forms as fused side groups onto polythiophene chains. The X-ray crystal structures of compounds 1 and 2 are reported. Tetrathianaphthalene (TTN) is an isomer of tetrathiafulvalene (TTF) however, monomer and polymer versions of 1 do not show any similarity to TTF in cyclic voltammetry (CV) or spectroelectrochemical measurements. CV experiments have shown that 1 and 3 are easier to oxidize than 2, whereas 1 also has an additional reduction peak, giving it a smaller HOMO-LUMO gap than the other two monomers. All three polymers of 1-3 have nearly the same oxidation and reduction potentials as well as band gaps; small variations can be attributed to the differences in the side groups. Spectroelectrochemical measurements revealed that the polymers showed electrochromic behavior; switching times and colorimetry 0 measurements are reported. From this data, all three polymers have a color change of red to yellow with poly(3) having the best color contrast and percentage change in absorbance from various switching times

KW - manganese(ii) dialkyls

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KW - adducts

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