Excited State Charge Separation in Solution and in Electropolymerized Films of Terthiophene-Fullerene Dyad and Phenothiazine-Terthiophene-Fullerene Triad

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This article reports synthesis, X-ray structure and excited state events occurring in a terthiophene-C₆₀ dyad (TT-C₆₀), and a phenothiazine-terthiophene-C₆₀ triad (PTZ-TT-C₆₀).

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Bodenstedt, Kurt; Lim, G. N.; Vdouychenko, Mark; Estrada, Tania; Subbaiyan, Navaneetha K.; Nesterov, Vladimir N. et al. December 23, 2016.

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This article reports synthesis, X-ray structure and excited state events occurring in a terthiophene-C₆₀ dyad (TT-C₆₀), and a phenothiazine-terthiophene-C₆₀ triad (PTZ-TT-C₆₀).

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7 p.

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Abstract: A covalently linked molecular dyad comprised of terthiophene and C₆₀, and a molecular triad comprised of phenothiazine, terthiophene and C₆₀ have been newly synthesized to probe photoexcited events in solution and at the electropolymerized film. The X-ray structure of the dyad revealed spatial disposition of the donor-acceptor entities without significant intermolecular type interactions. Optical absorbance, fluorescence, and the electrochemical studies were consistent with the structural integrity of the dyad and triad. Further, the TT-C₆₀ dyad (TT = terthiophene) was found to electropolymerize during multi-cycling of voltammograms. The frontier HOMO and LUMO orbitals of the phenothiazine-terthiophene-C₆₀ triad (PTZ-TT-C₆₀, PTZ = phenothiazine) were found to be located respectively on the phenothiazine-terthiophene and C60 entities. Free-energy calculations revealed that the excited state charge transfer resulting into the formation of TT•+-C₆₀•− in the case of the dyad, and (PTZ-TT)•+-C₆₀•− charge separated state in the case of triad to be thermodynamically feasible. Evidence for the occurrence of excited state singlet-singlet energy transfer from ¹TT* to form ¹C₆₀* followed by charge transfer was secured from studies involving femtosecond transient absorption studies in polar benzonitrile. Charge stabilization to some extent in the triad compared to that in the dyad was obtained. Attempts were also made to secure evidence of charge separation in the terthiophene-fullerene drop-casted and electropolymerized films on FTO surface.

This paper is part of the JSS Focus Issue on Nanocarbons – In Memory of Sir Harry Kroto.

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  • ECS Journal of Solid State Science and Technology, 6(6), The Electrochemical Society, December 23, 2016, pp. 1-7

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  • Publication Title: ECS Journal of Solid State Science and Technology
  • Volume: 6
  • Issue: 6
  • Page Start: 3007
  • Page End: 3013
  • Peer Reviewed: Yes

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  • December 23, 2016

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  • Sept. 24, 2018, 1:56 p.m.

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Bodenstedt, Kurt; Lim, G. N.; Vdouychenko, Mark; Estrada, Tania; Subbaiyan, Navaneetha K.; Nesterov, Vladimir N. et al. Excited State Charge Separation in Solution and in Electropolymerized Films of Terthiophene-Fullerene Dyad and Phenothiazine-Terthiophene-Fullerene Triad, article, December 23, 2016; Pennington, New Jersey. (https://digital.library.unt.edu/ark:/67531/metadc1248354/: accessed March 15, 2025), University of North Texas Libraries, UNT Digital Library, https://digital.library.unt.edu; crediting UNT College of Arts and Sciences.

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