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Incorporation of fused tetrathiafulvalenes (TTFs) into polythiophene architectures: Varying the electroactive dominance of the TTF species in hybrid systems

Lookup NU author(s): Dr Ross Harrington, Professor William Clegg

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Abstract

A novel polythienylenevinylene (PTV) and two new polythiophenes (PTs), featuring fused tetrathiafulvalene (TTF) units, have been prepared and characterized by ultraviolet-visible (UV-vis) and electron paramagnetic resonance (EPR) spectroelectrochemistry. All polymers undergo two sequential, reversible oxidation processes in solution. Structures in which the TTF species is directly linked to the polymer backbone (2 and 4) display redox behavior which is dictated by the fulvalene system. Once the TTF is spatially removed from the polymer chain by a nonconjugated link (polymer 3), the electroactivity of both TTF and polythiophene moieties can be detected. Computational studies confirm the delocalization of charge over both electroactive centers (TTF and PT) and the existence of a triplet dication intermediate. PTV 4 has a low band gap (1.44 eV), is soluble in common organic solvents, and is stable under ambient conditions. Organic solar cells of polymer 4:[6,6]-phenyl-C61 butyric acid methyl ester (PCBM) have been fabricated. Under illumination, a photovoltaic effect is observed with a power conversion efficiency of 0.13% under AM1.5 solar simulated light. The onset of photocurrent at 850 nm is consistent with the onset of the π-π absorption band of the polymer. Remarkably, UV-vis spectroelectrochemistry of polymer 4 reveals that the conjugated polymer chain remains unchanged during the oxidation of the polymer. © 2006 American Chemical Society.

Publication metadata

Author(s): Berridge R, Skabara PJ, Pozo-Gonzalo C, Kanibolotsky A, Lohr J, McDouall JJW, McInnes EJL, Wolowska J, Winder C, Sariciftci NS, Harrington RW, Clegg W

Publication type: Article

Publication status: Published

Journal: Journal of Physical Chemistry B

Year: 2006

Volume: 110

Issue: 7

Pages: 3140-3152

ISSN (print): 1520-6106

ISSN (electronic): 1520-5207

Publisher: American Chemical Society

URL: http://dx.doi.org/10.1021/jp057256h

DOI: 10.1021/jp057256h

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