The functionalisation of tetrathiafulvalene with thiophene units is reported via the synthesis of two multiredox compounds 4 and 5. The two molecules represent a fused structure (4) and a TTF-thiophene system directly linked by a single bond (5); both compounds are endowed with 'free' 2,5-positions within the thiophene ring, making them accessible to polymerisation reactions. The solution electrochemistry of 4 and 5 reveals the redox properties of the two components: a three-stage oxidation process is seen in each case. Charge-transfer complexes have been prepared, using TCNQ or TCNQF(4) as the electron acceptor, with conductivities in the range of 10(-4) to 0.22 S cm(-1). Compounds 4 and 5 have been studied by X-ray crystallography; the former exhibits kappa-packing whilst the latter shows a high degree of conjugation between the two donor moieties.
- conducting polymers
- organic metals
Skabara, P. J., Mullen, K., Bryce, M. R., Howard, J. A. K., & Batsanov, A. S. (1998). The synthesis, redox properties and X-ray crystal structures of two new tetrathiafulvalene-thiophene donors. Journal of Materials Chemistry, 8(8), 1719-1724. https://doi.org/10.1039/a803027h