101260
3-Octylthiophene
3-Substituted thiophenes (1) are very useful synthons in organic chemistry(2). They are key substrates for the synthesis of many natural products and intermediates with increasing pharmacological interest(3,4). In several fields such as agrochemistry (weedkillers, pesticides, fungicides), veterinary products, flavour agents, dyes and fluorescent compounds they are more and more useful. The organoleptic properties of these types of compounds have also been studied(5) and they are used as additives in perfumes. A very important new application of these products is their use as monomers for the synthesis of conducting polymers.
Numerous articles and reviews(6) have already been published on poly(3-substituted) thiophenes and in the last twenty years, 230 patents described the preparation and application of this type of material; among them 165 are dealing specifically with the 3-alkyl derivatives. These conducting polymers are at present intensively studied in view of their multiple potential technological applications. Indeed poly(3-methyl thiophene) exhibits a much higher electrical conductivity if compared to the poly(thiophene) itself. Introduction of a long linear alkyl chain at the third position on the poly(thiophene) backbone, and particularly an octyl chain, was proven to give rise to soluble organic conductors(7,8). These materials can be used as antistatic coatings (bulk utilizations) or as molecular devices such as organic electronic components. They are also precursors for the preparation of selective modified electrodes and sensors.
References:
| (1) | Fuller, L.S.; Pratt, J.W.; Yates, F.S. Informations chimie, 1979, 187, 147-51 |
| (2) | Fuller, L.S.; Pratt, J.W.; Yates, F.S. Informations chimie, 1979, 187, 147-51; Fuller, L.S.; Pratt, J.W.; Yates, F.S. Informations chimie, 1979, 194, 177-81 |
| (3) | Marwah, P.; Marwah, A.K.; Shankar Rao, G. Synth. Commun., 1989, 19, 2809-15 |
| (4) | Raynolds, P.W. J. Heterocycl. Chem. , 1984, 21, 1231-2 |
| (5) | Winter, M.; Gautschi, F.; Flament, I.; Stoll, M.; Goldman, I.M.; U.S. 3,989,713 (02 Nov. 1976), CA 86: 43556d |
| (6) | Roncali, J. Chem. Rev., 1992, 92, 711-38. Chem. Rev., 1997, 97, 173. |
| (7) | Lemaire, M.; Garreau, R.; Garnier, F.; Roncali, J. New.J.Chem., 1987, 11, 703-8 |
| (8) | Lemaire, M.; Büchner, W.; Garreau, R.; Guetté, J.-P.; Cotton, J.-P. New.J.Chem., 1992, 16, 1009-12 |
Available in kg quantities
