Abstract
The in terest f or t etrathiafulvalene (hereafter in dicated a s TTF) began a bout s eventy years ago, but before 1970 only a few articles appeared in the literature [1]. In 1970 Wudl and coworkers observed that TTF can be reversibly oxidized to monocationic radical and dication [3]; both the charged species are stable in solution for a long time, and the first and second oxidation potential values can be finely tuned by appropriate substituents [4]. Since 1970 the work dealing with TTF has increased enormously. A few years later Ferraris et al. [5] observed that TTF reacts in the solid state with 7,7’,8,8’-tetracyano-p-quinodimethane (a good π-electron accepting unit), forming a molecular solid, which for its high electrical conductivity and some similarity with metals was named the first organic metal. For its chemical and electrochemical properties TTF (and its derivatives) is today considered an important building block in many fields of scientific research, both in physics and chemistry [6].
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References
Narita, M. and Pittman, C.U. (1976) Synthesis 489.
Prinzbach, H., Berger, H., Lüttringhaus, A. (1965) Angew. Chem. 77,453.
Wudl, F., Smith, G.M., Hufnagel, E.J. (1970) J. Chem. Soc. Chem. Commun. 1453.
Jeppesen, J.O., Takimja, K.., Jensen, F., Becher, J. (1999) Org. Lett. 1, 1291.
Ferraris, J.P., Cowan, D.O., Valatka, V., Perlstein, J.H. (1973) J. Am. Chem. Soc. 95, 948.
(a) Jørgensen, T., Hansen, T.K.., Becher, J. (1994) Chem. Soc. Rev. 23, 41. (b) Adam, M. and Müller, K. (1994) Adv. Mater. 6439. (c) Bryce, M. (1999) Adv. Mater. 1, 11.
(a) Lehn, J.-M. (1988) Angew. Chem. Int. Ed. Engl. 27, 89. (b) Lehn, J.-M. (1990) Angew. Chem. Int. Ed. Engl. 29, 1304.
(a) Feynman, R.P. (1960) Eng. Sci. 23, 22. (b) Drexler, K.E. (1986) Engines of Creation. The Coming Era of Nanotechnology, Anchor Press, New York, (c) Drexler, K.E. (1992) Nanosystems. Molecular Machinery, Manufacturing, and Computation, Wiley, New York, (d) Balzani, V., Credi, A., Venturi, M. (2000) in Vögtle, F., Stoddart, J.F., Shibasaki, M. (eds.) Stimulating Concepts in Chemistry, Wiley, Weinheim, p. 255.
(a) Muller, D.A., Sorsch, T., Moccio, S., Baumann, F.H., Evans-Lutterodt, K., Timp, G. (1999) Nature 399, 758. (b) Whitesides, G. M, Love, J.C. (2001) Sci. Am. 285, 32. (c) Service, R.F. (2001) Science 293, 785. (d) Keyes, R.W. (2001) Proc. IEEE 89, 227.
Nielsen, M.B., Lomholt, C, Becher, J. (2000) Chem. Soc. Rev. 29, 153.
Ballardini, R., Balzani, V., Di Fabio, A., Gandolfi, M.T., Becher, J., Lau, J., Nielsen, M.B., Stoddart, J.F. (2001) New J. Chem 25, 293.
Schill, G. (1971) Catenanes, Rotaxanes, and Knots, Academic, New York.
Amabilino, D.B. and Stoddart, J.F. (1995) Chem. Rev. 2725.
(a) Anelli, P.L., Ashton, P.R., Ballardini, R., Balzani, V., Delgado, M., Gandolfi, M.T., Goodnow, T. T., Kaifer, A.E., Philp, D., Pietraszkiewicz, M., Prodi, L., Reddington, M.V., Slawin, A.M.Z., Spencer, N, Stoddart, J.F., Vincent, C, Williams, D.J. (1992) J. Am. Chem. Soc. 114, 193. (b) Ashton, P.R., Ballardini, R., Balzani, V., Credi, A., Gandolfi, M.T., Menzer, S., Pérez-García, L., Prodi, L., Stoddart, J.F., Venturi, M., White, A.J.P., Williams, D.J. (1995) J. Am. Chem. Soc. 117, 11171. (c) Vögtle, F., Dunnwald, T., Schmidt, T. (1996) Ace. Chem. Res. 29, 451. (d) Hamilton, D.G., Davies, J.E., Prodi, L., Sanders, J.K.M. (1998) Chem. Eur. J. 4, 608.
Balzani, V., Credi, A., Mattersteig, G., Matthews, O.A., Raymo, F.M., Stoddart, J.F., Venturi, M., White, A.J.P., Williams, D.J. (2000) J. Org. Chem. 65, 1924.
Ashton, P.R., Balzani, V., Becher, J., Credi, A., Fjfe, M.C.T., Mattersteig, G., Menzer, S., Nielsen, M.B., Raymo, F. M, Stoddart, J.F., Venturi, M, Williams, D.J. (1999) J. Am.Chem. Soc. 121, 3951.
(a) Ishow, E., Credi, A., Balzani, V., Spadola, F., Mandolini, L (1999) Chem. Eur. J. 5, 984. (b) Ashton, P.R., Ballardini, R., Balzani, V., Credi, A., Dress, R., Ishow, E., Kleverlaan, C.J., Kocian, O., Preece, J.A., Spencer, N., Stoddart, J.F., Venturi, M., Wagner, S. (2000), Chem. Eur. J. 6, 3558. (c) Ballardini, R., Balzani, V., Clemente-Leon, M., Credi, A., Gandolfi, M. T, Ishow., Perkins, J., Stoddart, J.F., Tseng, H.-R., Wenger, S. (2002) J. Am. Chem. Soc, in press.
Credi, A., Montalti, M., Balzani, V., Ungford, S.J., Raymo, F.M., Stoddart, J.F. (1998) New J. Chem. 1061.
Balzani, V., Gómez-López, M., Stoddart, J.F. (1998)) Acc. Chem. Res. 31, 405.
Leigh, D.A. and Murphy, A. (1999) Chem. Ind. 179.
Balzani, V., Credi, A., Venturi, M., (1999) in Ungaro, R.. and Dalcanale, E. (eds), Supramolecular Science: Where It Is and Where It Is Going, Kluwer, Dordrecht, p. 1.
Balzani, V., Credi, A., Raymo, F. M, Stoddart, J.F. (2000) Angew. Chem. Int. Ed. 33, 3349.
(a) Balzani, V. and Scandola, F. (1991) Supramolecular Photochemistry, Horwood, New York, (b) Balzani, V. (1992) Tetrahedron 48, 10443. (c) Bissel, R.A., de Silva, A.P., Guraratne, H.Q.N., Linch, P.L. M, Maguire, G.E.M., McCoy, C.P., Sandanayake, K.R.A.S. (1993) Top. Curr. Chem. 168, 223. (d) Fabbrizzi, L. and Poggi, A. (1995) Chem. Soc. Rev. 24, 197. (e) Benniston, A.C. (1996) Chem. Soc. Rev. 25, 427. (f) Gómez-López, M., Preece, J.A., Stoddart, J.F. (1996) Nanotechnology 7, 183. (g) Ward, M.D.(1997) Chem. Ind. 640. (h) Balzani, V., Credi, A., Scandola, F. (1997) Chim. Ind. (Rome) 79, 751. (i) Swager, T.M. (1998) Ace. Chem. Res. 31, 201. (j) Sauvage, J.-P. (1998) Ace. Chem. Res. 31, 611. (k) Chambron, J.-C. and Sauvage, J.-P. (1998) Chem. Eur. J. 4, 1362. (1) Venturi, M., Credi, A., Balzani, V. (1999) Coord. Chem. Rev. 185/186, 233. (m) Kaifer, A.E. (1999) Ace. Chem. Res. 32, 62.
Di Fabio, A., Ballardini, R., Balzani, V., Gandolfi, MX, Venturi, M., Stoddart, J.F., Tseng, H.-R. manuscript in preparation.
(a) Pascher, T., Chesick, J.P., Winkler, J.R., Gray, H.B. (1996) Science 271, 1558. (b)Chen, E., Wittung-Stafshede, P., Kliger, D.S. (1999)J Am. Chem. Soc. 121, 3811. (c) Lee, J.C., Gray, H.B., Winkler, J.R. (2001) Proc. Natl. Acad. Sci. USA, 98, 7760. (d) Dado, G.P., Gellman, S.H. (1993)J Am. Chem. Soc. 115, 12609.
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Di Fabio, A., Ballardini, R., Gandolfi, M.T. (2003). Tetrathiafulvalene and its Derivatives as π-Electron Donating Units in Pseudorotaxanes, Rotaxanes, and Catenanes. In: Barsanti, L., Evangelista, V., Gualtieri, P., Passarelli, V., Vestri, S. (eds) Molecular Electronics: Bio-sensors and Bio-computers. NATO Science Series, vol 96. Springer, Dordrecht. https://doi.org/10.1007/978-94-010-0141-0_3
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