Abstract
The sulfur-containing heterocycle, tetrathiafulvalene (TTF) and its derivatives have been intensively studied during the past two decades on account of their unique π electron donor properties. They were originally prepared for the development of electrically conducting materials and have, as such, been synonymous with the development of molecular organic metals. However, during the past few years, the utility of TTF derivatives as building blocks in macrocyclic and supramolecular chemistry has revealed that the TTF moiety is useful beyond the field of materials chemistry. Progress in synthetic TTF chemistry has enabled the preparation of elaborate molecular architectures and consequently TTF has been incorporated into a number of molecular and supramolecular systems, such as cyclophanes, catenanes, rotaxanes, dendrimers, and polymers. Molercular devices based on host-guest interactions may act as for example sensors or molecular switches. Among these systems mechanically-interlocked architectures such as catenanes and rotaxanes are now prime candidates for the construction of artificial molecular machines and the fabrication of molecular electronic devices.
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References
Nielsen, M.B., Lomholt, C. and Becher, J., (2000), Chem. Soc. Rev. 29, 153–164.
Segura, J.L. and Martín, N., (2001),Angew. Chem., Int. Ed. 40,1372–1409.
Simonsen, K.B. and Becher, J., (1997),Synlett, 1211–1220.
Vögtle, F., Ed., (1983) Cyclophanes I, Topics in Current Chemistry, 113, Springer, Berlin,.
Vögtle, F., Ed., (1983), Cyclophanes II, Topics in Current Chemistry, 115, Springer, Berlin,.
Vögtle, F., (1993), Cyclophane Chemistry, Wiley, Chichester.
Diederich, F., (1991), Cyclophanes, Monographs in Supramolecular Chemistry (Ed.: J. F. Stoddart), The Royal Society of Chemistry, London.
Boulas, P. L., Gomez-Kaifer M. and Echegoyen, L., (1998)Angew. Chem. Int. Ed, 37, 226–247
Takimiya, K., Thorup, N. and Becher, J., (2000)Chem. Eur. J., 6, 1947–1954.
Spanggaard, H., Prehn, J., Nielsen, M. B., Levillain, E., Allain, M., and Becher, J, (2000), J. Am. Chem. Soc., 122, 9486–9494.
Simonsen, K. B., Svenstrup, N., Lau, J, Thorup, N. and Becher, J., (1999)Angew. Chem. Int. Ed., 38, 1417–1420.
Jeppesen, J. O., Takimiya, K., Jensen, F. and Becher, J., (1999)Org. Lett. 1, 1291–1294.
,4-bis(2-cyanoethylsulfanyl)thiophenes P. Blanchard et al, (2002)J. Org. Chem., 67, 3961–3964.
Frere, P., Gallego-Planas, N., Blanchard P., (2002), Tetrahedron Letters, 43, 1825–1828.
Otsubo, T., Aso, Y. and Takimiya, K., (1996)Adv. Mater., 8, 203–211.
Only few TTF-belts have been reported, see:
Adam, M., Enkelmann, V., Rader, H. J., Rohrich, J. and Mullen, K. (1992)Angew. Chem. Int. Ed. Engl. 31, 309–310.
Takimiya, K., Imamura, K., Shibata, Y., Aso, Y., Ogura, F. and Otsubo, T., (1997)J. Org Chem., 62, 5567–5574.
Nielsen, K., Jeppesen, J. O., Thorup, N. and Becher, J., (2002)Org. Letters, 4, 1327–1330.
Sessler, J. L. and Gale, P. A. in The Porphyrin Handbook, Vol. 6 (Eds.: Kadish, K. M., Smith, K. M. and Guilard, R.), Academic Press, San Diego, (2000), 257–278.
Baeyer, A., (1886), Ber. Dtsch. Chem. Ges. 19, 2184–2185.
Anzenbacher, Jr. P., Try, A. C, Miyaji, H., Jursýkovà, K., Lynch, V. M., Marquez, M. and Sessler, J. L. (2000)J. Am. Chem. Soc., 122, 10268–10272.
Schmidtchen, F. P. (2002), Org. Lett. 4, 431–434.
Yoon, D.-W., Hwang, H. and Lee, C. H. (2002), Angew. Chem. Int. Ed., 41, 1757–1759.
Nielsen, K. A., Jeppesen, J. O., Levillain, E. And Jan Becher, (2003)Angew. Chem. Int. Ed, 42, 187–191.
Gale, P. A., Sessler, J. L., Kràl, V., and Lynch, A.J. Am. Chem. Soc. (1996), 118, 5140–5141.
Becher, J., Brimert, T., Jeppesen, J. O., Pedersen, J. Z., Zubarev, R., Bjørnholm, T., Reitzel, N., Jensen, T. R., Kjaer, K. and Levillain, E.,Angew. Chem. Int. Ed, (2001), 41, 2497–2500.
Jeppesen, J. O., Takimiya, K., Jensen, F., Brimert, T., Nielsen, K., Thorup, N., and BecherJ. Org. Chem., (2000), 65, 5794–5805.
Li, H., Jeppesen, J. O., Levillain, E., and Becher, J., Chem. Commun, (2003), 846–847.
For examples of catenanes, rotaxanes and pseudorotaxanes containing TTF, see:
Ashton, P. R., Bissell, R. A., Spencer, N., Stoddart, J. F. and Tolley, M. S., (1992)Synlett, 923–926;
Li, Z.-T., Stein, P. C, Svenstrup, N., Lund, K. H., and Becher, J., (1995), Angew. Chem. Int. Ed. Engl., 34, 2524–2528;
Li, Z.-T., and Becher, J., (1996), Chem. Commun., 639–640;
Li, Z.-T., Stein, P. C, Becher, J., Jensen, D., Mørk, P., and Svenstrup, N., (1996), Chem. Eur. J.2 624–633
Li, Z.-T., and J. Becher, (1997),Synlett, 557–560;
Nielsen, M. B., Li, Z.-T. and Becher, J., (1997),J. Mater. Chem., 7, 1175–1187
Asakawa, M., Ashton, P. R., Balzani, V., Credi, A., Mattersteig, G., Matthews, O., Montalti, N., Spencer, N., Stoddart, J. F., and Venturi, M.., (1997)Chem. Eur. J., 3, 1992–1996;
Asakawa, M., Ashton, P. R., Balzani, V., Credi, A., Hamers, C., Mattersteig, G., Montalti, M., Shipway, A. N., Spencer, N., Stoddart, J. F., Tolley, M. S., Venturi, M, White, A. J. P., and Williams, D. J., (1998)Angew. Chem. Int. Ed, 37, 333–337;
Nielsen, M. B., Nielsen, S. B, and J. Becher, (1998)Chem. Commun, 475–476;
Nielsen, M. B., Thorup, N., and Becher, J., (1998)J. Chem. Soc. Perkin Trans. I, 1305–1308;
Credi, A., Montalti, M., Balzani, V., Langford, S. J., Raymo, F. M., and Stoddart, J. F., (1998)New. J. Chem., 22, 1061–1065;
Asakawa, M., Ashton, P. R., Balzani, V., Boyd, S. E., Credi, A., Mattersteig, G., Menzer, S., Montalti, M., Raymo, F. M., Ruffilli, C., Stoddart, J. F., Venturi, M., and Williams, D. J., (1999)Eur. J. Org. Chem., 985–994;
Lau, J., Nielsen, M. B., Thorup, N., Cava, M. P., and Becher, J., (1999)Eur. J. Org. Chem., 3335–3341;
Asakawa, M., Higuchi, M., Mattersteig, G., Nakamura, T., Pease, A. R., Raymo, F. M., Shimizu, T., and Stoddart, J. F., (2000), Adv. Mater., 12, 1099–1102.
Nielsen, M. B., Jeppesen, J. O., Lau, J., Lomholt, C., Damgaard, D., Jacobsen, J. P., Becher, J., and Stoddart, J. F., (2001), J. Org. Chem., 66, 3559–3563.
For examples of molecular machines see:
Gómez-López, M, Preece, J. A., Stoddart, J. F., (1996)Nanotechnology, 7, 183–192.
Ward, M. D., (1997), Chem. Ind., 640–645.
Balzani, V., Gómez- López, M., Stoddart, J. F., (1998)Acc. Chem. Res., 31, 405–414.
Sauvage, J.-P., (1998)Acc. Chem. Res., 31, 611–619.
Niemz, A., Rotello, V. M., (1999), Acc. Chem. Res., 32, 42–52.
Kaifer, A. E., (1999)Acc. Chem. Res., 32, 62–71.
Fabbrizzi, L., Licchelli, M., Pallavicini, P., (1999)Acc. Chem. Res., 32, 846–853.
Leigh, D. A., Murphy, A., (1999), Chem. Ind., 178–183.
Ward, M. D., (2000), Chem. Ind., 22–26.
Balzani, V., Credi, A., Raymo, F. M., Stoddart, J. F., (2000)Angew. Chem. Int. Ed, 39, 3348–3391.
Ballardini, R., Balzani, V., Credi, A., Gandolfi, M. T., Venturi, M., (2001)Acc. Chem. Res., 34, 445–455.
Harada, A., (2001), Acc. Chem. Res., 34, 456–464.
Collin, J. P., Dietrich- Buchecker, C., Gavina, P., Jimenez-Molero, M. C., Sauvage, J.-P., (2001)Acc. Chem. Res., 34, 477–487.
Structure and Bonding, 99, (Special volume on Molecular Machines and Motors, Ed. J.-P. Sauvage).
Stanier, C. A., Alderman, S. J., Claridge, T. D. W., Anderson, H. L., (2002), Angew. Chem. Int. Ed., 41, 1769–1772.
For examples of molecular devices see:
Collier, C. P., Wong, E. W., Belohradsky, M., Raymo, F. M., Stoddart, J. F., Kuekes, P. J., Williams, R. S., and Heath, J. R., (1999)Science, 285, 391–394.
Wong, E. W., Collier, C. P., Belohradsky, M., Raymo, F. M., Stoddart, J. F., and Heath, J. R., (2000)J. Am. Chem. Soc, 122, 5831–5840.
Asakawa, M., Higuchi, M., Mattersteig, G., Nakamura, T., Pease, A. R., Raymo, F. M., Shimizu, T., and Stoddart, J. F., (2000)Adv. Mater., 12, 1099–1102.
Collier, C. P., Mattersteig, G., Wong, E. W., Lou, Y., Beverly, K., Sampaio, J., Raymo, F. M., Stoddart, and J. F., Heath, J. R., (2000)Science, 289, 1172–1175.
Service, R. F., (2001), Science, 291, 426–427.
Pease, A. R., Jeppesen, J. O., Stoddart, J. F., Luo, T., Collier, C. P., and Heath, J. R., (2001)Acc. Chem. Res. 34, 433–444.
Collier, C. P., Jeppesen, J. O., Luo, Y., Perkins, J., Wong, E. W., Heath, J. R. and Stoddart, J. F., (2001)J. Am. Chem. Soc, 123, 12632–12641.
Service, R. F., (2001)Science, 294, 2442–2443.
Luo, Y., Collier, C. P., Jeppesen, J. O., Nielsen, K. A., Delonno, E., Ho, G., Perkins, J., Tseng, H.-R., Yamamoto, T., Stoddart, J. F., and Heath, J. R., (2002), ChemPhysChem., 3, 519–525.
Jacoby, M., (2002)Chem. Eng. News38–43.
Balzani, V., Credi, A., Mattersteig, G., Matthews, O. A., Raymo, F. M., Stoddart, J. F., Venturi, M., White, A. J. P. and Williams, D. J., (2000)J. Org. Chem., 65, 1924–1936.
Jeppesen, J. O., Perkins, J., Becher, J., and Stoddart, J. F., (2000)Org. Lett., 2, 3547–3550.
Jeppesen, J. O., Perkins, J., Becher, J., and Stoddart, J. F., (2001)Angew. Chem. Int. Ed, 40, 1216–1221.
Jeppesen, J. O., Nielsen, K. A., Perkins, J., Vignon, S. A., Di Fabio, A., Ballardini, R., Gandolfi, M. T., Venturi, M., Balzani, V., Becher, J., and Stoddart, J. F., (2003), Chem. Eur. J., 9, 2982 - 3007.
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Becher, J., Nielsen, K., Jeppesen, J.O. (2004). Macrocyclic, Molecular, and Supramolecular TTF Systems. In: Ouahab, L., Yagubskii, E. (eds) Organic Conductors, Superconductors and Magnets: From Synthesis to Molecular Electronics. NATO Science Series, vol 139. Springer, Dordrecht. https://doi.org/10.1007/978-94-007-1027-6_1
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