Abstract
A novel redox-active calix[4]arene-TTF 5 was prepared by the reaction of p-tert-butylcalix[4]arene 4 with the tosylated TTF 3 in the presence of cesium fluoride. The structure of the dyad 5 was identified by X-ray diffraction analysis, and the preliminary electrochemical properties of 5 were investigated by cyclic voltammetry (CV), for which two reversible one-electron waves were observed. Moreover, the UV-vis absorption spectra studies show that the dyad 5 undergoes progressive oxidation at the TTF moiety in presence of increasing amounts of Cu2+ or Hg2+. 
[1] J.B. Regnouf de Vains, M. Sallé, R. Lamartine, J. Chem. Soc., Perkin Trans 2, 2461 (1997) 10.1039/a706640fSearch in Google Scholar
[2] D. Canevet, M. Sallé, G. Zhang, D. Zhang, D. Zhu, Chem. Commun. 2245 (2009) 10.1039/b818607nSearch in Google Scholar PubMed
[3] B.T. Zhao, M.J. Blesa, N. Mercier, F. Le Derf, M. Sallé, Supramol. Chem. 17, 465 (2005) http://dx.doi.org/10.1080/1061027050021174310.1080/10610270500211743Search in Google Scholar
[4] B.T. Zhao, M.J. Blesa, N. Mercier, F. Le Derf, M. Sallé, New. J. Chem. 29, 1164 (2005) http://dx.doi.org/10.1039/b504339e10.1039/b504339eSearch in Google Scholar
[5] B.T. Zhao, M.J. Blesa, N. Mercier, F. Le Derf, M. Sallé, J. Org. Chem. 70, 6254 (2005) http://dx.doi.org/10.1021/jo050587610.1021/jo0505876Search in Google Scholar PubMed
[6] J. Lyskawa, D. Canevet, M. Allain, M. Sallé, Tetrahedron. Lett. 51, 5868 (2010) http://dx.doi.org/10.1016/j.tetlet.2010.08.11210.1016/j.tetlet.2010.08.112Search in Google Scholar
[7] M.J. Blesa, B.T. Zhao, M. Allain, F. Le Derf, M. Sallé, Chem. Eur. J. 12, 1906 (2006) http://dx.doi.org/10.1002/chem.20050087810.1002/chem.200500878Search in Google Scholar PubMed
[8] J. Lyskawa, M. Sallé, J.Y. Balandier, F. Le Derf, E. Levillain, M. Allain, P. Viel, S. Palacin, Chem. Commun. 2233 (2006) 10.1039/b518275aSearch in Google Scholar PubMed
[9] B.T. Zhao, M.J. Blesa, F. Le Derf, D. Canevet, C. Benhaoua, M. Mazari, M. Allain, M. Sallé, Tetrahedron 63, 10768 (2007) http://dx.doi.org/10.1016/j.tet.2007.06.11910.1016/j.tet.2007.06.119Search in Google Scholar
[10] M.H. Düker, R. Gómez, C.M.L. Vande Velde, V.A. Azov, Tetrahedron Lett. 52, 2881 (2011) http://dx.doi.org/10.1016/j.tetlet.2011.03.14010.1016/j.tetlet.2011.03.140Search in Google Scholar
[11] M.H. Lee, Q.Y. Cao, S.K. Kim, J.L. Sessler, J.S. Kim, J. Org. Chem. 76, 870 (2011) http://dx.doi.org/10.1021/jo102171310.1021/jo1021713Search in Google Scholar
[12] B.T. Zhao, W.B. Guo, P.Z. Hu, Heterocycles 81, 1661 (2010) http://dx.doi.org/10.3987/COM-10-1196510.3987/COM-10-11965Search in Google Scholar
[13] B.T. Zhao, Z. Zhou, Z.N. Yan, E. Belhadj, F. Le Derf, M. Sallé, Tetrahedron Lett. 51, 5815 (2010) http://dx.doi.org/10.1016/j.tetlet.2010.08.11610.1016/j.tetlet.2010.08.116Search in Google Scholar
[14] M. Frei, F. Diederich, R. Tremont, T. Rodriguez, L Echegoyen, Helv. Chim. Acta 89, 2040 (2006) http://dx.doi.org/10.1002/hlca.20069019410.1002/hlca.200690194Search in Google Scholar
[15] G.M. Sheldrick, SHELXS-97, Program for the Solution of Crystal Structures (University of Göttingen, Germany, 1997) Search in Google Scholar
[16] G.M. Sheldrick, SHELXL-97 Program for the Refinement of Crystal Structures (University of Göttingen, Germany, 1997) Search in Google Scholar
[17] D.E. John, A.S. Batsanov, M.R. Bryce, J.A.K. Howard, Synthesis 824 (2000) 10.1055/s-2000-6279Search in Google Scholar
[18] N. Svenstrup, K.M. Rasmussen, T.K. Hansen, J. Becher, Synthesis 809 (1994) 10.1055/s-1994-25580Search in Google Scholar
[19] J. Lau, J. Becher, Synthesis 1015 (1997) 10.1055/s-1997-1300Search in Google Scholar
[20] I. Bitter, A. Grün, G. Toth, B. Balázs, L. Tőke, Tetrahedron 53, 9799 (1997) http://dx.doi.org/10.1016/S0040-4020(97)00627-310.1016/S0040-4020(97)00627-3Search in Google Scholar
[21] N. L. Allinger, X. Zhou, J. Bergsma, J. Mol. Struct. (THEOCHEM) 312, 69 (1994) http://dx.doi.org/10.1016/S0166-1280(09)80008-010.1016/S0166-1280(09)80008-0Search in Google Scholar
[22] N. Iki, S. Ogawa, T. Matsue, S. Miyano, J. Electroanal. Chem. 610, 90 (2007) http://dx.doi.org/10.1016/j.jelechem.2007.06.02310.1016/j.jelechem.2007.06.023Search in Google Scholar
[23] E. Isomura, K.I. Tokuyama, T. Nishinaga, M. Iyoda, Tetrahedron Lett. 48, 5895 (2007) http://dx.doi.org/10.1016/j.tetlet.2007.06.04810.1016/j.tetlet.2007.06.048Search in Google Scholar
[24] V.A. Azov, R. Gómez, J. Stelten, Tetrahedron 64, 1909 (2008) http://dx.doi.org/10.1016/j.tet.2007.11.11010.1016/j.tet.2007.11.110Search in Google Scholar
© 2011 Versita Warsaw
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.
