Abstract
α-Cyclodextrin having cinnamamide at 6- or 3-positions (6-CiNH-α-CD, 3-CiNH-α-CD) and β-cyclodextrin with cinnamamide on 6-position (6-CiNH-β-CD) have been prepared. Supramolecular structures were formed in the solid state or aqueous solutions and characterized by measurements of NMR and vapor pressure osmometry (VPO). The results indicate that 6-CiNH-β-CD formed insoluble supramolecular polymers in the solid state, while 6-CiNH-α-CD and 3-CiNH-α-CD formed supramolecular complexes in aqueous solutions. 6-CiNH-α-CD was found to form a dimer in an aqueous solution. 3-CiNH-α-CD formed intermolecular complexes to give supramolecular polymers. The differences of the position of guest part on cyclodextrins caused to give a variety of supramolecular structures in aqueous solutions.
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1.(a) J.-P. Sauvage and C. Dietrich-Buchecker: Molecular Catenanes, Rotaxanes and Knots, Wiley-VCH, Weinheim (1999); (b)’A.’Harada: Adv. Polym. Sci. 133, 141 (1997); (c) A. Harada: Acc. Chem. Res. 34, 456 (2001); (d) D.B. Amabilino and J.F. Stoddard: Chem. Rev. 95, 2725 (1995); (e) V. Balzani, A. Credi, F.M. Raymo, and J.F. Stoddart, Angew. Chem. Int. Ed. 39, 3348 (2000).
(a) K. Hamasaki, H. Ikeda, A. Nakamura, A. Ueno, F. Toda, I.’Suzuki, and T. Osa: J. Am. Chem. Soc. 115, 5035 (1993); (b)’A.’Ueno, S. Minato, I. Suzuki, M. Fukushima, M. Ohkubo, T.’Osa, F. Hamada, and K. Murai: Chem. Lett. 605 (1990); (c)’R.’Corradini, A. Dossena, R. Marchelli, A. Panagia, G. Sartor, M. Saviano, A. Lombardi, and V. Pavone: Chem. Eur. J. 2, 373 (1996); (d) R. Corradini, A. Dossena, G. Galaverna, R. Marchelli, A. Panagia, and G. Sartor: J. Org. Chem. 62, 6283 (1997); (e)’Y.’Wang, T. Ikeda, H. Ikeda, A. Ueno, and F. Toda: Bull. Chem. Soc. Jpn. 67, 1598 (1994).
(a) A. Zanotti-Gerosa, E. Sorali, L. Giannini, A. Chiesi-Villa, and C. Rizzoli: Chem. Commun. 119 (1996); (b) N. Yamaguchi, D.S. Nagvekar, and H.W. Gibson: Angew. Chem., Int. Ed. 37, 2361 (1998); (c) J. Bulger, N.M. Sommerdik, A.J.W.G. Visser, A. van Hoek, R.J. M.Nolte, J.F.J. Engbersen, and D.N. Houldt: J. Am. Chem. Soc. 121, 28 (1999).
L.H.- Tong Z.-J. Hou Y. Inoue A. Tai (1992) ArticleTitle␣ J Am Chem Soc Perkin Trans 2 1253
T Hoshino M Miyauchi Y Kawaguchi H Yamaguchi A Harada (2000) ArticleTitle␣ J Am Chem Soc 112 9876
(a) S.E. Brown, J.H. Coates, D.R. Coghlan, C.J. Easton, S.J. van Eyk, W. Janowski, A. Lepore, A.F. Lincolun, Y. Luo, B.L. May, D.S. Schiesser, P. Wang, and M.L. Williams: Aust. J. Chem. 46, 953 (1993); (b) K. Takahashi, K. Hattori, and F. Toda: Tetrahedron Lett. 25, 3331 (1984); (c) H. Ikeda, Y. Nagano, Y. Du, T. Ikeda, and F. Toda: Tetrahedron Lett. 31, 5045 (1990).
A. Harada Y. Kawaguchi T. Hoshino (2001) ArticleTitle␣ J Incl Phenom 41 115
M.B. Hursthouse C.Z. Smith M. Thornton-Pett J.H.P. Utley (1982) ArticleTitle␣ J Chem Soc Chem Commun ␣ 881
J.L. Atwood J.E.D. Davies D.D. MacNicol F. Vögtle (1996) Comprehensive Supramolecular Chemistry. Pergamon Oxford
(a) P. Stilbs. Prog. NMR. Spectrosc. 19, 1–45 (1987); (b) E.O. Stejskal and J.E. Tanner. J. Chem. Phys. 42, 288 (1965); (c) K.S. Cameron and L. Fielding. J. Org. Chem. 66, 6891 (2001).
L. Avram Y. Cohen (2002) ArticleTitle␣ J. Org. Chem. 67 2639
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Miyauchi, M., Kawaguchi, Y. & Harada, A. Formation of Supramolecular Polymers Constructed by Cyclodextrins with Cinnamamide. J Incl Phenom Macrocycl Chem 50, 57–62 (2004). https://doi.org/10.1007/s10847-003-8839-3
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DOI: https://doi.org/10.1007/s10847-003-8839-3