The monoprotonated bipyridinium cation can complex with dibenzo-24-crown-8 by means of ion-dipole and charge-transfer interactions. They both thread to form a [2]pseudorotaxane-like complex for further intercomplex association to produce pseudopolyrotaxane arrays through N+–H···N hydrogen bonding in the solid state.
Recent publications: (a) AshtonP.R., CampbellP.J., GlinkP.T., PhilpD., SpencerN., StoddartJ.F., CrystalE.J.T., MenzerS., WilliamsD.J., and TaskerP.A., Angew. Chem. Int. Ed. Engl., 1995, 34, 1865; (b) M. Lamsa, J. Huuskonen, K. Rissanen and J. Pursiainen, Chem. Eur. J., 1998, 4, 84; (c) S.J. Loeb and J.A. Wisner, Angew. Chem. Int. Ed. Engl., 1998, 37, 2838; (d) S. Kiviniemi, A.Sillanpaa, M. Nissinen, K. Rissanen, M. T. Lamsa and J. Pursiainen, Chem. Commun., 1999, 897; (e) S. Kiviniemi, M. Nissinen, M. T. Lamsa, J. Jalonen, K. Rissanen and J. Pursiainen, New J. Chem., 2000, 24, 47; (f) S. Kiviniemi, M. Nissinen, T. Kolli, J. Jalonen, K. Rissanen and J. Pursiainen. J. Inclusion Phenom. Macrocyclic Chem., 2001, 40, 153; (g) S.J. Loeb, J. Tiburão and S.J. Vella, Org. Lett., 2005, 7, 4923; (h) F. Huang, C. Slebodnick, A.E. Ratliff and H.W. Gibson, Tetrahedron Lett., 2005, 46, 6019; (i) A.B. Braunschweig, C.M. Ronconi, J.Y. Han, F. Aricó, S.J. Cantrill, J.F. Stoddart, S. I. Khan, A.J. P.White and D.J. Williams, Eur. J. Org. Chem., 2006, 1857; (j) P.N. Cheng, C.F. Lin, Y.H. Liu, C.C. Lai, S.M. Peng and S.H. Chiu, Org. Lett., 2006, 8, 435.
2.
TiburãoJ., DavidsonG.J.E., and LoebS.J., Chem. Commun., 2002, 1282.
3.
BalzaniV., CeronP., CrediA., Gomez-LopezM., HamersC., StoddartJ.F., and WolfR., New J. Chem., 2001, 25, 25.
(a) FyfeM.C.T., and StoddartJ.F., Coord. Chem. Rev., 1999, 183, 139; (b) D.C. Sherrington and K.A. Taskinen, Chem. Soc. Rev., 2001, 30, 83; (c) S. Yagai, T. Iwashima, T. Karatsu and A. Kitamura, Chem. Commun., 2004, 1114.
6.
(a) AsakawaM., AshtonP.R., BrownG.R., HayesW., MenzerS., StoddartJ.F., WhiteA.J.P., and WilliamsD.J., Adv. Mater., 1996, 8, 37; (b) P.R. Ashton, R. Ballardini, V. Balzani, M. Belohradsky, M.T. Gandolfi, D. Philp, L. Prodi, F.M. Raymo, M.V. Reddington, N. Spencer, J.F. Stoddart, M. Venturi and D.J. Williams, J. Am. Chem. Soc., 1996, 118, 4931.
7.
Crystal data for (2/DB24C8)·CF3SO3: yellow block, C35H41F3N2O11S, fw = 754.76, orthorhombic, T = 294(2) K, Pbcn, a = 19.539(3), b = 19.289(3), c = 19.541(3) Å, V = 7365(2) Å3, Z = 8, μ = 0.164 mm−1, independent reflections: 7894 (Rint = 0.1021). final R indices [I > 2σI]: R1 = 0.0497, wR2 = 0.0955, R indices (all data): R1 = 0.1467, wR2 = 0.1260, Goodness-of-fit (F2) = 0.984. CCDC 608599 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request.ãf.
8.
TsuchidaR., Bull. Chem. Soc. Jpn, 1935, 10, 27; P. Job, Compt. Rend., 1925, 180, 928; P. Job, Ann. Chim. Phys., 1928, 9, 113.
