Abstract
The [2]pseudorotaxane of cucurbit[6]uril (Q6) with 1,6-bis(imidazol-1-yl)hexane dihydrobromide was synthesized and its crystal structure was described. The structure of [2]pseudorotaxane was mainly stablized by host–guest C–H···O interactions. Self-assembly of the [2]pseudorotaxane produces infinite one-dimensional chains with intermolecular N–H···O, C–H···O, and π···π interactions; thus, a linear non-covalent pseudopolyrotaxane is formed.
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(a) F.M. Raymo and J.F. Stoddart: Chem. Rev. 99, 1643 (1999); (b) J.W. Lee, S. Samal, N. Selvapalam, H.-J. Kim, and K. Kim: Acc. Chem. Rev., 36, 621 (2003); (c) K. Kim, N. Selvapalam, and D.H. Oh: J. Incl. Phenom. Macro. 50, 31 (2004); (d) J.D. Badjic, V. Balzani, A. Credi, S. Silvi, and J.F. Stoddart: Science 303, 1845 (2004)
Zhang H.Z., Paulsen E.S., Walker K.A., Krakowiak K.E., Dearden D.V. J. Am. Chem. Soc.125 9284 (2003)
(a) D. Tuncel, and J.H.G. Steinke: Chem. Comm. 253 (2001); (b) J.W. Lee, K. Kim, and K. Kim: Chem.Comm. 1042 (2001); (c) K. Kim, W.S. Jeon, J.K. Kang, J.W. Lee, S.Y. Jon, T. Kim, and K. Kim: Angew. Chem. Int. Ed. 42, 2293 (2003); (d) D. Whang, J. Heo, C.-A. Kim, and K. Kim: Chem. Comm. 2361 (1997); (e) D. Tuncel and J.H.G. Steinke: Chem.Comm. 1509 (1999); (f) W. L. Mock, N.Y. Shih: J. Org.Chem. 51, 4440 (1986); (g) K.M. Park, D. Whang, E. Lee, J. Heo, and K. Kim: Chem. Eur. J. 8, 498 (2002); (h) D. Whang, Y.-M. Jeon, J. Heo, and K. Kim: J. Am. Chem. Soc. 118, 11333 (1996); (i) E. Lee, J. Kim, J. Heo, D. Whang, and K. Kim: Angew. Chem. Int. Ed. 40, 399 (2001); (j) Y. Tan, S.W. Choi, J.W. Lee, Y.H. Ko, and K. Kim: Macromolecules 35, 7161 (2002); (k) Y.-M. Jeon, D. Whang, J. Kim, and K. Kim: Chem. Lett. 503 (1996)
(a) W.A. Freeman, W.L. Mock, and N.Y. Shih: J. Am. Chem. Soc. 103, 7367 (1981); (b) A. Day, A.P. Arnold, R.J. Blanch, and B. Sunshall: J. Org. Chem. 66, 8094 (2001); (c) J. Kim, I.-S. Jung, S.-Y. Kim, E. Lee, J.-K. Kang, S. Sakamoto, K. Yamaguchi, and K. Kim: J. Am. Chem. Soc. 122, 540 (2000); (d) K. Kim, N. Selvapalam, and D.H. Oh: J. Incl. Phenom. Macro.Chem. 50, 31 (2004); (e) A.I. Day, R. J. Blanch, A.P. Arnold, S. Lorenzo, G.R. Lewis, and I. Dance: Angew. Chem. Int. Ed. 41, 275 (2002)
Shen X.-L., Chen H.-L., Yu F., Zhang Y.-C., Yang X.-H., Li Y.-Z.:(2004). Tetrahedron Lett.45, 6913
The guest molecule: Yeild 85%. 1H NMR (300 MHz, 25 °C, D2O): δ 8.53 (s, 2H), 7.31 (d, 4H), 4.05 (t, 4H, α-CH2), 1.71 (m, 4H, β-CH2), 1.16 (m, 4H, γ-CH2); 13C NMR (300 MHz, D2O): δ 136.60, 124.04, 121.96, 51.55, 31.40, 27.21; Elemental analysis (calcd. %): C, 37.89; N, 14.73; H, 5.26. Found: C, 37.66; N, 14.64; H, 5.23
General procedure for preparation of the [2] pseudorotaxane: A solution of 1, 6-bis(imidazol-1-yl)hexane dihydrobromide (0.1 mmol) in H2O (20 ml) was added CB[6] (0.1 mmol) in small portions and the mixture was stirred for 24 h at 80 °C. The solution was concentrated to 5 ml by evaporation. Addition of THF (30 ml) to the solution produced a white precipitate, which was filtered and dried in vacuum condition, affording the rotaxane complex. Yeild 76%. 1H NMR (300 MHz, 25 °C, D2O): δ 8.93 (s, 2H), 7.70 (s, 2H), 7.16 (s, 2H), 5.59 (d, 12H), 5.33 (s, 12H), 4.10 (d, 12H), 3.73 (t, 4H), 0.962 (m, 4H), 0.366 (m, 4H); 13C NMR (300 MHz, D2O): δ 158.2, 137.6, 125.7, 119.2, 72.6, 53.7, 50.9, 29.7, 25.2; Elemental analysis (calcd. %) for [C6H6N4O2]6 · C12H18N4 · 2HBr · 8H2O: C, 37.89; N, 25.78; H, 4.73. Found: C, 37.48; N, 25.42; H, 4.61
(a) F.M. Raymo, M.D. Bartberger, K.N. Houk, and J.F. Stoddart: J. Am.Chem.Soc. 123, 9264 (2001); (b) C. Dai, Z. Yuan, J.C. Collings, T.M. Fasina, R.L. Thomas, K.P. Roscoe, L.M. Stimson, D.S. Yufit, A.S. Batsanov, J.A.K. Howard, and T.B. Marder: Cryst. Eng. Comm. 6, 184 (2004); (c) T. Steiner: Chem.Comm. 727 (1997)
(a) P. Vishweshwar, A. Nangia, and V.M. Lynch: Cryst. Growth Des. 3, 783 (2003); (b) A. Spitaleri, C.A. Hunter, J.F. McCabe, M.J. Packer, and S.L. Cockroft: Cryst. Eng. Comm. 6, 489 (2004); (c) S. Tsuzuki, K. Honda, T. Uchimaru, M. Mikami, and K. Tanabe: J. Am. Chem. Soc. 124, 104 (2002); (d) F. Huang, L. Zhou, J.W. Jones, H.W. Gibson, and M. Ashraf-Khorassani: Chem. Commun. 2670 (2004); (e) H. Adams, C.A. Hunter, K.R. Lawson, J. Perkins, S.E. Spey, C.J. Urch, and J.M. Sanderson: Chem. Eur. J. 7, 4863 (2001)
The crystals suitable for single-crystal X-ray diffraction were grown from its water solution evaporating at room temperature for over a week. Crystallographic data were collected using a Bruker SMART 2000 CCD diffractometer with MoKα (λ=0.71073 Å). Intensities were integrated using the SAINT program and corrected for absorption and other effects using the SADABS program. Structures were solved and refined using the SHELXS-97 and SHELXL-97 programs. All hydrogens were located in a difference Fourier map and their geometry idealized, and refined by using a riding model with O–H=0.85 Å (s.u.=0.02) and Uiso(H)=1.2 Ueq(O). The positions of hydrogen atoms, bonded to carbon atoms, were idealized with their thermal parameters of 1.2 times those of attached atoms. Crystal data for C36H36N24O12 · C12H20N4 · 8H2O · 2Br: crystal size 0.2×0.2×0.2, monoclinic, space group P21/c (No.14). a=12.445(3) Å, b=20.081(4) Å, c=12.578(3) Å, β=113.088°, V=2891.6(10) Å3, Z=2, T=203 K, θmax=25.01°, 11578 reflections measured, 5029 unique (Rint=0.0412). Final residual for 476 parameters and 5029 reflections with I>2σ(I): R1=0.0440, wR2=0.0901 and GOF=0.872. CCDC 265575 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44-1223/336-033; e-mail: data_request@ccdc.cam.ac.uk
(a) S. Leininger, B. Olenyuk, and P.J. Stang: Chem. Rev. 100, 853 (2000); (b) L.A. Estroff, and A.D. Hamilton: Chem. Mater. 13, 3227 (2001)
(a) L. Brunsveld, B.J.B. Folmer, E.W. Meijer, and R.P. Sijbesma: Chem. Rev. 101, 4071 (2001); (b) K. Kim, D. Kim, J.W. Lee, Y.H. Ko, and K. Kim: Chem. Comm. 848 (2004)
(a) S.W. Choi, J.K. Lee, Y.H. Ko, and K. Kim: Macromolecules 35, 3526 (2002); (b) M. Asakawa, P.R. Ashton, G.R. Brown, W. Hayes, S. Menzer, J.F. Stoddart, A.J.P. White, and D.J. Williams: Adv. Mater. 8, 37 (1996); (c) P.R. Ashton, P.J. Campbell, E.J.T. Chrystal, P.T. Glink, S. Menzer, D. Philp, N. Spencer, J.F. Stoddart, P.A. Tasker, and D.J. Williams: Angew. Chem. Int. Ed. Engl. 34, 1865 (1995); (d) P.R. Ashton, E.J.T. Chrystal, P.J. Campbell, P.T. Glink, S. Menzer, C. Schiavo, J.F. Stoddart, P. A. Tasker, and D.J. Williams: Angew. Chem. Int. Ed. Engl. 34, 1869 (1995)
(a) K. Xia, T.-J. Hou, X.-J. Xu, and X.-H. Shen: Acta Phys.-Chim. Sin. 20, 5 (2004); (b) G. Li and L.B. McGown: Science 264, 249 (1994)
Lagona J., Mukhopadhyay P., Chakrabarti S., Isaacs L.: Angew. Chem. Int. Ed.44, 4844, (2005)
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We gratefully acknowledge the National Natural Science Foundation of China (No: 30470408, P. Yang) for the financial support of this work.
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HUO, FJ., YIN, CX. & YANG, P. Self-assembly of a [2]Pseudorotaxane Composed of Cucurbit[6]uril into Linear Pseudopolyrotaxanes by N–H···O, C–H···O and π···π Interactions. J Incl Phenom Macrocycl Chem 56, 193–196 (2006). https://doi.org/10.1007/s10847-006-9082-5
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DOI: https://doi.org/10.1007/s10847-006-9082-5