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Journal of Nanotechnology
Volume 2012 (2012), Article ID 216050, 10 pages
http://dx.doi.org/10.1155/2012/216050
Research Article

Self-Organization of 𝐊 + -Crown Ether Derivatives into Double-Columnar Arrays Controlled by Supramolecular Isomers of Hydrogen-Bonded Anionic Biimidazolate Ni Complexes

1Department of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka 1-3, Shinjuku-ku, Tokyo 162-8601, Japan
2Fukui University of Technology, Gakuen 3-6-1, Fukui 910-8505, Japan

Received 27 March 2012; Accepted 18 May 2012

Academic Editor: Hongmei Luo

Copyright © 2012 Makoto Tadokoro et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. J.-M. Lehn, “Supramolecular chemistry—scope and perspectives molecules, supermolecules, and molecular devices (Nobel Lecture),” Angewandte Chemie, vol. 27, no. 1, pp. 89–112, 1988. View at Google Scholar
  2. J.-M. Lehn, Supramolecular Chemistry-Concepts and Perspectives, Wiley-VCH, Weinheim, Germany, 1995.
  3. S. R. Batten and R. Robson, “Interpenetrating nets: ordered, periodic entanglement,” Angewandte Chemie, vol. 37, no. 11, pp. 1460–1494, 1998. View at Google Scholar
  4. M. Yoshizawa, M. Nagao, K. Umemoto et al., “Side chain-directed assembly of triangular molecular panels into a tetrahedron vs. open cone,” Chemical Communications, no. 15, pp. 1808–1809, 2003. View at Google Scholar
  5. J. Zubieta, P. J. Hagrman, and D. Hagrman, “Organic–inorganic hybrid materials: from “Simple” coordination polymers to organodiamine-templated molybdenum oxides,” Angewandte Chemie, vol. 38, no. 18, pp. 2638–2684, 1999. View at Google Scholar
  6. C. B. Aakeröy, A. M. Beatty, and K. R. Lorimer, “Assembly of 2-D inorganic/organic lamellar structures through a combination of copper(I) coordination polymers and selfcomplementary hydrogen bonds,” Journal of the Chemical Society, Dalton Transactions, no. 21, pp. 3869–3872, 2000. View at Publisher · View at Google Scholar · View at Scopus
  7. A. L. Gillon, G. R. Lewis, A. G. Orpen et al., “Organic–inorganic hybrid solids: control of perhalometallate solid state structures,” Journal of the Chemical Society, Dalton Transactions, no. 21, pp. 3897–3905, 2000. View at Google Scholar
  8. D. B. Mitzi, “Templating and structural engineering in organic–inorganic perovskites,” Journal of the Chemical Society, Dalton Transactions, no. 1, pp. 1–12, 2001. View at Google Scholar
  9. J.-C. Bünzli and C. Piguet, “Lanthanide-containing molecular and supramolecular polymetallic functional assemblies,” Chemical Reviews, vol. 102, no. 6, pp. 1897–1928, 2002. View at Google Scholar
  10. L. Carlucci, G. Ciani, and D. M. Proserpio, “Polycatenation, polythreading and polyknotting in coordination network chemistry,” Coordination Chemistry Reviews, vol. 246, no. 1-2, pp. 247–289, 2003. View at Publisher · View at Google Scholar · View at Scopus
  11. S. Subramanian and M. J. Zaworotko, “Exploitation of the hydrogen bond: recent developments in the context of crystal engineering,” Coordination Chemistry Reviews, vol. 137, pp. 357–401, 1994. View at Google Scholar · View at Scopus
  12. G. R. Desiraju, “Supramolecular synthons in crystal engineering—a new organic synthesis,” Angewandte Chemie, vol. 34, no. 21, pp. 2311–2327, 1995. View at Google Scholar
  13. A. D. Burrows, C.-W. Chan, M. M. Chowdhry, J. E. McGrady, and D. M. P. Mingos, “Multidimensional crystal engineering of bifunctional metal complexes containing complementary triple hydrogen bonds,” Chemical Society Reviews, vol. 24, no. 5, pp. 329–339, 1995. View at Google Scholar
  14. I. Dance, “Supramolecular inorganic chemistry,” in The Crystal as Supramolecular Entity, G. R. Desiraju, Ed., vol. 5, pp. 145–248, John Wiley & Sons, 1996. View at Google Scholar
  15. N. Ohata, H. Masuda, and O. Yamauchi, “Programmed self-assembly of copper(II)-L- and -D-arginine complexes with aromatic dicarboxylates to form chiral double-helical structures,” Angewandte Chemie, vol. 35, no. 5, pp. 531–532, 1996. View at Google Scholar
  16. A. D. Burrows, D. M. P. Mingos, A. J. P. White, and D. J. Williams, “Crystal engineering of metal complexes based on charge-augmented double hydrogen-bond interactions between thiosemicarbazides and carboxylates,” Chemical Communication, no. 1, pp. 97–100, 1996. View at Google Scholar
  17. C. B. Aakeröy and A. M. Beatty, “Supramolecular assembly of low-dimensional silver(I) architectures via amide–amide hydrogen bonds,” Chemical Communications, no. 10, pp. 1067–1068, 1998. View at Google Scholar
  18. C. B. Aakeröy, A. M. Beatty, and D. S. Leinen, “The oxime functionality: a versatile tool for supramolecular assembly of metal-containing hydrogen-bonded architectures,” Journal of the American Chemical Society, vol. 120, no. 29, pp. 7383–7384, 1998. View at Google Scholar
  19. C. B. Aakeröy, A. M. Beatty, and B. A. Helfrich, “Two-fold interpenetration of 3-D nets assembled via three-co-ordinate silver(I) ions and amide–amide hydrogen bonds,” Journal of the Chemical Society, Dalton Transactions, no. 12, pp. 1943–1946, 1998. View at Google Scholar
  20. D. Braga, L. Maini, and F. Grepioni, “Crystal engineering of organometallic compounds through cooperative strong and weak hydrogen bonds: a simple route to mixed-metal systems,” Angewandte Chemie, vol. 37, no. 16, pp. 2240–2242, 1998. View at Google Scholar
  21. J. C. Mareque Rivas and L. Brammer, “Hydrogen bonding in substituted-ammonium salts of the tetracarbonylcobaltate(−I) anion: some insights into potential roles for transition metals in organometallic crystal engineering,” Coordination Chemistry Reviews, vol. 183, no. 1, pp. 43–80, 1999. View at Google Scholar
  22. M. T. Allen, A. D. Burrows, and M. F. Mahon, “Hydrogen bond directed crystal engineering of nickel complexes: the effect of ligand methyl substituents on supramolecular structure,” Journal of the Chemical Society, Dalton Transactions, no. 2, pp. 215–222, 1999. View at Google Scholar
  23. D. Braga and F. Grepioni, “Complementary hydrogen bonds and ionic interactions give access to the engineering of organometallic crystals,” Journal of the Chemical Society, Dalton Transactions, no. 1, pp. 1–8, 1999. View at Google Scholar
  24. L. Brammer, J. C. Mareque Rivas, R. Atencio, S. Fang, and F. C. Pigge, “Combining hydrogen bonds with coordination chemistry or organometallic π-arene chemistry: strategies for inorganic crystal engineering,” Journal of the Chemical Society, Dalton Transactions, no. 21, pp. 3855–3867, 2000. View at Publisher · View at Google Scholar · View at Scopus
  25. M. M. Bishop, L. F. Lindoy, B. W. Skelton, and A. H. White, “Modification of supramolecular motifs: some effects of incorporation of metal complexes into supramolecular arrays,” Journal of the Chemical Society, Dalton Transactions, no. 3, pp. 377–382, 2002. View at Google Scholar · View at Scopus
  26. L. Brammer, “Metals and hydrogen bonds,” Journal of the Chemical Society, Dalton Transactions, no. 16, pp. 3145–3157, 2003. View at Google Scholar · View at Scopus
  27. M. Tadokoro, T. Shiomi, K. Isobe, and K. Nakasuji, “Cesium(I)-mediated 3-D superstructures by one-pot self-organization of hydrogen-bonded nickel complexes,” Inorganic Chemistry, vol. 40, no. 22, pp. 5476–5478, 2001. View at Publisher · View at Google Scholar · View at Scopus
  28. L. Öhrström and K. Larsson, “What kinds of three-dimensional nets are possible with tris-chelated metal complexes as building blocks?” Journal of the Chemical Society, Dalton Transactions, no. 3, pp. 347–353, 2004. View at Google Scholar
  29. C. S. Abrahams, R. L. Collin, and W. N. Lipscomb, “The crystal structure of hydrogen peroxide,” Acta Crystallographica, vol. 4, pp. 15–20, 1951. View at Google Scholar
  30. F. Robinson and M. J. Zaworotko, “Triple interpenetration in [Ag(4,4-bipyridine)][NO3], a cationic polymer with a three-dimensional motif generated by self-assembly of “T-shaped” building blocks,” Journal of the Chemical Society, Chemical Communications, no. 23, pp. 2413–2414, 1995. View at Google Scholar
  31. O. M. Yaghi and H. L. Li, “T-shaped molecular building units in the porous structure of Ag(4,4-bpy)·NO3,” Journal of the American Chemical Society, vol. 118, no. 1, pp. 295–296, 1996. View at Google Scholar
  32. O. M. Yaghi, C. E. Davis, G. M. Li, and H. L. Li, “Selective guest binding by tailored channels in a 3-D porous zinc(II)−benzenetricarboxylate network,” Journal of the American Chemical Society, vol. 119, no. 12, pp. 2861–2868, 1997. View at Publisher · View at Google Scholar · View at Scopus
  33. K. Biradha and M. Fujita, “A springlike 3D-coordination network that shrinks or swells in a crystal-to-crystal manner upon guest removal or readsorption,” Angewandte Chemie, vol. 41, no. 18, pp. 3392–3395, 2002. View at Google Scholar
  34. M. Fujita, Y. J. Kwon, S. Washizu, and K. Ogura, “Preparation, clathration ability, and catalysis of a two-dimensional square network material composed of cadmium(II) and 4,4-bipyridine,” Journal of the American Chemical Society, vol. 116, no. 3, pp. 1151–1152, 1994. View at Google Scholar · View at Scopus
  35. L. Carlucci, G. Cianni, D. M. Proserpio, and A. Sironi, “Polymeric helical motifs from the self-assembly of silver salts and pyridazine,” Inorganic Chemistry, vol. 37, no. 22, pp. 5941–5943, 1998. View at Google Scholar
  36. R. Atencio, K. Biradha, T. L. Hennigar et al., “Flexible bilayer architectures in the coodination polymers [MII(NO3)2(1,2-BIS(4-pyridyl)ethane)1.5]n (MII = Co, Ni),” Crystal Engineering, vol. 1, no. 3–4, pp. 203–212, 1998. View at Google Scholar
  37. S. S.-Y. Chui, S. M.-F. Lo, J. P. H. Charmant, A. G. Orpen, and I. D. Williams, “A chemically functionalizable nanoporous material [Cu3(TMA)2(H2O)3]n,” Science, vol. 283, no. 5405, pp. 1148–1150, 1999. View at Google Scholar
  38. O. R. Evans, R.-G. Xiong, Z. Wang, G. K. Wong, and W. Liu, “Crystal engineering of acentric diamondoid metal–organic coordination networks,” Angewandte Chemie, vol. 38, no. 4, pp. 536–538, 1999. View at Google Scholar
  39. A. J. Blake, N. R. Champness, P. Hubberstey, W.-S. Li, M. A. Withersby, and M. Schröder, “Inorganic crystal engineering using self-assembly of tailored building-blocks,” Coordination Chemistry Reviews, vol. 183, no. 1, pp. 117–138, 1999. View at Google Scholar
  40. A. J. Blake, N. R. Champness, P. A. Cooke, and J. E. B. Nicolson, “Synthesis of a chiral adamantoid network—the role of solvent in the construction of new coordination networks with silver(I),” Chemical Communications, no. 8, pp. 665–666, 2000. View at Google Scholar
  41. S. R. Batten, B. F. Hoskins, and R. Robson, “Interdigitation, interpenetration and intercalation in layered cuprous tricyanomethanide derivatives,” Chemistry, vol. 6, no. 1, pp. 156–161, 2000. View at Google Scholar
  42. S. Kitagawa, R. Kitaura, and S. Noro, “Functional porous coordination polymers,” Angewandte Chemie, vol. 43, no. 18, pp. 2334–2375, 2004. View at Google Scholar
  43. K. Takaoka, M. Kawano, M. Tominaga, and M. Fujita, “In situ observation of a reversible single-crystal-to-single-crystal apical-ligand-exchange reaction in a hydrogen-bonded 2D coordination network,” Angewandte Chemie, vol. 44, no. 14, pp. 2151–2154, 2005. View at Google Scholar
  44. M. Tadokoro, J. Toyoda, K. Isobe et al., “Dimeric hydrogen-bonded transition metal complex containing bidentate mono-deprotonated 2,2-biimidazolate ligand,” Chemistry Letters, vol. 24, no. 8, pp. 613–614, 1995. View at Google Scholar
  45. M. Tadokoro and K. Nakasuji, “Hydrogen bonded 2,2-biimidazolate transition metal complexes as a tool of crystal engineering,” Coordination Chemistry Reviews, vol. 198, no. 1, pp. 205–218, 2000. View at Google Scholar
  46. L. Öhrström, K. Larsson, S. Borg, and S. T. Norberg, “Crucial influence of solvent and chirality—the formation of helices and three-dimensional nets by hydrogen-bonded biimidazolate complexes,” Chemistry, vol. 7, no. 22, pp. 4805–4810, 2001. View at Google Scholar · View at Scopus
  47. R. Atencio, M. Chacon, T. Gonzalez, A. Brice, G. Agrifoglio, and A. Sierraalta, “Robust hydrogen-bonded self-assemblies from biimidazole complexes. Synthesis and structural characterization of [M(biimidazole)2(OH2)2]2+ (M = Co2+, Ni2+) complexes and carboxylate modules,” Dalton Transactions, no. 4, pp. 505–513, 2004. View at Google Scholar
  48. B. H. Ye, B. B. Ding, Y. Q. Weng, and X. M. Chen, “Multidimensional networks constructed with isomeric benzenedicarboxylates and 2,2-biimidazole based on mono-, bi-, and trinuclear units,” Crystal Growth & Design, vol. 5, no. 2, pp. 801–806, 2005. View at Google Scholar
  49. R. L. Sang and L. Xu, “Counteranion-induced formation of cis and trans singly and doubly H2biim-bridged Di-, Hexa-, and polymeric Ag–H2biim complexes,” European Journal of Inorganic Chemistry, vol. 2006, no. 6, pp. 1260–1267, 2006. View at Google Scholar
  50. L. Ion, D. Morales, J. Pérez et al., “Ruthenium biimidazole complexes as anion receptors,” Chemical Communications, no. 1, pp. 91–93, 2006. View at Publisher · View at Google Scholar · View at Scopus
  51. M. Tadokoro, H. Kanno, T. Kitajima et al., “Self-organizing super-structures formed from hydrogen-bonded biimidazolate metal complexes,” Proceedings of the National Academy of Sciences of the United States of America, vol. 99, no. 8, pp. 4950–4955, 2002. View at Publisher · View at Google Scholar · View at Scopus
  52. M. Tadokoro, K. Isobe, H. Uekusa et al., “Cation-dependent formation of superstructures by one-pot self-organization of hydrogen-bonded nickel complexes,” Angewandte Chemie, vol. 38, no. 1-2, pp. 95–98, 1999. View at Google Scholar · View at Scopus
  53. M. Tadokoro, T. Shiomi, M. Kaneyama, and Y. Miyazato, “Controlled super-structures of hydrogen bonding NiII complexes organizing one-dimensional double cationic arrays,” Journal of Nanoscience and Nanotechnology, vol. 9, no. 1, pp. 301–306, 2009. View at Publisher · View at Google Scholar · View at Scopus
  54. M. D. Hollingsworth and K. D. M. Harris, “Urea, thiourea, and selenourea,” in Comprehensive Supramolecular Chemistry, J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, and J.-M. Lehn, Eds., vol. 6, pp. 177–238, Pergamon Press, 1996. View at Google Scholar
  55. H. Gies and B. Marler, “Crystalline microporous silicas as host-guest systems,” in Comprehensive Supramolecular Chemistry, J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, and J.-M. Lehn, Eds., vol. 6 of Solid-State Supramolecular Chemistry: Crystal Engineering, pp. 851–883, Pergamon Press, 1996. View at Google Scholar
  56. M. E. Davis, “Ordered porous materials for emerging applications,” Nature, vol. 417, pp. 813–821, 2002. View at Google Scholar
  57. N. W. Ockwig, O. Delgado-Friedrichs, M. O'Keeffe, and O. M. Yaghi, “Reticular chemistry:  occurrence and taxonomy of nets and grammar for the design of frameworks,” Accounts of Chemical Research, vol. 38, no. 3, pp. 176–182, 2005. View at Google Scholar
  58. A. Altomare, G. Cascarano, C. Giacovazzo et al., “SIR92—a program for automatic solution of crystal structures by direct methods,” Journal of Applied Crystallography, vol. 27, no. 1, pp. 435–441, 1994. View at Google Scholar
  59. P. T. Beurskens, G. Admiraal, G. Beurskens et al., “The DIRDIF-99 program system”.