Self-Organization of -Crown Ether Derivatives into Double-Columnar Arrays Controlled by Supramolecular Isomers of Hydrogen-Bonded Anionic Biimidazolate Ni Complexes
Anionic tris (biimidazolate) nickelate (II) ([Ni(Hbim)3]？), which is a hydrogen-bonding (H-bonding) molecular building block, undergoes self-organization into honeycomb-sheet superstructures connected by complementary intermolecular H-bonds. The crystal obtained from the stacking of these sheets is assembled into channel frameworks, approximately 2？nm wide, that clathrate two cationic K+-crown ether derivatives organised into one-dimensional (1D) double-columnar arrays. In this study, we have shown that all five cationic guest-included crystals form nanochannel structures that clathrate the 1-D double-columnar arrays of one of the four types of K+-crown ether derivatives, one of which induces a polymorph. This is accomplished by adaptably fitting two types of anionic [Ni(Hbim)3]？ host arrays. One is a Δ Λ ？ Δ Λ ？ Δ Λ ？ network with H-bonded linkages alternating between the two different optical isomers of the Δ and Λ types with flexible H-bonded [Ni(Hbim)3]？. The other is a Δ Δ Δ ？ Λ Λ Λ ？ network of a racemate with 1-D H-bonded arrays of the same optical isomer for each type. Thus, [Ni(Hbim)3]？ can assemble large cations such as K+ crown-ether derivatives into double-columnar arrays by highly recognizing flexible H-bonding arrangements with two host networks of Δ Λ ？ Δ Λ ？ Δ Λ ？ and Δ Δ Δ ？ Λ Λ Λ ？ . 1. Introduction Self-assembled supramolecular architectures are currently of considerable interest owing to their intriguing network topologies and their potential applications in microelectronics, nonlinear optics, porous materials, and other technologies [1–10]. A tenet of crystal engineering, which belongs to supramolecular chemistry as well, is to control multidimensional network topologies in crystals constructed from molecular building blocks that are connected by means of mutual interactions of H-bonds and metal-coordination bonds [11–26]. For example, three-dimensional (3-D) molecular networks such as complicated (10,3)-a and (10,3)-b nets in crystals can also be produced in the field of crystal engineering by a rational design of artificial molecular building blocks [27–43]. In a previous report, we showed that 2,2′-biimidazolate monoanions (Hbim？) was convenient for fabricating, via one-pot self-organization, controlled crystal structures that are not only coordinated to a transition metal ion but also connected to each other through intermolecular H-bonds of the complementary dual N-H？N type [44–50]. The self-organizing superstructures formed from the H-bonded networks of the transition metal complexes with Hbim？ can be controlled in
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.
[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.
[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.
[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.
[6]
C. B. Aaker？y, 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.
[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.
[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.
[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.
[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.
[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.
[12]
G. R. Desiraju, “Supramolecular synthons in crystal engineering—a new organic synthesis,” Angewandte Chemie, vol. 34, no. 21, pp. 2311–2327, 1995.
[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.
[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.
[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.
[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.
[17]
C. B. Aaker？y 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.
[18]
C. B. Aaker？y, 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.
[19]
C. B. Aaker？y, 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.
[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.
[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.
[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.
[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.
[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.
[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.
[26]
L. Brammer, “Metals and hydrogen bonds,” Journal of the Chemical Society, Dalton Transactions, no. 16, pp. 3145–3157, 2003.
[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.
[28]
L. ？hrstr？m 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.
[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.
[30]
F. Robinson and M. J. Zaworotko, “Triple interpenetration in [Ag(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.
[31]
O. M. Yaghi and H. L. Li, “T-shaped molecular building units in the porous structure of Ag(4, -bpy)·NO3,” Journal of the American Chemical Society, vol. 118, no. 1, pp. 295–296, 1996.
[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.
[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.
[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, -bipyridine,” Journal of the American Chemical Society, vol. 116, no. 3, pp. 1151–1152, 1994.
[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.
[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.
[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.
[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.
[39]
A. J. Blake, N. R. Champness, P. Hubberstey, W.-S. Li, M. A. Withersby, and M. Schr？der, “Inorganic crystal engineering using self-assembly of tailored building-blocks,” Coordination Chemistry Reviews, vol. 183, no. 1, pp. 117–138, 1999.
[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.
[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.
[42]
S. Kitagawa, R. Kitaura, and S. Noro, “Functional porous coordination polymers,” Angewandte Chemie, vol. 43, no. 18, pp. 2334–2375, 2004.
[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.
[44]
M. Tadokoro, J. Toyoda, K. Isobe et al., “Dimeric hydrogen-bonded transition metal complex containing bidentate mono-deprotonated 2, -biimidazolate ligand,” Chemistry Letters, vol. 24, no. 8, pp. 613–614, 1995.
[45]
M. Tadokoro and K. Nakasuji, “Hydrogen bonded 2, -biimidazolate transition metal complexes as a tool of crystal engineering,” Coordination Chemistry Reviews, vol. 198, no. 1, pp. 205–218, 2000.
[46]
L. ？hrstr？m, 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.
[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.
[48]
B. H. Ye, B. B. Ding, Y. Q. Weng, and X. M. Chen, “Multidimensional networks constructed with isomeric benzenedicarboxylates and 2, -biimidazole based on mono-, bi-, and trinuclear units,” Crystal Growth & Design, vol. 5, no. 2, pp. 801–806, 2005.
[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.
[50]
L. Ion, D. Morales, J. Pérez et al., “Ruthenium biimidazole complexes as anion receptors,” Chemical Communications, no. 1, pp. 91–93, 2006.
[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.
[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.
[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.
[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. V？gtle, and J.-M. Lehn, Eds., vol. 6, pp. 177–238, Pergamon Press, 1996.
[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. V？gtle, and J.-M. Lehn, Eds., vol. 6 of Solid-State Supramolecular Chemistry: Crystal Engineering, pp. 851–883, Pergamon Press, 1996.
[56]
M. E. Davis, “Ordered porous materials for emerging applications,” Nature, vol. 417, pp. 813–821, 2002.
[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.
[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.
[59]
P. T. Beurskens, G. Admiraal, G. Beurskens et al., “The DIRDIF-99 program system”.
