Abstract
Employing N,N′-bis-(4-pyridinylmethylene)-1,5-naphthalenediamine (nbpy4) and iron(II) thiocyanate as building blocks, three coordination polymers, [Fe(NCS)2(nbpy4)(MeOH)2] n , 1, [Fe(NCS)2(nbpy4)2] n ·2nCHCl3·nH2O·2nEtOH, 2, and [Fe(NCS)2(nbpy4)(bpy)] n ·2.5nDCM·0.75nH2O, 3, have been prepared. The three metal–organic materials were prepared by varying the solvent systems used and the inclusion of a second pyridine containing ligand (4,4′-bipyridine, bpy). Single crystal X-ray diffraction revealed 1 to be a one-dimensional structure with hydrogen bonding between adjacent chains and 2–3 to be two-dimension network solids with (4,4)-topologies.
Similar content being viewed by others
References
Murray, L.J., Dinca, M., Long, J.R.: Hydrogen storage in metal-organic frameworks. Chem. Soc. Rev. 38, 1294–1314 (2009)
Lee, J., Farha, O.K., Roberts, J., Scheidt, K.A., Nguyen, S.T., Hupp, J.T.: Metal-organic framework materials as catalysts. Chem. Soc. Rev. 38, 1450–1459 (2009)
Perry IV, J.J., Perman, J.A., Zaworotko, M.J.: Design and synthesis of metal-organic frameworks using metal-organic polyhedra as supermolecular building blocks. Chem. Soc. Rev 38, 1400–1417 (2009)
Tranchemontagne, D.J., Mendoza-Cortes, J.L., O’Keeffe, M., Yaghi, O.M.: Secondary building units, nets and bonding in the chemistry of metal-organic frameworks. Chem. Soc. Rev. 38, 1257–1283 (2009)
Halder, G.J., Kepert, C.J., Moubaraki, B., Murray, K.S., Cashion, J.D.: Guest-dependent spin crossover in a nanoporous molecular framework material. Science 298, 1762–1765 (2002)
Maspoch, D., Ruiz-Molina, D., Veciana, J.: Old materials with new tricks: multifunctional open-framework materials. Chem. Soc. Rev. 36, 770–818 (2007)
Zou, R.-Q., Sakurai, H., Xu, Q.: Preparation, adsorption properties, and catalytic activity of 3D porous metal–organic frameworks composed of cubic building blocks and alkali-metal ions. Angew. Chem. Int. Ed. 118, 2604–2608 (2006)
Ohara, K., Kawano, M., Inokuma, Y., Fujita, M.: A porous coordination network catalyzes an olefin isomerization reaction in the pore. J. Am. Chem. Soc. 132, 30–31 (2009)
Kawamichi, T., Inokuma, Y., Kawano, M., Fujita, M.: Regioselecitive huisgen cycloaddition within porous coordination networks. Angew. Chem. Int. Ed. 49, 2375–2377 (2010)
Coronado, E., Gatteschi, D.: Trends and challenges in molecule-based magnetic materials. J. Mater. Chem. 16, 2513–2515 (2006)
Wang, D., Zhang, B., He, C., Wu, P., Duan, C.: A new chiral N-heterocyclic carbene silver(I) cylinder: synthesis, crystal structure and catalytic properties. Chem. Commun. 46, 4728–4730 (2010)
Kepert, C.J.: Supramolecular magnetic materials. Aust. J. Chem. 62, 1079–1080 (2009)
Neville, S.M., Halder, G.J., Chapman, K.W., Duriska, M.B., Moubaraki, B., Murray, K.S., Kepert, C.J.: Guest tunable structure and spin crossover properties in a nanoporous coordination framework material. J. Am. Chem. Soc. 131, 12106–12108 (2009)
Southon, P.D., Liu, L., Fellows, E.A., Price, D.J., Halder, G.J., Chapman, K.W., Moubaraki, B., Murray, K.S., Letard, J.-F., Kepert, C.J.: Dynamic interplay between spin-crossover and host-guest function in a nanoporous metal–organic framework material. J. Am. Chem. Soc. 131, 10998–11009 (2009)
Bechlars, B., D’Alessandro, D.M., Jenkins, D.M., Iavarone, A.T., Glover, S.D., Kubiak, C.P., Long, J.R.: High-spin ground states via electron delocalization in mixed-valence imidazolate-bridged divanadium complexes. Nat. Chem 2, 362–368 (2010)
Sato, S., Morohara, O., Fujita, D., Yamaguchi, Y., Kato, K., Fujita, M.: Parallel-stacked aromatic hosts for orienting small molecules in a magnetic field: induced residual dipolar coupling by encapsulation. J. Am. Chem. Soc. 132, 3670–3671 (2010)
Batten, S.R., Murray, K.S.: Structure and magnetism of coordination polymers containing dicyanamide and tricyanomethanide. Coord. Chem. Rev. 246, 103–130 (2003)
Iremonger, S.S., Southon, P.D., Kepert, C.J.: A nanoporous chiral metal-organic framework material that exhibits reversible guest adsorption. Dalton Trans. 44, 6103–6105 (2008)
Furukawa, H., Yaghi, O.M.: Storage of hydrogen, methane, and carbon dioxide in highly porous covalent organic frameworks for clean energy applications. J. Am. Chem. Soc. 131, 8875–8883 (2009)
Britt, D., Furukawa, H., Wang, B., Glover, T.G., Yaghi, O.M.: Highly efficient separation of carbon dioxide by a metal-organic framework replete with open metal sites. Proc. Natl. Acad. Sci. USA 106, 20637–20640 (2009)
Brown, C.M., Liu, Y., Yildirim, T., Peterson, V.K., Kepert, C.J.: Hydrogen adsorption in HKUST-1: a combined inelastic neutron scattering and first-principles study. Nanotechnology 20, 204025 (2009)
Duriska, M.B., Neville, S.M., Lu, J., Iremonger, S.S., Boas, J.F., Kepert, C.J., Batten, S.R.: Systematic Metal Variation and Solvent and Hydrogen-Gas Storage in Supramolecular Nanoballs. Angew. Chem., Int. Ed. 48, 8919–8922 (2009)
Clegg, J.K., Iremonger, S.S., Hayter, M.J., Southon, P.D., MacQuart, R.B., Duriska, M.B., Jensen, P., Turner, P., Jolliffe, K.A., Kepert, C.J., Meehan, G.V., Lindoy, L.F.: Hierarchical self-assembly of a chiral metal–organic framework displaying pronounced porosity. Angew. Chem. Int. Ed. 49, 1075–1078 (2010)
Janiak, C.: Engineering coordination polymers towards applications. Dalton. Trans. 14, 2781–2804 (2003)
Bünzli, J.-C.G., Piguet, C.: Lanthanide-containing molecular and supramolecular polymetallic functional assemblies. Chem. Rev. 102, 1897–1928 (2002)
de Sá, G.F., Malta, O.L., de Mello Donegá, C., Simas, A.M., Longo, R.L., Santa-Cruz, P.A., da Silva, E.F.: Spectroscopic properties and design of highly luminescent lanthanide coordination complexes. Coord. Chem. Rev. 196, 165–195 (2000)
Gass, I.A., Batten, S.R., Forsyth, C.M., Moubaraki, B., Schneider, C.J., Murray, K.S.: Supramolecular aspects of iron(II) crown-dipyridyl spin-crossover compounds. Coord. Chem. Rev. 255, 2058–2067 (2011)
Glasson, C.R.K., Lindoy, L.F., Meehan, G.V.: Recent developments in the d-block metallo-supramolecular chemistry of polypyridyls. Coord. Chem. Rev. 252, 940–963 (2008)
Halder, G.J., Kepert, C.J.: Iron(II) molecular framework materials with 4, 4’-azopyridine. Aust. J. Chem. 58, 311–314 (2005)
Schilter, D., Clegg, J.K., Harding, M.M., Rendina, L.M.: Platinum(II) and palladium(II) metallomacrocycles derived from cationic 4, 4’-bipyridinium, 3-aminopyrazinium and 2-aminopyrimidinium ligands. Dalton Trans. 39, 239–247 (2010)
Glasson, C.R.K., Clegg, J.K., McMurtrie, J.C., Meehan, G.V., Lindoy, L.F., Motti, C.A., Moubaraki, B., Murray, K.S., Cashion, J.D.: Unprecedented encapsulation of a [FeIIICl4]− anion in a cationic [FeII4L6]8+ tetrahedral cage derived from 5, 5′′′-dimethyl-2, 2′:5′, 5′′:2′′, 2′′′-quaterpyridine. Chem. Sci. 2, 540–543 (2011)
Glasson, C.R.K., Meehan, G.V., Clegg, J.K., Lindoy, L.F., Turner, P., Duriska, M.B., Willis, R.: A new FeII quaterpyridyl M4L6 tetrahedron exhibiting selective anion binding. Chem. Commun. 10, 1190–1192 (2008)
Glasson, C.R.K., Meehan, G.V., Clegg, J.K., Lindoy, L.F., Smith, J.A., Keene, F.R., Motti, C.: Microwave synthesis of a rare [Ru2L3]4+ triple helicate and its interaction with DNA. Chem. Eur. J. 14, 10535–10538 (2008)
Hristova, Y.R., Smulders, M.M.J., Clegg, J.K., Breiner, B., Nitschke, J.R.: Selective anion binding by a “Chameleon” capsule with a dynamically reconfigurable exterior. Chem. Sci. 2, 638–641 (2011)
Neville, S.M., Leita, B.A., Halder, G.J., Kepert, C.J., Moubaraki, B., Letard, J.-F., Murray, K.S.: Understanding the two-step spin-transition phenomenon in iron(II) 1D chain materials. Chem. Eur. J. 14, 10123–10133 (2008)
Neville, S.M., Halder, G.J., Chapman, K.W., Duriska, M.B., Southon, P.D., Cashion, J.D., Letard, J.-F., Moubaraki, B., Murray, K.S., Kepert, C.J.: Single-crystal to single-crystal structural transformation and photomagnetic properties of a porous iron(ii) spin-crossover framework. J. Am. Chem. Soc. 130, 2869–2876 (2008)
Mulyana, Y., Kepert, C.J., Lindoy, L.F., McMurtrie, J.C.: New cadmium(II) and iron(II) coordination frameworks incorporating a Di(4-pyridyl)isoindoline ligand. Eur. J. Inorg. Chem. 12, 2470–2475 (2005)
Halder, G.J., Kepert, C.J.: In situ single-crystal X-ray diffraction studies of desorption and sorption in a flexible nanoporous molecular framework material. J. Am. Chem. Soc. 127, 7891–7900 (2005)
Halder, G.J., Chapman, K.W., Neville, S.M., Moubaraki, B., Murray, K.S., Letard, J.-F., Kepert, C.J.: Elucidating the mechanism of a two-step spin transition in a nanoporous metal–organic framework. J. Am. Chem. Soc. 130, 17552–17562 (2008)
Cussen, E.J., Claridge, J.B., Rosseinsky, M.J., Kepert, C.J.: Flexible sorption and transformation behavior in a microporous metal–organic framework. J. Am. Chem. Soc. 124, 9574–9581 (2002)
Fletcher, A.J., Cussen, E.J., Prior, T.J., Rosseinsky, M.J., Kepert, C.J., Thomas, K.M.: Adsorption dynamics of gases and vapors on the nanoporous metal organic framework material Ni2(4, 4’-Bipyridine)3(NO3)4: guest modification of host sorption behavior. J. Am. Chem. Soc. 123, 10001–10011 (2001)
Beves, J.E., Constable, E.C., Housecroft, C.E., Kepert, C.J., Neuburger, M., Price, D.J., Schaffner, S.: The conjugate acid of bis{4’-(4-pyridyl)-2, 2′:6′, 2″-terpyridine}iron(II) as a self-complementary hydrogen-bonded building block. Cryst. Eng. Comm. 9, 1073–1077 (2007)
Beves, J.E., Bray, D.J., Clegg, J.K., Constable, E.C., Housecroft, C.E., Jolliffe, K.A., Kepert, C.J., Lindoy, L.F., Neuburger, M., Price, D.J., Schaffner, S., Schaper, F.: Expanding the 4, 4′-bipyridine ligand: Structural variation in {M(pytpy)2}2+ complexes (pytpy = 4’-(4-pyridyl)-2, 2′:6′, 2″-terpyridine, M = Fe, Ni, Ru) and assembly of the hydrogen-bonded, one-dimensional polymer {[Ru(pytpy)(Hpytpy)]} 3n+n . Inorg. Chim. Acta. 361, 2582–2590 (2008)
Beves, J.E., Dunphy, E.L., Constable, E.C., Housecroft, C.E., Kepert, C.J., Neuburger, M., Price, D.J., Schaffner, S.: Vectorial property dependence in bis{4’-(n-pyridyl)-2, 2′:6′, 2″-terpyridine}iron(II) and ruthenium(II) complexes with n = 2, 3 and 4. Dalton. Trans. 3, 386–396 (2008)
Beves, J.E., Constable, E.C., Housecroft, C.E., Kepert, C.J., Price, D.J.: The first example of a coordination polymer from the expanded 4, 4’-bipyridine ligand [Ru(pytpy)2]2 + (pytpy = 4’-(4-pyridyl)-2, 2′:6′, 2″-terpyridine). Cryst. Eng. Comm. 9, 456–459 (2007)
Amoore, J.J.M., Neville, S.M., Moubaraki, B., Iremonger, S.S., Murray, K.S., Letard, J.-F., Kepert, C.J.: Thermal- and light-induced spin crossover in a guest-dependent dinuclear iron(II) system. Chem. Eur. J. 16, 1973–1982 (2010)
Amoore, J.J.M., Kepert, C.J., Cashion, J.D., Moubaraki, B., Neville, S.M., Murray, K.S.: Structural and magnetic resolution of a two-step full spin-crossover transition in a dinuclear iron(II) pyridyl-bridged compound. Chem. Eur. J. 12, 8220–8227 (2006)
Su, C.-Y., Goforth, A.M., Smith, M.D., zur Loye, H.-C.: Assembly of large simple 1D and rare polycatenated 3D molecular ladders from T-shaped building blocks containing a new, long N, N′-bidentate ligand. Chem. Commun. 19, 2158–2159 (2004)
Liu, Y.-R., Li, X.-P., Zhang, J.-A., Su, C.-Y.: N, N′-Bis(4-pyridylmethylene)naphthalene-1, 5-diamine. Acta. Cryst. 61, o2089–o2090 (2005)
Jang, Y.O., Lee, S.W.: Homoleptic silver-bis(pyridine) coordination polymers: [Ag(L1)2] (PF6), [Ag(L1)2] (SbF6), [Ag(L1)2] (BF4), [Ag(L2)] (PF6), and [Ag(L3)1.5] (CF3SO3) (H2O)2 {L1 = (4-py)-CH=N–C10H6–N=CH–(4-py); L2 = (2-py)–CH=N–C10H6–N=CH–(2-py); L3 = (3-py)–CH=N–C14H12–N=CH–(3-py)}. Polyhedron 29, 2731–2738 (2010)
Jung, Y.-M., Lee, S.W.: Relative coordinating abilities of bis(pyridine)-type ligands when forming mixed-ligand coordination polymers: preparation and structure of [Cd2(L1)2(L2)(NO3)4].infin. {(n-py)-CH=N–C10H6–N=CH–(n-py) [n = 3 (L1), 4 (L2)]}. Bull. Korean Chem. Soc. 31, 2668–2671 (2010)
Min, D., Cho, B.-Y., Lee, S.W.: Novel long bipyridine-type linking ligands containing an intervening naphthalene fragment: [Zn(L1)(NO3)2], [Zn(L2)(NO3)2], and [Cd(L1)1.5(NO3)2] (L1 = (4-py)–CHN–C10H6–NCH–(4-py); L2 = (3-py)–CHN–C10H6–NCH–(3-py)). Inorg. Chim. Acta. 359, 577–584 (2006)
Kim, S.H., Huh, H.S., Lee, S.W.: Cobalt(II) coordination polymers based on dicarboxylates and dipyridyl-type ligands: [CoL1.5(NO3)2], [Co1.5(bpdc)1.5(dma) (dma) (EtOH), [Co1.5(ndc)1.5(dma)2], [Co3(ndc)3(dmf)4], and [CoL(bpdc)] (EtOH) (bpdcH2 = biphenyl-4, 4’-dicarboxylic acid, ndcH2 = 2, 6-naphthalene dicarboxylic acid, L = pyCH=N–C10H6–N=CHpy). J. Mol. Struct. 841, 78–87 (2007)
Huh, H.S., Lee, S.W.: {μ-N,N’-Bis[(E)-4-pyridylmethylidene]naphthalene-1,5-diamine}bis[dichlorido(dimethyl sulfide)platinum(II)]. Acta. Cryst. E64, m1138 (2008)
Bruker-Nonius: APEX v2.1, SAINT v.7 and XPREP v.6.14. Bruker AXS Inc., Madison (2003)
Bruker: SMART, SAINT and XPREP. Bruker Analytical X-ray Instruments Inc., Wisconsin (1995)
Farrugia, L.J.: WinGX suite for small-molecule single-crystal crystallography. J. Appl. Cryst. 32, 837–838 (1999)
Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giocavazzo, C., Gaugliardi, A., Moliterni, G.C., Polidori, G., Spagna, S.: SIR97, A package for crystal structure solution by direct methods and refinement. J. Appl. Cryst. 32, 115–119 (1999)
Sheldrick, G.M.: SADABS. Empirical absorption and correction software. University of Göttingen, Germany (1996–2008)
Sheldrick, G.M.: A short history of SHELX. Acta. Cryst. A 64, 112–122 (2008)
Sheldrick, G.M.: SHELXL-97: programs for crystal structure analysis. University of Göttingen, Germany (1997)
Xia, H.-L., Ardo, S., Narducci Sarjeant, A.A., Huang, S., Meyer, G.J.: Photodriven spin change of Fe(II) benzimidazole compounds anchored to nanocrystalline TiO2 thin films. Langmuir 25, 13641–13652 (2009)
Létard, J.F., Nguyen, O., Soyer, H., Mingotaud, C., Delhaès, P., Kahn, O.: First evidence of the LIESST effect in a Langmuir–Blodgett film. Inorg. Chem. 38, 3020–3021 (1999)
Vigato, P.A., Tamburini, S.: The challenge of cyclic and acyclic schiff bases and related derivatives. Coord. Chem. Rev. 248, 1717–2128 (2004)
Capitán-Vallvey, L.F., Jimenez, C.: Spectrophotometric extractive determination of thiocyanate as a mixed-ligand iron-thiocyanate-2-(phenyliminomethyl)pyridine complex. Microchem. J. 28, 118–125 (1983)
Wells, A.F.: Three-dimensional nets and polyhedra. Wiley-Interscience, New York (1977)
Acknowledgments
We thank the Australian Research Council and J.K.C. acknowledges the Marie Curie IIF scheme of the 7th EU Framework Program for support. The authors thank Dr Deanna D’Alessandro for comments on UV–Vis Spectra.
Author information
Authors and Affiliations
Corresponding author
Additional information
This work is dedicated to Professor Len Lindoy on the occasion of his 75th birthday.
Rights and permissions
About this article
Cite this article
Li, F., Clegg, J.K. & Kepert, C.J. Structural diversity in coordination polymers constructed from a naphthalene-spaced dipyridyl ligand and iron(II) thiocyanate. J Incl Phenom Macrocycl Chem 71, 381–388 (2011). https://doi.org/10.1007/s10847-011-0016-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10847-011-0016-5