Skip to main content
SpringerLink
Log in

Structural diversity in coordination polymers constructed from a naphthalene-spaced dipyridyl ligand and iron(II) thiocyanate

  • Original Article
  • Published:
Journal of Inclusion Phenomena and Macrocyclic Chemistry Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Scheme 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. Murray, L.J., Dinca, M., Long, J.R.: Hydrogen storage in metal-organic frameworks. Chem. Soc. Rev. 38, 1294–1314 (2009)

    Article  CAS  Google Scholar 

  2. 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)

    Article  CAS  Google Scholar 

  3. 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)

    Article  CAS  Google Scholar 

  4. 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)

    Article  CAS  Google Scholar 

  5. 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)

    Article  CAS  Google Scholar 

  6. Maspoch, D., Ruiz-Molina, D., Veciana, J.: Old materials with new tricks: multifunctional open-framework materials. Chem. Soc. Rev. 36, 770–818 (2007)

    Article  CAS  Google Scholar 

  7. 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)

    Article  Google Scholar 

  8. 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)

    Article  Google Scholar 

  9. Kawamichi, T., Inokuma, Y., Kawano, M., Fujita, M.: Regioselecitive huisgen cycloaddition within porous coordination networks. Angew. Chem. Int. Ed. 49, 2375–2377 (2010)

    CAS  Google Scholar 

  10. Coronado, E., Gatteschi, D.: Trends and challenges in molecule-based magnetic materials. J. Mater. Chem. 16, 2513–2515 (2006)

    Article  Google Scholar 

  11. 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)

    Article  CAS  Google Scholar 

  12. Kepert, C.J.: Supramolecular magnetic materials. Aust. J. Chem. 62, 1079–1080 (2009)

    Article  CAS  Google Scholar 

  13. 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)

    Article  CAS  Google Scholar 

  14. 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)

    Article  CAS  Google Scholar 

  15. 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)

    Article  CAS  Google Scholar 

  16. 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)

    Article  CAS  Google Scholar 

  17. Batten, S.R., Murray, K.S.: Structure and magnetism of coordination polymers containing dicyanamide and tricyanomethanide. Coord. Chem. Rev. 246, 103–130 (2003)

    Article  CAS  Google Scholar 

  18. 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)

    Article  Google Scholar 

  19. 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)

    Article  CAS  Google Scholar 

  20. 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)

    Article  CAS  Google Scholar 

  21. 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)

    Google Scholar 

  22. 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)

    CAS  Google Scholar 

  23. 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)

    Article  CAS  Google Scholar 

  24. Janiak, C.: Engineering coordination polymers towards applications. Dalton. Trans. 14, 2781–2804 (2003)

    Article  Google Scholar 

  25. Bünzli, J.-C.G., Piguet, C.: Lanthanide-containing molecular and supramolecular polymetallic functional assemblies. Chem. Rev. 102, 1897–1928 (2002)

    Article  Google Scholar 

  26. 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)

    Article  Google Scholar 

  27. 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)

    Google Scholar 

  28. 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)

    Article  CAS  Google Scholar 

  29. Halder, G.J., Kepert, C.J.: Iron(II) molecular framework materials with 4, 4’-azopyridine. Aust. J. Chem. 58, 311–314 (2005)

    Article  CAS  Google Scholar 

  30. 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)

    Article  CAS  Google Scholar 

  31. 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)

    Article  CAS  Google Scholar 

  32. 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)

    Article  Google Scholar 

  33. 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)

    Article  CAS  Google Scholar 

  34. 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)

    Article  CAS  Google Scholar 

  35. 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)

    Article  CAS  Google Scholar 

  36. 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)

    Article  CAS  Google Scholar 

  37. 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)

    Article  Google Scholar 

  38. 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)

    Article  CAS  Google Scholar 

  39. 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)

    Article  CAS  Google Scholar 

  40. 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)

    Article  CAS  Google Scholar 

  41. 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)

    Article  CAS  Google Scholar 

  42. 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)

    CAS  Google Scholar 

  43. 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)

    Article  CAS  Google Scholar 

  44. 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)

    Article  Google Scholar 

  45. 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)

    CAS  Google Scholar 

  46. 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)

    Article  CAS  Google Scholar 

  47. 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)

    Article  CAS  Google Scholar 

  48. 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)

    Article  Google Scholar 

  49. 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)

    Google Scholar 

  50. 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)

    Article  CAS  Google Scholar 

  51. 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)

    Article  CAS  Google Scholar 

  52. 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)

    Article  CAS  Google Scholar 

  53. 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)

    Article  CAS  Google Scholar 

  54. 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)

  55. Bruker-Nonius: APEX v2.1, SAINT v.7 and XPREP v.6.14. Bruker AXS Inc., Madison (2003)

    Google Scholar 

  56. Bruker: SMART, SAINT and XPREP. Bruker Analytical X-ray Instruments Inc., Wisconsin (1995)

    Google Scholar 

  57. Farrugia, L.J.: WinGX suite for small-molecule single-crystal crystallography. J. Appl. Cryst. 32, 837–838 (1999)

    Article  CAS  Google Scholar 

  58. 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)

    Article  CAS  Google Scholar 

  59. Sheldrick, G.M.: SADABS. Empirical absorption and correction software. University of Göttingen, Germany (1996–2008)

  60. Sheldrick, G.M.: A short history of SHELX. Acta. Cryst. A 64, 112–122 (2008)

    Article  Google Scholar 

  61. Sheldrick, G.M.: SHELXL-97: programs for crystal structure analysis. University of Göttingen, Germany (1997)

    Google Scholar 

  62. 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)

    Article  CAS  Google Scholar 

  63. 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)

    Article  Google Scholar 

  64. Vigato, P.A., Tamburini, S.: The challenge of cyclic and acyclic schiff bases and related derivatives. Coord. Chem. Rev. 248, 1717–2128 (2004)

    Article  CAS  Google Scholar 

  65. 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)

    Article  Google Scholar 

  66. Wells, A.F.: Three-dimensional nets and polyhedra. Wiley-Interscience, New York (1977)

    Google Scholar 

Download references

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

  1. School of Chemistry, The University of Sydney, Sydney, NSW, 2006, Australia

    Feng Li, Jack K. Clegg & Cameron J. Kepert

  2. Department of Chemistry, The University of Cambridge, Lensfield Rd, Cambridge, CB2 1EW, UK

    Jack K. Clegg

Authors
  1. Feng Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jack K. Clegg
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Cameron J. Kepert
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Cameron J. Kepert.

Additional information

This work is dedicated to Professor Len Lindoy on the occasion of his 75th birthday.

Rights and permissions

Reprints 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

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-011-0016-5

Keywords

Search

Navigation