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Supramolecular compounds with coordination polymeric chains of Ag ions, p-sulfonatocalix[4]arene and ethylenediamine

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Abstract

Complexes (en)0.5[{Ag2(en)2}{Ag4(en)4}2(SC4)2]·17H2O(1) and [Ag5(en)5(H2O)2][Ag8(en)8(H2O)2(SC4)2][Na(H2O)4][Na6(H2O)16(SC4)2]·50H2O (2), SC4 = p-sulfonatocalix[4]arene pentaanion, en = ethylenediamine, were synthesized from sodium p-sulfonatocalix[4]arene (Na4SC4), Ag+ ions in aqueous solution of pH = 11 at room temperature. Single-crystal structures were determined by X-ray diffraction. In 1, two 20-membered macrocycles consisting of four Ag+ ions and four en molecules are combined together by weak Ag–Ag metal bonds in which the Ag+ ions are coordinated by sulfonate oxygen atoms of SC4 with a weak Ag–O interaction. Two Ag+ ions in a ten-membered ring, Ag2(en)2, link two hydroxyl oxygen atoms of two SC4, forming a chain extending along the a-axis. In 2 four Ag+ ions and four en molecules form a chain with SC4 as pendants through Ag–O interaction. Another SC4 coordinates to three Na+ ions, forming a Na3-SC4-H2O chain through sharing a water molecule. The third chain is formed by three Ag+ ions and three en molecules. These chains stretch towards different directions forming a 3D supramolecular architecture stabilized by hydrogen bonds.

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References

  1. Atwood, J.L., Bott, S.G., Morley, S.D.: Novel layer structure of sodium calix[4]arenesulfonate complexes—a class of organic clay mimics. Angew. Chem. Int. Ed. Engl. 27, 1361–1362 (1988)

    Article  Google Scholar 

  2. Dalgarno, S.J., Atwood, J.L., Raston, C.L.: Host–guest complexes with p-sulfonatocalix[4,5]arenas charged crown ethers snd lanthanides: factors affecting molecular capsule formation. Cryst. Growth Des. 6, 174–180 (2006)

    Article  CAS  Google Scholar 

  3. Dalgarno, S.J., Atwood, J.L., Raston, C.L.: Structural versatility in praseodymium complexes of p-Sulfonatocalix[4]arene. Cryst. Growth Des. 7, 1762–1770 (2007)

    Article  CAS  Google Scholar 

  4. Liu, Y., Chen, K., Guo, S.-J., Li, Q., Song, H.-B.: Comparable inclusion and aggregation structures of p-Sulfonatothiacalix[4]arene and p-sulfonatocalix[4]arene upon complexation with quinoline guests. Cryst. Growth Des. 7, 2601–2608 (2007)

    Article  CAS  Google Scholar 

  5. Ling, I., Alias, Y., Sobolev, A.N., Raston, C.L.: p-Sulfonatocalix[4]arene–pyrrolidinium complexation in building multicomponent layered arrays. Cryst. Growth Des. 10, 1312–1318 (2010)

    Article  CAS  Google Scholar 

  6. Zhang, J., Guo, D., Liu, Y.: Solid-state supramolecular architectures by p-sulfonatocalix[4]arene with bispyridinium derivatives. Chin. J. Chem. 28, 1575–1579 (2010)

    Article  CAS  Google Scholar 

  7. Francisco, V., Basilio, N., García-Río, L.: Counterion exchange as a decisive factor in the formation of host:guest complexes by p-sulfonatocalix[4]arene. J. Phys. Chem. B 116, 5308–5315 (2012)

    Article  CAS  Google Scholar 

  8. Qian, H., Guo, D.-S., Liu, Y.: p-Sulfonatocalix[4]arene supramolecular polymers: formation by host–guest interactions and light response. Asian J. Org. Chem. 1, 155–159 (2012)

    Article  Google Scholar 

  9. Basílio, N., Piñeiro, Á., Silva, J.P.D., García-Río, L.: Cooperative assembly of discrete stacked aggregates driven by supramolecular host–guest complexation. J. Org. Chem. 78, 9113–9119 (2013)

    Article  Google Scholar 

  10. Sun, R., Xue, C., Ma, X., Gao, M., Tian, H., Li, Q.: Light-driven linear helical supramolecular polymer formed by molecular-recognition-directed self-assembly of bis(p-sulfonatocalix[4]arene) and pseudorotaxane. J. Am. Chem. Soc. 135, 5990–5993 (2013)

    Article  CAS  Google Scholar 

  11. Zhao, H.-X., Guo, D.-S., Liu, Y.: Binding behaviors of p-Sulfonatocalix[4]arene with gemini guests. J. Phys. Chem. B 117, 1978–1987 (2013)

    Article  CAS  Google Scholar 

  12. Hardie, M.J., Raston, C.L.: Russian doll assembled superanion capsule–metal ion complexes: combinatorial supramolecular chemistry in aqueous media. J. Chem. Soc., Dalton Trans. 15, 2483–2492 (2000)

    Article  Google Scholar 

  13. Nichols, P.J., Raston, C.L., Steed, J.W.: Engineering of porous π-stacked solids using mechanochemistry. Chem. Commun. 12, 1062–1063 (2001)

    Article  Google Scholar 

  14. Dalgarno, J., Raston, C.L.: Capture of di-protonated [2.2.2]cryptand in the cavity of two p-sulfonato calixarenes as part of 2-D bi-layer lanthanide coordination polymers. Chem. Commun. 19, 2216–2217 (2002)

    Article  Google Scholar 

  15. Liu, Y., Guo, D.S., Zhang, H.Y., Kang, S., Song, H.B.: Diverse conformation and extended structure of p-Sulfonatothiacalix[4]arene manipulated by guest molecules. Cryst. Growth Des. 6, 1399–1406 (2006)

    Article  CAS  Google Scholar 

  16. Guo, D.S., Su, X., Liu, Y.: Benzyl effects of supramolecular architectures constructed by p-sulfonatocalix[4]arene and viologen guests: from simple 2:1 complex to polymeric capsules. Cryst. Growth Des. 8, 3514–3517 (2008)

    Article  CAS  Google Scholar 

  17. Webb, H.R., Hardie, M.J., Raston, C.L.: Scandium (III) coordination polymers containing capsules based on two p-sulfonatocalix[4]arenas. Chem. Eur. J. 7, 3616–3620 (2001)

    Article  CAS  Google Scholar 

  18. Liu, C., Luo, F., Liao, W., Li, D., Wang, X., Dronskowski, R.: pH-Dependent syntheses and structures of two copper(II)/phenanthroline/p-sulfonatocalix[4]arene supramolecular compounds with 1D water-filled channels. Cryst. Growth Des. 7, 2282–2285 (2007)

    Article  CAS  Google Scholar 

  19. Bi, Y., Liao, W., Zhang, H.: Assembly of supramolecular compounds with water-soluble calix[4]arenes. Cryst. Growth Des. 8, 3630–3635 (2008)

    Article  CAS  Google Scholar 

  20. Mattoussi, N., Pilet, G., Novitchi, G., Meganem, F., Luneau, D.: Synthesis, crystal structure, and magnetic properties of a bis-dinuclear oxo-bridged iron(iii) complex with p-sulfonatocalix[4]arene. Eur. J. Inorg. Chem. 14, 2652–2656 (2013)

    Article  Google Scholar 

  21. Wu, M., Yuan, D., Han, L., Wu, B., Xu, Y. and Hong, M.: Inclusion of metal complexes into cavities of 2d coordination networks built from p-sulfonatothiacalix[4]arene tetranuclear clusters. Eur. J. Inorg. Chem. 526–530 (2006)

  22. Liao, W., Bi, Y., Gao, S., Li, D., Zhang, H., Dronskowski, R.: Lanthanide-hinged calixarene bicapsules: discrete hexanuclear LnIII/phenanthroline/p-sulfonatocalix[4]arene oligomers (Ln = Gd, Tb). Eur. J. Inorg. Chem. 19, 2959–2962 (2008)

    Article  Google Scholar 

  23. Skripacheva, V., Mustafina, A., Rusakova, N., Yanilkin, V., Nastapova, N., Amirov, R., Burilov, V., Zairov, R., Kost, S., Solovieva, S., Korovin, Y., Antipin, I., Konovalov, A.: Heterometallic CoIII–LnIII (Ln = Gd, Tb, Dy) complexes on a p-sulfonatothiacalix[4]arene platform exhibiting redox-switchable metal-to-metal energy transfer. Eur. J. Inorg. Chem. 25, 3957–3963 (2008)

    Article  Google Scholar 

  24. Zheng, G., Zhang, F., Lia, Y., Zhang, H.: Guest inducing p-sulfonatocalix[4]arene into three-dimensional capsule architecture and a mixed A-B double layer framework. CrystEngComm 10, 1560–1564 (2008)

    Article  CAS  Google Scholar 

  25. Liao, W.P., Liu, C., Wang, X., Zhu, G.S., Zhao, X.J., Zhang, H.J., Liao, W.P.: 3D metal–organic frameworks incorporating water-soluble tetra-p-sulfonatocalix[4]arene. CrystEngComm 11, 2282–2284 (2009)

    Article  CAS  Google Scholar 

  26. Zheng, G., Fan, W., Song, S., Guo, H., Zhang, H.: Guests inducing p-sulfonatocalix[4]arenes into nanocapsule and layer structure. J. Solid State Chem. 183, 1457–1463 (2010)

    Article  CAS  Google Scholar 

  27. Gándara, F., Gutiérrez-Puebla, E., Iglesias, M., Snejko, N., Monge, M.Á.: Isolated hexanuclear hydroxo lanthanide secondary building units in a rare-earth polymeric framework based on p-sulfonatocalix[4]arene. Cryst. Growth Des. 10, 128–134 (2010)

    Article  Google Scholar 

  28. Wang, X., Xiong, Y., Liao, W.: Two lanthanide(III)/phenanthroline/p-sulfonatocalix[4]arene supramolecular compounds with 1D ‘molecular capsule’ chains. J. Mol. Struct. 967, 20–24 (2010)

    Article  CAS  Google Scholar 

  29. Mislin, G., Graf, E., Hoddeini, M.W., Cian, A.D., Kyritsakas, N., Fischer, J.: Synthesis and structural analysis of an infinite linear coordination network formed by the self-assembly of tetracyanocalix[4]arene ligands and silver cations. Chem. Commun. 22, 2545–2546 (1998)

    Article  Google Scholar 

  30. Zheng, G.-L., Zhang, H.-J., Song, S.-Y., Li, Y.-Y., Guo, H.-D.: Self-assembly of p-sulfonatocalix[4]arene and a Ag–hmt coordination polymer into a porous structure. Eur. J. Inorg. Chem. 11, 1756–1759 (2008)

    Article  Google Scholar 

  31. Graf, K.E., Hosseini, M.W., Cian, A.D., Fischer, J., Kleina, C.: Metallatubulane: synthesis and structural analysis of an infinite tubular coordination network formed by the self-assembly of a tetracyanocyclophane and silver cations. Chem. Commun. 3, 239–240 (2000)

    Google Scholar 

  32. Wu, M., Yuan, D., Huang, Y., Wei, W., Gao, Q., Jiang, F., Hong, M.: Captures of Copper(II) − 2,2′-bpy complexes in conformation-fixed homometallic anionic dimers and heterometallic clusters. Cryst. Growth Des. 7, 1446–1451 (2007)

    Article  CAS  Google Scholar 

  33. Su, C.-Y., Kang, B.-S., Du, C.-X., Yang, Q.-C., Mak, T.C.W.: Formation of mono-, bi-, tri-, and tetranuclear Ag(I) complexes of C 3-symmetric tripodal benzimidazole ligands. Inorg. Chem. 39, 4843–4849 (2000)

    Article  CAS  Google Scholar 

  34. Loo, K., Degtyareva, N., Park, J., Sengupta, B., Reddish, M., Rogers, C.C., Bryant, A., Petty, J.T.: Ag+-mediated assembly of 5′-guanosine monophosphate. J. Phys. Chem. B 114, 4320–4326 (2010)

    Article  CAS  Google Scholar 

  35. Sailaja, S., Rajasekharan, M.V.: Synthesis and structure of coordination polymers of Ag(I) with isomeric (aminomethyl)pyridines. formation of a novel circular helicate and 2-D networks via Ag···Ag contacts and coordination shell expansion under anion control. Inorg. Chem. 42, 5675–5684 (2003)

    Article  CAS  Google Scholar 

  36. Liu, Y., Pan, M., Yang, Q.-Y., Fu, L., Li, K., Wei, S.-C., Su, C.-Y.: Dual-emission from a single-phase Eu–Ag metal-organic framework: an alternative way to get white-light phosphor. Chem. Mater. 24, 1954–1960 (2012)

    Article  CAS  Google Scholar 

  37. Abu-Youssef, M.A.M., Soliman, S.M., Langer, V., Gohar, Y.M., Hasanen, A.A., Makhyoun, M.A., Zaky, A.H., Öhrström, L.R.: Synthesis, crystal structure, quantum chemical calculations, DNA interactions, and antimicrobial activity of [Ag(2-amino-3-methylpyridine)2] NO3 and [Ag(pyridine-2-carboxaldoxime)NO3]. Inorg. Chem. 49, 9788–9797 (2010)

    Article  CAS  Google Scholar 

  38. Isab, A.A., Wazeer, M.I.M., Fettouhi, M., Al-Maythalony, B.A., Al-Arfaj, A.R., Al-Zamil, N.O.: Solid state and solution NMR, X-ray and antimicrobial studies of 1:1 and 2:1 complexes of silver(I) cyanide with alkanediamine ligands. Inorg. Chim. Acta 360, 3719–3726 (2007)

    Article  CAS  Google Scholar 

  39. Liu, Z.-D., Zhu, H.-L.: Catena-poly[[μ-ethylenediamine-κ2 N:N’-bis[(ethylenediamine-κ2 N, N’)silver(I)] bis[silver(I)-μ-barbiturato-κ2 N:N’]] dihydrate]. Acta Cryst. E60, m1883–m1885 (2004)

    Google Scholar 

  40. Wang, Y.-T., Wang, Y.-L., Wang, J.-G., Fan, Y.-T.: μ-Ethylenediamine-κ2 N:N’-bis[(quinoline-2-carboxylato-κ2 N, O)silver(I)] tetrahydrate. Acta Cryst. E62, m1927–m1929 (2006)

    Google Scholar 

  41. Sun, D., Yan, Z.-H.: A novel one-dimensional silver cylinder stabilized by mixed 2-mercaptobenzoic acid and ethylene-diamine ligands. Acta Cryst. C68, m229–m232 (2012)

    Google Scholar 

  42. Usman, A., Fun, H.-K., Chantrapromma, S., Zhu, H.-L., Wang, X.-J.: Polymeric structure of (ethylenediamine)silver(I) 3-nitrobenzoate monohydrate. Acta Cryst. C59, m97–m99 (2003)

    CAS  Google Scholar 

  43. Zhu, H.-L., Wang, X.-J., Meng, F.-J., Liu, X.-Y.: Polymeric (ethylenediamine)silver(I) 2,4,6-trinitrophenolate. Acta Cryst. E59, m698–m699 (2003)

    Google Scholar 

  44. You, Z.-L., Yang, L., Zou, Y., Zeng, W.-J., Liu, W.-S. and Zhu, H.-L.:catena-Poly[[silver(I)-μ-ethane-1,2-diamine-κ2 N:N’] 3-fluorobenzoate monohydrate]. Acta Cryst. C60, m117-m118 (2004)

  45. Zhu, H.-L., Sun, Z.-Y., Rong, N.-N., Zhang, B., Zhang, M., Li, Y.: catena-Poly[[silver(I)-μ-1,2-diaminoethane] hexafluoroarsenate]. Acta Cryst. E59, m906–m907 (2003)

    Google Scholar 

  46. Gutsche, C.D., Dhawan, B., Leonis, M.: p-tert-Butylcalix[6]arene. Org. Synth. 68, 238–239 (1990)

    Article  CAS  Google Scholar 

  47. Gutsche, C.D., Lin, L.-G.: Calixarenes 12: the synthesis of functionalized calixarenes. Tetrahedron 42, 1633–1640 (1986)

    Article  CAS  Google Scholar 

  48. Atwood, J.L., Orr, G.W., Means, N.C.: Metal ion complexes of water-soluble calix[4]arenes. Inorg. Chem. 31, 603–606 (1992)

    Article  CAS  Google Scholar 

  49. Higashi, T.: Program for absorption correction. Rigaku Corporation, Tokyo (1995)

    Google Scholar 

  50. Sheldrick, G.M.: SHELXS-97. A program for automatic solution of crystal structure. university of goettingen, Germany (1997)

    Google Scholar 

  51. Sheldrick, G.M.: SHELXL-97. A programs for crystal structure refinement; university of goettingen, Germany (1997)

    Google Scholar 

  52. Xiong, K., Wu, M., Zhang, Q., Wei, W., Yang, M., Jiang, F., Hong, M.:1D Infinite silver(I) chains reside in the big cavities built by the novel p-sulfonatocalix[4]arene-trisilver blocks. Chem. Commun. 1840–1842 (2009)

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  1. Faculty of Chemistry, Northeast Normal University, Changchun, 130024, People’s Republic of China

    Jianxin Li, Shengdong Zhang, Ya-Guang Chen, Xiguang Du, Helong Yu & Jing Yu

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  1. Jianxin Li
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  2. Shengdong Zhang
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Correspondence to Ya-Guang Chen.

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Li, J., Zhang, S., Chen, YG. et al. Supramolecular compounds with coordination polymeric chains of Ag ions, p-sulfonatocalix[4]arene and ethylenediamine. J Incl Phenom Macrocycl Chem 81, 485–491 (2015). https://doi.org/10.1007/s10847-015-0478-y

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