Citation: Bo Li, Xu-Zhuo Sun. Dimensional effects of organic anion templates in modulating the assembly of water clusters in cucurbit[6]uril supramolecular systems[J]. Chinese Chemical Letters, ;2016, 27(03): 417-422. doi: 10.1016/j.cclet.2015.12.003 shu

Dimensional effects of organic anion templates in modulating the assembly of water clusters in cucurbit[6]uril supramolecular systems

Bo Li ,
Xu-Zhuo Sun ^,

1.
College of Chemistry and Chemical Engineering, Henan University of Technology, Zhengzhou 450001, China

Corresponding author: Xu-Zhuo Sun,
Received Date: 19 October 2015
Available Online: 13 November 2015
Fund Project:

Two new supramolecular architectures {(HC₂O₄)₂^2-[C₆H₁₈N₂²⁺⊂C₃₆H₃₆N₂₄O₁₂]}·12H₂O (1) and {(C₆H₅SO₃)₂^2-[C₆H₁₈N₂²⁺⊂C₃₆H₃₆N₂₄O₁₂]}·12H₂O (2) were synthesized and characterized by singlecrystal X-ray diffraction, thermogravimetric analysis and X-ray powder diffraction. Compound 1 contains infinite two dimensional (2D) L18(8)14(8)8(4) type anion-water aggregates[(HC₂O₄)₄ (H₂O)₂₂]^4- and results in the construction of sandwich-like three dimensional (3D) networks. In compound 2, honeycomβ-like three dimensional (3D) networks are fabricated by one dimensional (1D) "W"-like T5(0)A2 type anion-water clusters[(C₆H₅SO₃)(H₂O)₆]^-. These results indicate that anionic groups play a crucial role in modulating the structures of water clusters with their spatial structure and binding sites. In these two structures, the majority of interactions are O...H and H...Hinteractions on the Hirshfeld surface, which means that hydrogen bonding and hydrophobic interactions are the dominate drive forces in forming these supramolecular systems.
- Cucurbit[6]uril,
- Supramolecular,
- Water clusters,
- Anion templates,
- Pseudorotaxane
1. [1]
  [1] D. Eisenberg, W. Kauzmannc, The Structure and Properties of Water, Oxford University Press, Oxford, UK, 1969.
2. [2]
  [2] P. Ball, H₂O:a Biography of Water, Weidenfeld & Nicolson, London, 1999.
3. [3]
  [3] R. Ludwig, Water:from clusters to the bulk, Angew. Chem. (Ⅰ)nt. Ed. 40(2001) 1808-1827.
4. [4]
  [4] N. Pugliano, R.J. Saykally, Measurement of quantum tunneling between chiral isomers of the cyclic water trimer, Science 257(1992) 1937-1940.
5. [5]
  [5] U. Buck, F. Huisken, (Ⅰ)nfrared spectroscopy of size-selected water and methanol clusters, Chem. Rev. 100(2000) 3863-3890.
6. [6]
  [6] T. Head-Gordon, G. Hura, Water structure from scattering experiments and simulation, Chem. Rev. 102(2002) 2651-2670.
7. [7]
  [7] X.B. Wang, X. Yang, J.B. Nicholas, L.S. Wang, Bulk-like features in the photoemission spectra of hydrated doubly charged anion clusters, Science 294(2001) 1322-1325.
8. [8]
  [8] W.H. Robertson, E.G. Diken, E.A. Price, J.W. Shin, M.A. Johnson, Spectroscopic determination of the OH-solvation shell in the OH^-·(H₂O)_n clusters, Science 299(2003) 1367-1372.
9. [9]
  [9] R. Custelcean, M.G. Gorbunova, A metal-organic framework functionalized with free carboxylic acid sites and its selective binding of a Cl(H₂O)₄^- cluster, J. Am. Chem. Soc. 127(2005) 16362-16363.
10. [10]
  [10] C.K. Lam, F. Xue, J.P. Zhang, X.M. Chen, T.C.W. Mak, Hydrogen-Bonded anionic rosette networks assembled with guanidinium and C₃-symmetric oxoanion building blocks, J. Am. Chem. Soc. 127(2005) 11536-11537.
11. [11]
  [11] A. Bakhoda, H.R. Khavasi, N. Safari, Discrete cubane-like bromide-water cluster, Cryst. Growth Des. 11(2011) 933-935.
12. [12]
  [12] M.A. Hossain, P. Morehouse, D. Powell, K. Bowman-James, Tritopic (Cascade) and ditopic complexes of halides with an azacryptand, (Ⅰ)norg. Chem. 44(2005) 2143-2149.
13. [13]
  [13] Q.H. Pan, R.J. Tian, S.J. Liu, et al.,[Co(NH₃)₆]₂[Cd₈(C₂O₄)₁₁(H₂O)₄]·8H₂O:a 5-connected sqp topological metal-organic framework co-templated by Co(NH₃)₆³⁺ cation and (H₂O)₄ cluster, Chin. Chem. Lett. 24(2013) 861-865.
14. [14]
  [14] G.G. Luo, S.H. Wu, Z.H. Pan, Z.J. Xiao, J.C. Dai, Formation of different polymeric water clusters via organic anionic templates:more carboxylate groups used, more water molecules gathered, (Ⅰ)norg. Chem. Comm. 39(2014) 34-38.
15. [15]
  [15] G.G. Luo, H.B. Xiong, J.C. Dai, Syntheses, structural characterization, and properties of {[Cu(bpp)₂(H₂O)₂] (tp)·7H₂O} and {[Cu(bpp)₂(H₂O)](ip)·7H₂O} complexes, New examples of the organic anionic template effect on induced assembly of water clusters (bpp=1, 3-Bis(4-pyridyl)propane, tp=Terephthalate, ip=(Ⅰ)sophthalate), Cryst. Growth Des. 11(2011) 507-515.
16. [16]
  [16] S. Ganguly, R. Mondal, Coordination driven self-assembly in Co(Ⅱ) coordination polymers displaying unprecedented topology, water cluster, chirality, and spincanted magnetic behavior, Cryst. Growth Des. 15(2015) 2211-2222.
17. [17]
  [17] (a) N. Nijem, P. Canepa, U. Kaipa, et al., Water cluster confinement and methane adsorption in the hydrophobic cavities of a fluorinated metal-organic framework, J. Am. Chem. Soc. 135(2013) 12615-12626;
18. [18]
  (b) H. (Ⅰ)sobe, S. Sato, E. Nakamura, Synthesis of disubstituted cucurbit[6] uril and its rotaxane derivative, Org. Lett. 4(2002) 1287-1289.
19. [19]
  [18] (a) H. Yin, G. Hummer, J.C. Rasaiah, Metastable water clusters in the nonpolar cavities of the thermostable protein tetrabrachion, J. Am. Chem. Soc. 129(2007) 7369-7377;
20. [20]
  (b) W.A. Freeman, W.L. Mock, N. Shih, Cucurbituril, J. Am. Chem. Soc. 103(1981) 7367-7368.
21. [21]
  [19] (a) S. Parthasarathy, A. Altuve, S. Terzyan, et al., Accommodating a nonconservative internal mutation by water-mediated hydrogen bonding between β-sheet strands:a comparison of human and rat type B (Mitochondrial) cytochrome b5, Biochemistry 50(2011) 5544-5554;
22. [22]
  (b) W.L. Mock, N. Shih, Organic ligand-receptor interactions between cucurbituril and alkylammonium ions, J. Am. Chem. Soc. 110(1988) 4706-4710.
23. [23]
  [20] J. Lagona, P. Mukhopadhyay, S. Chakrabarti, L. (Ⅰ)saacs, The Cucurbit[n]uril family, Angew. Chem. (Ⅰ)nt. Ed. 44(2005) 4844-4870.
24. [24]
  [21] E. Lee, J. Heo, K. Kim, A three-dimensional polyrotaxane network, Angew. Chem. (Ⅰ)nt. Ed. 39(2000) 2699-2701.
25. [25]
  [22] E. Lee, J. Kim, J. Heo, D. Whang, K. Kim, A two-dimensional polyrotaxane with large cavities and channels:a novel approach to metal-organic open-frameworks by using supramolecular building blocks, Angew. Chem. (Ⅰ)nt. Ed. 40(2001) 399-402.
26. [26]
  [23] S.G. Roh, K.M. Park, S. Sakamoto, K. Tamaguchi, K. Kim, Synthesis of a fivemembered molecular necklace:a 2+2 approach, Angew. Chem. (Ⅰ)nt. Ed. 38(1999) 637-641.
27. [27]
  [24] K.M. Park, S.Y. Kim, J. Heo, et al., Designed self-assembly of molecular necklaces, J. Am. Chem. Soc. 124(2002) 2140-2147.
28. [28]
  [25] M.V. Rekharsky, H. Yamamura, M. Kawai, et al., Sequential formation of a ternary complex among dihexylammonium, cucurbit[6] uril, and cyclodextrin with positive cooperativity, Org. Lett. 8(2006) 815-818.
29. [29]
  [26] Y. Liu, X.Y. Li, H.Y. Zhang, C.J. Li, F. Ding, Cyclodextrin-driven movement of cucurbit[7] uril, J. Org. Chem. 72(2007) 3640-3645.
30. [30]
  [27] X.Z. Sun, B. Li, J. Cao, et al., Pseudopolyrotaxanes of cucurbit[6] uril:a threedimensional network self-assembled by ClO₄^-(H₂O)₂^- water clusters, Chin. J. Chem. 30(2012) 941-946.
31. [31]
  [28] S. Angelos, Y.W. Yang, K. Patel, J.F. Stoddart, J.(Ⅰ). Zink, pH-Responsive supramolecular nanovalves based on cucurbit[6] uril, Angew. Chem. (Ⅰ)nt. Ed. 47(2008) 2222-2226.
32. [32]
  [29] Y.W. Yang, Y.L. Sun, N. Song, Switchable host-guest systems on surfaces, Acc. Chem. Res. 47(2014) 1950-1960.
33. [33]
  [30] X.Z. Sun, B. Li, Q.B. Zhou, et al., Pseudopolyrotaxanes of cucurbit[6] uril:a novel three-dimensional network self-assembled by (H₂O)₃ clusters and Br^-(H₂O)₃ anion clusters, Cryst. Growth Des. 8(2008) 2970-2974.
34. [34]
  [31] X.Z. Sun, B. Li, C.L. Xia, X.H. Zhou, H.B. Zhang, "Liquid-like" type (COO^-)₂(H₂O)₁₀ anion water clusters in three dimensional supramolecular structure of cucurbit[6] uril, CrystEngComm 14(2012) 8525-8529.
35. [35]
  [32] L.J. Barbour, G.W. Orr, J.L. Atwood, An intermolecular (H₂O)₁₀ cluster in a solidstate supramolecular complex, Nature 393(1998) 671-673.
36. [36]
  [33] R. Custalcean, C. Afloroaiei, M. Vlassa, M. Polverejan, Formation of extended tapes of cyclic water hexamers in an organic molecular crystal host, Angew. Chem. (Ⅰ)nt. Ed. 39(2000) 3094-3096.
37. [37]
  [34] S.K. Seth, (Ⅰ). Saha, C. Estarellas, et al., Supramolecular self-assembly of M-(Ⅰ)DA complexes involving lone-pair·π interactions:crystal structures, hirshfeld surface analysis, and DFT calculations[H₂(Ⅰ)DA=iminodiacetic acid.M=Cu(Ⅱ), Ni(Ⅱ)], Cryst. Growth Des. 11(2011) 3250-3265.
38. [38]
  [35] M.A. Spackman, P.G. Byrom, A novel definition of a molecule in a crystal, Chem. Phys. Lett. 267(1997) 215-220.
39. [39]
  [36] S.K. Wolff, D.J. Grimwood, J.J. McKinnon, D. Jayatilaka, M.A. Spackman, Crystal-Explorer 3.1, University of Western Australia, Perth, Australia, 2007.
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