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Inclusion of ferrocene within the deepened cavities formed from the hydrogen bonding self-assembly of calix[4]resorcinarenes with bis-pyridines

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Abstract

Co-crystallization of C-ethyl-calix[4]resorcinarene (1) and 4,4′-bipyridine (4,4′-bipy) from ethanol in the presence of ferrocene (FcH) yielded a multi-component complex FcH@1·2(4,4′-bipy) (3) that consists of a one-dimensional wave-like polymer, 1·2(4,4′-bipy), in which the cavity of 1 is deepened supramolecularly to enclose ferrocene as a guest. Heating mixture of C-methyl-calix[4]resorcinarene (2), trans-1,4-bis-(pyridyl)ethylene (bpe) and FcH in ethanol led to isolation of a similar host–guest complex FcH@2·2(bpe)·0.5C6H14 (4) in which the FcH guests have been assembled within a wave-like framework (2)·2(bpe).

Graphical Abstract

Ferrocene acts as the guest molecule for the self-assembly of the 1:2:1 C-ethyl-calix[4]resorcinarene/4,4′-bipyridine/ferrocene and the 1:2:1 C-methyl-calix[4]resorcinarene/trans-1,4-bis(pyridyl)ethylene/ferrocene supramolecular co-crystals.

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References

  1. MacGillivray, L.R., Atwood, J.L.: A chiral spherical molecular assembly held together by 60 hydrogen bonds. Nature 389, 469–472 (1997)

    Article  CAS  Google Scholar 

  2. MacGillivray, L.R., Atwood, J.L.: Structural classification and general principles for the design of spherical molecular hosts. Angew. Chem. Int. Ed. Engl. 38, 1018–1033 (1999)

    Article  CAS  Google Scholar 

  3. Atwood, J.L., Barbour, L.J., Jerga, A.: Hydrogen-bonded molecular capsules are stable in polar media. Chem. Commun. 22, 2376–2377 (2001)

    Article  Google Scholar 

  4. Cave, G.W.V., Ferrarelli, M.C., Atwood, J.L.: Nano-dimensions for the pyrogallol[4]arenecavity. Chem. Commun 22, 2787–2789 (2005)

    Google Scholar 

  5. Ma, B.Q., Zhang, Y.G., Coppens, P.: Structural variation and supramolecular isomerism in the C-methylcalix[4]resorcinarene/bipyridine system. Cryst. Growth Des. 2, 7–13 (2002)

    Article  CAS  Google Scholar 

  6. Brown, P.O., Enright, G.D., Ripmeester, J.A.: Cationic guests in extended anionic C-methylcalix[4]resorcinarene-inorganic frameworks: exercising conformational control over C-methylcalix[4]resorcinarene. J. Supramol. Chem. 2, 497–500 (2002)

    Article  CAS  Google Scholar 

  7. MacGillivray, L.R., Holman, K.T., Atwood, J.L.: Hydrogen bonds assist the organization of up to 11 guests within self-assembling cavities of nanometer dimensions. J. Supramol. Chem. 1, 125–130 (2001)

    Article  CAS  Google Scholar 

  8. MacGillivray, L.R., Atwood, J.L.: Rational design of multicomponent calix[4]arenes and control of their alignment in the solid state. J. Am. Chem. Soc. 119, 6931–6932 (1997)

    Article  CAS  Google Scholar 

  9. Nakamura, A., Sato, T., Kuroda, R.: Novel layered structures of the crystals based on C-methylcalix[4]resorcinarene formed at high temperature. CrystEngComm 5, 318–325 (2003)

    Article  CAS  Google Scholar 

  10. Ma, B.Q., Coppens, P.: Transformation of a C-methylcalix[4]resorcinarene-based host–guest complex from a wave-like to a novel triangular brick-wall architecture. Chem. Commun. 4, 504–505 (2003)

    Article  Google Scholar 

  11. Ma, B.Q., Coppens, P.: Three-fold interpenetrating three-dimensional networks based on C-methylcalix[4]resorcinarene incorporating benzophenone guest molecules. Chem. Commun. 3, 412–413 (2003)

    Article  Google Scholar 

  12. MacGillivray, L.R., Reid, J.L., Ripmeester, J.A.: Conformational isomerism leads to supramolecular isomerism and nanoscale inclusion in 2D extended framework solids based on C-methylcalix[4]resorcinarene. Chem. Commun 11, 1034–1035 (2001)

    Article  Google Scholar 

  13. Zhang, Y.G., Kim, C.D., Coppens, P.: Does C-methylcalix[4]resorcinarene always adopt the crown shape conformation? a resorcinarene/bipyridine/decamethylruthenocene supramolecular clathrate with a novel framework structure. Chem. Commun. 23, 2299–2300 (2000)

    Article  Google Scholar 

  14. MacGillivray, L.R., Diamente, P.R., Reid, J.L., Ripmeester, J.A.: Encapsulation of two aromatics by a carcerand-like capsule of nanometre-scale dimensions. Chem. Commun. 5, 359–360 (2000)

    Article  Google Scholar 

  15. Ma, B.Q., Coppens, P.: Variable conformation of benzophenone in a series of resorcinarene-based supramolecular frameworks. Cryst. Growth Des. 4, 1377–1385 (2001)

    Article  Google Scholar 

  16. MacGillivray, L.R., Papaefstathiou, G.S., Reid, J.L., Ripmeester, J.A.: A rod-shaped guest leads to architectural isomerism in a multicomponent crystalline framework based on a resorcin[4]arene. Cryst. Growth Des. 1, 373–375 (2001)

    Article  CAS  Google Scholar 

  17. Ma, B.Q., Zhang, Y.G., Coppens, P.: Multiple structures in supramolecular solids: Benzophenone embedded in three different C-methylcalix[4]resorcinarene/bipyridine frameworks. Cryst. Growth Des. 1, 271–275 (2001)

    Article  CAS  Google Scholar 

  18. Ma, B.Q., Zhang, Y.G., Coppens, P.: The chair conformation of C-methylcalix[4]-resorcinarene in a novel, stepped, supramolecular framework. CrystEngComm 3, 78–80 (2001)

    Article  Google Scholar 

  19. MacGillivray, L.R., Reid, J.L., Ripmeester, J.A.: Solvent provides a trap for the guest-induced formation of 1D host frameworks based upon supramolecular, deep-cavity resorcin[4]arenes. CrystEngComm 1, 1–4 (1999)

    Article  Google Scholar 

  20. Colquhoun, H.M., Stoddart, J.F., Williams, D.J.: Second-sphere coordination—a novel rǒle for molecular receptors. Angew. Chem. Int. Ed. Engl. 25, 487–507 (1986)

    Article  Google Scholar 

  21. Klingert, B., Rihs, G.: Molecular encapsulation of transition-metal complexes in cyclodextrins. 1. Synthesis and x-ray crystal structure of [(η5-C5H5)Fe(η6-C6H6)]PF6.2α-CD·8H2O. Organometallics 9, 1135–1141 (1990)

    Article  CAS  Google Scholar 

  22. Klingert, B., Rihs, G.: Molecular encapsulation of transition metal complexes in cyclodextrins. Part 2. Synthesis and crystal structures of 2:1 adducts between α-cyclodextrin and metallocenium hexafluorophosphates [η5-C5H5)2 M]PF6 (M=Fe Co, Rh). J. Incl. Phenom. 10, 255–265 (1991)

    Article  Google Scholar 

  23. Klingert, B., Rihs, G.: Molecular encapsulation of transition metal complexes in cyclodextrins. Part 3. Structural consequences of varying the guest geometry in channel-type inclusion compounds. J. Chem. Soc. Dalton Trans. 6, 2749–2760 (1991)

    Article  Google Scholar 

  24. Odagaki, Y., Hirotsu, K., Higuchi, T., Harada, A., Takahashi, S.: X-Ray structure of the α-cyclodextrin–ferrocene (2 : 1) inclusion compound. J. Chem. Soc., Perkin Trans. 1, 1230–1231 (1990)

    Article  Google Scholar 

  25. MacGillivray, L.R., Spinney, H.A., Reid, J.L., Ripmeester, J.A.: Entrapment of ferrocenes within supramolecular, deep-cavity resorcin[4]arenes. Chem. Commun. 6, 517–518 (2000)

    Article  Google Scholar 

  26. Friščič, T., MacGillivray, L.R.: Double inclusion of ferrocene within a doubly interpenetrated three-dimensional framework based on a resorcin[4]arene. J. Organomet. Chem. 666, 43–48 (2003)

    Article  Google Scholar 

  27. Hardie, M.J.: Solid state confinement of ferrocene by calixarenes. Supramol. Chem. 14, 7–10 (2002)

    Article  CAS  Google Scholar 

  28. Cram, D.J., Karbach, S., Kim, H.E., Knobler, C.B., Maverick, E.F., Ericson, J.L., Helgeson, R.C.: Host-guest complexation. 46. Cavitands as open molecular vessels form solvates. J. Am. Chem. Soc. 110, 2229–2237 (1988)

    Article  CAS  Google Scholar 

  29. SMART and SAINT + for Windows NT Version 6.02a. Bruker Analytical X-ray Instruments Inc., Madison, Wisconsin, USA (1998)

  30. Sheldrick, G.M.: SADABS. University of Göttingen, Germany (1996)

    Google Scholar 

  31. Sheldrick, G.M.: SHELXTL Software Reference Manual. Version 5.1. Bruker AXS Inc., Madison, USA (1997)

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

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This project was supported by Natural Science Foundation of China (90922008).

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Correspondence to Qian-Feng Zhang.

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Wang, YJ., Liu, JL., Yang, HM. et al. Inclusion of ferrocene within the deepened cavities formed from the hydrogen bonding self-assembly of calix[4]resorcinarenes with bis-pyridines. J Incl Phenom Macrocycl Chem 85, 105–110 (2016). https://doi.org/10.1007/s10847-016-0609-0

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