Skip to main content
SpringerLink
Log in

Porous molecular crystals of calix[4]arenes

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

X-ray diffraction, thermogravimetric, and adsorption measurements were applied to study the thermal decomposition of the complexes of 25,26,27,28-tetrahydroxycalix[4]arene and 4-tert-butylcalix[4]arene with the solvents resulting in the formation of porous phases. Diffusion of the "guest" (solvent, gas) through the molecular crystal of calixarene-host proceeds via the consecutive formation of a series of thermodynamically unstable porous phases of the "host." Owing to the structural reorganization of calixarene, the transport of the "guest" occurs through the "host" matrix followed by complexation and formation of the thermodynamically stable structure.

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

Similar content being viewed by others

References

  1. S. Horike, S. Shimomura, S. Kitagawa, Nat. Chem., 2009, 1, 695.

    Article  CAS  Google Scholar 

  2. A. I. Cooper, Angew. Chem., Int. Ed., 2011, 50, 996.

    Article  CAS  Google Scholar 

  3. J. R. Holst, A. Trewin, A. I. Cooper, Nat. Chem., 2010, 2, 915.

    Article  CAS  Google Scholar 

  4. N. B. McKeown. J. Mater. Chem., 2010, 20, 10588.

    Article  CAS  Google Scholar 

  5. J. Tian, P. K. Thallapally, B. P. McGrail, CrystEngComm, 2012, 14, 1909.

    Article  CAS  Google Scholar 

  6. M. Mastalerz, M. W. Schneider, I. M. Oppel, O. A. Presly, Angew. Chem., Int. Ed., 2011, 50, 1046.

    Article  CAS  Google Scholar 

  7. M. W. Schneider, I. M. Oppel, H. Ott, L. G. Lechner, H.-J. S. Hauswald, R. Stoll, M. Mastalerz, Chem.-Eur. J., 2012, 18, 836.

    Article  CAS  Google Scholar 

  8. K. E. Jelfs, W. Xiaofeng, M. Schmidtmann, J. T. A. Jones, J. E. Warren, D. J. Adams, A. I. Cooper, Angew. Chem., Int. Ed., 2011, 50, 10653.

    Article  CAS  Google Scholar 

  9. T. Hasell, S. Y. Chong, K. E. Jelfs, D. J. Adams, A. I. Cooper, J. Am. Chem. Soc., 2012, 134, 588.

    Article  CAS  Google Scholar 

  10. T. Tozawa, J. T. A. Jones, S. I. Swamy, S. Jiang, D. J. Adams, S. Shakespeare, R. Clowes, D. Bradshaw, T. Hasell, S. Y. Chong, C. Tang, S. Thompson, J. Parker, A. Trewin, J. Bacsa, A. M. Z. Slawin, A. Steiner, A. I. Cooper, Nat. Mater., 2009, 8, 973.

    Article  CAS  Google Scholar 

  11. J. T. A. Jones, T. Hasell, X. Wu, J. Bacsa, K. E. Jelfs, M. Schmidtmann, S. Y. Chong, D. J. Adams, A. Trewin, F. Schiffman, F. Cora, B. Slater, A. Steiner, G. M. Day, A. I. Cooper, Nature, 2011, 474, 367.

    Article  CAS  Google Scholar 

  12. M. Mastalerz, I. M. Oppel, Angew. Chem., Int. Ed., 2012, 51, 5252.

    Article  CAS  Google Scholar 

  13. C. G. Bezzu, M. Helliwell, J. E. Warren, D. R. Allan, N. B. McKeown, Science, 2010, 327, 1627.

    Article  CAS  Google Scholar 

  14. J. T. A. Jones, D. Holden, T. Mitra, T. Hasell, D. J. Adams, K. E. Jelfs, A. Trewin, D. J. Willock, G. M. Day, J. Bacsa, A. Steiner, A. I. Cooper, Angew. Chem., Int. Ed., 2011, 50, 749.

    Article  CAS  Google Scholar 

  15. T. Mitra, K. E. Jelfs, M. Schmidtmann, A. Ahmed, S. Y. Chong, D. J. Adams, A. I. Cooper, Nat. Chem., 2013, 5, 276.

    Article  CAS  Google Scholar 

  16. S. J. Dalgarno, P. K. Thallapally, L. J. Barbour, J. L. Atwood, Chem. Soc. Rev., 2007, 36, 236.

    Article  CAS  Google Scholar 

  17. J. L. Atwood, L. J. Barbour, A. Jerga, B. L. Schottel, Science, 2002, 298, 1000.

    Article  CAS  Google Scholar 

  18. J. A. Ripmeester, G. D. Enright, C. I. Ratcliffe, K. A. Udachin, I. L. Moudrakovski, Chem. Commun., 2006, 4986.

    Google Scholar 

  19. J. W. Steed, J. L. Atwood, Supramolecular Chemistry, John Wiley & Sons, Chichester, 2nd ed., 2009.

    Book  Google Scholar 

  20. W. Sliwa, C. Kozlowski, Calixarenes and Resorcinarenes: Synthesis, Properties and Applications, Wiley-VCH Verlag GmbH & Co., Weinheim, 2009.

    Google Scholar 

  21. C. D. Gutsche, Calixarenes. An Introduction, The Royal Society of Chemistry, Cambridge, 2nd ed., 2008.

    Google Scholar 

  22. J. Vicens, J. Harrowfield, L. Baklouti, Calixarenes in the Nanoworld, Springer, Dordrecht, 2007.

    Book  Google Scholar 

  23. Z. Asfari, V. Bцhmer, J. Harrowfield, J. Vicens, Calixarenes 2001, Kluwer Academic Publishers, Dordrecht, 2001.

    Google Scholar 

  24. E. B. Brouwer, K. A. Udachin, G. D. Enright, J. A. Ripmeester, K. J. Ooms, P. A. Halchuk, Chem. Commun., 2001, 565.

    Google Scholar 

  25. P. K. Thallapally, P. B. McGrail, S. J. Dalgarno, H. T. Schaef, J. Tian, J. L. Atwood, Nat. Mater., 2008, 7, 146.

    Article  CAS  Google Scholar 

  26. E. B. Brouwer, G. D. Enright, K. A. Udachin, S. Lang, K. J. Ooms, P. A. Halchuk, J. A. Ripmeester, Chem. Commun., 2003, 1416.

    Google Scholar 

  27. J. L. Atwood, L. J. Barbour, A. Jerga, Chem. Commun., 2002, 2952.

    Google Scholar 

  28. Cambridge Structural Database System, Version 1.18, Cambridge, 2015.

  29. J. L. Atwood, L. J. Barbour, G. O. Lloyd, P. K. Thallapally, Chem. Commun., 2004, 922.

    Google Scholar 

  30. P. K. Thallapally, P. B. McGrail, S. J. Dalgarno, J. L. Atwood, Cryst. Growth Des., 2008, 8, 2090.

    Article  CAS  Google Scholar 

  31. J. L. Atwood, L. J. Barbour, A. Jerga, Angew. Chem., Int. Ed., 2004, 43, 2948.

    Article  CAS  Google Scholar 

  32. P. K. Thallapally, L. Dobrzaсska, T. R. Gingrich, T. B. Wirsig, L. J. Barbour, J. L. Atwood, Angew. Chem., Int. Ed., 2006, 45, 6506.

    Article  CAS  Google Scholar 

  33. P. K. Thallapally, T. B. Wirsig, L. J. Barbour, J. L. Atwood, Chem. Commun., 2005, 4420.

    Google Scholar 

  34. J. L. Atwood, L. J. Barbour, P. K. Thallapally, T. B. Wirsig, Chem. Commun., 2005, 51.

    Google Scholar 

  35. P. K. Thallapally, G. O. Lloyd, T. B. Wirsig, M. W. Bredenkamp, J. L. Atwood, L. J. Barbour, Chem. Commun., 2005, 5272.

    Google Scholar 

  36. P. K. Thallapally, K. A. Kirby, J. L. Atwood, New J. Chem., 2007, 31, 628.

    Article  CAS  Google Scholar 

  37. P. K. Thallapally, B. P. McGrail, J. L. Atwood, Chem. Commun., 2007, 1521.

    Google Scholar 

  38. O. V. Surov, V. P. Barannikov, M. I. Voronova, CrystEng-Comm, 2014, 16, 8700.

    Article  CAS  Google Scholar 

  39. M. Thommes, Chem. Ing. Tech., 2010, 82, 1059.

    Article  CAS  Google Scholar 

  40. D. H. Brouwer, I. L. Moudrakovski, K. A. Udachin, G. D. Enright, J. A. Ripmeester, Cryst. Growth Des., 2008, 8, 1878.

    Article  CAS  Google Scholar 

  41. K. A. Udachin, I. L. Moudrakovski, G. D. Enright, C. I. Ratcliffe, J. A. Ripmeester, Phys. Chem. Chem. Phys., 2008, 10, 4636.

    Article  CAS  Google Scholar 

  42. Z. Asfari, A. Bilyk, C. Bond, J. M. Harrowfield, G. A. Koutsantonis, N. Lengkeek, M. Mocerino, B. W. Skelton, A. N. Sobolev, S. Strano, J. Vicens, A. H. White, Org. Biomol. Chem., 2004, 2, 387.

    Article  CAS  Google Scholar 

  43. W. Xu, R. J. Puddephatt, L. Manojlovic-Muir, K. W. Muir, C. S. Frampton, J. Inclusion Phenom. Mol. Recognit. Chem., 1994, 19, 277.

    Article  CAS  Google Scholar 

  44. X. Gu, L. Zhang, X. Gong, W. M. Lau, Z. F. Liu, J. Phys. Chem. B, 2008, 112, 14851.

    Article  CAS  Google Scholar 

  45. O. V. Surov, E. V. Plevina, M. I. Voronova, V. V. Vinogradov, N. Zh. Mamardashvili, Russ. J. Phys. Chem. (Engl. Transl.), 2013, 87, 783 [Zh. Fiz. Khim., 2013, 87, 804].

    Article  CAS  Google Scholar 

  46. A. Adamson, Physical Chemistry of Surfaces, Wiley-Interscience, New York, 1976, 698 pp.

    Google Scholar 

  47. J. L. Atwood, L. J. Barbour, A. Jerga, Science, 2002, 296, 2367.

    Article  CAS  Google Scholar 

  48. R. Ungaro, A. Pochini, G. D. Andreetti, V. Sangermano, J. Chem. Soc., Perkin Trans. 2, 1984, 12, 1979.

    Article  Google Scholar 

  49. O. V. Surov, M. I. Voronova, E. V. Plevina, V. P. Barannikov, P. R. Smirnov, N. Zh. Mamardashvili, Russ. J. Phys. Chem. (Engl. Transl.), 2014, 88, 1329 [Zh. Fiz. Khim., 2014, 88, 1146].

    Article  CAS  Google Scholar 

  50. O. V. Surov, M. I. Voronova, V. P. Barannikov, G. P. Shaposhnikov, J. Phys. Chem. C, 2014, 118, 338.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Chemistry of Macroheterocyclic Compounds, Ivanovo State University of Chemistry and Technology, 7 Sheremetevskii prosp., 153000, Ivanovo, Russian Federation

    O. I. Koifman

  2. G. A. Krestov Institute of Solution Chemistry, Russian Academy of Sciences, 1 ul. Akademicheskaya, 153045, Ivanovo, Russian Federation

    O. I. Koifman, N. Zh. Mamardashvili & O. V. Surov

Authors
  1. O. I. Koifman
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. Zh. Mamardashvili
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. O. V. Surov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to O. I. Koifman.

Additional information

Dedicated to Academician of the Russian Academy of Sciences R. Z. Sagdeev on the occasion of his 75th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0241—0253, February, 2017.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Koifman, O.I., Mamardashvili, N.Z. & Surov, O.V. Porous molecular crystals of calix[4]arenes. Russ Chem Bull 66, 241–253 (2017). https://doi.org/10.1007/s11172-017-1724-9

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-017-1724-9

Key words

Search

Navigation