Nanoporous and mesoporous organic structures: new openings for materials research

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P. J. Langley and J. Hulliger


Abstract

Organic solid state and molecular architectures providing nano- or mesoporous space for the inclusion of guest species open up new opportunities for the synthesis of materials showing designed chemical and physical properties. Porous materials are reviewed by taking into account recent progress in inorganic zeolites, metalloorganic and organic networks including carbon nanotubes and condensed cyclodextrins. Various properties requiring a parallel alignment of close-packed guests are addressed. As a particular example of physical property design, spontaneous polarity formation in channel-type inclusion compounds is discussed.


References

  1. (a) T. Bein, Chem. Mater., 1996, 8, 1636 CrossRef CAS; (b) V. Ramamurthy and D. F. Eaton, Chem. Mater., 1994, 6, 1128 CrossRef CAS; (c) G. A. Ozin, A. Kuperman and A. Stein, Angew. Chem., 1989, 101, 373 CAS; (d) J. Hulliger, P. J. Langley, A. Quintel, P. Rechsteiner and S. W. Roth, in Supramolecular Engineering of Synthetic Metallic Materials, eds. J. Veciana, C. Rovira, D. B. Amabilino, NATO ASI series C, vol. 518, p. 67, Kluwer, London, 1999 Search PubMed.
  2. (a) J. Y. Ying, C. P. Mehnert and M. S. Wong, Angew. Chem., Int. Ed. Engl., 1999, 38, 56 CrossRef CAS; (b) S. Mann, S. L. Burkett, S. A. Davis, C. E. Fowler, N. H. Mendelson, S. D. Sims, D. Walsh and N. T. Whilton, Chem. Mater., 1997, 9, 2300 CrossRef CAS.
  3. H.-B. Bürgi, J. Hulliger and P. J. Langley, Curr. Opin. Solid State Mater. Sci., 1998, 3, 425 CrossRef CAS.
  4. A. I. Kitaigorodsky, Molecular Crystals and Molecules, Academic Press, New York, London, 1973 Search PubMed.
  5. E. Weber, Top. Curr. Chem., 1987, 140, 3.
  6. (a) R. Hoss, O. König, V. Kramer-Hoss, U. Berger, P. Rogin and J. Hulliger, Angew. Chem., Int. Ed. Engl., 1996, 35, 1664 CrossRef CAS; (b) M. Farina, G. Di Silvestro and P. Sozzani, in Comprehensive Supramolecular Chemistry, eds. J. L. Atwood, J. E. D. Davies, D. D. MacNicol and F. Vögtle, Elsevier Science Ltd., Oxford, vol. 6, 1996, ch. 12, p. 371 Search PubMed.
  7. K. D. M. Harris, Chem. Soc. Rev., 1997, 26, 279 RSC.
  8. Special issue on ‘Cyclodextrins’, eds. V. T. D'Souza and K. B. Lipkowitz, Chem. Rev., 1998, 98, 1741 Search PubMed.
  9. O. König, H.-B. Bürgi, T. Armbruster, J. Hulliger and T. Weber, J. Am. Chem. Soc., 1997, 119, 10632 CrossRef.
  10. G. R. Desiraju, Crystal Engineering: The Design of Organic Solids, Elsevier, New York, 1989 Search PubMed.
  11. J. D. Wuest, in Mesomolecules: From Molecules to Materials, eds. G. D. Mendenhall, A. Greenberg and J. F. Liebman, Chapman & Hall, New York, 1995, ch. 4, p. 107 Search PubMed.
  12. G. R. Desiraju, Angew. Chem., Int. Ed. Engl., 1995, 34, 2311 CrossRef CAS.
  13. M. C. Etter, J. Phys. Chem., 1991, 95, 4601 CrossRef CAS.
  14. O. Ermer and L. Lindenberg, Helv. Chim. Acta, 1991, 74, 825 CrossRef CAS.
  15. V. A. Russell, C. C. Evans, W. Li and M. D. Ward, Science, 1997, 276, 575 CrossRef CAS.
  16. D. Braga, F. Grepioni and G. R. Desiraju, Chem. Rev., 1998, 98, 1375 CrossRef CAS.
  17. P. J. Stang and B. Olenyuk, Acc. Chem. Res., 1997, 30, 502 CrossRef CAS.
  18. O. M. Yaghi and H. Li, J. Am. Chem. Soc., 1995, 117, 10401 CrossRef CAS.
  19. P. M. Ajayan and S. Iijima, Nature, 1993, 361, 333 CrossRef CAS.
  20. S. Subramoney, Adv. Mater., 1998, 10, 1157 CrossRef CAS.
  21. A. Thess, R. Lee, P. Nikolaev, H. Dai, P. Petit, J. Robert, C. Xu, Y. H. Lee, S. G. Kim, A. G. Rinzler, D. T. Colbert, G. E. Scuseria, D. Tománek, J. E. Fischer and R. E. Smalley, Science, 1996, 273, 483 CrossRef CAS.
  22. (a) J. D. Hartgerink, T. D. Clark and M. R. Ghadiri, Chem. Eur. J., 1998, 4, 1367 CrossRef CAS; (b) M. R. Ghadiri, J. R. Granja, R. A. Milligan, D. E. McRee and N. Khazanovich, Nature, 1993, 366, 324 CrossRef CAS.
  23. P. De Santis, S. Morosetti and R. Rizzo, Macromolecules, 1974, 7, 52 CrossRef CAS.
  24. X. Sun and G. P. Lorenzi, Helv. Chim. Acta, 1994, 77, 1520 CrossRef CAS.
  25. A. Harada, J. Li and M. Kamachi, Nature, 1993, 364, 516 CrossRef CAS.
  26. (a) Y.-S. Lee, J.-Z. Yang, T. M. Sisson, D. A. Frankel, J. T. Gleeson, E. Aksay, S. L. Keller, S. M. Gruner and D. F. O'Brien, J. Am. Chem. Soc., 1995, 117, 5573 CrossRef CAS; (b) J. Malthête, A.-M. Levelut and J.-M. Lehn, J. Chem. Soc., Chem. Commun., 1992, 1434 RSC; (c) J. C. Nelson, J. G. Saven, J. S. Moore and P. G. Wolynes, Science, 1997, 277, 1793 CrossRef CAS.
  27. E. Maverick and D. J. Cram, in Comprehensive Supramolecular Chemistry, eds. J. L. Atwood, J. E. D. Davies, D. D. MacNicol and F. Vöghe, Elśsevier Science Ltd., Oxford, vol. 6, ch. 12, p. 413 Search PubMed.
  28. K. Endo, T. Koike, T. Sawaki, O. Hayashida, H. Masuda and Y. Aoyama, J. Am. Chem. Soc., 1997, 119, 4117 CrossRef.
  29. F. Toda, Acc. Chem. Res., 1995, 28, 480 CrossRef CAS.
  30. J. D. Wright, Molecular Crystals, 2nd edn., Cambridge University Press, Cambridge, 1995 Search PubMed.
  31. R. Arad-Yellin, B. S. Green, M. Knossow and G. Tsoucaris, in Inclusion Compounds, vol. 3, eds. J. L. Atwood, J. E. D. Davies and D. D. MacNicol, Academic Press, London, 1984, ch. 9, p. 263 Search PubMed.
  32. H. Sakuraba, H. Ishizaki, T. Nakai and Y. Tanaka, J. Inclusion Phenom. Mol. Recognit. Chem., 1997, 27, 341 CrossRef CAS.
  33. W. E. Moerner and L. Kador, Phys. Rev. Lett., 1989, 62, 2535 CrossRef CAS.
  34. N. Gfeller, S. Megelski and G. Calzaferri, J. Phys. Chem. B, 1999, 103, 1250 CrossRef CAS.
  35. D. Fichou, S. Delysse and J.-M. Nunzi, Adv. Mater., 1997, 9, 1178 CrossRef CAS.
  36. G. Ihlein, F. Schüth, O. Krauss, U. Vietze and F. Laeri, Adv. Mater., 1998, 10, 1117 CrossRef CAS.
  37. (a) S. Tomaru, S. Zembutsu, M. Kawachi and M. Kobayashi, J. Chem. Soc., Chem. Commun., 1984, 1207 RSC; (b) D. F. Eaton, A. G. Anderson, W. Tam and Y. Wang, J. Am. Chem. Soc., 1987, 109, 1886 CrossRef CAS.
  38. J. Hulliger, P. J. Langley and S. W. Roth, Cryst. Eng., 1998, 1, 177 Search PubMed.
  39. (a) W. E. Moerner and S. M. Silence, Chem. Rev., 1994, 94, 127 CrossRef CAS; (b) A. Quintel and J. Hulliger, Synth. Met., in the press Search PubMed.
  40. K. Sutter, J. Hulliger and P. Günter, Solid State Commun., 1990, 74, 867 CrossRef CAS.
  41. A. Kraft, A. C. Grimsdale and A. B. Holmes, Angew. Chem., Int. Ed. Engl., 1998, 37, 402 CrossRef.
  42. A. J. Banister and I. B. Gorrell, Adv. Mater., 1998, 10, 1415 CrossRef CAS.
  43. P. J. Langley, J. M. Rawson, J. N. B. Smith, M. Schuler, R. Bachmann, A. Schweiger, F. Palacio. G. Antorrena, G. Gescheidt, A. Quintel, P. Rechsteiner and J. Hulliger, J. Mater. Chem., 1999, 9, 1431 RSC.
  44. J. Hulliger, Z. Kristallogr., 1999, 214, 9 CAS.
  45. M. S. Dresselhaus, G. Dresselhaus and R. Saito, Carbon, 1995, 33, 883 CrossRef CAS.
  46. J. Caro, F. Marlow and M. Wübbenhorst, Adv. Mater., 1994, 6, 413 CrossRef CAS.
  47. A. Comotti, R. Simonatti, S. Stramare and P. Sozzami, Nanotechnol., 1999, 10, 70 Search PubMed personal communication.
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