Skip to main content
SpringerLink
Log in

Mechanical mixing of molecular crystals

A green route to co-crystals and coordination networks

  • Published:
Journal of Thermal Analysis and Calorimetry Aims and scope Submit manuscript

Abstract

Supramolecular reactions between crystalline materials can be exploited to prepare both hydrogen bonded co-crystals and coordination networks. Mechanical mixing of molecular crystals as well as kneading provide an alternative, solvent-free, route to novel materials hence these methods represent a green route to supramolecular solid-state chemistry.

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. D. Braga, F. Grepioni and G. R. Desiraju, Chem. Rev., 98 (1998) 1375.

    Article  CAS  Google Scholar 

  2. A. J. Blake, N. R. Champness, P. Hubberstey, W.-S. Li, M. A. Withersby and M. Schroder, Coord. Chem. Rev., 183 (1999) 117.

    Article  CAS  Google Scholar 

  3. D. Braga, G. R. Desiraju, J. S. Miller, A. G. Orpen and S. L. Price, Cryst. Eng. Comm., 4 (2002) 500.

    CAS  Google Scholar 

  4. D. Braga, L. Brammer and N. R. Champness, Cryst. Eng. Comm., 7 (2005) 1.

    CAS  Google Scholar 

  5. J. Chem. Soc., Dalton Trans. (2000) 3705–3998, Proceedings of the Dalton Discussion on Inorganic Crystal Engineering.

  6. M. D. Hollingsworth, Science, 295 (2002) 2410.

    CAS  Google Scholar 

  7. L. Brammer, Chem. Soc. Rev., 33 (2004) 476.

    Article  CAS  Google Scholar 

  8. M. W. Hosseini, Cryst. Eng. Comm., 6 (2004) 318.

    CAS  Google Scholar 

  9. D. Braga and F. Grepioni, Angew. Chem. Int. Ed., 43 (2004) 4002.

    Article  CAS  Google Scholar 

  10. D. Braga, D. D’Addario, S. L. Giaffreda, L. Maini, M. Polito and F. Grepioni, Top. Curr. Chem., 254 (2005) 71.

    CAS  Google Scholar 

  11. A. V. Trask and W. Jones, Top. Curr. Chem., 254 (2005) 41.

    CAS  Google Scholar 

  12. G. Kaupp, Top. Curr. Chem., 254 (2005) 95.

    CAS  Google Scholar 

  13. G. W. V. Cave, C. L. Raston and J. L. Scott, Chem. Commun., (2001) 2159.

  14. G. Rothenberg, A. P. Downie, C. L. Raston and J. L. Scott, J. Am. Chem. Soc., 123 (2001) 8701.

    Article  CAS  Google Scholar 

  15. D. Braga and F. Grepioni, Chem. Commun., (2005) 3635.

  16. J. F. Fernandez-Bertran, Pure Appl. Chem., 71 (1999) 581.

    CAS  Google Scholar 

  17. V. V. Boldyrev and K. Tkacova, J. Mater. Synth. Process., 8 (2000) 121.

    Article  CAS  Google Scholar 

  18. C. Suryanarayana, E. Ivanov and V. V. Boldyrev, Mater. Sci. Eng., A 304 (2001) 151.

    Google Scholar 

  19. G. M. J. Schmidt, Pure Appl. Chem., 27 (1971) 647.

    CAS  Google Scholar 

  20. G. S. Papaefstathiou, A. J. Kipp and L. R. MacGillivray, Chem. Commun., (2001) 2462.

  21. T. Friscic and L. R. MacGillivray, Chem. Commun., (2005) 5748.

  22. X. C. Gao, T. Friscic and L. R. MacGillivray, Angew. Chem. Int. Ed., 43 (2004) 232.

    Article  CAS  Google Scholar 

  23. L. R. MacGillivray, G. S. Papaefstathiou, T. Friscic, D. B. Varshney and T. D. Hamilton, Top. Curr. Chem., 248 (2004) 201.

    Google Scholar 

  24. T. Friscic and L. R. Macgillivray, Chem. Commun., (2003) 1306.

  25. J. Xiao, M. Yang, J. W. Lauher and F. W. Fowler, Angew. Chem. Int. Ed., 39 (2000) 2132.

    Article  CAS  Google Scholar 

  26. J. R. Scheffer and W. J. Xia, Top. Curr. Chem., 254 (2005) 233.

    CAS  Google Scholar 

  27. A. Matsumoto, Top. Curr. Chem., 254 (2005) 263.

    CAS  Google Scholar 

  28. S. Yamamoto, K. Matsuda and M. Irie, Angew. Chem. Int. Ed., 42 (2003) 1636.

    Article  CAS  Google Scholar 

  29. M. Morimoto, S. Kobatake and M. Irie, Chem. Eur. J., 9 (2003) 621.

    Article  CAS  Google Scholar 

  30. M. Irie, S. Kobatake and M. Horichi, Science, 291 (2001) 1769.

    Article  CAS  Google Scholar 

  31. K. Novak, V. Enkelmann, G. Wegner and K. B. Wagener, Angew. Chem., Int. Ed. Engl., 32 (1993) 1614.

    Article  Google Scholar 

  32. L. Yu, Adv. Drug Delivery Rev., 48 (2001) 27.

    Article  CAS  Google Scholar 

  33. Y. Shirota, J. Mater. Chem., 15 (2005) 75.

    Article  CAS  Google Scholar 

  34. R. P. Rastogi, P. S. Bassi and S. L. Chadha, J. Phys. Chem.-Us, 67 (1963) 2569.

    Article  CAS  Google Scholar 

  35. R. P. Rastogi and N. B. Singh, J. Phys. Chem.-Us, 72 (1968) 4446.

    Article  CAS  Google Scholar 

  36. T. P. Rastogi and N. B. Singh, J. Phys. Chem.-Us, 70 (1966) 3315.

    Article  CAS  Google Scholar 

  37. A. O. Patil, D. Y. Curtin and I. C. Paul, J. Am. Chem. Soc., 106 (1984) 348.

    Article  CAS  Google Scholar 

  38. C. C. Chiang, C. T. Lin, H. J. Wang, D. Y. Curtin and I. C. Paul, J. Am. Chem. Soc., 99 (1977) 6303.

    Article  CAS  Google Scholar 

  39. I. C. Paul and D. Y. Curtin, Acc. Chem. Res., 6 (1973) 217.

    Article  CAS  Google Scholar 

  40. M. C. Etter, S. M. Reutzel and C. G. Choo, J. Am. Chem. Soc., 115 (1993) 4411.

    Article  CAS  Google Scholar 

  41. W. H. Ojala and M. C. Etter, J. Am. Chem. Soc., 114 (1992) 10288.

    Article  CAS  Google Scholar 

  42. F. K. Urakaev, V. S. Shevchenko and V. V. Boldyrev, Dokl. Phys. Chem., 377 (2001) 59.

    Article  Google Scholar 

  43. V. V. Boldyrev, Ultrason. Sonochem., 2 (1995) S143.

    Article  CAS  Google Scholar 

  44. M. A. Mikhailenko, T. N. Drebushchak, V. A. Drebushchak, E. V. Boldyreva and V. V. Boldyrev, J. Cryst. Growth, 274 (2005) 569.

    Article  CAS  Google Scholar 

  45. V. V. Boldyrev, J. Mater. Sci., 39 (2004) 5117.

    Article  CAS  Google Scholar 

  46. M. A. Mikhailenko, T. P. Shakhtshneider and V. V. Boldyrev, J. Mater. Sci., 39 (2004) 5435.

    Article  CAS  Google Scholar 

  47. G. Kaupp, Cryst. Eng. Comm., 5 (2003) 117.

    CAS  Google Scholar 

  48. J. M. Cairney, S. G. Harris, L. W. Ma, P. R. Munroe and E. D. Doyle, J. Mater. Sci., 39 (2004) 3569.

    Article  CAS  Google Scholar 

  49. Y. A. Kim, T. Hayashi, Y. Fukai, M. Endo, T. Yanagisawa and M. S. Dresselhaus, Chem. Phys. Lett., 355 (2002) 279.

    Article  CAS  Google Scholar 

  50. K. Wieczorek-Ciurowa, K. Gamrat and K. Fela, Solid State Ionics, 164 (2003) 193.

    Article  CAS  Google Scholar 

  51. S. Watano, T. Okamoto, M. Tsuhari, I. Koizumi and Y. Osako, Chem. Pharm. Bull., 50 (2002) 341.

    Article  CAS  Google Scholar 

  52. S. Watano, J. Furukawa, K. Miyanami and Y. Osako, Adv. Powder Technol., 12 (2001) 427.

    Article  CAS  Google Scholar 

  53. N. Shan, F. Toda and W. Jones, Chem. Commun., (2002) 2372.

  54. A. V. Trask, N. Shan, W. D. S. Motherwell, W. Jones, S. Feng, R. B. H. Tan and K. J. Carpenter, Chem. Commun., (2005) 880.

  55. A. V. Trask, W. D. S. Motherwell and W. Jones, Chem. Commun., (2004) 890.

  56. N. Morin, A. Chilouet, J. Millet and J. C. Rouland, J. Therm. Anal. Cal., 62 (2000) 187.

    Article  CAS  Google Scholar 

  57. G. Bruni, A. Marini, V. Berbenni, R. Riccardi and M. Villa, J. Inclusion Phenom. Macr. Chem., 35 (1999) 517.

    Article  CAS  Google Scholar 

  58. F. Taneri, T. Gueneri, Z. Aigner and M. Kata, J. Inclusion Phenom. Macr. Chem., 44 (2002) 257.

    Article  CAS  Google Scholar 

  59. R. Saikosin, T. Limpaseni and P. Pongsawasdi, J. Inclusion Phenom. Macr. Chem., 44 (2002) 191.

    Article  CAS  Google Scholar 

  60. A. V. Trask, W. D. S. Motherwell and W. Jones, Cryst. Growth Des., 5 (2005) 1013.

    Article  CAS  Google Scholar 

  61. A. V. Trask, D. A. Haynes, W. D. S. Motherwell and W. Jones, Chem. Commun., (2006) 51.

  62. M. J. Zaworotko, Chem. Soc. Rev., 23 (1994) 283.

    Article  CAS  Google Scholar 

  63. T. Steiner, Angew. Chem. Int. Ed., 41 (2002) 48.

    Article  CAS  Google Scholar 

  64. M. J. Calhorda, Chem. Commun., (2000) 801.

  65. D. Braga, L. Maini, M. Polito and F. Grepioni, Struct. Bonding, 111 (2004) 1.

    CAS  Google Scholar 

  66. M. Nishio, Cryst. Eng. Comm., 6 (2004) 130.

    CAS  Google Scholar 

  67. L. Brammer, Dalton Trans., (2003) 3145.

  68. A. D. Burrows, Struct. Bonding, 108 (2004) 55.

    CAS  Google Scholar 

  69. A. Nangia, Cryst. Eng. Comm., (2002) 1.

  70. M. C. Etter and G. M. Frankenbach, Chem. Mater., 1 (1989) 10.

    Article  CAS  Google Scholar 

  71. V. R. Pedireddi, W. Jones, A. P. Chorlton and R. Docherty, Chem. Commun., (1996) 987.

  72. M. R. Caira, L. R. Nassimbeni and A. F. Wildervanck, J. Chem. Soc., Perkin Trans., 2 (1995) 2213.

    Google Scholar 

  73. D. Braga, L. Maini, G. de Sanctis, K. Rubini, F. Grepioni, M. R. Chierotti and R. Gobetto, Chem. Eur. J., 9 (2003) 5538.

    Article  CAS  Google Scholar 

  74. D. Braga, L. Maini, M. Polito, L. Mirolo and F. Grepioni, Chem. Eur. J., 9 (2003) 4362.

    Article  CAS  Google Scholar 

  75. D. Braga, L. Maini, M. Polito, L. Mirolo and F. Grepioni, Chem. Commun., (2002) 2960.

  76. D. Braga, L. Maini, M. Polito and F. Grepioni, Organometallics, 18 (1999) 2577.

    Article  CAS  Google Scholar 

  77. D. Braga, L. Maini, M. Polito and F. Grepioni, Chem. Commun., (2002) 2302.

  78. D. Braga, L. Maini, S. L. Giaffreda, F. Grepioni, M. R. Chierotti and R. Gobetto, Chem. Eur. J., 10 (2004) 3261.

    Article  CAS  Google Scholar 

  79. A. N. Khlobystov, A. J. Blake, N. R. Champness, D. A. Lemenovskii, A. G. Majouga, N. V. Zyk and M. Schroder, Coord. Chem. Rev., 222 (2001) 155.

    Article  CAS  Google Scholar 

  80. L. Pan, M. B. Sander, X. Huang, J. Li, M. Smith, E. Bittner, B. Bockrath and J. K. Johnson, J. Am. Chem. Soc., 126 (2004) 1308.

    Article  CAS  Google Scholar 

  81. F. A. Cotton, C. Lin and C. A. Murillo, J. Chem. Soc., Dalton Trans., (2001) 499.

  82. N. L. Rosi, J. Eckert, M. Eddaoudi, D. T. Vodak, J. Kim, M. O’Keeffe and O. M. Yaghi, Science, 300 (2003) 1127.

    Article  CAS  Google Scholar 

  83. N. L. Rosi, M. Eddaoudi, J. Kim, M. O’Keeffe and O. M. Yaghi, Cryst. Eng. Comm., 4 (2002) 401.

    CAS  Google Scholar 

  84. M. Oh, J. A. Reingold, G. B. Carpenter and D. A. Sweigart, Coord. Chem. Rev., 248 (2004) 561.

    Article  CAS  Google Scholar 

  85. S. R. Batten and K. S. Murray, Coord. Chem. Rev., 246 (2003) 103.

    Article  CAS  Google Scholar 

  86. L. Carlucci, G. Ciani and D. M. Proserpio, Coord. Chem. Rev., 246 (2003) 247.

    Article  CAS  Google Scholar 

  87. K. Biradha and M. Fujita, Angew. Chem. Int. Ed., 41 (2002) 3392.

    Article  CAS  Google Scholar 

  88. D. Braga, S. L. Giaffreda, F. Grepioni and M. Polito, Cryst. Eng. Comm., 6 (2004) 458.

    CAS  Google Scholar 

  89. P. J. Nichols, C. L. Raston and J. W. Steed, Chem. Commun., (2001) 1062.

  90. W. J. Belcher, C. A. Longstaff, M. R. Neckenig and J. W. Steed, Chem. Commun., (2002) 1602.

  91. W. C. McCrone, Physics and Chemistry of the Organic Solid State, John Wily and Sons, 1965 p. 726.

  92. J. Bernstein, Polymorphism in Molecular Crystals, Oxford University Press, Oxford 2002, p. 352.

    Google Scholar 

  93. J. O. Henck, J. Bernstein, A. Ellern and R. Boese, J. Am. Chem. Soc., 123 (2001) 1834.

    Article  CAS  Google Scholar 

  94. D. Braga and F. Grepioni, Chem. Soc. Rev., 29 (2000) 229.

    Article  CAS  Google Scholar 

  95. D. Braga and F. Grepioni, Top. Organomet. Chem., 4 (1999) 47.

    Article  CAS  Google Scholar 

  96. D. Braga, G. Cojazzi, A. Abati, L. Maini, M. Polito, L. Scaccianoce and F. Grepioni, Dalton, (2000) 3969.

  97. M. R. Caira, Top. Curr. Chem., 198 (1998) 163.

    CAS  Google Scholar 

  98. M. R. Caira, L. R. Nassimbeni and M. Timme, J. Pharm. Sci., 84 (1995) 884.

    Article  CAS  Google Scholar 

  99. R. J. Webb, T. Y. Dong, C. G. Pierpont, S. R. Boone, R. K. Chadha and D. N. Hendrickson, J. Am. Chem. Soc., 113 (1991) 4806.

    Article  CAS  Google Scholar 

  100. M. M. De Villiers, J. G. Van der Watt and A. P. Lotter, Drug Dev. Ind. Pharm., 17 (1991) 1295.

    Google Scholar 

  101. D. Braga, L. Maini and F. Grepioni, Chem. Commun., (1999) 937.

  102. D. Braga and L. Maini, Chem. Commun., (2004) 976.

  103. C. C. Wilson, Acta Crystallogr., Sect. B: Struct. Sci., B57 (2001) 435.

    Article  CAS  Google Scholar 

  104. D. Wiechert and D. Mootz, Angew. Chem. Int. Ed., 38 (1999) 1974.

    Article  CAS  Google Scholar 

  105. D. Braga, K. Rubini and L. Maini, Cryst. Eng. Comm., 6 (2004) 236.

    CAS  Google Scholar 

  106. D. Braga, L. Scaccianoce, F. Grepioni and S. M. Draper, Organometallics, 15 (1996) 4675.

    Article  CAS  Google Scholar 

  107. F. Grepioni, G. Cojazzi, S. M. Draper, N. Scully and D. Braga, Organometallics, 17 (1998) 296.

    Article  CAS  Google Scholar 

  108. D. Braga, D. Paolucci, G. Cojazzi and F. Grepioni, Chem. Commun., (2001) 803.

  109. R. J. Davey, N. Blagden, G. D. Potts and R. Docherty, J. Am. Chem. Soc., 119 (1997) 1767.

    Article  CAS  Google Scholar 

  110. H. Koshima and M. Miyauchi, Cryst. Growth Des., 1 (2001) 355.

    Article  CAS  Google Scholar 

  111. D. Braga, G. Cojazzi, D. Paolucci and F. Grepioni, Cryst. Eng. Comm., 3 (2001) 159.

    Google Scholar 

  112. A. J. Blake, N. R. Brooks, N. R. Champness, M. Crew, A. Deveson, D. Fenske, D. H. Gregory, L. R. Hanton, P. Hubberstey and M. Schroder, Chem. Commun., (2001) 1432.

  113. D. V. Soldatov, J. A. Ripmeester, S. I. Shergina, I. E. Sokolov, A. S. Zanina, S. A. Gromilov and Y. A. Dyadin, J. Am. Chem. Soc., 121 (1999) 4179.

    Article  CAS  Google Scholar 

  114. B. Rather and M. J. Zaworotko, Chem. Commun., (2003) 830.

  115. B. Moulton and M. J. Zaworotko, Chem. Rev., 101 (2001) 1629.

    Article  CAS  Google Scholar 

  116. K. D. M. Harris and E. Y. Cheung, Chem. Soc. Rev., 33 (2004) 526.

    Article  CAS  Google Scholar 

  117. P. Seiler and J. D. Dunitz, Acta Crystallogr., Sect. B: Struct. Sci., B38 (1982) 1741.

    CAS  Google Scholar 

  118. J. D. Dunitz and J. Bernstein, Acc. Chem. Res., 28 (1995) 193.

    Article  CAS  Google Scholar 

  119. G. Kaupp, Cryst. Eng. Comm., (2006) DOI: 10.1039/b609053b.

  120. F. Toda and Editor, Organic Solid State Reactions, Springer, Berlin, Germany 2005, p. 305.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Dipartimento di Chimica G. Ciamician, University of Bologna, Via Selmi 2, 40126, Bologna, Italy

    D. Braga, S. L. Giaffreda, M. Curzi, Lucia Maini, M. Polito & Fabrizia Grepioni

Authors
  1. D. Braga
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. L. Giaffreda
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. Curzi
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Lucia Maini
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. M. Polito
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Fabrizia Grepioni
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to D. Braga.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Braga, D., Giaffreda, S.L., Curzi, M. et al. Mechanical mixing of molecular crystals. J Therm Anal Calorim 90, 115–123 (2007). https://doi.org/10.1007/s10973-007-8484-y

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10973-007-8484-y

Keywords

Search

Navigation