One-pot mechanosynthesis with three levels of molecular self-assembly: coordination bonds, hydrogen bonds and host-guest inclusion

Chemistry - A European Journal

Volumn 15, Issue 46, 2009, Pages 12644-12652

  Friščić, Tomislav ^a   Meštrović, Ernest ^b   Šamec, Dijana Škalec ^b   Kaitner, Branko ^c   Fábián, László ^d  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b PLIVA CROATIA LTD   (Croatia)

^c UNIVERSITY OF ZAGREB   (Croatia)

^d CAMBRIDGE CRYSTALLOGRAPHIC DATA CENTRE   (United Kingdom)

Author keywords

Green chemistry; Inclusion compounds; Mechanochemistry self assembly; Supramolecular chemistry

Indexed keywords

COORDINATION BONDS; COORDINATION-DRIVEN; DIBENZOYLMETHANATE; GREEN CHEMISTRY; HOST-GUESTS; IN-SITU; INCLUSION COMPOUNDS; INCLUSION PROPERTIES; ISONICOTINAMIDE; LIQUID PHASE; MECHANO-CHEMISTRY; MECHANOCHEMICALS; MECHANOSYNTHESIS; METAL-ORGANIC; MOLECULAR SELF ASSEMBLY; ONE POT; ONE POT PROCESS; SELF-ASSEMBLY SUPRAMOLECULAR CHEMISTRY; SINGLE-CRYSTAL AND POWDER; SOLUTION SYNTHESIS; STRUCTURAL INFORMATION; SYNTHONS;

AMIDES; COBALT; COBALT COMPOUNDS; COORDINATION REACTIONS; GRINDING (COMMINUTION); GRINDING (MACHINING); HYDROGEN BONDS; LIQUIDS; MACROMOLECULES; METAL IONS; METALS; SELF ASSEMBLY; SINGLE CRYSTALS; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS (CHEMICAL); WHEELS;

COMPLEXATION;

COBALT; ORGANOMETALLIC COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; HYDROGEN BOND; SYNTHESIS;

COBALT; HYDROGEN BONDING; MODELS, MOLECULAR; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS;

EID: 71549128037     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901058     Document Type: Article

References (104)

1. a) T. Friščić, A. V. Trask, W. Jones, W. D. S. Motherwell, Angew. Chem. 2006, 118, 7708-7712;
2. Angew. Chem. Int. Ed. 2006, 45, 7546-7550;
3. b) T. Friščić, L. Fábián, J. C. Burley, W. Jones, W. D. S. Motherwell, Chem. Commun. 2006, 5009-5011;
4. c) N. Shan, F. Toda, W. Jones, Chem. Commun. 2002, 2372-2373.
5. a) D. Braga, F. Grepioni, Angew. Chem. 2004, 116, 4092-4102;
6. Angew. Chem. Int. Ed. 2004, 43, 4002-4011;
7. b) D. Braga, S. L. Giaffreda, F. Grepioni, A. Pettersen, L. Maini, M. Curzi, M. Polito, Dalton 2006, 1249 -1263;
8. c) K. Tanaka, F. Toda, Chem. Rev. 2000, 100, 1025-1074.
9. a) D. R. Weyna, T. Shattock, P. Vishweshwar, M. J. Zaworotko, Cryst. Growth Des. 2009, 9, 1106-1123;
10. b) D. J. Berry, C. C. Seaton, W. Clegg, R. W. Harrington, S. J. Coles, P. N. Horton, M. B. Hursthouse, R. Storey, W. Jones, T. Frišč ić, N. Blagden, Cryst. Growth Des. 2008, 8, 1697-1712;
11. c) S. Karki, L. Fábián, T. Friščić, W. Jones, Org. Lett. 2007, 9, 3133-3136.
12. a) D. Cinčić, T. Friščić, W. Jones, J. Am. Chem. Soc. 2008, 130, 7524-7525;
13. b) D. Cinčić, T. Friščić, W. Jones, Chem. Mater. 2008, 20, 6623-6626;
14. c) D. Cinčić, T. Friščić, W. Jones, Chem Eur. J. 2008, 14, 747-753.
15. a) K. L. Nguyen, T. Friščić, G. M. Day, L. F. Gladden, W. Jones, Nat. Mater. 2007, 6, 206-209;
16. b) G. A. Bowmaker, N. Chaichit, C. Pakawatchai, B. W. Skelton, A. H. White, Dalton 2008, 2926-2928.
17. T. Friščić, W. Jones, Cryst. Growth Des. 2009, 9, 1621-1637.
18. T. Friščić, A. V. Trask, W. Jones, W. D. S. Motherwell, Cryst. Growth Des. 2008, 8, 1605-1609.
19. B. Içli, N. Christinat, J. Tönnemann, C. Schüttler, R. Scopelliti, K. Severin, J. Am. Chem. Soc. 2009, 131, 3154-3155.
20. D. Braga, M. Curzi, A. Johansson, M. Polito, K. Rubini, F. Grepioni, Angew. Chem. 2006, 118, 148-152;
21. Angew. Chem. Int. Ed. 2006, 45, 142-146.
22. a) A. Pichon, S. L. James, CrystEngComm 2008, 10, 1839-1847;
23. b) A. Pichon, A. Lazuen-Garay, S. L. James, CrystEngComm 2006, 8, 211-214.
24. T. Friščić, L. Fábián, CrystEngComm 2009, 11, 743-745.
25. One-pot mechanochemical assembly through hydrogen bonds and ππ interactions was recently utilised in a mechanochromic procedure that can distinguish enantiomerically pure compounds from racemates, see : a) R. Kuroda, T. Sato, Y. Imai, CrystEngComm 2008, 10, 1881-1890;
26. b) Y. Imai, N. Tajima, T. Sato, R. Kuroda, Org. Lett. 2006, 8, 2941-2944;
27. c) E.Y. Cheung, S. J. Kitchin, K. D. M. Harris, Y. Imai, N. Tajima, R. Kuroda, J. Am. Chem. Soc. 2003, 125, 14658-14659.
28. The ability to combine such mechanochemical reactions in a sequence was demonstrated, see: a) A. N. Swinburne, J. W. Steed, CrystEngComm 2009, 11, 433-438;
29. b) P. J. Nichols, C. L. Raston, J. W. Steed, Chem Commun. 2001, 1062-1063.
30. a) T. Friščić, S. L. Childs, S. A. A. Rizvi, W. Jones, CrystEngComm 2009, 11, 418-426;
31. b) D. Braga, S. L. Giaffreda, F. Grepioni, G. Palladino, M. Polito, New J. Chem. 2008, 32, 820-828.
32. a) A. Lazuen-Garay, A. Pichon, S. L. James, Chem. Soc. Rev. 2007, 36, 846-855;
33. b) C. J. Adams, M. A. Kurawa, M. Lusi, A. G. Orpen, CrystEngComm 2008, 10, 1790-1795;
34. c) C. J. Adams, H. M. Colquhoun, P. C. Crawford, M. Lusi, A. G. Orpen, Angew. Chem. 2007, 119, 1142-1146;
35. Angew. Chem. Int. Ed. 2007, 46, 1124-1128;
36. e) D. Braga, M. Polito, E. Dichiarante, K. Rubini, F. Grepioni, Chem. Commun. 2007, 1594-1596.
37. 2] compounds, see: a) B. Kaitner, E. Meštrović, Acta Crystallogr. E, 2007, E63, m1549-m1550;
38. b) E. Meštrović, B. Kaitner, J. Chem. Crystallogr. 2006, 36, 599-603;
39. c) N. Judaš, I. Halasz, D.-K. Bučar, Acta Crystallogr. 2006, E62, m283-m285.
40. a) C.-L. Chen, A. M. Beatty, J. Am. Chem. Soc. 2008, 130, 17222-17223;
41. b) A. M. Beatty, Coord Chem. Rev. 2003, 246, 131-143;
42. c) A. M. Beatty, B. A. Helfrich, G. A. Hogan, B. A. Reed, Cryst. Growth Des. 2006, 6, 122-126.
43. For recent reviews pertinent to SSMs, see: a) D. V. Soldatov J. Chem. Cryst. 2006, 36, 747-768;
44. b) D. Soldatov, J. Inclusion Phenom. Macrocyclic Chem. 2004, 48, 3-9.
45. a) F. Toda, D. L. Ward, H. Hart, Tetrahedron Lett. 1981, 22, 3865-3868;
46. b) H. Hart, L.-T. W. Lin, D. L. Ward, J. Am. Chem. Soc. 1984, 106, 4043-4045;
47. c) F. Maharaj, R. Bishop, D. C. Craig, P. Jensen, M. L. Scudder, N. Kumar, Cryst. Growth Des. 2009, 9, 1334-1338;
48. d) L. Johnson, L. Nassimbeni, E. Weber, K. Skobridis, Perkin Trans. 2 1992, 2131-2136;
49. e) K. K. D. Ng, H. Hart, Tetrahedron 1995, 51, 7883-7906;
50. f) F. Toda, K. Akagi, Tetrahedron Lett. 1968, 9, 3695-3698.
51. a) D. V. Soldatov, G. D. Enright, C. I. Ratcliffe, A. T. Henegouwen, J. A. Ripmeester, Chem. Mater. 2001, 13, 4322-4334;
52. b) D. V. Soldatov, P. Tinnemans, G. D. Enright, C. I. Ratcliffe, P. R. Diamente, J. A. Ripmeester, Chem. Mater. 2003, 15, 3826-3840;
53. c) D. V. Soldatov, I. L. Moudrakovski, C. I. Ratcliffe, R. Dutrisac, J. A. Ripmeester, Chem. Mater. 2003, 15, 4810-4818;
54. d) D. V. Soldatov, G. D. Enright, J. A. Ripmeester, Supramol. Chem. 1999, 11, 35-47.
55. For other metal-organic designs of wheel-and-axle host compounds, see: a) A. Bacchi, M. Carcelli, T. Chiodo, F. Mezzadri, CrystEngComm 2008, 10, 1916-1927;
56. b) A. Bacchi, E. Bosetti, M. Carcelli, P. Pelagatti, D. Rogolino, G. Pelizzi, Inorg. Chem. 2005, 44, 431-442;
57. c) A. Bacchi, E. Bosetti, M. Carcelli, CrystEngComm 2005, 7, 527-537;
58. d) Y. Diskin-Posner, G. K. Patra, I. Goldberg, Dalton 2001, 2775-2782;
59. e) S. B. Sembiring, S. B. Colbran, R. Bishop, D. C. Craig, A. D. Rae, Inorg. Chim. Acta 1995, 228, 109-117.
60. M. J. Rosseinsky, Microporous Mesoporous Mater. 2004, 73, 15-30.
61. [25]
62. For similar mechanochemical ligand substitution reactions, see: a) W. J. Belcher, C. A. Longstaff, M.R. Neckenig, J.W Steed, Chem. Commun. 2002, 1602-1603;
63. b) D. Braga, F. Grepioni, L. Maini, R. Brescello, L. Cotarca, CrystEngComm 2008, 10, 469-471.
64. a) D. V. Soldatov, A. T. Henegouwen, G. D. Enright, C. I. Ratcliffe, J. A. Ripmeester, Inorg. Chem. 2001, 40, 1626-1636;
65. b) D. V. Soldatov, J. A. Ripmeester, Chem. Eur. J. 2001, 7, 2979-2994.
66. C. B. Aakeröy, J. Desper, J. Valdés-Martínez, CrystEngComm 2004, 6, 413-418.
67. [25b]
68. a) T. Steiner, Angew. Chem 2002, 114, 50-80;
69. Angew. Chem. Int. Ed. 2002, 41, 48-76;
70. b) M. Nishio, CrystEngComm 2004, 6, 130-158.
71. 2] within 3 min exposure to air.
72. 2] have been previously described, see: M. Doring, W. Ludwig, E. Uhlig, Z. Anorg. Allg. Chem. 1991, 595, 45-52.
73. For other known structures of imidazole adducts of metal(II) β-diketonates, see: a) S. Delgado, A. Munoz, M. E. Medina, C. J. Pastor, Inorg. Chim. Acta 2006, 359, 109 (CCDC code NECGAE);
74. b) G. Mago, M. Hinago, H. Miyasaka, N. Matsumoto, H. Okawa, Inorg. Chim. Acta 1997, 254, 145 (CCDC code TOBYIS).
75. [26]
76. The positioning of broad reflections in the pattern suggests that the product is most likely a mixture of phases similar to 1 and 2. This assumption was further supported by comparison with the PXRD pattern of a neat ground mixture of 1 and 2, previously prepared by LAG with nitromethane.
77. 2O with na and imi using FT-IR spectroscopy revealed that the spectra of both products are similar to the spectra of corresponding crystalline wheel-and-axle compounds obtained by LAG.
78. -1.
79. a) K. D. M. Harris, Comp. Mater. Sci. 2009, 45, 16-20;
80. b) Z. F. Zhou, K. D. M. Harris, J. Phys. Chem. A 2008, 112, 4863-4868;
81. c) C. C. Seaton, M. Tremayne, Chem. Commun. 2002, 880-881;
82. d) K. D. M. Harris, E. Y. Cheung, Chem. Soc. Rev. 2004, 33, 526-538;
83. e) M. Tremayne, Phil. Trans. R. Soc. Lond. A 2004, 362, 2691-2707.
84. W. I. F. David, K. Shankland, J. van de Streek, E. Pidcock, W. D. S. Motherwell, J. C. Cole, J. Appl. Crystallogr. 2006, 39, 910-915.
85. For other examples of structure solution using DASH, see : a) T. Friščić, L. Fábián, J. C. Burley, D. G. Reid, M. J. Duer, W. Jones, Chem. Commun. 2008, 1644-1666;
86. b) G. P. Stáhly, S. Bates, M. C. Andres, B. A. Cowans, Cryst. Growth Des. 2006, 6, 925-932;
87. c) A. J. Florence, N. Shankland, K. Shankland, W. I. F. David, E. Pidcock, X. Xu, A. Johnston, A. R. Kennedy, P. J. Cox, J. S. O. Evans, G. Steele, S. D. Cosgrove, C. S. Frampton, J. Appl. Crystallogr. 2005, 38, 249-259.
88. C. B. Aakeröy, B. M. T. Scott, J. Desper, New J. Chem. 2007, 31, 2044-2051.
89. The field of supramolecular ladders was recently reviewed, see: A. N. Sokolov, L. R. MacGillivray, Cryst. Growth Des. 2006, 6, 2615-2624.
90. a) B. R. Bhogala, A. Nangia, New J. Chem. 2008, 32, 800-807;
91. b) B. K. Saha, A. Nangia, CrystEngComm 2006, 8, 440-443;
92. c) B. R. Bhogala, S. Basavoju, A. Nangia, Cryst. Growth Des. 2005, 5, 1683-1686;
93. d) P. Brunet, M. Simard, J. D. Wuest, J. Am. Chem. Soc. 1997, 119, 2737-2738.
94. The composition of the material was difficult to establish using TG due to the rapid loss of included solvent upon exposure to air. Consequently, the composition was established from single crystal X-ray structure determination. Simulated PXRD pattern coincided with the measured pattern for the fresh material prepared by LAG.
95. 2] is reminiscent of the supramolecular wheeland-axle host 4-tritylbenzamide that readily adopts three types of arrangement due to the availability of two types of hydrogen-bond acceptors: a) C. Malla Reddy, L. Sreenivas Reddy, S. Aitipamula, A. Nangia, C.-K. Lam, T. C. W. Mak, CrystEngComm 2005, 7, 44-52;
96. b) R. K. R. Jetti, S. S. Kuduva, D. S. Reddy, F. Xue, T. C. W. Mak, A. Nangia, G. R. Desiraju, Tetrahedron Lett. 1998, 39, 913-916.
97. [45]
98. For recent reviews on SCSC reactivity, see: a) T. Frišč ić, L. R. MacGillivray, Z. Kristallogr. 2005, 220, 351-363;
99. b) A. E. Keating, M. A. Garcia-Garibay "Photochemical Solid-to-Solid Reactions" in: Mol. Supramol. Photochem. Vol.2 (Eds. V. Ramamurthy, K. Schanze), pp. 195-248, Marcel Dekker 1998.
100. 2] ·acetone produces 1.
101. The same rationalisation can also be used to explain the difference between LAG and solution experiments involving nitromethane, that is, the inability to construct significant amounts of 1 from solution.
102. a) A. Jayasankar, Z. J. Shao, N. Rodríguez-Hornedo, Pharm. Res. 2006, 23, 2381-2392;
103. b) D. Braga, S. L. Giaffreda, F. Grepioni, M. R. Chierotti, R. Gobetto, G. Palladino, M. Polito, CrystEngComm 2007, 9, 879-881;
104. c) K. Fujii, Y. Ashida, H. Uekusa, S. Hirano, S. Toyota, F. Toda, Z. Pan, K. D. M. Harris, Cryst. Growth Des. 2009, 9, 1201-1201