The interplay of coordinative, hydrogen bonding and π-π stacking interactions in sustaining supramolecular solid-state architectures. A study case of bis(4-pyridyl)- and bis(4-pyridyl-N-oxide) tectons

Coordination Chemistry Reviews

Volumn 236, Issue 1-2, 2003, Pages 91-119

  Roesky, Herbert W ^a   Andruh, Marius ^b  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b UNIVERSITY OF BUCHAREST   (Romania)

Author keywords

Coordination polymers; Crystal engineering; Extended structures; Hydrogen bonds; Stacking interactions

Indexed keywords

1,2 BIS(4 PYRIDYL)ETHANE; 1,2 BIS(PYRIDYL)ETHYLENE; 4,4' AZOPYRIDINE; 4,4' BIPYRIDINE; 4,4' BIPYRIDINE N,N' DIOXIDE; BRIDGED COMPOUND; COORDINATION COMPOUND; ETHANE; LIGAND; METAL COMPLEX; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

CHEMICAL ENGINEERING; CHEMICAL STRUCTURE; COVALENT BOND; CRYSTAL STRUCTURE; HYBRID; HYDROGEN BOND; MATERIALS; MOLECULAR INTERACTION; REVIEW; SOLID STATE; STOICHIOMETRY; STRUCTURE ANALYSIS;

EID: 0037266139     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0010-8545(02)00218-7     Document Type: Review

References (126)

1. (a) D. Venkataraman, G.B. Gardner, S. Lee, J.S. Moore, J. Am. Chem. Soc. 117 (1995) 11600;
2. (b) O.M. Yaghi, G. Li, H. Li, Nature 378 (1995) 703;
3. (c) C.J. Kepert, M.J. Rosseinsky, Chem. Commun. (1999) 375;
4. (d) K. Biradha, Y. Hongo, M. Fujita, Angew. Chem. Int. Ed. Engl. 39 (2000) 3843;
5. (e) M. Eddaoudi, D.B. Moler, H. Li, B. Chen, T.M. Reinecke, M. O'Keeffe, O.M. Yaghi, Acc. Chem. Res. 34 (2001) 319;
6. K. Seiki, S. Takamizawa, W. Mori, Chem. Lett. (2001) 332.
7. M. Fujita, Y.J. Kwon, S. Washizu, K. Ogura, J. Am. Chem. Soc. 116 (1994) 1151.
8. See for example: (a) O. Kahn, Molecular Magnetism, VCH, New York, 1993;
9. (b) J.S. Miller, A.J. Epstein, Angew. Chem. Int. Ed. Engl. 33 (1994) 385;
10. (c) M. Ohba, H. Okawa, Coord. Chem. Rev. 198 (2000) 313;
11. (d) K.R. Dunbar, R.A. Heintz, Progr. Inorg. Chem. 45 (1997) 283;
12. (e) E. Coronado, J.R. Galán-Mascarós, C.J. Gómez-Garcia, J. Ensling, P. Gütlich, Chem. Eur. J. 6 (2000) 552;
13. (f) H.O. Stumpf, L. Ouahab, Y. Pei, P. Bergerat, O. Kahn, J. Am. Chem. Soc. 116 (1994) 3866;
14. (g) E. Coronado, M. Clemente-León, J.R. Galán-Mascarós, C. Giménez-Saiz, C.J. Gómez-García, E. Martínez-Ferrero, J. Chem. Soc. Dalton Trans. (2000) 3955.
15. (a) J.-M. Lehn, Science 260 (1993) 1762;
16. (b) B.J. Holliday, C.A. Mirkin, Angew. Chem. Int. Ed. Engl. 40 (2001) 2022.
17. R.W. Gable, B.F. Hoskins, R. Robson, J. Chem. Soc. Chem. Commun. (1990) 1677.
18. (a) M. Andruh, H.W. Roesky, M. Noltemeyer, H.-G. Schmidt, Z. Naturforsch. Teil b 49 (1994) 31;
19. (b) J. Lu, C. Yu, T. Niu, T. Paliwala, G. Crisci, F. Somosa, A.J. Jacobson, Inorg. Chem. 37 (1998) 4637;
20. (c) A.S. Batsanov, M.J. Begley, P. Hubberstay, J. Stroud, J. Chem. Soc. Dalton Trans. (1996) 1947;
21. (d) C. Chen, D. Xu, Y. Xu, C. Cheng, Acta Crystallogr. Sect. C 48 (1992) 1231.
22. See for example: (a) L.R. MacGillivray, S. Subramanain, M.J. Zaworotko, J. Chem. Soc. Chem. Commun. (1994) 1325;
23. (b) L. Carlucci, G. Ciani, D.M. Proserpio, A. Sironi, J. Chem. Soc. Chem. Commun. (1994) 2755;
24. (c) T. Kuroda-Sowa, M. Yamamoto, M. Munakata, M. Seto, M. Maekawa, Chem. Lett. (1996) 349.
25. See for example: S. Subramanian, M.J. Zaworotko, Angew. Chem. Int. Ed. Engl. 34 (1995) 2127.
26. (a) O.M. Yaghi, H. Li, C. Davis, D. Richardson, T.L. Groy, Acc. Chem. Res. 31 (1998) 474;
27. (b) S. Kitagawa, M. Kondo, Bull. Chem. Soc. Jpn. 71 (1998) 1739;
28. (c) S.R. Batten, R. Robson, Angew. Chem. Int. Ed. Engl. 37 (1998) 1460;
29. (d) P.J. Hagram, D. Hagram, J. Zubieta, Angew. Chem. Int. Ed. Engl. 38 (1999) 2638;
30. (e) M.J. Zaworotko, Chem. Commun. (2001) 1;
31. (f) R. Robson, J. Chem. Soc. Dalton Trans. (2000) 3735;
32. (g) A.N. Khlobystov, A.J. Blake, N.R. Champness, D.A. Lemenovskii, A.G. Majouga, N.V. Zyk, M. Schröder, Coord. Chem. Rev. 222 (2001) 155.
33. (a) M.C. Etter, Acc. Chem. Res. 23 (1990) 120;
34. (b) S. Subramanian, M.J. Zaworotko, Coord. Chem. Rev. 137 (1994) 357.
35. (a) J.C. MacDonald, G.M. Whitesides, Chem. Rev. 94 (1994) 2383;
36. (b) C.B. Aakeröy, K.R. Seddon, Chem. Rev. 93 (1993) 397;
37. (c) G.R. Desiraju, in: F. Vögtle, J.F. Stoddart, M. Shibasaki (Eds.), Stimulating Concepts in Chemistry, Wiley VCH, Weinheim, 2000, p. 293.
38. J.W. Steed, J.L. Atwood, Supramolecular Chemistry, Wiley, Chichester, 2000.
39. W.L. Jorgensen, D.L. Severance, J. Am. Chem. Soc. 112 (1990) 4768.
40. C. Janiak, J. Chem. Soc. Dalton Trans. (2000) 3885.
41. (a) G. Marinescu, M. Andruh, R. Lescouëzec, M.C. Muñoz, J. Cano, F. Lloret, M. Julve, New J. Chem. 24 (2000) 527;
42. (b) M.C. Muñoz, M. Julve, F. Lloret, J. Faus, M. Andruh, J. Chem. Soc. Dalton Trans. (1998) 3125.
43. S.F. Lai, C.Y. Chen, K.J. Lin, Chem. Commun. (2001) 1082.
44. (a) K.S. Min, M.P. Suh, Eur. J. Inorg. Chem. (2001) 449;
45. (b) M. Munakata, J. Dai, M. Maekawa, T. Kuroda-Sowa, J. Fukui, J. Chem. Soc. Chem. Commun. (1994) 2331.
46. (a) C.V.K. Sharma, M.J. Zaworotko, Chem. Commun. (1996) 2655;
47. (b) K. Sivashankar, V.R. Pedireddi, C.N.R. Rao, J. Mol. Struct. 559 (2001) 41;
48. (c) V.R. Pedireddi, S. Chatterjee, A. Ranganathan, C.N.R. Rao, J. Am. Chem. Soc. 119 (1997) 10867;
49. (d) A. Ranganathan, V.R. Pedireddi, G. Sanjayan, K.N. Ganesh, C.N.R. Rao, J. Mol. Struct. 522 (2000) 87;
50. (e) S.B. Copp, S. Subramanian, M.J. Zaworotko, Angew. Chem. Int. Ed. Engl. 32 (1993) 706.
51. C. He, B.G. Zhang, C.Y. Duan, J.H. Li, Q.J. Meng, Eur. J. Inorg. Chem. (2000) 2549.
52. (a) J.F. Létard, P. Guionneau, E. Codjovi, O. Lavastre, G. Bravic, D. Chasseau, O. Kahn, J. Am. Chem. Soc. 119 (1997) 10861;
53. (b) J.F. Létard, P. Guionneau, L. Rabardel, J.A.K. Howard, A.E. Goeta, D. Chasseau, O. Kahn, Inorg. Chem. 37 (1998) 4432;
54. (c) M. Wesolek, D. Meyer, J.A. Osborn, A. De Cian, J. Fisher, A. Derory, P. Logoll, M. Drillon, Angew. Chem. Int. Ed. Engl. 33 (1994) 1592;
55. (d) A.J. Amoroso, J.C. Jeffery, P.L. Jones, J.A. McCleverty, P. Thornton, M.D. Ward, Angew. Chem. Int. Ed. Engl. 34 (1995) 1443.
56. L. Carlucci, G. Ciani, D.M. Proserpio, A. Sironi, J. Chem. Soc. Dalton Trans. (1997) 1801.
57. A.J. Blake, S.J. Hill, P. Hubberstay, W.S. Li, J. Chem. Soc. Dalton Trans. (1997) 913.
58. X.M. Chen, M.L. Tong, Y.J. Luo, Z.N. Chen, Aust. J. Chem. 49 (1996) 835.
59. S.D. Huang, R.G. Xiong, Polyhedron 16 (1997) 3929.
60. M.X. Li, G.Y. Xie, Y.D. Gu, J. Chen, P.J. Zheng, Polyhedron 14 (1995) 1235.
61. S. Noro, M. Kondo, T. Ishii, S. Kitagawa, H. Matsuzaka, J. Chem. Soc. Dalton Trans. (1999) 1569.
62. J. Lu, T.P. Shiao, C. Yu, T. Niu, A.J. Jacobson, Inorg. Chem. 36 (1997) 923.
63. G. De Munno, D. Armentano, T. Poerio, M. Julve, J.A. Real, J. Chem. Soc. Dalton Trans. (1999) 1813.
64. M. Andruh, in: G. Ondrejovic, A. Sirota (Eds.), Coordination Chemistry at the Turn of the Century, STU Press, Bratislava, 1999, p. 31.
65. (a) M.L. Tong, B.H. Ye, J.W. Cai, X.M. Chen, S.W. Ng, Inorg. Chem. 37 (1998) 2645;
66. (b) M.L. Tong, S.L. Zheng, X.M. Chen, Polyhedron 19 (2000) 1809.
67. K. Biradha, K.V. Domasevitch, B. Moulton, C. Seward, M.J. Zaworotko, Chem. Commun. (1999) 1327.
68. O.M. Yaghi, H. Li, T.L. Groy, Inorg. Chem. 36 (1997) 4292.
69. M.L. Tong, H.K. Lee, X.M. Chen, R.B. Huang, T.C.W. Mak, J. Chem. Soc. Dalton Trans. (1999) 3657.
70. (a) M.L. Tong, X.M. Chen, X.L. Yu, T.C.W. Mak, J. Chem. Soc. Dalton Trans. (1998) 5;
71. (b) L.M. Zheng, X. Fang, K.H. Lii, H.H. Song, X.Q. Xin, H.K. Fun, K. Chinnakali, I.A. Razak, J. Chem. Soc. Dalton Trans. (1999) 231;
72. (c) J. Lu, C. Yu, T. Niu, T. Paliwala, G. Crisci, F. Somosa, A.J. Jacobson, Inorg. Chem. 37 (1998) 4637;
73. (d) Y.S. Zhang, G.D. Enright, S.R. Breeze, S. Wang, New J. Chem. 23 (1999) 625;
74. (e) Z. Shi, L. Zhang, S. Gao, G. Yang, J. Hua, L. Gao, S. Feng, Inorg. Chem. 39 (2000) 1990;
75. (f) J. Li, H. Zeng, J. Chen, Q. Wang, X. Wu, Chem. Commun. (1997) 1213; Y. Rodriguez-Martin, C. Ruiz-Pérez, J. Sanchiz, F. Lloret, M. Julve, Inorg. Chim. Acta 318 (2001) 159;
76. (f) J. Li, H. Zeng, J. Chen, Q. Wang, X. Wu, Chem. Commun. (1997) 1213; Y. Rodriguez-Martin, C. Ruiz-Pérez, J. Sanchiz, F. Lloret, M. Julve, Inorg. Chim. Acta 318 (2001) 159;
77. (g) L.R. MacGillivray, R.H. Groeneman, J.L. Atwood, J. Am. Chem. Soc. 120 (1998) 2676;
78. (h) B.W. Sun, B.Q. Ma, Z.M. Wang, New J. Chem. 24 (2000) 853;
79. (i) J. Tao, M.L. Tong, J.X. Shi, X.M. Chen, S.W. Ng, Chem. Commun. (2000) 2043;
80. (j) J. Tao, M.L. Tong, X.M. Chen, J. Chem. Soc. Dalton Trans. (2000) 3669;
81. (k) L. Pan, N. Ching, X. Huang, J. Li, Chem. Commun. (2001) 1064;
82. (l) Q. Wang, X. Wu, W. Zhang, T. Sheng, P. Lin, J. Li, Inorg. Chem. 38 (1999) 2223;
83. (m) A.M. Chippindale, A.R. Cowley, K.J. Peacock, Acta Crystallogr. Sect. C 56 (2000) 651;
84. (n) S.R. Batten, B.F. Hoskins, R. Robson, Chem. Eur. J. 6 (2000) 156;
85. (o) C.H. Huang, L.H. Huang, K.H. Lii, Inorg. Chem. 40 (2001) 2625;
86. (p) H. Hou, Y. Wei, Y. Fan, C. Du, Y. Zhu, Y. Song, Y. Niu, X. Xin, Inorg. Chim. Acta 319 (2001) 212.
87. M.L. Tong, H.J. Chen, X.M. Chen, Inorg. Chem. 39 (2000) 2235.
88. (a) F. Robinson, M.J. Zaworotko, J. Chem. Soc. Chem. Commun. (1995) 2413;
89. (b) K.N. Power, T.L. Hennigar, M.J. Zaworotko, New J. Chem. (1998) 177.
90. M. Bukowska-Strzyzewska, A. Tosik, Inorg. Chim. Acta 30 (1978) 189.
91. (a) C.V. Krishnamohan Sharma, R.D. Rogers, Chem. Commun. (1999) 83;
92. (b) K.T. Al-Rasoul, M.G.B. Drew, Acta Crystallogr. Sect. C 43 (1987) 2081.
93. K.T. Al-Rasoul, T.J.R. Weakley, Inorg. Chim. Acta 63 (1982) 161.
94. T.J.R. Weakley, Inorg. Chim. Acta 95 (1984) 317.
95. V.A. Trush, J. Swiatek-Kozlowska, V.V. Skopenko, V.M. Amyrkhanov, Z. Naturforsch. Teil b 56 (2001) 249.
96. C. Seward, N.X. Hu, S. Wang, J. Chem. Soc. Dalton Trans. (2001) 134.
97. (a) C.Y. Su, B.S. Kang, H.Q. Liu, Q.G. Wang, T.C.W. Mak, Chem. Commun. (1998) 1551;
98. (b) C.Y. Su, B.S. Kang, Q.C. Yang, T.C.W. Mak, J. Chem. Soc. Dalton Trans. (2000) 1857.
99. (a) A.L. Gillon, G.R. Lewis, A.G. Orpen, S. Rotter, J. Starbuck, X.M. Wang, Y. Rodríguez-Martín, C. Ruiz-Pérez, J. Chem. Soc. Dalton Trans. (2000) 3897;
100. (b) L.J. Barbour, L.R. MacGillivray, J.L. Atwood, Supramol. Chem. 7 (1996) 167.
101. H.J. Chen, L.Z. Zhang, Z.G. Cai, G. Yang, X.M. Chen, J. Chem. Soc. Dalton Trans. (2000) 2463.
102. (a) M.J. Plater, M.R.St.J. Foreman, A.M.Z. Slawin, Inorg. Chim. Acta 303 (2000) 132;
103. (b) S. Bruda, M. Andruh, H.W. Roesky, Y. Journaux, M. Noltemeyer, E. Rivière, Inorg. Chem. Commun. 4 (2001) 111.
104. (a) B.Q. Ma, S. Gao, H.L. Sun, G.X. Xu, J. Chem. Soc. Dalton Trans. (2001) 130;
105. (b) B.Q. Ma, H.L. Sun, S. Gao, G.X. Xu, Inorg. Chem. 40 (2001) 6247.
106. D.L. Long, A.J. Blake, N.R. Champness, M. Schröder, Chem. Commun. (2000) 2273.
107. D. Visinescu, G.I. Pascu, M. Andruh, J. Magull, H.W. Roesky, Inorg. Chim. Acta, in press.
108. A. Nedelcu, Z. Žák, A.M. Madalan, J. Pinkas, M. Andruh, unpublished.
109. (a) D.L. Long, A.J. Blake, N.R. Champness, M. Schröder, Chem. Commun. (2000) 1369;
110. (b) D.L. Long, A.J. Blake, N.R. Champness, C. Wilson, M. Schröder, J. Am. Chem. Soc. 123 (2001) 3401.
111. S. Tanase, M. Andruh, A. Müller, M. Schmidtmann, C. Mathonière, G. Rombaut, Chem. Commun. (2001) 1084.
112. (a) M. Fujita, Y.J. Kwon, M. Miyazawa, K. Ogura, J. Chem. Soc. Chem. Commun. (1994) 1977;
113. (b) M. Fujita, M. Aoyaghi, K. Okura, Bull. Chem. Soc. Jpn. 71 (1998) 1799.
114. (a) T.L. Hennigar, D.C. MacQuarrie, P. Loisier, R.D. Rogers, M.J. Zaworotko, Angew Chem. Int. Ed. Engl. 36 (1997) 972;
115. (b) B. Moulton, M.J. Zaworotko, Chem. Rev. 101 (2001) 1629.
116. Networks constructed from both bpeta molecules and bridging anions: (a) K.N. Power, T.L. Hennigar, M.J. Zaworotko, Chem. Commun. (1998) 595; (b) Q.M. Wang, G.C. Guo, T.C.W. Mak, Chem. Commun. (1999) 1849; (c) L. Carlucci, G. Ciani, D.M. Proserpio, S. Rizzato, Chem. Commun. (2000) 1319; (d) Y.B. Dong, R.C. Layland, M.D. Smith, N.G. Pschirer, U.H.F. Bunz, H.C. zur Loe, Inorg. Chem. 38 (1999) 3056; (e) M.L. Hernández, M. Gotzone Barandika, M.K. Urtiaga, R. Cortés, L. Lezama, M.I. Arruortua, J. Chem. Soc. Dalton Trans. (2000) 79.
117. Networks constructed from both bpeta molecules and bridging anions: (a) K.N. Power, T.L. Hennigar, M.J. Zaworotko, Chem. Commun. (1998) 595; (b) Q.M. Wang, G.C. Guo, T.C.W. Mak, Chem. Commun. (1999) 1849; (c) L. Carlucci, G. Ciani, D.M. Proserpio, S. Rizzato, Chem. Commun. (2000) 1319; (d) Y.B. Dong, R.C. Layland, M.D. Smith, N.G. Pschirer, U.H.F. Bunz, H.C. zur Loe, Inorg. Chem. 38 (1999) 3056; (e) M.L. Hernández, M. Gotzone Barandika, M.K. Urtiaga, R. Cortés, L. Lezama, M.I. Arruortua, J. Chem. Soc. Dalton Trans. (2000) 79.
118. Networks constructed from both bpeta molecules and bridging anions: (a) K.N. Power, T.L. Hennigar, M.J. Zaworotko, Chem. Commun. (1998) 595; (b) Q.M. Wang, G.C. Guo, T.C.W. Mak, Chem. Commun. (1999) 1849; (c) L. Carlucci, G. Ciani, D.M. Proserpio, S. Rizzato, Chem. Commun. (2000) 1319; (d) Y.B. Dong, R.C. Layland, M.D. Smith, N.G. Pschirer, U.H.F. Bunz, H.C. zur Loe, Inorg. Chem. 38 (1999) 3056; (e) M.L. Hernández, M. Gotzone Barandika, M.K. Urtiaga, R. Cortés, L. Lezama, M.I. Arruortua, J. Chem. Soc. Dalton Trans. (2000) 79.
119. Networks constructed from both bpeta molecules and bridging anions: (a) K.N. Power, T.L. Hennigar, M.J. Zaworotko, Chem. Commun. (1998) 595; (b) Q.M. Wang, G.C. Guo, T.C.W. Mak, Chem. Commun. (1999) 1849; (c) L. Carlucci, G. Ciani, D.M. Proserpio, S. Rizzato, Chem. Commun. (2000) 1319; (d) Y.B. Dong, R.C. Layland, M.D. Smith, N.G. Pschirer, U.H.F. Bunz, H.C. zur Loe, Inorg. Chem. 38 (1999) 3056; (e) M.L. Hernández, M. Gotzone Barandika, M.K. Urtiaga, R. Cortés, L. Lezama, M.I. Arruortua, J. Chem. Soc. Dalton Trans. (2000) 79.
120. Networks constructed from both bpeta molecules and bridging anions: (a) K.N. Power, T.L. Hennigar, M.J. Zaworotko, Chem. Commun. (1998) 595; (b) Q.M. Wang, G.C. Guo, T.C.W. Mak, Chem. Commun. (1999) 1849; (c) L. Carlucci, G. Ciani, D.M. Proserpio, S. Rizzato, Chem. Commun. (2000) 1319; (d) Y.B. Dong, R.C. Layland, M.D. Smith, N.G. Pschirer, U.H.F. Bunz, H.C. zur Loe, Inorg. Chem. 38 (1999) 3056; (e) M.L. Hernández, M. Gotzone Barandika, M.K. Urtiaga, R. Cortés, L. Lezama, M.I. Arruortua, J. Chem. Soc. Dalton Trans. (2000) 79.
121. (a) M. Ferbinteanu, G. Marinescu, H.W. Roesky, M. Noltemeyer, H.G. Schmidt, M. Andruh, Polyhedron 18 (1999) 243;
122. (b) F.D. Rochon, M. Andruh, R. Melanson, Can. J. Chem. 76 (1998) 1564.
123. C.S. Hong, Y. Do, Inorg. Chem. 37 (1998) 4470.
124. C.S. Hong, S.K. Son, Y.S. Lee, M.J. Jun, Y. Do, Inorg. Chem. 38 (1999) 5602.
125. S.A. Bourne, J. Lu, B. Moulton, M.J. Zaworotko, Chem. Commun. (2001) 861.
126. I. Haiduc, F.T. Edelmann, Supramolecular Organometallic Chemistry, Wiley-VCH, Weinheim, 1999.