Metallo-supramolecular self-assembly: The case of triangle-square equilibria

Inorganic Chemistry

Volumn 47, Issue 17, 2008, Pages 7588-7598

  Weilandt, Torsten ^a,b   Troff, Ralf W ^a   Saxell, Heidi ^c,d   Rissanen, Kari ^c   Schalley, Christoph A ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b UNIVERSITY OF BONN   (Germany)

^c UNIVERSITY OF JYVÄSKYLÄ   (Finland)

^d BASF SE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 51849132424     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic800334k     Document Type: Article

References (129)

1. Fujita, M.; Yazaki, J.; Ogura, K. J. Am. Chem. Soc. 1990, 112, 5645-5647.
2. (a) Stang, P. J.; Cao, D. H. J. Am. Chem. Soc. 1994, 116, 4981-4982.
3. Also see: (b) Stang, P. J.; Zhdankin, V. V. J. Am. Chem. Soc. 1993, 115, 9808-9809.
4. For reviews on polynuclear, self-assembling metal complexes, see: (a) Leininger, S.; Olenyuk, B.; Stang, P. J. Chem. Rev. 2000, 100, 853-908.
5. (b) Holliday, B. J.; Mirkin, C. A. Angew. Chem. 2001, 113, 2076-2097.
6. Angew. Chem., Int. Ed. 2001, 40, 2022-2043.
7. (c) Albrecht, M. Chem. Rev. 2001, 101, 3457-3498.
8. (d) Cotton, F. A.; Lin, C.; Murillo, C. A. Acc. Chem. Res. 2001, 34, 759-771.
9. (e) Sun, S.-S.; Lees, A. J. Coord. Chem. Rev. 2002, 230, 170-192.
10. (f) Würthner, F.; You, C.-C.; Saha-Möller, C. R. Chem. Soc. Rev. 2004, 33, 133-146.
11. (g) Hofmeier, H.; Schubert, U. S. Chem. Soc. Rev. 2004, 33, 373-399.
12. (h) Fujita, M.; Tominaga, M.; Hori, A.; Therrien, B. Acc. Chem. Res. 2005, 38, 369-380.
13. (i) Kaiser, A.; Bäuerle, P. Top. Curr. Chem. 2005, 249, 127-201.
14. (j) You, C.-C.; Dobrawa, R.; Saha-Möller, C. R.; Würthner, F. Top. Curr. Chem. 2005, 258, 39-82.
15. (k) Nitschke, J. R. Acc. Chem. Res. 2007, 40, 103-112.
16. (l) Georgiev, I. G.; MacGillivray, L. R. Chem. Soc. Rev. 2007, 36, 1239-1248.
17. (m) Gunnlaugsson, T.; Stomeo, F. Org. Biomol. Chem. 2007, 5, 1999-2009.
18. For selected recent examples, see: (a) Müller, I. M.; Möller, D.; Schalley, C. A. Angew. Chem. 2005, 117, 485-488.
19. Angew. Chem., Int. Ed. 2005, 44, 480-484.
20. (b) Yoshizawa, M.; Sato, N.; Fujita, M. Chem. Lett. 2005, 34, 1392-1393.
21. (c) Amouri, H.; Mimassi, L.; Rager, M. N.; Mann, B. E.; Guyard-Duhayon, C.; Raehm, L. Angew. Chem. 2005, 117, 4619-4622.
22. Angew. Chem., Int. Ed. 2005, 44, 4543-4546.
23. (d) Tashiro, S.; Tominaga, M.; Yamaguchi, Y.; Kato, K.; Fujita, M. Angew. Chem. 2006, 118, 247-250;
24. Angew. Chem., Int. Ed. 2006, 45, 241-244.
25. (e) Fiedler, D.; Bergman, R. G.; Raymond, K. N. Angew. Chem. 2006, 118, 759-762;
26. Angew. Chem., Int. Ed. 2006, 45, 745-748.
27. (f) Das, S.; Bharadwaj, P. K. Inorg. Chem. 2006, 45, 5257-5259.
28. (g) Albrecht, M.; Janser, I.; Burk, S.; Weis, P. Dalton Trans. 2006, 2875-2880.
29. (h) Haino, T.; Kobayashi, M.; Fukazawa, Y. Chem. - Eur. J. 2006, 12, 3310-3319.
30. (i) Pluth, M. D.; Berman, R. G.; Raymond, K. N. Chem. Soc. Rev. 2007, 36, 161-171.
31. (j) Tashiro, K.; Aida, T. Chem. Soc. Rev. 2007, 36, 189-197.
32. (k) Pluth, M. D.; Berman, R. G.; Raymond, K. N. Science 2007, 316, 85-88.
33. (l) John, R. P.; Moon, D.; Lah, M. S. Supramol. Chem. 2007, 19, 295-308.
34. (m) Leung, D. H.; Berman, R. G.; Raymond, K. N. J. Am. Chem. Soc. 2007, 129, 2746-2747.
35. (n) Pluth, M. D.; Berman, R. G.; Raymond, K. N. J. Am. Chem. Soc. 2007, 129, 11459-11467.
36. For examples of metallo-supramolecular squares, see: (a) Stang, P. J.; Whiteford, J. A. Organometallics 1994, 13, 3776-3777.
37. (b) Slone, R. V.; Yoon, D. I.; Calburn, R. M.; Hupp, J. T. J. Am. Chem. Soc. 1995, 117, 11813-11814.
38. (c) Würthner, F.; Sautter, A.; Schmid, D.; Weber, P. J. A. Chem. - Eur. J. 2001, 7, 894-902.
39. (d) Sun, S.-S.; Lees, A. J. Inorg. Chem. 2001, 40, 3154-3160.
40. (e) Safarowsky, C.; Merz, L.; Rang, A.; Broekmann, P.; Herrmann, B. A.; Schalley, C. A. Angew. Chem. 2004, 116, 1311-1314;
41. Angew. Chem., Int. Ed. 2004, 43, 1291-1294.
42. (f) Janka, M.; Anderson, G. K.; Rath, N. P. Organometallics 2004, 23, 4382-4390.
43. (g) Lee, S. J.; Kim, J. S.; Lin, W. Inorg. Chem. 2004, 43, 6579-6588.
44. (h) Cheng, K. F.; Thai, N. A.; Teague, L. C.; Grohmanna, K.; Drain, C. M. Chem. Commun. 2005, 37, 4678-4680.
45. (i) Jiang, L.; Lu, T. B.; Feng, X.-L. Inorg. Chem. 2005, 44, 7056-7062.
46. (j) Kraft, S.; Hanuschek, E.; Beckhaus, R.; Haase, D.; Saak, W. Chem. - Eur. J. 2005, 11, 969-978.
47. (k) Abrahams, F. B.; Price, D. J.; Robson, R. Angew. Chem. 2006, 118, 820-824;
48. Angew. Chem., Int. Ed. 2006, 45, 806-810.
49. (l) Cotton, F. A.; Liu, C. Y.; Murillo, C. A.; Wang, X. Inorg. Chem. 2006, 45, 2619-2626.
50. (m) You, C.-C.; Hippius, C.; Grüne, M.; Würthner, F. Chem. - Eur. J. 2006, 12, 7510-7519.
51. (n) Fyles, T. M.; Tong, C. C. New J. Chem. 2007, 31, 296-304.
52. (o) Mounir, M.; Lorenzo, J.; Ferrer, M.; Prieto, M. J.; Rossell, O.; Avilès, F. X.; Moreno, V. J. Inorg. Biochem. 2007, 101, 660-666.
53. (p) Fyles, T. M.; Tong, C. C. New J. Chem. 2007, 31, 655-661.
54. For examples of triangles, see: (a) Fujita, M.; Aoyagi, M.; Ogura, K. Inorg. Chim. Acta 1996, 246, 53-57.
55. (b) Schnebeck, R.-D.; Randaccio, L.; Zangrando, E.; Lippert, B. Angew. Chem. 1998, 110, 128-130;
56. Angew. Chem., Int. Ed. 1998, 37, 119-121.
57. (c) Lai, S.-W.; Chan, M. C.-W.; Peng, S.-M.; Che, C.-M. Angew. Chem. 1999, 111, 708-710;
58. Angew. Chem., Int. Ed. 1999, 38, 669-671.
59. (d) Habereder, T.; Warchhold, M.; Nöth, H.; Severin, K. Angew. Chem. 1999, 111, 3422-3425;
60. Angew. Chem., Int. Ed. 1999, 38, 3225-3228.
61. (e) Sun, S.-S.; Lees, A. J. Inorg. Chem. 1999, 38, 4181-4182.
62. (f) Schneebeck, R.- D.; Friesinger, E.; Glahé, F.; Lippert, B. J. Am. Chem. Soc. 2000, 122, 1381-1390.
63. (g) Yu, X.-Y.; Maekawa, M.; Kondo, M.; Kitagawa, S.; Jin, G.-X. Chem. Lett. 2001, 168-169.
64. (h) Schweiger, M.; Seidel, S. R.; Arif, A. M.; Stang, P. J. Angew. Chem. 2001, 113, 3575-3577;
65. Angew. Chem., Int. Ed. 2001, 40, 3467-3469.
66. (i) Lee, S. J.; Hu, A.; Lin, W. J. Am. Chem. Soc. 2002, 124, 12948-12949.
67. (j) Fornies, J.; Gomez, J.; Lalinde, E.; Moreno, M. T. Chem. - Eur. J. 2004, 10, 888-898.
68. (k) Gosh, S.; Turner, D. R.; Batten, S. R.; Mukherjee, P. S. Dalton Trans. 2007, 1869-1871.
69. (a) Drain, C. M.; Lehn, J. M. J. Chem Soc., Chem. Commun. 1994, 2313-2315.
70. (b) Romero, F. M.; Ziessel, R.; Dupont-Gervais, A.; van Dorsselaer, A. J. J. Chem. Soc., Chem. Commun. 1996, 551-553.
71. (c) Manna, J.; Whiteford, J. A.; Stang, P. J.; Muddiman, D. C.; Smith, R. D. J. Am. Chem. Soc. 1996, 118, 8731-8732.
72. (d) Hall, J.; Loeb, S. J.; Shimizu, G. K. H.; Yap, G. P. A. Angew. Chem. 1998, 110, 130-133;
73. Angew. Chem., Int. Ed. Engl. 1998, 37, 121-123.
74. (e) Mukherjee, P. S.; Das, N.; Kryschenko, Y. K.; Arif, A. M.; Stang, P. J. J. Am. Chem. Soc. 2004, 126, 2464-2473.
75. (f) Tarkany, G.; Jude, H.; Palinkas, G.; Stang, P. J. Org. Lett. 2005, 7, 4971-4973.
76. (g) Das, N.; Gosh, A.; Arif, A. M.; Stang, P. J. Inorg. Chem. 2005, 44, 7130-7137.
77. (h) Megyes, T.; Jude, H.; Grosz, T.; Bako, I.; Radnai, T.; Tarkanyi, G.; Palinkas, G.; Stang, P. J. J. Am. Chem. Soc. 2005, 127, 10731-10738.
78. (i) Jude, H.; Disteldorf, H.; Fischer, S.; Wedge, T.; Hawkridge, A. M.; Arif, A. M.; Hawthorne, M. F.; Muddiman, D. C.; Stang, P. J. J. Am. Chem. Soc. 2005, 127, 12131-12139.
79. (j) Jude, H.; Sinclair, D. J.; Das, N.; Sherburn, M. S.; Stang, P. J. J. Org. Chem. 2006, 71, 4155-4163.
80. (k) Dias, H. V. R.; Gamage, C. S. P.; Keltner, J.; Diyabalanage, H. V. K.; Omari, I.; Eyobo, Y.; Dias, N. R.; Roehr, N.; McKinney, L.; Poth, T. Inorg. Chem. 2007, 46, 2979-2987.
81. For some examples see: (a) Beauchamp, D. A.; Loeb, S. J. Chem. Commun. 2002, 2484-2485.
82. (b) Tuna, F.; Hamblin, J.; Jackson, A.; Clarkson, G.; Alcock, N. W.; Hannon, M. J. Dalton Trans. 2003, 2141-2148.
83. (c) Graves, C. R.; Merlau, M. L.; Morris, G. A.; Sun, S.-S.; Nguyen, S. B. T.; Hupp, J. T. Inorg. Chem. 2004, 43, 2013-2017.
84. (d) Jeong, K. S.; Kim, S. Y.; Shin, U.-S.; Nguyen, T. M. H.; Kogej, M.; Broekmann, P.; Jeong, N.; Kirchner, B.; Reiher, M.; Schalley, C. A. J. Am. Chem. Soc. 2005, 127, 17672-17685.
85. (e) Kiplinger, J. L.; Pool, J. A.; Schelter, E. J.; Thompson, J. D.; Scott, B. L.; Morris, D. E. Angew. Chem. 2006, 118, 2090-2095;
86. Angew. Chem., Int. Ed. 2006, 45, 2036-2041.
87. (f) Clegg, J. K.; Lindoy, L. F.; McMurtrie, J. C.; Schilter, D. Dalton Trans. 2006, 3114-3121.
88. (g) Chand, D. K.; Biradha, K.; Kawano, M.; Sakamoto, S.; Yamaguchi, K.; Fujita, M. Chem. Asian J. 2006, 1, 82-90.
89. (h) Cotton, F. A.; Murillo, C. A.; Stiriba, S.-E.; Wang, X.; Yu, R. Inorg. Chem. 2006, 44, 8223-8233.
90. (i) Heo, J.; Jeon, Y.-M.; Mirkin, C. A. J. Am. Chem. Soc. 2007, 129, 7712-7713.
91. (j) Baradjí, E. G.; Freisinger, E.; Costisella, B.; Schalley, C. A.; Brüning, W.; Sabat, M.; Lippert, B. Chem. - Eur. J. 2007, 13, 6019-6039.
92. (k) Derossi, S.; Casanova, M.; Iengo, E.; Zangrando, E.; Stener, M.; Alessio, E. Inorg. Chem. 2007, 46, 11243-11253.
93. (a) Lee, S. B.; Hwang, S.; Chung, D. S.; Yun, H.; Hong, J.-I. Tetrahedron Lett. 1998, 39, 873-876.
94. (b) Schnebeck, R.-D.; Freisinger, E.; Lippert, B. Eur. J. Inorg. Chem. 2000, 1193-1200.
95. (c) Sautter, A.; Schmid, D. G.; Jung, G.; Würthner, F. J. Am. Chem. Soc. 2001, 123, 5424-5430.
96. (d) Schalley, C. A.; Müller, T.; Linnartz, P.; Witt, M.; Schäfer, M.; Lützen, A. Chem. Eur. J. 2002, 8, 3538-3551.
97. (e) Zhang, L.; Niu, Y.-H.; Jen, A. K.-Y.; Lin, W. Chem. Commun. 2005, 1002-1004.
98. (f) Cotton, F. A.; Murillo, C. A.; Yu, R. Dalton Trans. 2006, 3900-3905.
99. (g) Uehara, K.; Kasai, K.; Mizuno, N. Inorg. Chem. 2007, 46, 2563-2570.
100. (a) Ferrer, M.; Mounir, M.; Rossell, O.; Ruiz, E.; Maestro, M. A. Inorg. Chem. 2003, 42, 5890-5899.
101. (b) Ferrer, M.; Gutierrez, A.; Mounir, M.; Rossel, O.; Riuz, E.; Rang, A.; Engeser, M. Inorg. Chem. 2007, 46, 3395-3406.
102. (a) Bark, T.; Düggeli, M.; Stoeckli-Evans, H.; Zelewsky, A. v. Angew. Chem. 2001, 113, 2924-2927;
103. Angew. Chem., Int. Ed. 2001, 40, 2848-2851.
104. (b) Mamula, O.; Monlien, F. J.; Porquet, A.; Hopfgartner, G.; Merbach, A. E.; Zelewsky, A. v. Chem. - Eur. J. 2001, 7, 533-539.
105. Fujita, M.; Sasaki, O.; Mitsuhashi, T.; Fujita, T.; Yazaki, J.; Yamaguchi, K.; Ogura, K. Chem. Commun. 1996, 1535-1536.
106. Berben, L. A.; Faia, C. M.; Crawford, N. R. M.; Long, J. R. Inorg. Chem. 2006, 45, 6378-6386.
107. Engeser, M.; Rang, A.; Ferrer, M.; Gutiérrez, A.; Schalley, C. A. Int. J. Mass Spectrom. 2006, 255-256, 185-194.
108. (a) Lukoyanov, A. N.; Fedushkin, I. L.; Schumann, H.; Hummert, M. Z. Anorg. Allg. Chem. 2006, 632, 1471-1476.
109. (b) Rang, A.; Engeser, M.; Maier, N. M.; Nieger, M.; Lindner, W.; Schalley, C. A. Chem. - Eur. J. 2008, 14, 3855-3859.
110. (a) Sakamoto, S.; Fujita, M.; Kim, K.; Yamaguchi, K. Tetrahedron 2000, 56, 955-964.
111. (b) Sakamoto, S.; Yoshizawa, M.; Kusukawa, T.; Fujita, M.; Yamaguchi, K. Org. Lett. 2001, 3, 1601-1604.
112. (c) Tominaga, M.; Suzuki, K.; Kawano, M.; Kusukawa, T.; Ozeki, T.; Sakamoto, S.; Yamaguchi, K.; Fujita, M. Angew. Chem. 2004, 116, 5739-5743;
113. Angew. Chem., Int. Ed. 2004, 42, 5621-5625.
114. For a review, see: (d) Yamaguchi, K. J. Mass Spectrom. 2003, 38, 473-490.
115. (a) Cohen, Y.; Avram, L.; Frish, L. Angew. Chem. 2005, 117, 524-560;
116. Angew. Chem., Int. Ed. 2005, 44, 520-554.
117. (b) Cohen, Y., Avram, L.; Evan-Salem, T.; Frish, L. Diffusion NMR in Supramolecular Chemistry. In Analytical Methods in Supramolecular Chemistry; Schalley, C. A., Ed.; Wiley-VCH: Weinheim 2007.
118. (c) Macchioni, A.; Ciancaleoni, G.; Zuccaccia, C.; Zuccaccia, D. Chem. Soc. Rev. 2008, 37, 479-489.
119. CACHE 5.0 for Windows; Fujitsu Ltd.: Krakow, Poland, 2001.
120. Schweiger, M.; Seidel, S. R.; Arif, A. M.; Stang, P. J. Inorg. Chem. 2002, 41, 2556-2559.
121. Sun, S.-S.; Lees, A. J.; Zavalij, P. Y. Inorg. Chem. 2003, 42, 3445-3453.
122. Pansanel, J.; Jouaiti, A.; Ferlay, S.; Hosseine, M. W.; Planeix, J.-M.; Kyritsakas, N. New J. Chem. 2006, 71-76.
123. Stang, P. J.; Cao, D. H.; Saito, S.; Arif, A. M. J. Am. Chem. Soc. 1995, 117, 6273-6283.
124. Appleton, T. G.; Bennett, M. A.; Tomkins, I. B. J. Chem. Soc., Dalton Trans. 1976, 439-446.
125. Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307-326.
126. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 1990, 46, 467-473.
127. Sheldrick, G. M.; Schneider, T. R. Methods Enzymol. 1997, 277, 319- 343.
128. Blessing, R. H. Acta Crystallogr., Sect. A: Found. Crystallogr. 1995, 51, 33-38.
129. Van der Sluis, P.; Spek, A. L. Acta Crystallogr., Sect. A: Found. Crystallogr. 1990, 46, 194-201.