Systematic investigation of silver-carbon bonding in coordination frameworks with aryl ligands that contain ethynyl and ethenyl substituents

Chemistry - A European Journal

Volumn 19, Issue 17, 2013, Pages 5387-5400

  Hau, Sam C K ^a   Mak, Thomas C W ^a  

^a CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

coordination modes; crystal engineering; metal organic frameworks; silver; X ray diffraction

Indexed keywords

COORDINATION FRAMEWORKS; COORDINATION MODES; COORDINATION NETWORKS; METAL ORGANIC FRAMEWORK; SINGLE CRYSTAL X-RAY DIFFRACTION; SYSTEMATIC INVESTIGATIONS; TRIFLUOROACETATES; VINYL SUBSTITUENTS;

AROMATIC COMPOUNDS; CARBON; CARBON DIOXIDE; COMPLEX NETWORKS; CRYSTAL ENGINEERING; CRYSTAL ORIENTATION; CRYSTALLINE MATERIALS; LIGANDS; NAPHTHALENE; X RAY DIFFRACTION;

SILVER;

EID: 84876210765     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201204225     Document Type: Article

References (121)

1. P. Braunstein, C. Frison, N. Oberbeckmann-Winter, X. Morise, A. Messaoudi, M. Bénard, M.-M. Rohmer, R. Welter, Angew. Chem. 2004, 116, 6246-6251
2. Angew. Chem. Int. Ed. 2004, 43, 6120-6125
3. T. K. Ronson, T. Lazarides, H. Adams, S. J. A. Pope, D. Sykes, S. Faulkner, S. J. Coles, M. B. Hursthouse, W. Clegg, R. W. Harrington, M. D. Ward, Chem. Eur. J. 2006, 12, 9299-9313
4. D. Salazar-Mendoza, S. A. Baudron, M. W. Hosseini, Chem. Commun. 2007, 2252-2254
5. C. Fernández-Cortabitarte, F. García, J. V. Morey, M. McPartlin, S. Singh, A. E. H. Wheatley, D. S. Wright, Angew. Chem. 2007, 119, 5521-5523
6. Angew. Chem. Int. Ed. 2007, 46, 5425-5427.
7. M. I. Bruce, Chem. Rev. 1991, 91, 197-257
8. H. Lang, D. S. A. George, G. Rheinwald, Coord. Chem. Rev. 2000, 206-207, 101-197
9. N. J. Long, C. K. Williams, Angew. Chem. 2003, 115, 2690-2722
10. Angew. Chem. Int. Ed. 2003, 42, 2586-2617
11. V. W.-W. Yam, J. Organomet. Chem. 2004, 689, 1393-1401
12. S. S. Y. Chui, M. F. Y. Ng, C.-M. Che, Chem. Eur. J. 2005, 11, 1739-1749
13. W.-Y. Wong, Coord. Chem. Rev. 2007, 251, 2400-2427.
14. C. P. McArdle, J. J. Vittal, R. J. Puddephatt, Angew. Chem. 2000, 112, 3977-3980
15. Angew. Chem. Int. Ed. 2000, 39, 3819-3822
16. C. P. McArdle, M. C. Jennings, J. J. Vittal, R. J. Puddephatt, Chem. Eur. J. 2001, 7, 3572-3593
17. C. P. McArdle, M. J. Irwin, M. C. Jennings, J. J. Vittal, R. J. Puddephatt, Chem. Eur. J. 2002, 8, 723-734
18. C. P. McArdle, S. Van, M. C. Jennings, R. J. Puddephatt, J. Am. Chem. Soc. 2002, 124, 3959-3965
19. F. Mohr, M. C. Jennings, R. J. Puddephatt, Eur. J. Inorg. Chem. 2003, 217-233
20. T. J. Burchell, M. C. Jennings, R. J. Puddephatt, Inorg. Chim. Acta 2006, 359, 2812-2818
21. N. C. Habermehl, D. J. Eisler, C. K. Kirby, N. L.-S. Yue, R. J. Puddephatt, Organometallics 2006, 25, 2921-2928.
22. S. Barlow, D. O'Hare, Chem. Rev. 1997, 97, 637-669
23. I. R. Whittall, A. M. McDonagh, M. G. Humphrey, Adv. Organomet. Chem. 1998, 42, 291-362
24. M. P. Cifuentes, M. G. Humphrey, J. Organomet. Chem. 2004, 689, 3968-3981.
25. M. Younus, A. Kohler, S. Cron, N. Chawdhury, M. R. A. Al-Madani, M. S. Khan, N. J. Long, R. H. Friend, P. R. Raithby, Angew. Chem. 1998, 110, 3180-3183
26. Angew. Chem. Int. Ed. 1998, 37, 3036-3039
27. V. W.-W. Yam, Acc. Chem. Res. 2002, 35, 555-563
28. Q.-H. Wei, L.-Y. Zhang, G.-Q. Yin, L.-X. Shi, Z.-N. Chen, J. Am. Chem. Soc. 2004, 126, 9940-9941
29. H.-B. Xu, L.-X. Shi, E. Ma, L.-Y. Zhang, Q.-H. Wei, Z.-N. Chen, Chem. Commun. 2006, 1601-1603
30. H.-B. Xu, J. Ni, K.-J. Chen, L.-Y. Zhang, Z.-N. Chen, Organometallics 2008, 27, 5665-5671
31. H.-B. Xu, L.-Y. Zhang, J. Ni, H.-Y. Chao, Z.-N. Chen, Inorg. Chem. 2008, 47, 10744-10752
32. H.-B. Xu, L.-Y. Zhang, X.-M. Chen, X.-L. Li, Z.-N. Chen, Cryst. Growth Des. 2009, 9, 569-576.
33. F. Paul, C. Lapinte, Coord. Chem. Rev. 1998, 178-180, 431-509
34. V. W.-W. Yam, K. M.-C. Wong, Top. Curr. Chem. 2005, 257, 1-32
35. S. Rigaut, C. Olivier, K. Costuas, S. Choua, O. Fadhel, J. Massue, P. Turek, J. Y. Saillard, P. H. Dixneuf, D. Touchard, J. Am. Chem. Soc. 2006, 128, 5859-5876
36. G. A. Koutsantonis, G. I. Jenkins, P. A. Schauer, B. Szczepaniak, B. W. Skelton, C. Tan, A. H. White, Organometallics 2009, 28, 2195-2205
37. K. J. Kilpin, M. L. Gower, S. G. Telfer, G. B. Jameson, J. D. Crowley, Inorg. Chem. 2011, 50, 1123-1134.
38. H.-X. Zhang, B.-S. Kang, A.-W. Xu, H.-Q. Liu, Z.-N. Chen, Comments Inorg. Chem. 2002, 23, 231-235
39. V. Balamurugan, W. Jacob, J. Mukherjee, R. Mukherjee, CrystEngComm 2004, 6, 396-400
40. J. Burgess, J. R. A. Cottam, P. J. Steel, Aust. J. Chem. 2006, 59, 295-297
41. A. D. Naik, M. M. Dîrtu, A. Léonard, B. Tinant, J. Marchand-Brynaert, B.-L. Su, Y. Garcia, Cryst. Growth Des. 2010, 10, 1798-1807
42. D. L. Reger, A. Debreczeni, M. D. Smith, Inorg. Chem. 2011, 50, 11754-11764
43. J. Zukerman-Schpector, I. Haiduc, E. R. T. Tiekink, Chem. Commun. 2011, 47, 12682-12684.
44. P. Pyykkö, Chem. Rev. 1988, 88, 563-594
45. P. Pyykkö, Chem. Rev. 1997, 97, 597-636
46. P. Pyykkö, Chem. Soc. Rev. 2008, 37, 1967-1997
47. S. Grimme, J.-P. Djukic, Inorg. Chem. 2010, 49, 2911-2919
48. J. Muñiz, C. Wang, P. Pyykkö, Chem. Eur. J. 2011, 17, 368-377.
49. G. R. Desiraju, Angew. Chem. 1995, 107, 2541-2558
50. Angew. Chem. Int. Ed. Engl. 1995, 34, 2311-2327
51. G. R. Desiraju, Angew. Chem. 2007, 119, 8492-8508
52. Angew. Chem. Int. Ed. 2007, 46, 8342-8356.
53. S. C. K. Hau, P.-S. Cheng, T. C. W. Mak, J. Am. Chem. Soc. 2012, 134, 2922-2925, and references therein.
54. T. C. W. Mak, X.-L. Zhao, Q.-M. Wang, G.-C. Guo, Coord. Chem. Rev. 2007, 251, 2311-2333
55. T. C. W. Mak, L. Zhao, Chem. Asian J. 2007, 2, 456-467
56. T. C. W. Mak, L. Zhao, X.-L. Zhao, Supramolecular Assembly of Silver(I) Complexes with Argentophilic, and, Silver.Carbon Interactions. In, The Importance of Pi-Interactions in Crystal Engineering-Frontiers in Crystal Engineering III (Eds.:, E. R. T. Tiekink, J. Zukerman-Schpector,), Wiley, Chichester, 2012, Chapter 3, pp. 323 -366.
57. S. R. Batten, R. Robson, Angew. Chem. 1998, 110, 1558-1595
58. Angew. Chem. Int. Ed. 1998, 37, 1460-1494
59. B. Moulton, M. J. Zaworotko, Chem. Rev. 2001, 101, 1629-1658
60. M. Eddaoudi, J. Kim, N. Rosi, D. Vodak, J. Wachter, M. O'Keeffe, O. Yaghi, Science 2002, 295, 469-472
61. C. Carlucci, C. Ciani, D. M. Proserpio, Coord. Chem. Rev. 2003, 246, 247-289
62. S. Kitagawa, R. Kitaura, S.-J. Noro, Angew. Chem. 2004, 116, 2388-2430
63. Angew. Chem. Int. Ed. 2004, 43, 2334-2375
64. N. W. Ockwig, O. Delgardo-Friedrichs, M. Eddaoudi, D. B. Moler, H. Li, B. Chen, T. M. Reineke, M. O'Keeffe, O. Yaghi, Acc. Chem. Res. 2005, 38, 176-182.
65. S.-Q. Zang, L. Zhao, T. C. W. Mak, Organometallics 2008, 27, 2396-2398
66. S.-Q. Zang, T. C. W. Mak, Inorg. Chem. 2008, 47, 7094-7105
67. S.-Q. Zang, J. Han, T. C. W. Mak, Organometallics 2009, 28, 2677-2683.
68. L. Zhao, W.-Y. Wong, T. C. W. Mak, Chem. Eur. J. 2006, 12, 4865-4872
69. L. Zhao, M. Du, T. C. W. Mak, Chem. Asian J. Chem. Asian. J. 2007, 2, 1240-1257.
70. G.-C. Guo, G.-D. Zhou, T. C. W. Mak, J. Am. Chem. Soc. 1999, 121, 3136-3141
71. G.-C. Guo, G.-D. Zhou, Q.-G. Wang, T. C. W. Mak, Angew. Chem. 1998, 110, 652-654
72. Angew. Chem. Int. Ed. 1998, 37, 630-632
73. Q.-G. Wang, T. C. W. Mak, J. Am. Chem. Soc. 2001, 123, 1501-1502
74. Q.-M. Wang, T. C. W. Mak, Angew. Chem. 2001, 113, 1164-1167
75. Angew. Chem. Int. Ed. 2001, 40, 1130-1133
76. Q.-M. Wang, T. C. W. Mak, Chem. Commun. 2001, 807-808.
77. K.-M. Chi, C.-T. Lin, S.-M. Peng, G.-H. Lee, Organometallics 1996, 15, 2660-2663.
78. T. Nishinaga, T. Kawamura, K. Komatsu, Chem. Commun. 1998, 2263-2264.
79. M. Iyoda, T. Horino, F. Takahashi, M. Hasegawa, M. Yoshida, Y. Kuwatani, Tetrahedron Lett. 2001, 42, 6883-6886.
80. P. Schulte, U. Behrens, J. Organomet. Chem. 1998, 563, 235-249.
81. R. Gleiter, T. von Hirschheydt, F. Rominger, Eur. J. Inorg. Chem. 2000, 2127-2130
82. R. Koschabek, R. Gleiter, F. Rominger, Eur. J. Inorg. Chem. 2006, 609-620
83. A. Kunze, R. Gleiter, F. Rominger, Eur. J. Inorg. Chem. 2006, 621-627.
84. H. V. R. Dias, J. A. Flores, J. Wu, P. Kroll, J. Am. Chem. Soc. 2009, 131, 11249-11255.
85. C. Janiak, J. Chem. Soc. Dalton Trans. 2000, 3885-3896.
86. H. V. R. Dias, Z. Wang, W. Jin, Inorg. Chem. 1997, 36, 6205-6215
87. H. V. R. Dias, X. Wang, Dalton Trans. 2005, 2985-2987
88. H. V. R. Dias, J. Wu, X. Wang, K. Rangan, Inorg. Chem. 2007, 46, 1960
89. X. Kou, H. V. R. Dias, Dalton Trans. 2009, 7529-7536.
90. I. Krossing, A. Reisinger, Angew. Chem. 2003, 115, 5903-5906
91. Angew. Chem. Int. Ed. 2003, 42, 5725-5728
92. A. Reisinger, N. Trapp, I. Krossing, Organometallics 2007, 26, 2096-2105
93. A. Reisinger, N. Trapp, C. Knapp, D. Himmel, F. Breher, H. Rüegger, I. Krossing, Chem. Eur. J. 2009, 15, 9505-9520.
94. P. D. Prince, P. J. Cragg, J. W. Steed, Chem. Commun. 1999, 1179-1180
95. P. Arya, A. Channa, P. J. Cragg, P. D. Prince, J. W. Steed, New J. Chem. 2002, 26, 440-447.
96. E. S. Chernyshova, R. Goddard, K.-R. Pörschke, Organometallics 2007, 26, 4872-4880
97. K. C. Lim, F. Marchetti, C. Pettinari, B. W. Skelton, B. J. Smith, A. H. White, Inorg. Chim. Acta 2006, 359, 1594-1602.
98. J. R. A. Cottam, P. J. Steel, J. Organomet. Chem. 2006, 691, 2286-2290.
99. S. Q. Liu, T. Kuroda-Sowa, H. Konaka, Y. Suenaga, M. Maekawa, T. Mizutani, G. L. Ning, M. Munakata, Inorg. Chem. 2005, 44, 1031-1036.
100. P. I. Richards, J. F. Bickley, R. Boomishankar, A. Steiner, Chem. Commun. 2008, 1656-1658.
101. M. Munakata, L. P. Wu, T. Kuroda-Sowa, M. Maekawa, Y. Suenaga, G. L. Ning, T. Kojima, J. Am. Chem. Soc. 1998, 120, 8610-8618
102. M. Munakata, L. P. Wu, G. L. Ning, T. Kuroda-Sowa, M. Maekawa, Y. Suenaga, N. Maeno, J. Am. Chem. Soc. 1999, 121, 4968-4976
103. M. Munakata, L. P. Wu, K. Sugimoto, T. Kuroda-Sowa, M. Maekawa, Y. Suenaga, N. Maeno, M. Fujita, Inorg. Chem. 1999, 38, 5674-5680
104. M. Munakata, G. L. Ning, Y. Suenaga, T. Kuroda-Sowa, M. Maekawa, T. Ohta, Angew. Chem. 2000, 112, 4729-4731
105. Angew. Chem. Int. Ed. 2000, 39, 4555-4557.
106. S.-L. Zheng, M.-L. Tong, S.-D. Tan, Y. Wang, J.-X. Shi, Y.-X. Tong, H. K. Lee, X.-M. Chen, Organometallics 2001, 20, 5319-5325.
107. A. P. Côté, A. G. K. H. Shimizu, Inorg. Chem. 2004, 43, 6663-6673.
108. E. L. Elliott, G. A. Hernández, A. Lindenc, J. S. Siegel, Org. Biomol. Chem. 2005, 3, 407-413.
109. R. Cacciapaglia, S. D. Stefano, L. Mandolini, P. Mencarelli, F. Ugozzoli, Eur. J. Org. Chem. 2008, 186-195.
110. H. C. Kang, A. W. Hanson, B. Eaton, V. Boekelheide, J. Am. Chem. Soc. 1985, 107, 1979-1985.
111. A. Ikeda, H. Tsuzuki, S. Shinkai, J. Chem. Soc. Perkin Trans. 2 1994, 2073-2080.
112. J. Gross, G. Harder, F. Vögtle, H. Stephan, K. Gloe, Angew. Chem. 1995, 107, 523-526
113. Angew. Chem. Int. Ed. Engl. 1995, 34, 481-484.
114. O. Struck, L. A. J. Chrisstoffels, R. J. W. Lugtenberg, W. Verboom, G. J. van Hummel, S. Harkema, D. N. Reinhoudt, J. Org. Chem. 1997, 62, 2487-2493.
115. H.-P. Wu, C. Janiak, G. Rheinwald, H. Lang, J. Chem. Soc. Dalton Trans. 1999, 183-190.
116. B. P. Hay, V. S. Bryantsev, Chem. Commun. 2008, 2417-2428
117. T. J. Mooibroek, C. A. Black, P. Gamez, J. Reedijk, Cryst. Growth Des. 2008, 8, 1082-1093
118. I. A. Gural'skiy, D. Escudero, A. Frontera, P. V. Solntsev, E. B. Rusanov, A. N. Chernega, H. Krautscheidd, K. V. Domasevitch, Dalton Trans. 2009, 2856-2864
119. O. B. Berrymanab, D. W. Johnson, Chem. Commun. 2009, 3143-3153.
120. G. M. Sheldrick, SADABS: Program for Empirical Absorption Correction of Area Detector Data; University of Göttingen: Göttingen, Germany (1996).
121. G. M. Sheldrick, SHELXTL 5.10 for Windows Structure Determination Software Programs; Bruker Analytical X-ray Systems, Inc.; Madison, WI, 1997.