Control of light-promoted [2+2] cycloaddition reactions by a remote ancillary regulatory group that is covalently attached to rhenium rectangles

Chemistry - A European Journal

Volumn 18, Issue 49, 2012, Pages 15714-15721

  Lu, Zong Zhan ^a,b   Lee, Chung Chou ^a   Velayudham, Murugesan ^a   Lee, Li Wei ^a   Wu, Jing Yun ^a   Kuo, Ting Shen ^c   Lu, Kuang Lieh ^a  

^a INSTITUTE OF CHEMISTRY   (Taiwan)

^b NATIONAL CENTRAL UNIVERSITY   (Taiwan)

^c NATIONAL TAIWAN NORMAL UNIVERSITY   (Taiwan)

Author keywords

cycloaddition; photochemistry; rectangles; rhenium; self assembly

Indexed keywords

COORDINATION COMPOUNDS; CYCLOADDITION REACTION; CYCLOBUTANES; HYDROTHERMAL CONDITIONS; METHYL GROUP; PHOTOCYCLOADDITION REACTION; REACTION CENTER; RECTANGLES; SINGLE CRYSTAL X-RAY DIFFRACTION; SPECTROSCOPIC TECHNIQUE;

BUTANE; CYCLOADDITION; ETHYLENE; FUNCTIONAL GROUPS; IRRADIATION; LIGANDS; PHOTOCHEMICAL REACTIONS; RHENIUM; SELF ASSEMBLY; X RAY DIFFRACTION;

GEOMETRY;

LIGAND; ORGANOMETALLIC COMPOUND; RHENIUM;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; LIGHT; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; LIGANDS; LIGHT; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; RHENIUM; X-RAY DIFFRACTION;

EID: 84870040711     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201202301     Document Type: Article

References (94)

1. W. R. Browne, B. L. Feringa, Nat. Nanotechnol. 2006, 1, 25-35 and references therein
2. J. Vicario, M. Walko, A. Meetsma, B. L. Feringa, J. Am. Chem. Soc. 2006, 128, 5127-5135
3. A. N. Sokolov, D.-K. Bučar, J. Baltrusaitis, S. X. Gu, L. R. MacGillivray, Angew. Chem. 2010, 122, 4369-4373
4. Angew. Chem. Int. Ed. 2010, 49, 4273-4277.
5. S. Takeuchi, S. Ruhman, T. Tsuneda, M. Chiba, T. Taketsugu, T. Tahara, Science 2008, 322, 1073-1077
6. M. Irie, S. Kobatake, M. Horichi, Science 2001, 291, 1769-1772
7. N. Koumura, R. W. J. Zijlstra, R. A. van Delden, N. Harada, B. L. Feringa, Nature 1999, 401, 152-155
8. R. Ballardini, V. Balzani, A. Credi, M. T. Gandolfi, M. Venturi, Acc. Chem. Res. 2001, 34, 445-455.
9. E. Gindensperger, H. Köppel, C. Daniel, Chem. Commun. 2010, 46, 8225-8227
10. H. Nishihara, Coord. Chem. Rev. 2005, 249, 1468-1475
11. A. O. T. Patrocínio, N. Y. M. Iha, Inorg. Chem. 2008, 47, 10851-10857
12. V. W.-W. Yam, Y. Yang, J. Zhang, B. W.-K. Chu, N. Zhu, Organometallics 2001, 20, 4911-4918.
13. K. Tanaka, F. Toda, Chem. Rev. 2000, 100, 1025-1074
14. D. G. Amirsakis, M. A. Garcia-Garibay, S. J. Rowan, J. F. Stoddart, A. J. P. White, D. J. Williams, Angew. Chem. 2001, 113, 4386-4391
15. Angew. Chem. Int. Ed. 2001, 40, 4256-4261
16. J. J. Vittal, Coord. Chem. Rev. 2007, 251, 1781-1795.
17. F. Li, J. Zhuang, G. Jiang, H. Tang, A. Xia, L. Jiang, Y. Song, Y. Li, D. Zhu, Chem. Mater. 2008, 20, 1194-1196
18. J. Svoboda, B. König, Chem. Rev. 2006, 106, 5413-5430
19. S. Yamada, N. Uematsu, K. Yamashita, J. Am. Chem. Soc. 2007, 129, 12100-12101
20. L. R. MacGillivray, CrystEngComm 2004, 6, 77-78
21. T. Friščić, D. M. Drab, L. R. MacGillivray, Org. Lett. 2004, 6, 4647-4650
22. L. R. MacGillivray, J. Org. Chem. 2008, 73, 3311-3317
23. W. L. Leong, J. J. Vittal, Chem. Rev. 2011, 111, 688-764.
24. A. M. P. Peedikakkal, L. L. Koh, J. J. Vittal, Chem. Commun. 2008, 441-443
25. M. Nagarathinam, J. J. Vittal, Chem. Commun. 2008, 438-440
26. Y. Hill, A. Briceño, Chem. Commun. 2007, 3930-3932
27. G. S. Papaefstathiou, T. Friščić, L. R. MacGillivray, J. Am. Chem. Soc. 2005, 127, 14160-14161
28. D. B. Varshney, X. Gao, T. Friščić, L. R. MacGillivray, Angew. Chem. 2006, 118, 662-666
29. Angew. Chem. Int. Ed. 2006, 45, 646-650
30. X.-Y. Wang, Z.-M. Wang, S. Gao, Chem. Commun. 2007, 1127-1129
31. J. F. Eubank, V. Ch. Kravtsov, M. Eddaoudi, J. Am. Chem. Soc. 2007, 129, 5820-5821
32. A. Michaelides, S. Skoulika, M. G. Siskos, Chem. Commun. 2004, 2418-2419.
33. K. Tanaka, F. Toda, E. Mochizuki, N. Yasui, Y. Kai, I. Miyahara, K. Hirotsu, Angew. Chem. 1999, 111, 3733-3736
34. Angew. Chem. Int. Ed. 1999, 38, 3523-3525
35. F. Toda, Top. Curr. Chem. 2005, 254, 1-40
36. L. R. MacGillivray, G. S. Papaefstathiou, T. Friščić , D. B. Varshney, T. D. Hamilton, Top. Curr. Chem. 2004, 248, 201-221
37. M. Nagarathinam, A. M. P. Peedikakkal, J. J. Vittal, Chem. Commun. 2008, 5277-5288
38. A. M. P. Peedikakkal, J. J. Vittal, Chem. Eur. J. 2008, 14, 5329-5334.
39. Y.-F. Han, Y.-J. Lin, W.-G. Jia, G.-L. Wang, G.-X. Jin, Chem. Commun. 2008, 1807-1809
40. J. A. Tsui, B. T. Sterenberg, Organometallics 2009, 28, 4906-4908
41. W.-Z. Zhang, Y.-F. Han, Y.-J. Lin, G.-X. Jin, Organometallics 2010, 29, 2842-2849
42. W.-B. Yu, Y.-F. Han, Y.-J. Lin, G.-X. Jin, Chem. Eur. J. 2011, 17, 1863-1871
43. W. L. Nie, G. Erker, G. Kehr, R. Froehlich, Angew. Chem. 2004, 116, 313-317
44. Angew. Chem. Int. Ed. 2004, 43, 310-313.
45. I. G. Georgiev, L. R. MacGillivray, Chem. Soc. Rev. 2007, 36, 1239-1248
46. G. S. Papaefstathiou, Z. Zhong, L. Geng, L. R. MacGillivray, J. Am. Chem. Soc. 2004, 126, 9158-9159
47. L. R. MacGillivray, CrystEngComm 2002, 4, 37-41
48. N. Shan, W. Jones, Tetrahedron Lett. 2003, 44, 3687-3689.
49. J. Nishimura, Y. Nakamura, Y. Hayashida, T. Kudo, Acc. Chem. Res. 2000, 33, 679-686.
50. H. Hopf, Angew. Chem. 2003, 115, 2928-2931
51. Angew. Chem. Int. Ed. 2003, 42, 2822-2825
52. J. S. Sinninghe Damsté, M. Strous, W. I. C. Rijpstra, E. C. Hopmans, J. A. J. Geenevasen, A. C. T. van Duin, L. A. van Niftrik, M. S. M. Jetten, Nature 2002, 419, 708-712
53. A. Matsumoto, Top. Curr. Chem. 2005, 254, 263-305
54. X. Gao, T. Friščić, L. R. MacGillivray, Angew. Chem. 2004, 116, 234-238
55. Angew. Chem. Int. Ed. 2004, 43, 232-236.
56. A. M. P. Peedikakkal, J. J. Vittal, Inorg. Chem. 2010, 49, 10-12
57. M. Nagarathinam, J. J. Vittal, Angew. Chem. 2006, 118, 4443-4447
58. Angew. Chem. Int. Ed. 2006, 45, 4337-4341
59. N. L. Toh, M. Nagarathinam, J. J. Vittal, Angew. Chem. 2005, 117, 2277-2281
60. Angew. Chem. Int. Ed. 2005, 44, 2237-2241.
61. G. S. Papaefstathiou, I. G. Georgiev, T. Friščić, L. R. MacGillivray, Chem. Commun. 2005, 3974-3976
62. D. Liu, Z.-G. Ren, H.-X. Li, J.-P. Lang, N.-Y. Li, B. F. Abrahams, Angew. Chem. 2010, 122, 4877-4880
63. Angew. Chem. Int. Ed. 2010, 49, 4767-4770.
64. Q. Chu, D. C. Swenson, L. R. MacGillivray, Angew. Chem. 2005, 117, 3635-3638
65. Angew. Chem. Int. Ed. 2005, 44, 3569-3572
66. R. Santra, K. Biradha, Cryst. Growth Des. 2010, 10, 3315-3320.
67. J. Y. Lee, S. J. Hong, C. Kim, Y. Kim, Dalton Trans. 2005, 3716-3718.
68. D.-K. Bučar, G. S. Papaefstathiou, T. D. Hamilton, Q. L. Chu, I. G. Georgiev, L. R. MacGillivray, Eur. J. Inorg. Chem. 2007, 4559-4568
69. T. Friščić, L. R. MacGillivray, Chem. Commun. 2003, 1306-1307
70. L. R. MacGillivray, J. L. Reid, J. A. Ripmeester, J. Am. Chem. Soc. 2000, 122, 7817-7818
71. T. D. Hamilton, G. S. Papaefstathiou, L. R. MacGillivray, J. Am. Chem. Soc. 2002, 124, 11606-11607.
72. I. G. Georgiev, D.-K. Bučar, L. R. MacGillivray, Chem. Commun. 2010, 46, 4956-4958.
73. L. R. MacGillivray, G. S. Papaefstathiou, T. Friščić , T. D. Hamilton, D.-K. Bučar, Q. Chu, D. B. Varshney, I. G. Georgiev, Acc. Chem. Res. 2008, 41, 280-291
74. M. H. Mir, L. L. Koh, G. K. Tan, J. J. Vittal, Angew. Chem. 2010, 122, 400-403
75. Angew. Chem. Int. Ed. 2010, 49, 390-393
76. G. S. Papaefstathiou, L. R. MacGillivray, Angew. Chem. 2002, 114, 2174-2177
77. Angew. Chem. Int. Ed. 2002, 41, 2070-2073.
78. M. Sathiyendiran, R.-T. Liao, P. Thanasekaran, T.-T. Luo, N. S. Venkataramanan, G.-H. Lee, S.-M. Peng, K.-L. Lu, Inorg. Chem. 2006, 45, 10052-10054.
79. K. D. Benkstein, J. T. Hupp, C. L. Stern, Angew. Chem. 2000, 112, 3013-3015
80. Angew. Chem. Int. Ed. 2000, 39, 2891-2893
81. R.-T. Liao, W.-C. Yang, P. Thanasekaran, C.-C. Tsai, M. Sathiyendiran, Y.-H. Liu, T. Rajendran, H.-M. Lin, T.-W. Tseng, K.-L. Lu, Chem. Commun. 2008, 3175-3177.
82. G. M. Schmidt, J. Pure Appl. Chem. 1971, 27, 647-678.
83. A. Briceño, D. Leal, R. Atencio, G. D. de Delgado, Chem. Commun. 2006, 3534-3536.
84. V. Enkelmann, G. Wegner, K. Novak, K. B. Wagener, J. Am. Chem. Soc. 1993, 115, 10390-10391.
85. S. Ariel, S. Askari, J. R. Scheffer, J. Trotter, L. Walsh, J. Am. Chem. Soc. 1984, 106, 5726-5728
86. M. D. Cohen, G. M. J. Schmidt, F. I. Sonnt, J. Chem. Soc. 1964, 2000-2013.
87. L. Wang, Y.-C. Huang, Y. Liu, H.-K. Fun, Y. Zhang, J.-H. Xu, J. Org. Chem. 2010, 75, 7757-7768
88. J. H. Penn, L.-X. Gan, E. Y. Chan, P. D. Loesel, J. Org. Chem. 1989, 54, 601-606.
89. M. A. Fernandes, D. C. Levendis, C. B. de Koning, Cryst. Eng. 2001, 4, 215-231.
90. H. Greiving, H. Hopf, P. G. Jones, P. Bubenitschek, J. P. Desvergne, H. Bouas-Lauren, J. Chem. Soc. Chem. Commun. 1994, 1075-1076
91. Y. Xu, M. D. Smith, J. A. Krause, L. S. Shimizu, J. Org. Chem. 2009, 74, 4874.
92. G. M. Sheldrick, SHELXS-86, Program for Crystal Structure Determination, University of Göttingen, Göttingen, Germany, 1986.
93. G. M. Sheldrick, SHELX-97 (including SHELXS and SHELXL), University of Göttingen, Göttingen, Germany, 1997.
94. WINGX:, L. J. Farrugia, J. Appl. Crystallogr. 1999, 32, 837-838.