Photoswitchable N-heterocyclic carbenes: Using light to modulate electron-donating properties

Angewandte Chemie - International Edition

Volumn 50, Issue 44, 2011, Pages 10322-10326

  Neilson, Bethany M ^a   Lynch, Vincent M ^a   Bielawski, Christopher W ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

carbenes; cyclization; nitrogen heterocycles; photochromism; photoswitch

Indexed keywords

CARBENES; CHALCOGENS; ELECTROCYCLIC RINGS; ELECTRON DONATING PROPERTIES; ELECTRON-DONATING ABILITY; METAL ADDUCTS; N-HETEROCYCLIC CARBENES; NITROGEN HETEROCYCLES; PHOTO-INDUCED; PHOTO-SWITCHABLE; PHOTOCYCLIZATION REACTION; PHOTOSWITCH; UV IRRADIATION; VISIBLE LIGHT;

CARBON INORGANIC COMPOUNDS; CHLORINE COMPOUNDS; IRIDIUM; LIGANDS; PHOTOCHROMISM;

ORGANIC COMPOUNDS;

EID: 80054999132     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201105032     Document Type: Article

References (95)

1. For reviews on NHCs and their coordination chemistry, see: F. E. Hahn, M. C. Jahnke, Angew. Chem. 2008, 120, 3166-3216
2. Angew. Chem. Int. Ed. 2008, 47, 3122-3172
3. W. A. Herrmann, Angew. Chem. 2002, 114, 1342-1363
4. Angew. Chem. Int. Ed. 2002, 41, 1290-1309
5. D. Bourissou, O. Guerret, F. P. Gabbaï, G. Bertrand, Chem. Rev. 2000, 100, 39-91
6. W. A. Herrmann, C. Köcher, Angew. Chem. 1997, 109, 2256-2282
7. Angew. Chem. Int. Ed. Engl. 1997, 36, 2162-2187
8. S. Díez-González, N. Marion, S. P. Nolan, Chem. Rev. 2009, 109, 3612-3676
9. T. Dröge, F. Glorius, Angew. Chem. 2010, 122, 7094-7107
10. Angew. Chem. Int. Ed. 2010, 49, 6940-6952.
11. For studies of tuning the electron-donating ability of NHCs as a means to influence catalytic reactions, see: D. M. Khramov, E. L. Rosen, J. A. V. Er, P. D. Vu, V. M. Lynch, C. W. Bielawski, Tetrahedron 2008, 64, 6853-6862
12. M. D. Sanderson, J. W. Kamplain, C. W. Bielawski, J. Am. Chem. Soc. 2006, 128, 16514-16515
13. D. M. Khramov, V. M. Lynch, C. W. Bielawski, Organometallics 2007, 26, 6042
14. L. Benhamou, N. Vujkovic, V. César, H. Gornitzka, N. Lugan, G. Lavigne, Organometallics 2010, 29, 2616-2630
15. M. Süßner, H. Plenio, Chem. Commun. 2005, 5417-5419
16. V. Sashuk, L. H. Peeck, H. Plenio, Chem. Eur. J. 2010, 16, 3983-3993
17. T. W. Hudnall, J. P. Moerdyk, C. W. Bielawski, Chem. Commun. 2010, 46, 4288-4290
18. J. P. Moerdyk, C. W. Bielawski, Organometallics 2011, 30, 2278-2284
19. A. Fürstner, M. Alcarazo, H. Krause, C. W. Lehmann, J. Am. Chem. Soc. 2007, 129, 12676-12677
20. T. W. Hudnall, A. G. Tennyson, C. W. Bielawksi, Organometallics 2010, 29, 4569-4578
21. C. J. O'Brien, E. A. B. Kantchev, G. A. Chass, H. Niloufar, A. C. Hopkinson, M. G. Organ, D. H. Setiadi, T. Tang, D. Fan, Tetrahedron 2005, 61, 9723-9735.
22. For examples of switchable NHCs and related catalysts, see: A. G. Tennyson, V. M. Lynch, C. W. Bielawski, J. Am. Chem. Soc. 2010, 132, 9420-9429
23. M. Süßner, H. Plenio, Angew. Chem. 2005, 117, 7045-7048
24. Angew. Chem. Int. Ed. 2005, 44, 6885-6888
25. E. L. Rosen, C. D. Varnado, Jr., A. G. Tennyson, D. M. Khramov, J. W. Kamplain, D. H. Sung, P. T. Cresswell, V. M. Lynch, C. W. Bielawski, Organometallics 2009, 28, 6695-6706
26. L. H. Peeck, S. Leuthäusser, H. Plenio, Organometallics 2010, 29, 4339-4345
27. S. L. Balof, S. J. P'Pool, N. J. Berger, E. J. Valente, A. M. Shiller, H.-J. Schanz, Dalton Trans. 2008, 5791-5799
28. S. L. Balof, B. Yu, A. B. Lowe, Y. Ling, Y. Zhang, H.-J. Schanz, Eur. J. Inorg. Chem. 2009, 1717-1722
29. S. J. P'Pool, H.-J. Schanz, J. Am. Chem. Soc. 2007, 129, 14200-14212.
30. Photochromism: Molecules and Systems (Eds.:, H. Durr, H. Bouas-Laurent,), Elsevier, Amsterdam, 2003
31. Special Issue: "Photochromism: Memories and Switches" (Ed.: M. Irie), Chem. Rev. 2000, 100, 1683.
32. M. Irie, Chem. Rev. 2000, 100, 1685-1716
33. K. Matsuda, M. Irie, J. Photochem. Photobiol. C 2004, 169-182
34. H. Tian, S. Yang, Chem. Soc. Rev. 2004, 33, 85-97
35. H. Tian, S. Wang, Chem. Commun. 2007, 781-792
36. C. Yun, J. You, J. Kim, J. Huh, E. Kim, J. Photochem. Photobiol. C 2009, 10, 111-129
37. M. Akita, Organometallics 2011, 30, 43-51.
38. For an investigation of the photophysical properties of metal complexes supported by 1,3-dimethyl-4,5-dithienylimidazolylidenes, see: V. W.-W. Yam, J. K. Lee, C. Ko, N. Zhu, J. Am. Chem. Soc. 2009, 131, 912-913
39. P. H.-M. Lee, C.-C. Ko, N. Zhu, V. W.-W. Yam, J. Am. Chem. Soc. 2007, 129, 6058-6059.
40. A. R. Siamaki, D. A. Black, B. A. Arndtsen, J. Org. Chem. 2008, 73, 1135-1138.
41. In support of this hypothesis, ring-opened 4,5-dithienylimidazolium salts were found to be more electrophilic than their ring-closed isomers; see: G. Duan, N. Zhu, V. W.-W. Yam, Chem. Eur. J. 2010, 16, 13199-13209
42. T. Nakashima, M. Goto, S. Kawai, T. Kawai, J. Am. Chem. Soc. 2008, 130, 14570-14575.
43. Y. Odo, K. Matsuda, M. Irie, Chem. Eur. J. 2006, 12, 4283-4288
44. V. Lemieux, M. D. Spantulescu, K. K. Baldridge, N. R. Branda, Angew. Chem. 2008, 120, 5112-5115
45. Angew. Chem. Int. Ed. 2008, 47, 5034-5037
46. H. D. Samachetty, N. R. Branda, Chem. Commun. 2005, 2840
47. D. Sud, T. B. Norsten, N. R. Branda, Angew. Chem. 2005, 117, 2055-2057
48. Angew. Chem. Int. Ed. 2005, 44, 2019-2021
49. M. Herder, M. Pätzel, L. Grubert, Hecht, Chem. Commun. 2011, 47, 460-462
50. S. H. Kawai, S. L. Gilat, J. M. Lehn, Eur. J. Org. Chem. 1999, 2359-2366
51. V. Lemieux, S. Gauthier, N. R. Branda, Angew. Chem. 2006, 118, 6974-6978
52. Angew. Chem. Int. Ed. 2006, 45, 6820-6824
53. D. Sud, T. J. Wigglesworth, N. R. Branda, Angew. Chem. 2007, 119, 8163-8165
54. Angew. Chem. Int. Ed. 2007, 46, 8017-8019
55. H. D. Samachetty, V. Lemieux, N. R. Branda, Tetrahedron 2008, 64, 8292-8300
56. R. S. Stoll, S. Hecht, Angew. Chem. 2010, 122, 5176-5200
57. Angew. Chem. Int. Ed. 2010, 49, 5054-5075
58. T. Hirose, K. Matsuda, M. Irie, J. Org. Chem. 2006, 71, 7499-7508
59. T. Hirose, M. Irie, K. Matsuda, Adv. Mater. 2008, 20, 2137-2141
60. M. Singer, A. Jäschke, J. Am. Chem. Soc. 2010, 132, 8372-8377.
61. D. Sud, R. McDonald, N. R. Branda, Inorg. Chem. 2005, 44, 5960-5962
62. Y. Tanaka, A. Inagaki, M. Akita, Chem. Commun. 2007, 1169-1171
63. K. Motoyama, T. Koike, M. Akita, Chem. Commun. 2008, 5812-5814
64. Y. Tanaka, A. Inagaki, T. Koike, C. Lapinte, M. Akita, Chem. Eur. J. 2010, 16, 4762-4776
65. K. Uchida, A. Inagaki, M. Akita, Organometallics 2007, 26, 5030-5041.
66. For other examples of photochromic 4,5-diarylimidazolones, see:, M. M. Krayushkin, S. N. Ivanov, A. Y. Martynkin, B. V. Lichitsky, A. A. Dudinov, L. G. Vorontsova, Z. A. Starikova, B. M. Uzhinov, Russ. Chem. Bull. Int. Ed. 2002, 51, 1731-1736.
67. L. I. Belen'kii, V. Z. Shirinyan, G. P. Gromova, A. V. Kolotaev, Y. A. Strelenko, S. N. Tandura, A. N. Shumskii, M. M. Krayushkin, Chem. Heterocycl. Compd. 2003, 39, 1570-1578.
68. F. Toda, K. Tanaka, H. Tange, J. Chem. Soc. Perkin Trans. 1 1989, 1555-1556.
69. B. L. Benac, E. M. Burgess, A. J. Arduengo, Org. Synth. 1986, 64, 92.
70. CO typical of amides while that of 1 c was more characteristic of aliphatic ketones; see:, E. Pretsch, P. Buhlmann, M. Badertscher, Structure Determination of Organic Compounds: Tables of Spectral Data, 4 th ed., Springer, Berlin, 2009, pp. 310-324.
71. C. N. R. Rao, Chemical Applications of Infrared Spectroscopy, Academic Press, New York, 1963, pp. 298-303
72. M. Davies, J. Jones, J. Chem. Soc. 1958, 955-958.
73. R. B. Woodward, R. Hoffmann, The Conservation of Orbital Symmetry, Verlag Chemie, Weinheim, 1970.
74. The solid-state structure of 1 c was slightly disordered due to the existence of two enantiomers in the sample, with one having the S,S configuration at C6 and C7 and the other having the R,R configuration at the same atoms. See Supporting Information for additional discussion. Similar disorder has been observed in previously reported structures of ring-closed perfluorocyclopentene-based dithienylethenes; see: S. Kobatake, M. Yamada, T. Yamada, M. Irie, J. Am. Chem. Soc. 1999, 121, 8450-8456
75. M. Morimoto, M. Irie, J. Am. Chem. Soc. 2010, 132, 14172-14178
76. H. Choi, H. Lee, Y. Kang, E. Kim, S.-O. Kang, J. Ko, J. Org. Chem. 2005, 70, 8291-8297
77. M. Irie, T. Lifka, S. Kobatake, N. Kato, J. Am. Chem. Soc. 2000, 122, 4871-4876
78. S. Kobatake, K. Shibata, K. Uchida, M. Irie, J. Am. Chem. Soc. 2000, 122, 12135-12141
79. M. Irie, S. Kobatake, M. Horichi, Science 2001, 291, 1769-1772
80. M. Morimoto, S. Kobatake, M. Irie, Chem. Eur. J. 2003, 9, 621-627
81. M. Morimoto, S. Kobatake, M. Irie, Photochem. Photobiol. Sci. 2003, 2, 1088-1094
82. T. Kodani, K. Matsuda, T. Yamada, S. Kobatake, M. Irie, J. Am. Chem. Soc. 2000, 122, 9631-9637.
83. bur) were calculated for 1 o (30.1 %) and 1 c (30.2 %). The calculations were performed using the web application SamVca with Bondi radii scaled by 1.17, R=3.5 Å for the sphere radius, d=2.10 Å for the distance between C1 and O1, and s=0.05 Å for the mesh spacing; see:, A. Poater, B. Cosenza, A. Correa, S. Giudice, F. Ragone, V. Scarano, L. Cavallo, Eur. J. Inorg. Chem. 2009, 1759-1766.
84. A. R. Chianese, X. Li, M. C. Janzen, J. W. Faller, R. H. Crabtree, Organometallics 2003, 22, 1663-1667
85. H. M. J. Wang, I. J. B. Lin, Organometallics 1998, 17, 972-975.
86. R. A. Kelly III, H. Clavier, S. Giudice, N. M. Scott, E. D. Stevens, J. Bordner, I. Samardjiev, C. D. Hoff, L. Cavallo, S. P. Nolan, Organometallics 2008, 27, 202-210
87. C. A. Tolman, Chem. Rev. 1977, 77, 313-348.
88. Decarbonylation was observed by IR spectroscopy when 3 o was irradiated in acetonitrile or dichloromethane; see Supporting Information.: See Supporting Information for the UV/Vis spectral data accompanying the cyclization of 3 o to 3 c.: The conversion of 3 o to 3 c was calculated to be 18 % by IR spectroscopy after 10 min of irradiation at 297 nm. After 45 min of irradiation, the conversion was calculated to be 29 % by IR spectroscopy (see Supporting Information). These conversions are in accord with other reported photochromic DAE-containing metal complexes; see: S. Kume, H. Nishihara, Dalton Trans. 2008, 3260-3271
89. W. Tan, J. Zhou, F. Li, T. Yi, H. Tian, Chem. Asian J. 2011, 6, 1263-1268
90. The results reported herein demonstrate that the bonding characteristics of carbamides may be modulated using only electronics as opposed to stereoelectronic approaches; see: C. Chan, R. Heid, S. Zheng, J. Guo, B. Zhou, T. Furuuchi, S. J. Danishefsky, J. Am. Chem. Soc. 2005, 127, 4596-4598
91. J. Clayden, W. Moran, Angew. Chem. 2006, 118, 7276-7278
92. Angew. Chem. Int. Ed. 2006, 45, 7118-7120
93. K. Tani, B. M. Stoltz, Nature 2006, 441, 731-734
94. M. Szostak, L. Yao, V. W. Day, D. R. Powell, J. Aubé, J. Am. Chem. Soc. 2010, 132, 8836-8837
95. T. W. Hudnall, C. W. Bielawski, J. Am. Chem. Soc. 2009, 131, 16039-16041.