Consequences of the one-electron reduction and photoexcitation of unsymmetric bis-imidazolium salts

Chemistry - A European Journal

Volumn 18, Issue 34, 2012, Pages 10677-10688

  Gierz, Verena ^b   Melomedov, Jascha ^a   Förster, Christoph ^a   Deißler, Christine ^c   Rominger, Frank ^c   Kunz, Doris ^b   Heinze, Katja ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

^b UNIVERSITY OF TÜBINGEN   (Germany)

^c UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

bis imidazolium salts; chromophores; excited state dynamics; photochemistry; redox chemistry

Indexed keywords

C-C BONDS; CARBENES; EPR SPECTROSCOPY; EXCITED-STATE DYNAMICS; FLUORESCENCE BEHAVIORS; GROUND-STATE MOLECULES; IMIDAZOLIUM; IN-SITU; N-HETEROCYCLIC CARBENES; ONE-ELECTRON REDUCTIONS; RADICAL CATIONS; REDOX CHEMISTRY; ROOM TEMPERATURE; SQUARE WAVE VOLTAMMETRY; TIME-DEPENDENT DENSITY; TWISTING MOTION; TWO-ELECTRON REDUCTION;

CHEMICAL BONDS; CHROMOPHORES; ELECTRONS; EMISSION SPECTROSCOPY; GROUND STATE; IRRADIATION; PHOTOCHEMICAL REACTIONS; PHOTOEXCITATION; SALTS; STEEL BEAMS AND GIRDERS; VOLTAMMETRY;

DENSITY FUNCTIONAL THEORY;

EID: 84865012723     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201200323     Document Type: Article

References (122)

1. M. Glasbeek, H. Zhang, Chem. Rev. 2004, 104, 1929-1954.
2. T. Weil, T. Vosch, J. Hofkens, K. Peneva, K. Müllen, Angew. Chem. 2010, 122, 9252-9278
3. Angew. Chem. Int. Ed. 2010, 49, 9068-9093
4. K. E. Sapsford, L. Berti, I. L. Medintz, Angew. Chem. 2006, 118, 4676-4704
5. Angew. Chem. Int. Ed. 2006, 45, 4562-4589
6. A. Mishra, R. K. Behera, P. K. Behera, B. K. Mishra, G. B. Behera, Chem. Rev. 2000, 100, 1973-2011
7. J. Fabian, Chem. Rev. 1992, 92, 1197-1226.
8. G. J. Hedley, A. Ruseckas, A. Harriman, I. D. W. Samuel, Angew. Chem. 2011, 123, 6764-6767
9. Angew. Chem. Int. Ed. 2011, 50, 6634-6637
10. J.-F. Huang, H. Luo, C. Liang, I.-W. Sun, G. A. Baker, S. Dai, J. Am. Chem. Soc. 2005, 127, 12784-12785
11. S. Wang, Y.-T. Chang, J. Am. Chem. Soc. 2006, 128, 10380-10381
12. B. S. Harrison, M. B. Ramey, J. R. Reynolds, K. S. Schanze, J. Am. Chem. Soc. 2000, 122, 8561-8562
13. H. Y. Woo, D. Korystov, A. Mikhailovsky, T.-Q. Nguyen, G. C. Bazan, J. Am. Chem. Soc. 2005, 127, 13794-13795
14. H. Y. Woo, B. Liu, B. Kohler, D. Korystov, A. Mikhailovsky, G. C. Bazan, J. Am. Chem. Soc. 2005, 127, 14721-14729.
15. A. J. Boydston, P. D. Vu, O. L. Dykhno, V. Chang, A. R. Wyatt II, A. S. Stockett, E. T. Ritschdorff, J. B. Shear, C. W. Bielawski, J. Am. Chem. Soc. 2008, 130, 3143-3156.
16. A. J. Boydston, C. S. Pecinovsky, S. T. Chao, C. W. Bielawski, J. Am. Chem. Soc. 2007, 129, 14550-14551.
17. J. W. Kamplain, V. M. Lynch, C. W. Bielawski, Org. Lett. 2007, 9, 5401-5404.
18. M. Ostermeier, C. Limberg, B. Ziemer, V. Karunakaran, Angew. Chem. 2007, 119, 5423-5426
19. Angew. Chem. Int. Ed. 2007, 46, 5329-5331.
20. J. A. Murphy, S. Zhou, D. W. Thomson, F. Schoenebeck, M. Mahesh, S. R. Park, T. Tuttle, L. E. A. Berlouis, Angew. Chem. 2007, 119, 5270-5275
21. Angew. Chem. Int. Ed. 2007, 46, 5178-5183.
22. J. A. Murphy, T. A. Khan, S. Zhou, D. W. Thomson, M. Mahesh, Angew. Chem. 2005, 117, 1380-1384
23. Angew. Chem. Int. Ed. 2005, 44, 1356-1360.
24. J. R. Ames, M. A. Houghtaling, D. L. Terrian, T. P. Mitchell, Can. J. Chem. 1997, 75, 28-36.
25. Z. Shi, V. Goulle, R. P. Thummel, Tetrahedron Lett. 1996, 37, 2357-2360.
26. Z. Shi, R. P. Thummel, Tetrahedron Lett. 1995, 36, 2741-2744.
27. Z. Shi, R. P. Thummel, J. Org. Chem. 1995, 60, 5935-5945.
28. Z. Shi, R. P. Thummel, Tetrahedron Lett. 1994, 35, 33-36.
29. M. J. S. Gynane, M. F. Lappert, P. I. Riley, P. Rivière, M. Rivière-Baudet, J. Organomet. Chem. 1980, 202, 5-12.
30. M. J. S. Gyname, M. F. Lappert, J. Organomet. Chem. 1976, 114, C 4 -C 6.
31. T. P. Vaid, J. Am. Chem. Soc. 2011, 133, 15838-15841.
32. G. T. Spence, C. J. Serpell, J. Sardinha, P. J. Costa, V. Félix, P. D. Beer, Chem. Eur. J. 2011, 17, 12955-12966.
33. P. Wasserscheid, T. Welton, (Eds.), Ionic Liquids in Synthesis, Wiley-VCH, Weinheim, 2008
34. N. V. Plechkova, K. R. Seddon, Chem. Soc. Rev. 2008, 37, 123-150
35. V. I. Pârvulescu, C. Hardacre, Chem. Rev. 2007, 107, 2615-2665
36. S.-g. Lee, Chem. Commun. 2006, 1049-1063
37. J. Dupont, Acc. Chem. Res. 2011, 44, 1223-1229
38. H. Olivier-Bourbigou, L. Magna, D. Morvan, Applied Catalysis A: General 2010, 373, 1-56
39. T. Welton, Chem. Rev. 1999, 99, 2071-2083.
40. J. B. Goodenough, Y. Kim, Chem. Mater. 2010, 22, 587-603.
41. S. Seki, Y. Kobayashi, H. Miyashiro, Y. Ohno, A. Usami, Y. Mita, N. Kihira, M. Watanabe, N. Terada, J. Phys. Chem. B 2006, 110, 10228-10230.
42. H. Choi, C. Baik, S. O. Kang, J. Ko, M. S. Kang, M. K. Nazeeruddin, M. Grätzel, Angew. Chem. 2008, 120, 333-336
43. Angew. Chem. Int. Ed. 2008, 47, 327-330.
44. D. Kuang, S. Uchida, R. Humphry-Baker, S. M. Zakeeruddin, M. Grätzel, Angew. Chem. 2008, 120, 1949-1953
45. Angew. Chem. Int. Ed. 2008, 47, 1923-1927.
46. V. A. Cocalia, K. E. Gutowski, R. D. Rogers, Coord. Chem. Rev. 2006, 250, 755-764.
47. A. J. Arduengo III, R. L. Harlow, M. Kline, J. Am. Chem. Soc. 1991, 113, 361-363.
48. review on the synthesis of NHC complexes:, F. E. Hahn, M. C. Jahnke, Angew. Chem. 2008, 120, 3166-3216
49. Angew. Chem. Int. Ed. 2008, 47, 3122-3172
50. review on the synthesis of NHC precursors:, L. Benhamou, E. Chardon, G. Lavigne, S. Bellemin-Laponnaz, V. César, Chem. Rev. 2011, 111, 2705-2733.
51. M. Regitz, Angew. Chem. 1996, 108, 791-794
52. Angew. Chem. Int. Ed. Engl. 1996, 35, 725-728
53. W. A. Herrmann, C. Köcher, Angew. Chem. 1997, 109, 2256-2282
54. Angew. Chem. Int. Ed. Engl. 1997, 36, 2162-2187
55. A. J. Arduengo III, Acc. Chem. Res. 1999, 32, 913-921
56. D. Bourissou, O. Guerret, F. P. Gabbaï, G. Bertrand, Chem. Rev. 2000, 100, 39-92
57. T. Dröge, F. Glorius, Angew. Chem. 2010, 122, 7094-7107
58. Angew. Chem. Int. Ed. 2010, 49, 6940-6952.
59. W. A. Herrmann, Angew. Chem. 2002, 114, 1342-1363
60. Angew. Chem. Int. Ed. 2002, 41, 1290-1309
61. O. Kühl, Chem. Soc. Rev. 2007, 36, 592-607
62. V. Cesar, S. Bellemin-Laponnaz, L. H. Gade, Chem. Soc. Rev. 2004, 33, 619-636
63. O. Schuster, L. Yang, H. G. Raubenheimer, A. Albrecht, Chem. Rev. 2009, 109, 3445-3478
64. A. T. Biju, N. Kuhl, F. Glorius, Acc. Chem. Res. 2011, 44, 1182-1195.
65. L. Mercs, M. Albrecht, Chem. Soc. Rev. 2010, 39, 1903-1912
66. M. C. Deblock, M. J. Panzner, C. A. Tessier, C. L. Cannon, W. J. Youngs, in N-Heterocyclic Carbenes (Ed:, S. Díez-González,), The Royal Society of Chemistry, Cambridge, 2011, pp. 119-133
67. I. J. B. Lin, C. S. Vasam, Can. J. Chem. 2005, 83, 812-825.0
68. Y. Wang, G. H. Robinson, Dalton Trans. 2012, 41, 337-345
69. M. Yamashita, Angew. Chem. 2010, 122, 2524-2526
70. Angew. Chem. Int. Ed. 2010, 49, 2474-2475.
71. N. Kuhn, R. Fawzi, T. Kratz, M. Steimann, G. Henkel, Phosphorus Sulfur Silicon Relat. Elem. 1996, 112, 225-233
72. J. J. Weigand, K.-O. Feldmann, F. D. Henne, J. Am. Chem. Soc. 2010, 132, 16321-16323
73. P. Bissinger, H. Braunschweig, A. Damme, R. D. Dewhurst, T. Kupfer, K. Radacki, K. Wagner, J. Am. Chem. Soc. 2011, 133, 19044-19047
74. M. Y. Abraham, Y. Wang, X. Yuzhong, W. P. Yaoming, H. F. Schaefer, P. V. R. Schleyer, G. H. Robinson, J. Am. Chem. Soc. 2011, 133, 8874-8876.
75. M. F. Lappert, J. Organomet. Chem. 1988, 358, 185-214.
76. H.-W. Wanzlick, E. Schikora, Angew. Chem. 1960, 72, 494.
77. F. E. Hahn, L. Wittenbecher, D. Le Van, R. Fröhlich, Angew. Chem. 2000, 112, 551-554
78. Angew. Chem. Int. Ed. 2000, 39, 541-544.
79. Y. Liu, P. E. Lindner, D. M. Lemal, J. Am. Chem. Soc. 1999, 121, 10626-10627.
80. T. A. Taton, P. Chen, Angew. Chem. 1996, 108, 1098-1100
81. Angew. Chem. Int. Ed. Engl. 1996, 35, 1011-1013.
82. D. Kunz, C. Deißler, V. Gierz, F. Rominger, T. Oeser, Z. Naturforsch. 2010, 65b, 861-872.
83. F. Vollmer, W. Rettig, E. Birckner, J. Fluoresc. 1994, 4, 65-69.
84. A. O. Doroshenko, Theor. Exp. Chem. 2002, 38, 135-155.
85. N. Kuhn, G. Weyers, D. Bläser, R. Boese, Z. Naturforsch. 2001, 56b, 1235-1237.
86. H. Meerwein, W. Florian, N. Schön, G. Stopp, Liebigs Ann. Chem. 1961, 641, 1-39.
87. K. Hafner, G. Schulz, K. Wagner, Liebigs Ann. Chem. 1964, 678, 39-53.
88. D. Kunz, E. O. Johnsen, B. Monsler, F. Rominger, Chem. Eur. J. 2008, 14, 10909-10914.
89. D. W. Karkhanis, L. Field, Phosphorus Sulfur Relat. Elem. 1985, 22, 49-57
90. P. S. Athey, G. E. Kiefer, J. Org. Chem. 2002, 67, 4081-4085.
91. W. Tyrra, D. Naumann, H. Pohl, I. Pantenburg, Z. Anorg. Allg. Chem. 2003, 629, 1039-1043.
92. M. Nonnenmacher, D. Kunz, F. Rominger, T. Oeser, J. Organomet. Chem. 2005, 690, 5647-5653
93. b) M. Nonnenmacher, D. Kunz in ", Modeling of Molecular Properties ", P. Comba (Ed.), Chapter 22, p. 349-363, Wiley-VCH, Weinheim, 2011.
94. H. A. Bent, Chem. Rev. 1961, 61, 275-311.
95. M. V. Baker, D. H. Brown, V. J. Hesler, B. W. Skelton, A. H. White, Organometallics 2007, 26, 250-252.
96. N. Nagel, H. Bock, P. Eller, Z. Kristallogr. 2000, 215, 39-44.
97. M. Lemke, F. Knoch, H. Kirsch, J. Salbeck, Chem. Ber. 1995, 128, 131-136.
98. H. Bock, K. Ruppert, K. Merzweiler, D. Fenske, H. Goesmann, Angew. Chem. 1989, 101, 1715-1717
99. Angew. Chem. Int. Ed. Engl. 1989, 28, 1684-1685.
100. D. Enders, K. Breuer, G. Raabe, J. Simonet, A. Ghanimi, H. B. Stegmann, J. H. Teles, Tetrahedron Lett. 1997, 38, 2833-2836.
101. T. Ramnial, I. McKenzie, B. Gorodetsky, E. M. W. Tsang, J. A. C. Clyburne, Chem. Commun. 2004, 1054-1055.
102. N. G. Connelly, W. E. Geiger, Chem. Rev. 1996, 96, 877-910.
103. I. A. Shkrob, T. W. Marin, S. D. Chemerisov, J. L. Hatcher, J. F. Wishart, J. Phys. Chem. B 2011, 115, 3889-3902.
104. I. A. Shkrob, J. Phys. Chem. B 2010, 114, 368-375.
105. C. N. Sherren, C. Mu, M. I. Webb, I. McKenzie, B. M. McCollum, J.-C. Brodovitch, P. W. Percival, T. Storr, K. R. Seddon, J. A. C. Clyburne, C. J. Walsby, Chem. Sci. 2011, 2, 2173-2177.
106. J. C. Walton, M. M. Brahmi, J. Monot, L. Fensterbank, M. Malacria, D. P. Curran, E. Lacôte, J. Am. Chem. Soc. 2011, 133, 10312-10321.
107. U. Siemeling, C. Färber, M. Leibold, C. Bruhn, P. Mücke, R. F. Winter, B. Sarkar, M. von Hopffgarten, G. Frenking, Eur. J. Inorg. Chem. 2009, 4607-4612.
108. E. Çetinkaya, P. B. Hitchcock, H. Küçükbay, M. F. Lappert, S. Al-Juaid, J. Organomet. Chem. 1994, 481, 89-95.
109. M. Kasha, Faraday Discuss. 1950, 9, 14-19.
110. G. Swiatkowski, R. Menzel, W. Rapp, J. Lumin. 1987, 37, 183-189.
111. G. Grabner, K. Rechthaler, G. Köhler, J. Phys. Chem. A 1998, 102, 689-696.
112. M. Barboiu, L. Prodi, M. Montalti, N. Zaccheroni, N. Kyritsakas, J.-M. Lehn, Chem. Eur. J. 2004, 10, 2953-2959.
113. K. Heinze, M. Schlenker, Eur. J. Inorg. Chem. 2005, 66-71.
114. T. Muraoka, K. Kinbara, Y. Kobayashi, T. Aida, J. Am. Chem. Soc. 2003, 125, 5612-5613.
115. V. Balzani, A. Credi, M. Venturi, Moleular Devices and Machines, Wiley-VCH Weinheim, 2008.
116. E. R. Kay, D. A. Leigh, F. Zerbetto, Angew. Chem. 2007, 119, 72-196
117. Angew. Chem. Int. Ed. 2007, 46, 72-191.
118. C. A. Parker, T. J. Joyce, Trans. Faraday Soc. 1966, 62, 2785-2792.
119. G. M. Sheldrick, Bruker Analytical X-ray Instruments Inc., Madison, Wisconsin (USA) 2008.
120. G. M. Sheldrick, Acta Cryst. 2008, A64, 112-122.
121. Gaussian 09, Revision A.02, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian, Inc., Wallingford CT, 2009.
122. V. Barone, in Recent Advances in Density Functional Methods; (Ed.: D. P. Chong) World Scientific: Singapore, 1995; Part 1.