Localization/delocalization of charges in bay-linked perylene bisimides

Chemistry - A European Journal

Volumn 18, Issue 22, 2012, Pages 6764-6775

  Jiang, Wei ^a   Xiao, Chengyi ^a   Hao, Linxiao ^a   Wang, Zhaohui ^a   Ceymann, Harald ^b   Lambert, Christoph ^b   Di Motta, Simone ^c,d   Negri, Fabrizia ^c,d  

^a INSTITUTE OF CHEMISTRY   (China)

^b UNIVERSITY OF WÜRZBURG   (Germany)

^c UNIVERSITY OF BOLOGNA   (Italy)

^d INSTM   (Italy)

Author keywords

charge transfer; copper; cross coupling; perylenes bisimides; Ullmann reaction

Indexed keywords

ABSORPTION AND FLUORESCENCE SPECTROSCOPY; CONJUGATION EFFECTS; CROSS-COUPLINGS; CT BANDS; DEGREE OF INTERACTION; EXCITON COUPLING; HOMOCOUPLING; LOCALIZATION/DELOCALIZATION; MIXED VALENCE; PERYLENE BISIMIDES; PERYLENES; TIME-DEPENDENT; ULLMANN REACTION;

CHARGE TRANSFER; COPPER; DENSITY FUNCTIONAL THEORY; FLUORESCENCE SPECTROSCOPY; SPECTROELECTROCHEMISTRY;

ELECTRON TRANSITIONS;

EID: 84861552768     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201103954     Document Type: Article

References (94)

1. R. E. Martin, F. Diederich, Angew. Chem. 1999, 111, 1440
2. Angew. Chem. Int. Ed. 1999, 38, 1350
3. M. Gross, D. C. Müller, H. G. Nothofer, U. Scherf, D. Neher, C. Brauchle, K. Meerholz, Nature 2000, 405, 661
4. J. M. Tour, Chem. Rev. 1996, 96, 537
5. T. Dutta, K. B. Woody, S. R. Parkin, M. D. Watson, J. Gierschner, J. Am. Chem. Soc. 2009, 131, 17321
6. A. Tsuda, A. Osuka, Science 2001, 293, 79
7. M. Baumgarten, M. Müller, A. Bohnen, K. Müllen, Angew. Chem. 1992, 104, 482
8. Angew. Chem. Int. Ed. Engl. 1992, 31, 448
9. J. Wu, M. D. Watson, N. Tchebotareva, Z. Wang, K. Müllen, J. Org. Chem. 2004, 69, 8194.
10. A. Heckmann, C. Lambert, Angew. Chem. Int. Ed. 2012, 51, 326
11. J. Hankache, O. S. Wenger, Chem. Rev. 2011, 111, 5138.
12. J. L. Brédas, D. Beljonne, V. Coropceanu, J. Cornil, Chem. Rev. 2004, 104, 4971.
13. J. L. Brédas, G. B. Street, Acc. Chem. Res. 1985, 18, 309.
14. M. B. Robin, P. Day, Adv. Inorg. Chem. Radiochem. 1967, 9, 247.
15. B. S. Brunschwig, C. Creutz, Chem. Soc. Rev. 2002, 31, 168
16. S. F. Nelsen, Chem. Eur. J. 2000, 6, 581
17. K. D. Demadis, C. M. Hartshorn, T. J. Meyer, Chem. Rev. 2001, 101, 2655
18. J. P. Launay, C. Coudret, C. Hortholary, J. Phys. Chem. B 2007, 111, 6788.
19. R. A. Marcus, Pure Appl. Chem. 1997, 69, 13
20. R. A. Marcus, N. Sutin, Comments Inorg. Chem. 1986, 5, 119.
21. P. Chen, T. J. Meyer, Chem. Rev. 1998, 98, 1439
22. S. F. Nelsen, H. Q. Tran, J. Phys. Chem. A 1999, 103, 8139
23. B. S. Brunschwig, S. Ehrenson, N. Sutin, J. Phys. Chem. 1986, 90, 3657
24. S. F. Nelsen, D. A. Trieber, R. F. Ismagilov, Y. Teki, J. Am. Chem. Soc. 2001, 123, 5684.
25. K. Hunger, Industrial Dyes: Chemistry, Properties, Applications, Wiley-VCH, Weinheim, 2003.
26. F. Würthner, Chem. Commun. 2004, 1564
27. T. van der Boom, R. T. Hayer, Y. Zhao, P. J. Bushar, E. A. Weiss, M. R. Wasielewski, J. Am. Chem. Soc. 2002, 124, 9582
28. Y. Che, A. Datar, K. Balakrishnan, L. Zang, J. Am. Chem. Soc. 2007, 129, 7234
29. C. Addicott, I. Oesterling, T. Yamamoto, K. Müllen, P. J. Stang, J. Org. Chem. 2005, 70, 797
30. X. He, H. Liu, Y. Li, S. Wang, Y. Li, N. Wang, J. Xiao, X. Xu, D. Zhu, Adv. Mater. 2005, 17, 2811.
31. M. P. O'Neil, M. P. Niemczyk, W. A. Svec, D. Gosztda, G. L. Gaines, M. R. Wasielewski, Science 1992, 257, 63
32. J. J. Dittmer, E. A. Marseglia, R. H. Friend, Adv. Mater. 2000, 12, 1270
33. B. A. Jones, M. J. Ahrens, M. Yoon, A. Facchetti, T. J. Marks, M. R. Wasielewski, Angew. Chem. 2004, 116, 6523
34. Angew. Chem. Int. Ed. 2004, 43, 6363
35. B. A. Jones, A. Facchetti, M. R. Wasielewski, T. J. Marks, J. Am. Chem. Soc. 2007, 129, 15259
36. Y. Che, H. Huang, M. Xu, C. Zhang, B. R. Bunes, X. Yang, L. Zang, J. Am. Chem. Soc. 2011, 133, 1087.
37. X. Zhan, Z. Tan, B. Domercq, Z. An, X. Zhang, S. Barlow, Y. Li, D. Zhu, B. Kippelen, S. R. Marder, J. Am. Chem. Soc. 2007, 129, 7246
38. J. H. Oh, W. Y. Lee, T. Noe, W. C. Chen, M. Könemann, Z. Bao, J. Am. Chem. Soc. 2011, 133, 4204.
39. C. Kohl, S. Becker, K. Müllen, Chem. Commun. 2002, 2778
40. N. G. Pschirer, C. Kohl, F. Nolde, J. Qu, K. Müllen, Angew. Chem. 2006, 118, 1429
41. Angew. Chem. Int. Ed. 2006, 45, 1401.
42. Q. Yan, D. Zhao, Org. Lett. 2009, 11, 3426
43. Z. Yuan, Y. Xiao, X. Qian, Chem. Commun. 2010, 46, 2772.
44. J. Hassan, M. Sévignon, C. Gozzi, E. Schulz, M. Lemaire, Chem. Rev. 2002, 102, 1359
45. D. Ma, Q. Cai, Acc. Chem. Res. 2008, 41, 1450
46. S. V. Ley, A. W. Thomas, Angew. Chem. 2003, 115, 5558
47. Angew. Chem. Int. Ed. 2003, 42, 5400
48. I. P. Beletskaya, A. V. Cheprakov, Coord. Chem. Rev. 2004, 248, 2337
49. F. Monnier, M. Taillefer, Angew. Chem. 2009, 121, 7088
50. Angew. Chem. Int. Ed. 2009, 48, 6954
51. Y. Li, L. Tan, Z. Wang, H. Qian, Y. Shi, W. Hu, Org. Lett. 2008, 10, 529
52. Y. Li, C. Li, W. Yue, W. Jiang, R. Kopecek, J. Qu, Z. Wang, Org. Lett. 2010, 12, 2374.
53. Y. Zhen, W. Yue, Y. Li, W. Jiang, S. Di Motta, E. Di Donato, F. Negri, S. Ye, Z. Wang, Chem. Commun. 2010, 46, 6078.
54. H. Qian, Z. Wang, W. Yue, D. Zhu, J. Am. Chem. Soc. 2007, 129, 10664
55. Y. Shi, H. Qian, Y. Li, W. Yue, Z. Wang, Org. Lett. 2008, 10, 2337
56. H. Qian, F. Negri, C. Wang, Z. Wang, J. Am. Chem. Soc. 2008, 130, 17970
57. H. Qian, W. Yue, Y. Zhen, S. Di Motta, E. Di Donato, F. Negri, J. Qu, W. Xu, D. Zhu, Z. Wang, J. Org. Chem. 2009, 74, 6275
58. Y. Zhen, H. Qian, J. Xiang, J. Qu, Z. Wang, Org. Lett. 2009, 11, 3084
59. Y. Zhen, C. Wang, Z. Wang, Chem. Commun. 2010, 46, 1926
60. Y. Wu, Y. Zhen, Y. Ma, R. Zheng, Z. Wang, H. Fu, J. Phys. Chem. Lett. 2010, 1, 2499
61. H. Wang, H. Su, H. Qian, Z. Wang, X. Wang, A. Xia, J. Phys. Chem. A 2010, 114, 9130.
62. W. Jiang, Y. Li, W. Yue, Y. Zhen, J. Qu, Z. Wang, Org. Lett. 2010, 12, 228.
63. A. D. Schlüter, M. Löffler, V. Enkelmann, Nature 1994, 368, 831
64. C. Xu, A. Wakamiya, S. Yamaguchi, J. Am. Chem. Soc. 2005, 127, 1638
65. U. Scherf, K. Müllen, Makromol. Chem. Rapid Commun. 1991, 12, 489
66. Y. Wu, J. Zhang, Z. Fei, Z. Bo, J. Am. Chem. Soc. 2008, 130, 7192.
67. C. You, R. Dobrawa, C. R. S. Möller, F. Würthner, Top. Curr. Chem. 2005, 258, 39.
68. M. Kasha, H. R. Rawls, M. Ashraf El-Bayoumi, Pure Appl. Chem. 1965, 11, 371.
69. N. S. Hush, Coord. Chem. Rev. 1985, 64, 135
70. N. S. Hush, Electrochim. Acta 1968, 13, 1005
71. S. F. Nelsen, R. F. Ismagilov, D. A. Trieber, Science 1997, 278, 846.
72. F. Cisnetti, R. Ballardini, A. Credi, M. T. Gandolfi, S. Masiero, F. Negri, S. Pieraccini, G. P. Spada, Chem. Eur. J. 2004, 10, 2011.
73. V. Coropceanu, J. Cornil, D. A. da Silva, Y. Olivier, R. Silbey, J. L. Bredas, Chem. Rev. 2007, 107, 926.
74. E. Di Donato, R. P. Fornari, S. Di Motta, Y. Li, Z. Wang, F. Negri, J. Phys. Chem. B 2010, 114, 5327
75. S. Di Motta, M. Siracusa F. Negri, J. Phys. Chem. C 2011, 115, 20754.
76. Y. Geerts, H. Quante, H. Platz, R. Mahrt, M. Hopmeier, A. Bohm, K. Müllen, J. Mater. Chem. 1998, 8, 2357
77. H. Quante, K. Müllen, Angew. Chem. 1995, 107, 1487
78. Angew. Chem. Int. Ed. Engl. 1995, 34, 1323
79. L. Fan, Y. Xu, H. Tian, Tetrahedron Lett. 2005, 46, 4443
80. W. Qiu, S. Chen, X. Sun, Y. Liu, D. Zhu, Org. Lett. 2006, 8, 867.
81. T. Yanai, D. P. Tew, N. C. Handy, Chem. Phys. Lett. 2004, 393, 51.
82. M. Renz, K. Theilacker, C. Lambert, M. Kaupp, J. Am. Chem. Soc. 2009, 131, 16292
83. M. Kaupp, M. Renz, M. Parthey, M. Stolte, F. Würthner, C. Lambert, Phys. Chem. Chem. Phys. 2011, 13, 16973.
84. D. Jacquemin, V. Wathelet, E. A. Perpète, C. Adamo, J. Chem. Theory Comput. 2009, 5, 2420
85. F. Santoro, V. Barone, R. Improta, J. Comput. Chem. 2008, 29, 957.
86. M. J. G. Peach, P. Benfield, T. Helgaker, D. J. Tozer, J. Chem. Phys. 2008, 128, 044118-1 -8.
87. D. Fazzi, E. V. Canesi, F. Negri, C. Bertarelli, C. Castiglioni, ChemPhysChem 2010, 11, 3685
88. S. Di Motta, F. Negri, D. Fazzi, C. Castiglioni, E. V. Canesi, J. Phys. Chem. Lett. 2010, 1, 3334.
89. A. Kikuchi, H. Ito, J. Abe, J. Phys. Chem. B 2005, 109, 19448
90. P. M. Lahti, A. S. Ichimura, J. A. Sanborn, J. Phys. Chem. A 2001, 105, 251.
91. S. Portmann, H. P. Lüthi, Molekel, version 4.3, Chimia 2000, 54, 766.
92. M. J. Frisch et al., Gaussian 09, revision A.02, Gaussian, Inc., Wallingford CT, 2009.
93. W. Liu, V. Settels, P. H. P. Harbach, A. Dreuw, R. F. Fink, B. Engels, J. Comput. Chem. 2011, 32, 1971
94. H. Zhao, J. Pfister, V. Settels, M. Renz, M. Kaupp, V. C. Dehm, F. Würthner, R. F. Fink, B. Engels, J. Am. Chem. Soc. 2009, 131, 15660.