Conformational effects of bay substituents on optical, electrochemical and dynamic properties of perylene bisimides: Macrocyclic derivatives as effective probes

Chemistry - A European Journal

Volumn 13, Issue 26, 2007, Pages 7395-7409

  Osswald, Peter ^a   Würthner, Frank ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Dyes pigments; Dynamic properties; Fluorescence; Optical properties; Perylene bisimide

Indexed keywords

CONFORMATIONS; DERIVATIVES; DYES; ELECTROCHEMICAL PROPERTIES; FLUORESCENCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTICAL PROPERTIES; SYNTHESIS (CHEMICAL);

DYNAMIC PROPERTIES; ELECTRON TRANSFER; PERYLENE BISIMIDE;

AROMATIC COMPOUNDS;

EID: 34548730244     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200700601     Document Type: Article

References (101)

1. a) G. Seybold, G. Wagenblast, Dyes Pigm. 1987, 11, 303-317;
2. b) G. Seybold, A. Stange (BASF AG), Ger. Pat., DE 3545004, 1987 (Chem. Abstr. 1988, 108, 77134c).
3. a) F. Würthner, Chem. Commun. 2004, 1564-1579;
4. b) A. C. Grimsdale, K. Müllen, Angew. Chem. 2005, 117, 5732-5772;
5. Angew. Chem. Int. Ed. 2005, 44, 5592-5629;
6. c) F. Würthner, Pure Appl. Chem. 2006, 78, 2341-2350;
7. d) M. R. Wasielewski, J. Org. Chem. 2006, 71, 5051-5066.
8. R. Gvishi, R. Reisfeld, Z. Burshstein, Chem. Phys. Lett. 1993, 213, 338-344.
9. a) T. D. M. Bell, S. Habuchi, S. Masuo, I. Österling, K. Müllen, P. Tinnefeld, M. Sauer, M. van der Auweraer, J. Hofkens, F. C. De Schryver, Aust. J. Chem. 2004, 57, 1169-1173;
10. b) A. Margineanu, J. Hofkens, M. Cotlet, S. Habuchi, A. Stefan. J. Qu, C. Kohl, K. Müllen, J. Vercammen, Y. Engelborghs, T. Gensch, F. C. De Schryver, J. Phys. Chem. B 2004, 108, 12242-12251;
11. c) F. C. De Schryver, T. Vosch, M. Cotlet, M. van der Auweraer, K. Müllen, J. Hofkens, Acc. Chem. Res. 2005, 38, 514-522;
12. d) E. Lang, F. Würthner, J. Köhler, ChemPhysChem 2005, 6, 935-941;
13. E. Lang, F. Würthner, J. Köhler, ChemPhysChem 2006, 7, 292.
14. For OLEDs, see: a) P. Ranke, I. Bleyl, J. Simmer, D. Haarer, A. Bacher, H. W. Schmidt, Appl. Phys. Lett. 1997, 71, 1332-1334;
15. b) P. Posch, M. Thelakkat, H.W. Schmidt, Synth. Met. 1999, 102, 1110-1112;
16. c)F. Würthner, C. Thalacker, S. Diele, C. Tschierske, Chem. Eur. J. 2001, 7, 2245-2253;
17. d) L. Fan, W. Zhu, J. Li, H. Tian, Synth. Met. 2004, 145, 203-210; for PLEDs, see:
18. e) C. Ego, D. Marsitzky, S. Becker, J. Zhang, A. C. Grimsdale, K. Müllen, J. D. MacKenzie, C. Silva, R. H. Friend, J. Am. Chem. Soc. 2003, 125, 437-443.
19. J. Baggerman, D. C. Jagesar, R. E. Vallée, J. Hofkens, F. C. De Schryver, F. Schelhase, F. Vögtle, A. M. Brouwer, Chem. Eur. J. 2007, 13, 1291-1299.
20. a) F. Würthner, A. Sautter, D. Schmidt, P. J. A. Weber, Chem. Eur. J. 2001, 7, 894-902;
21. b) C.-C. You, F. Würthner, J. Am. Chem. Soc. 2003, 125, 9716-9725;
22. c) C.-C. You, C. Hippius, M. Grüne, F. Würthner, Chem. Eur. J. 2006, 12, 7510-7519.
23. C. Addicott, I. Österling, T. Yamamoto, K. Müllen, P. J. Stang, J. Org. Chem. 2005, 70, 797-801.
24. a) R. Dobrawa, M. Lysteska, P. Ballester, M. Grüne, F. Würthner, Macromolecules 2005, 38, 1315-1325;
25. b) Y. Li, N. Wang, H. Gan, H. Liu, H. Li, Y. Li, X. He, C. Huang, S. Cui, S. Wang, D. Zhu, J. Org. Chem. 2005, 70, 9686-9692.
26. a) F. Würthner, B. Hanke, M. Lysetska, G. Lambright, G. S. Harms, Org. Lett. 2005, 7, 967-970; for organogels based on diaryloxy-substituted perylene bisimides, see :
27. b) K. Sugiyasu, N. Fujita, S. Shinkai, Angew. Chem. 2004, 116, 1249-1253;
28. Angew. Chem. Int. Ed. 2004, 43, 1229-1233;
29. c) Y. Liu, Y. Li, H. Gan, H. Liu, Y. Li, J. Zhuang, F. Lu, D. Zhu, J. Org. Chem. 2004, 69, 9049-9054.
30. a) Y. Liu, J. Zhuang, H. Liu, Y. Li, F. Lu, H. Gan, T. Xiu, N. Wang, X. He, D. Zhu, ChemPhysChem 2004, 5, 1210-1215;
31. b) C. Hippius, F. Schlosser, M. O. Vysotsky, V. Böhmer, F. Würthner, J. Am. Chem. Soc. 2006, 128, 3870-3871; for examples of diaryloxy-substituted perylene bisimides, see:
32. c) A. S. Lukas, Y. Zhao, S. E. Miller, M. R. Wasielwski, J. Phys. Chem. B 2002, 106, 1299-1306;
33. d) M. J. Ahrens, L. E. Sinks, B. Rybtchinski, W. Liu, B. A. Xones, J. M. Giaimo, A. V. Gusev, A. J. Goshe, D. M. Tiede, M. R. Wasielwski; J. Am. Chem. Soc. 2004, 126, 8284-8294.
34. a) D. Liu, S. De Feyter, M. Cotlet, A. Stefan, U.-M. Wiesler, A. Herrmann, D. Grebel-Koehler, J. Qu, K. Müllen, F. C. De Schryver, Macromolecules 2003, 36, 5918-5925;
35. b) J. Qu, N. G. Pschirer, D. Liu, A. Stefan, F. C. De Schryver, K. Müllen, Chem. Eur. J. 2004, 10, 528-537;
36. c) C.-C. You, C. R. Sana-Möller, F. Würthner, Chem. Commun. 2004, 2030-2031;
37. d) J. Pan, W. Zhu, S. Li, W. Zeng, Y. Cao, H. Tian, Polymer 2005, 46, 7658-7669;
38. e) J. Pan, W. Zhu, S. Li, J. Xu, H. Tian, Eur. J. Org. Chem. 2006, 986-1001;
39. f) M. D. Yilmaz, O. A. Bozdemir, E. U. Akkaya, Org. Lett. 2006, 8, 2871-2873; for a 1,7-disubstituted perylene bisimde, see:
40. g) T. Ishi-i, K.-i. Murakami, Y. Imai, S. Mataka, J. Org. Chem. 2006, 71, 5752-5760.
41. a) A. P. H. J. Schenning, J. v. Herrikhuyzen, P. Jonkheijm, Z. Chen, F. Würthner, E. W. Meijer, J. Am. Chem. Soc. 2002, 124, 10252-10253;
42. b) E. H. A. Beckers, S. C. J. Meskers, A. P. H. J. Schenning, Z. Chen, F. Würthner, P. Marsal, D. Beljonne, J. Cornil, R. A. J. Janssen, J. Am. Chem. Soc. 2006, 128, 649-657;
43. c) E. H. A. Beckers, Z. Chen, S. C. J. Meskers, P. Jonkheijm, A. P. H. J. Schenning, X.-Q. Li, P. Osswald, F. Würthner, R. A. J. Janssen, J. Phys. Chem. B 2006, 110, 16967-16978.
44. a) C.-C. You, F. Würthner, Org. Lett. 2004, 6, 2401-2404;
45. b) A. Prodi, C. Chiroboli, F. Scandola, E. Iengo, E. Alessio, R. Dobrawa, F. Würthner, J. Am. Chem. Soc. 2005, 127, 1454-1462;
46. c) N. Wang, F. Lu, C. Huang, Y. Li, M. Yuan. X. Liu, H. Liu, L. Gan, L. Jiang, D. Zhu, J. Poly. Sci. A 2006, 44, 5863-5874; for examples of diaryloxy-substituted perylene bisimides, see :
47. d) T. van der Boom, R. T. Hayes, Y. Zhao, P. J. Bushard, E. A. Weiss, M. R. Wasielewski, J. Am. Chem. Soc. 2002, 124, 9582-9590;
48. e) X. He, H. Liu, Y. Li, Y. Liu, F. Lu, Y. Li, D. Zhu, Macromol. Chem. Phys. 2005, 206, 2199-2205;
49. f) S. Xiao, M. E. El-Khouly, Y. Li, Z. Gan, H. Liu, L. Xiang, Y. Araki, O. Ito, D. Zhu, J. Phys. Chem. B 2005, 109, 3658-3667.
50. B. K. Kaletas, R. Dobrawa, A. Sautter, F. Würthner, M. Zimine, L. De Cola, R. M. Williams, J. Phys. Chem. A 2004, 108, 1900-1909.
51. a) Y. Liu, S. Xiao, H. Li, Y. Li, H. Liu. F. Lu, J. Zhuang, D. Zhu, J. Phys. Chem. B 2004, 108, 6256-6260;
52. b) J. Hua, F. Ding F. S. Meng, H. Tian, Chin. Chem. Lett. 2004, 15, 1373-1376;
53. c) J. Hua, F. Meng, F. Ding, F. Li, H. Tian, J. Mater. Chem. 2004, 14, 1849-1853; for examples of diaryloxy-substituted perylene bisimides, see:
54. d) Y. Liu, N. Wang. Y. Li, H. Liu, Y. Li, J. Xiao, X. Xu, C. Huang. S. Cui, D. Zhu, Macromolecules 2005, 38, 4880-4887;
55. e) J. Zhuang, W. Zhou, X. Li, Y. Li, N. Wang, X. He, H. Liu, Y. Li, L. Jiang, C. Huang, S. Cui, S. Wang, D. Zhu, Tetrahedron 2005, 61, 8686-8693.
56. a) M. A. Abdalla, J. Bayer, J. O. Rädler, K. Müllen, Angew. Chem. 2004, 116, 4057-4060;
57. Angew. Chem. Int. Ed. 2004, 43, 3967-3970;
58. b) C. Kohl, T. Weil, J. Qu, K. Müllen, Chem. Eur. J. 2004, 10, 5297-5310;
59. c) S. Krauß, M. Lysetska, F. Würthner, Lett. Org. Chem. 2005, 2, 349-353.
60. J. Ren. X.-L. Zhao, Q.-C. Wang, C.-F. Ku. D.-H. Qu, C.-P. Chang, H. Tian, Dyes Pigm. 2005, 64, 193-200.
61. J. Hofkens, T. Vosch, M. Maus, F. Köhn, M. Cotlet, T. Weil, A. Herrmann, K. Müllen, F. C. De Schryver, Chem. Phys. Lett. 2001, 333, 255-263.
62. A. Sautter, C. Thalacker, F. Würthner, Angew. Chem. 2001, 113, 4557-4560;
63. Angew. Chem. Int. Ed. 2001, 40, 4425-4428.
64. a) M. Cotlet, S. Masuo, M. Lor, E. Fron, M. van der Auweraer, K. Müllen, X. Hofkens, F. C. De Schryver, Angew. Chem. 2004, 116, 6242-6246;
65. Angew. Chem. Int. Ed. 2004, 43, 6116-6120;
66. b) C. Flors, I. Oesterling, E. Fron, G. Schweitzer, M. Sliwa, A. Herrmann, M. van der Auweraer, F. C. De Schryver, K. Müllen, J. Hofkens, J. Phys. Chem. C 2007, 111, 4861-4870; for a recent comparison of different diarylsubstituted perylene bisimides, see:
67. c) C.-C. Chao, M.-k. Leung, Y. O. Su, K.-Y. Chiu, T.-H. Lin, S.-J. Shieh, S.-C. Lin, J. Org. Chem. 2005, 70, 4323-4331.
68. A part of this work has been communicated: P. Osswald, D. Leusser, D. Stalke, F. Würthner, Angew. Chem. 2005, 117, 254-257;
69. Angew. Chem. Int. Ed. 2005, 44, 250-253.
70. S. Hien, PhD Thesis, University of Regensburg (Germany), 1995.
71. a) U. Lüning, M. Müller, Chem. Ber. 1990, 123, 643-645;
72. b) G. Ferguson, A. J. Lough, A. Notti, S. Pappalardo, M. F. Parasi, A. Petringa, J. Org. Chem. 1998, 63, 9703-9710;
73. c) J. A. Wisner, P. D. Beer, M. G. B. Drew, Angew. Chem. 2001, 113, 3718-3721;
74. Angew. Chem. Int. Ed. 2001, 40, 3610-3612;
75. for a review on macrocyclisation, see: d) P. Knops, N. Sendhoff, H. B. Mekelburger, F. Vögtle, Top. Curr. Chem. 1992, 161, 1-36.
76. a) B. Dietrich, P. Viout, J.-M. Lehn, Macrocyclic Chemistry, Wiley VCH, Weinheim, 1993:
77. b) A. Ostrowicki, E. Koepp, F. Vögtle, Top. Curr. Chem. 1992, 161, 31-61.
78. a) W. L. Mattice, Macromolecules 1979, 12, 944-948;
79. b) M. A. Winnik, Chem. Rev. 1981, 81, 491-524.
80. M. Hesse, H. Meier, B. Zeeh, Spectroscopic Methods in Organic Chemistry, Thieme, Stuttgart, 1997, pp. 88-100.
81. K. Müllen, W. Heinz, F.-G. Klärner, W. R. Roth, I. Kindermann, O. Adamczak, M. Wette, J. Lex, Chem. Ber. 1990, 123. 2349-2371.
82. a) I. Petterson, K. Gundertofte, J. Comput. Chem. 1991, 12, 839-843;
83. b) C. Etzlstorfer, H. Falk, N. Müller, Monatsh. Chem. 1993, 124, 431-439;
84. c) C. Etzlstorfer, H. Falk, N. Müller, W. Schmitzberger, U. G. Wagner, Monatsh. Chem. 1993, 124, 751-761:
85. d) C. Etzlstorfer, H. Falk, Monatsh. Chem. 1993, 124, 1031-1039;
86. e) S. S. Yilmaz, R. Abbasoglu, B. Hazer, J. Mol. Model. 2003, 9, 230-234.
87. C.-C. You, F. Würthner, J. Am. Chem. Soc. 2003, 125, 9716-9725.
88. a) D. Rehm, A. Weller, Ber. Bunsenges. Phys. Chem. 1969, 73, 834-845;
89. b) A. Weller, Z. Phys. Chem. (Muenchen Ger.) 1982, 133, 93-98;
90. c) N. P. Redmore, I. V. Rubtsov, M. J. Therien, J. Am. Chem. Soc. 2003, 125, 8769-8778;
91. d) M. W. Holman, R. Liu, L. Zang, P. Yan, S. A. DiBenedetto, R. D. Bowers, D. A. Adams, J. Am. Chem. Soc. 2004, 126, 16126-16133.
92. C.-C. You, R. Dobrawa, C. R. Saha-Möller, F. Würthner, Top. Curr. Chem. 2005, 258, 39-82.
93. C. Vande Velde, E. Bultinck, K. Tersago, C. Van Alsenoy, F. Blockhuys, Int. J. Quantum Chem. 2007, 107, 670-679.
94. T. H. Goodwin, M. Przybylska, X. M. Robertson, Acta Crystallogr. 1950, 3, 279-284.
95. H. J. Talberg, Acta Chem. Scand. 1978, 32, 373-374.
96. The electrochemical potentials in dichloromethane have been taken from the following literature and referred to ferrocene by applying the potential of ferrocene (+ 0.52 V) vs SCE : T. Higuchi, C. Satake, M. Hirobe, J. Am. Chem. Soc. 1995, 117, 8879-8880.
97. a) D. Marquis, J.-P. Desvergne, H. Bouas-Laurent, J. Org. Chem. 1995, 60, 7984-7996;
98. b) S. Chatti, M. Bortolussi, A. Loupy, Tetrahedron 2000, 56, 5877-5883.
99. J. R. Lakowitz, Principles of Flourescence Spectroscopy, Kluwer Academic/Plenum, New York, 2nd ed., 1999, pp. 52-55.
100. A. J. Fry in Laboratory Techniques in Electroanalytical Chemistry (Eds.: P. T. Kessing, W. R. Heineman), Marcel Dekker, New York, 2nd ed., 1996, p. 481.
101. C. J. Adam, S. J. Clark, G. J. Ackland, J. Crain, Phys. Rev. E 1997, 55, 5641-5650.