Coreéxtended terrylene diimide on the bay region: Synthesis and optical and electrochemical properties

Organic Letters

Volumn 13, Issue 24, 2011, Pages 6484-6487

  Bai, Qianqian ^a   Gao, Baoxiang ^a   Ai, Qi ^a   Wu, Yonggang ^a   Ba, Xinwu ^a  

^a HEBEI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANTHRACENE DERIVATIVE; FUSED HETEROCYCLIC RINGS; IMIDE; TERRYLENE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROCHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

ANTHRACENES; ELECTROCHEMISTRY; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; IMIDES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXIDATION-REDUCTION;

EID: 84055223941     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202775b     Document Type: Article

References (60)

1. (a)Demmig, S.; Langhals,H.Chem.Ber. 1988, 121, 225.
2. (b)Herbst, W.; Hunger, K. Industrial Organic Pigments, 2nd completely revised ed.; Wiley-VCH: Weinheim, 1997.
3. (c) Zollinger, H. Color Chemistry, 3rd ed.; VCH: Weinheim, 2003.
4. (d) Würthner, F. Chem. Commun. 2004, 1564.
5. (a) Kaiser, T. E.; Wang, H.; Stepanenko, V.;Würthner, F. Angew. Chem., Int. Ed. 2007, 46, 5541.
6. (b) Zhang, X.; Chen, Z.; Würthner, F. J. Am. Chem. Soc. 2007, 129, 4886.
7. (c) Zhang, X.; Rehm, S.; Safont- Sempere, M. M.; Würthner, F. Nat. Chem. 2009, 1, 623.
8. (d) Gebers, J.; Rolland, D.; Frauenrath, H. Angew. Chem., Int. Ed. 2009, 48, 4480.
9. (e) Krieg, E.; Shirman, E.; Weissman, H.; Shimoni, E.; Wolf, S. G.; Pinkas, I.;Rybtchinski, B. J.Am.Chem. Soc. 2009, 131, 14365.
10. (f) Baram, J.; Shirman, E.; Ben-Shitrit, N.; Ustinov, A.; Weissman, H.; Pinkas, I.; Wolf, S. G.; Rybtchinski, B. J. Am. Chem. Soc. 2008, 130, 14966.
11. (a) Zhan, X.; Facchetti, A.; Barlow, S.; Marks, T. J.; Ratner, M. A.; Wasielewski, M. R.; Marder, S. R. Adv. Mater. 2011, 23, 268.
12. (b) Huang, C.; Barlow, S.; Marder, S. R. J. Org. Chem. 2011, 76, 2386.
13. (a) Nagao, Y.; Misono, T. Dyes Pigm. 1984, 5, 171.
14. (b) Haugland, R. P. Handbook of Fluorescent Probes and Research Chemicals; Molecular Probes Inc.: Eugene, 1989.
15. (c) Chen, Z.; Lohr, A.; Saha-Möller, C. R.; Würthner, F. Chem. Soc. Rev. 2009, 38, 564.
16. (a)Würthner, F.; Thalacker, C.; Diele, S.; Tschierske,C. Chem.; Eur. J. 2001, 7, 2245.
17. (b) Chen, Z.; Baumeister, U.; Tschierske, C.; Würthner, F. Chem.;Eur. J. 2007, 13, 450.
18. (c) Dehm, V.; Chen, Z.; Baumeister, U.; Prins, P.; Siebbeles, L. D. A.; Würthner, F. Org. Lett. 2007, 9, 1085.
19. (d) Xu, Y.; Leng, S.; Xue, C.; Sun, R.; Pan, J.; Ford, J.; Jin, S. Angew. Chem., Int. Ed. 2007, 46, 3896.
20. (e) Kato, T.; Yasuda, T.; Kamikawa, Y.; Yoshio, M. Chem. Commun. 2009, 729.
21. (f) Wicklein, A.; Lang, A.; Muth, M.; Thelakkat, M. J. Am. Chem. Soc. 2009, 131, 14442.
22. (g)Wicklein, A.;Kohn,P.;Ghazaryan,L.; Thurn-Albrecht, T.;Thelakkat, M. Chem. Commun. 2010, 46, 2328.
23. (a) Rohr, U.; Schlichting, P.; Böhm, A.; Gross, M.; Meerholz, K.; Bräuchle, C.; Müllen, K. Angew. Chem., Int. Ed. 1998, 37, 1434.
24. (b) Rohr, U.; Kohl, C.; Müllen, K.; van de Draats, A.; Warman, J. J. Mater. Chem. 2001, 11, 1789.
25. (c) An, Z.; Yu, J.; Domercq, B.; Jones, S. C.; Barlow, S.; Kippelen, B.; Marder, S. R. J. Mater. Chem. 2009, 19, 6688.
26. (a) Wegner, H. A.; Scott, L. T.; de Meijere, A. J. Org. Chem. 2003, 68, 883.
27. (b) Müller, S.; Müllen, K. Chem. Commun. 2005, 4045.
28. (c) Avlasevich, Y.; Li, C.; Müllen, K. J. Mater. Chem. 2010, 20, 3814.
29. (a) Franceschin, M.; Alvino, A.; Casagrande, V.; Mauriello, C.; Pascucci, E.; Savino, M.; Ortaggi, G.; Bianco, A. Bioorg. Med. Chem. 2007, 15, 1848.
30. (b) Franceschin, M.; Alvino, A.; Ortaggi, G.; Bianco, A. Tetrahedron Lett. 2004, 45, 9015.
31. (a) Herrmann, A.; Müllen, K. Chem. Lett. 2006, 35, 978.
32. (b) Samorí, P.; Severin, N.; Simpson, C. D.; Müllen, K.; Rabe, J. P. J. Am. Chem. Soc. 2002, 124, 9454.
33. (a) Nolde, F.; Pisula, W.;Müller, S.; Kohl, C.;Müllen, K. Chem. Mater. 2006, 18, 3715.
34. (b) An, Z.; Yu, J.; Domercq, B.; Jones, S. C.; Barlow, S.; Kippelen, B.; Marder, S. R. J. Mater. Chem. 2009, 19, 6688.
35. (a) Eversloh, C. L.; Li, C.;Müllen, K. Org. Lett. 2011, 13, 4148.
36. (b) Li, Y.; Xu, L.; Liu, T.; Yu, Y.; Liu, H.; Li, Y.; Zhu, D. Org. Lett. 2011, 13, 5692.
37. (a) Qian, H.; Liu, C.; Wang, Z.; Zhu, D. Chem. Commun. 2006, 44, 4587.
38. (b) Choi, H.; Paek, S.; Song, J.; Kim, C.; Cho, N.; Ko, J. Chem. Commun. 2011, 47, 5509.
39. (a) Jiang, W.; Li, Y.; Yue, W.; Zhen, Y.; Qu, J.; Wang, Z. Org. Lett. 2010, 12, 228.
40. (b) Li, Y.; Li, Y.; Li, J.; Li, C.; Liu, X.; Yuan, M.; Liu, H.; Wang, S. Chem.;Eur. J. 2006, 12, 8378.
41. (a) Holtrup, F. O.; M̈uller, G. R. J.; Quante, H.; De Feyter, S.; De Schryver, F. C.;M̈ullen, K. Chem.;Eur. J. 1997, 2, 219.
42. (b) Weil, T.; Reuther, E.; Beer, C.; Müllen, K. Chem.;Eur. J. 2004, 10, 1398.
43. (c) Fron, E.; Puhl, L.; Oesterling, I.; Li, C.;Müllen, K.; De Schryver, F. C.; Hofkens, J.; Vosch, T. ChemPhysChem 2011, 12, 595.
44. (a) Jung, C.;Müller, B. K.; Lamb, D. C.; Nolde, F.;M̈ullen, K.; Br̈auchle, C. J. Am. Chem. Soc. 2006, 128, 5283.
45. (b) Jung, C.; Ruthardt, N.; Lewis, R.; Michaelis, J.; Sodeik, B.; Nolde, F.; Peneva, K.;M̈ullen, K.; Bräuchle, C. ChemPhysChem 2009, 10, 180.
46. (c) Davies, M.; Jung, C.; Wallis, P.; Schnitzler, T.; Li, C.; Müllen, K.; Bräuchle, C. Chem- PhysChem 2011, 12, 1588.
47. (a) Gao, B. X.; Li, H. X.; Liu, H. M.; Zhang, L. C.; Bai, Q. Q.; Ba, X. W. Chem. Commun. 2011, 47, 3894.
48. (b) Gao, B. X.; Xia, D. F.; Zhang, L. C.; Bai, Q. Q.; Bai, L. B.; Yang, T.; Ba, X. W. J. Mater. Chem. 2011, 21, 15975.
49. Eversloh, C. L.; Liu, Z.; Müller, B.; Stangl, M.; Li, C.; Müllen, K. Org. Lett. 2011, 13, 5528.
50. Nolde, F.; Qu, J.; Kohl, C.; Pschirer, N. G.; Reuther, E.;Müllen, K. Chem.;Eur. J. 2005, 11, 3959.
51. 3 (1.7 equiv per hydrogen to be removed) did not produce the completely closed CETDI 3, even after the reaction time was extended to 48 h. The formation of partially closed compound 6 is due to the hindrance induced by the twisting of the terrylene diimides 6.
52. Feng, X.; Wu, J.; Enkelmann, V.;Müllen, K. Org. Lett. 2006, 8, 1145.
53. (a) Hunter, C. A.; Sanders, J.K.M. J. Am. Chem. Soc. 1990, 112, 5525.
54. (b) Watson, M. D.; Debije, M. G.; Warman, J. M.; Müllen, K. J. Am. Chem. Soc. 2004, 126, 766.
55. (c) Gao, B. X.; Wang, M.; Cheng, Y. X.; Wang, L. X.; Jing, X. B.; Wang, F. S. J. Am. Chem. Soc. 2008, 130, 8297.
56. Cheng, Y. J.; Yang, S. H.; Hsu, C. S. Chem. Rev. 2009, 109, 5868.
57. (a) Agrawal, A. K.; Jenekhe, S. A. Chem. Mater. 1996, 8, 579.
58. (b) Yang, C. J.; Jenekhe, S. A. Macromolecules 1995, 28, 1180.
59. (c) Alam, M. M.; Jenekhe, S. A. J. Phys. Chem. B 2002, 106, 11172.
60. Lee, S. K.; Zu, Y.; Herrmann, A.; Geerts, Y.;Müllen, K.; Bard, A. J. J. Am. Chem. Soc. 1999, 121, 3513.