Facile synthesis of 1-bromo-7-alkoxyl perylene diimide dyes: Toward unsymmetrical functionalizations at the 1,7-positions

Tetrahedron Letters

Volumn 53, Issue 9, 2012, Pages 1094-1097

  Zhang, Xin ^a,c   Pang, Shufeng ^a   Zhang, Zhigang ^b,c   Ding, Xunlei ^d   Zhang, Shanlin ^c   He, Shenggui ^d   Zhan, Chuanlang ^c  

^a BEIJING INSTITUTE OF TECHNOLOGY   (China)

^b HEBEI NORMAL UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^c PEKING UNIVERSITY   (China)

^d INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

Nucleophile; Nucleophilic substitution; Perylene diimide; Unsymmetrical functionalization

Indexed keywords

1 BROMO 7 ALKOXYL PERYLENE DIIMIDE; 4 HYDROXYLPYRIDINE; ALKANOL; BROMINE; DYE; POTASSIUM CARBONATE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; NUCLEOPHILICITY; OPTICS; STOICHIOMETRY; SUBSTITUTION REACTION;

EID: 84862780167     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.12.080     Document Type: Article

References (40)

1. C.L. Zhan, and A.D.Q. Li Curr. Org. Chem. 15 2011 1314 1339
2. L. Zang, Y.K. Che, and J.S. Moore Acc. Chem. Res. 41 2008 1596 1608
3. M.R. Wasielewski J. Org. Chem. 71 2006 5051 5066
4. F. Würthner Chem. Commun. 2004 1564 1579
5. L. Zhu, W. Wu, M.-Q. Zhu, J.J. Han, J.K. Hurst, and A.D.Q. Li J. Am. Chem. Soc. 129 2007 3524 3526
6. K. Peneva, G. Mihov, F. Nolde, S. Rocha, J.-I. Hotta, K. Braeckmans, J. Hofkens, H. Uji-i, A. Herrmann, and K. Müllen Angew. Chem., Int. Ed. 47 2008 3372 3375
7. J.J. Han, W. Wang, and A.D.Q. Li J. Am. Chem. Soc. 128 2006 672 673
8. S.M. Melnikov, E.K.L. Yeow, H. Uji-i, M. Cotlet, K. Müllen, F.C. De Schryver, J. Enderlein, and J. Hofkens J. Phys. Chem. B 111 2007 708 719
9. C.W. Tang Appl. Phys. Lett. 48 1986 183 185
10. L. Schmidt-Mende, A. Fechtenkötter, K. Müllen, E. Moons, R.H. Friend, and J.D. MacKenzie Science 293 2001 1119 1122
11. P. Peumans, S. Uchida, and S.R. Forrest Nature 425 2003 158 162
12. B.A. Jones, M.J. Ahrens, M.-H. Yoon, A. Facchetti, T.J. Marks, and M.R. Wasielewski Angew. Chem., Int. Ed. 43 2004 6363 6366
13. R. Schmidt, J.H. Oh, Y.-S. Sun, M. Deppisch, A.-M. Krause, K. Radacki, H. Braunschweig, M. Könemann, P. Erk, Z. Bao, and F. Würthner J. Am. Chem. Soc. 131 2009 6215 6228
14. R.T. Weitz, K. Amsharov, U. Zschieschang, E.B. Villas, D.K. Goswami, M. Burghard, H. Dosch, M. Jansen, K. Kern, and H. Klauk J. Am. Chem. Soc. 130 2008 4637 4645
15. K. Balakrishnan, A. Datar, T. Naddo, J. Huang, Oitker, R.M. Yen, J. Zhao, and L. Zang J. Am. Chem. Soc. 128 2006 7390 7398
16. W. Wang, L.-S. Li, G. Helms, H.-H. Zhou, and A.D.Q. Li J. Am. Chem. Soc. 125 2003 1120 1121
17. R. Zhang, Z. Wang, Y. Wu, H. Fu, and J. Yao Org. Lett. 10 2008 3065 3068
18. M. Rodríguez-Morgade, T. Torres, C. Atienza-Castellanos, and D.M. Guldi J. Am. Chem. Soc. 128 2006 15145 15154
19. C.-C. You, and F. Würthner J. Am. Chem. Soc. 125 2003 9716 9725
20. L. Fan, Y. Xu, and H. Tian Tetrahedron Lett. 46 2005 4443 4447
21. X. He, H. Liu, Y. Li, S. Wang, Y. Li, N. Wang, J. Xiao, X. Xu, and D. Zhu Adv. Mater. 17 2005 2811 2815
22. S. Xu, J. Sun, D. Ke, G. Song, W. Zhang, and C. Zhan J. Colloid Interface Sci. 349 2010 142 147
23. W. Wang, A.D. Shaller, and A.D.Q. Li J. Am. Chem. Soc. 130 2008 8271 8279
24. A.D. Shaller, W. Wang, H. Gan, and A.D.Q. Li Angew. Chem., Int. Ed. 47 2008 7705 7709
25. X. Zhan, Z. Tan, B. Domercq, Z. An, X. Zhang, S. Barlow, Y. Li, D. Zhu, B. Kippelen, and S.R. Marder J. Am. Chem. Soc. 129 2007 7246 7247
26. M. Sommer, A.S. Lang, and M. Thelakkat Angew. Chem., Int. Ed. 47 2008 7901 7904
27. X. Yang, X. Xu, and H.-F. Ji J. Phys. Chem. B 112 2008 7196 7202
28. X. Zhang, Z. Chen, and F. Würthner J. Am. Chem. Soc. 129 2007 4886 4887
29. R. Sun, C. Xue, M. Owak, R.M. Peetz, and S. Jin Tetrahedron Lett. 48 2007 6696 6699
30. G. Golubkov, H. Weissman, E. Shirman, S.G. Wolf I. Pinkas, and B. Rybtchinski Angew. Chem., Int. Ed. 48 2009 926 930
31. J. Baram, E. Shirman, N. Ben-Shitrit, A. Ustinov, H. Weissman, I. Pinkas, S.G. Wolf, and B. Rybtchinski J. Am. Chem. Soc. 130 2008 14966 14967
32. A. Wicklein, A. Lang, M. Muth, and M. Thelakkat J. Am. Chem. Soc. 131 2009 14442 14453
33. Y. Nagao, and T. Misono Dyes Pigments 5 1984 171 188
34. Y. Nagao, and T. Misono Bull. Chem. Soc. Jpn. 54 1981 1191 1194
35. H. Kaiser, J. Lindner, and H. Langhals Chem. Ber. 124 1991 529 535
36. H. Huang, Y. Che, and L. Zang Tetrahedron Lett. 51 2010 6651 6653
37. Y. Li, H. Zheng, Y. Li, S. Wang, Z. Wu, P. Liu, Z. Gao, H. Liu, and D. Zhu J. Org. Chem. 72 2007 2878 2885
38. P. Rajasingh, R. Cohen, E. Shirman, L.J.W. Shimon, and B. Rybtchinski J. Org. Chem. 72 2007 5973 5979
39. PDI 12 was previously synthesized in our lab, please see: D. Ke, C. Zhan, S. Xu, X. Ding, A. Peng, J. Sun, S. He, A.D.Q. Li, and J. Yao J. Am. Chem. Soc. 133 2011 11022 11025
40. Z. Chen, U. Baumeister, C. Tschierske, and F. Würthner Chem. Eur. J. 13 2007 450 465