N-Annulated perylene dyes with adjustable photophysical properties

Tetrahedron Letters

Volumn 52, Issue 48, 2011, Pages 6411-6414

  Zhu, Lijun ^a,b   Jiao, Chongjun ^b   Xia, Daohong ^a   Wu, Jishan ^b,c  

^a CHINA UNIVERSITY OF PETROLEUM   (China)

^b NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^c INSTITUTE OF MATERIALS RESEARCH AND ENGINEERING   (Singapore)

Author keywords

Absorption; Dye; Emission; N Annulated perylene; Push pull chromophore

Indexed keywords

DYE; PERYLENE;

ABSORPTION SPECTROSCOPY; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHROMATOPHORE; CYCLIC POTENTIOMETRY; LIGHT ABSORPTION; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 80255140502     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.09.077     Document Type: Article

References (32)

1. (a) Grimsdale, A. C.; Chan, K. L.; Martin, R. E.; Jokisz, P. G.; Holmes, A. B. Chem. Rev. 2009, 109, 897-1091;
2. (b) Zhong, C.; Duan, F.; Wu, H.; Cao, Y. Chem. Mater. 2011, 23, 326-340.
3. (a) Mishra, A.; Fischer, M. K. R.; Bäuerle, P. Angew. Chem., Int. Ed. 2009, 48, 2474-2499;
4. (b) Li, C.; Liu, M.; Pschirer, N. G.; Baumgaten, M.; Müllen, K. Chem. Rev. 2010, 110, 6817-6855.
5. (a) Zaumseil, J.; Sirringhaus, H. Chem. Rev. 2007, 107, 1296-1323;
6. (b) Wu, W.; Liu, Y.; Zhu, D. Chem. Soc. Rev. 2010, 39, 1489-1502.
7. (a) Kim, H. M.; Cho, B. R. Chem. Commun. 2009, 153-164;
8. (b) Pawlicki, M.; Collins, H. A.; Denning, R. G.; Anderson, H. L. Angew. Chem., Int. Ed. 2009, 48, 3244-3266.
9. (a) Tang, C. W. Appl. Phys. Lett. 1986, 48, 183-185;
10. (b) Schmidt-Mende, L.; Fechtenkötter, A.; Müllen, K.; Moons, E.; Friend, R. H.; MacKenzie, J. D. Science 2001, 293, 1119-1122;
11. (c) Zhan, X.; Tan, Z.; Domercq, B.; An, Z.; Zhang, X.; Barlow, S.; Li, Y.; Zhu, D.; Kippelen, B.; Marder, S. R. J. Am. Chem. Soc. 2007, 129, 7246-7247.
12. Schlichting, P.; Rohr, U.; Müllen, K. Liebigs Ann./Recueil. 1997, 395-407.
13. (a) Looker, J. J. J. Org. Chem. 1972, 37, 3379-3381;
14. (b) Jiang, W.; Qian, H.; Li, Y.; Wang, Z. J. Org. Chem. 2008, 73, 7369-7372.
15. (a) Li, Y.; Wang, Z. Org. Lett. 2009, 11, 1385-1388;
16. (b) Li, Y.; Gao, J.; Motta, S. D.; Negri, F.; Wang, Z. J. Am. Chem. Soc. 2010, 132, 4208-4213.
17. (a) Jiao, C.; Huang, K.-W.; Luo, J.; Zhang, K.; Chi, C.; Wu, J. Org. Lett. 2009, 11, 4508-4511;
18. (b) Jiao, C.; Huang, K.-W.; Guan, Z.; Xu, Q.-H.; Wu, J. Org. Lett. 2010, 12, 4046-4049;
19. (c) Jiao, C.; Huang, K.-W.; Wu, J. Org. Lett. 2011, 13, 632-635.
20. (a) Wenger, O. S. Acc. Chem. Res. 2011, 44, 25-35;
21. (b) Qian, G.; Wang, Z. Chem. Asian J. 2010, 5, 1006-1029.
22. (a) Vilsmeier, A.; Haack, A. Ber. 1927, 60, 119;
23. (b) Meth-Cohn, O.; Stanforth, S. P. Comp. Org. Syn. 1991, 2, 777-794.
24. Kedrowski, B. L.; Hoppe, R. W. J. Org. Chem. 2008, 73, 5177-5179.
25. Guldi, D. M.; Swartz, A.; Luo, C.; Gomez, R.; Segura, J. L.; Martin, N. J. Am. Chem. Soc. 2002, 124, 10875-10886.
26. (a) Kochurani, J.; Becker, J. Y.; Ellern, A.; Khodorkovsky, V. Tetrahedron Lett. 1999, 40, 8625-8628;
27. (b) Sanguinet, L.; Williams, J. C.; Yang, Z.; Twieg, R. J.; Mao, G.; Singer, K. D.; Wiggers, G.; Petschek, R. G. Chem. Mater. 2006, 18, 4259-4269;
28. (c) Lartia, R.; Allain, C.; Bordeau, G.; Schmidt, F.; Fiorini-Debuisschert, C.; Charra, F.; Teulade-Fichou, M. P. J. Org. Chem. 2008, 73, 1732-1744.
29. Würthner, F.; Kaiser, T. E.; Saha-Möller, C. R. Angew. Chem., Int. Ed. 2011, 50, 3376-3410.
30. (a) Reichardt, C. Chem. Rev. 1994, 94, 2319-2358;
31. (b) Grabowski, Z. R.; Rotkiewicz, K. Chem. Rev. 2003, 103, 3899-4031.
32. Kellogg, R. E.; Bennett, R. G. J. Chem. Phys. 1964, 41, 3042-3045.