One-pot synthesis of core-expanded naphthalene diimides: Enabling N-substituent modulation for diverse n-type organic materials

Organic Letters

Volumn 14, Issue 1, 2012, Pages 292-295

  Hu, Yunbin ^a   Qin, Yunke ^a   Gao, Xike ^a   Zhang, Fengjiao ^b   Di, Chong An ^b   Zhao, Zheng ^a   Li, Hongxiang ^a   Zhu, Daoben ^a,b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b INSTITUTE OF CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDE; NAPHTHALENE; NAPHTHALENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTRON; SYNTHESIS;

ELECTRONS; IMIDES; MOLECULAR STRUCTURE; NAPHTHALENES;

EID: 84862908287     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol203059r     Document Type: Article

References (29)

1. Bhosale, S. V.; Jani, C. H.; Langford, S. J. Chem. Soc. Rev. 2008, 37, 331
2. Sakai, N.; Mareda, J.; Vauthey, E.; Matile, S. Chem. Commun. 2010, 46, 4225
3. Zhan, X.; Facchetti, A.; Barlow, S.; Marks, T. J.; Ratner, M. A.; Wasielewski, M. R.; Marder, S. R. Adv. Mater. 2011, 23, 268
4. Jung, B. J.; Tremblay, N. J.; Yeh, M.-L.; Katz, H. E. Chem. Mater. 2011, 23, 568
5. Würthner, F.; Stolte, M. Chem. Commun. 2011, 47, 5109
6. Jones, B. A.; Facchetti, A.; Marks, T. J.; Wasielewski, M. R. Chem. Mater. 2007, 19, 2703
7. Oh, J. H.; Suraru, S.-L.; Lee, W.-Y.; Könemann, M.; Höffken, H. W.; Röger, C.; Schmidt, R.; Chung, Y.; Chen, W.-C.; Würthner, F.; Bao, Z. Adv. Funct. Mater. 2010, 20, 2148
8. Yan, H.; Chen, Z.; Zheng, Y.; Newman, C.; Quinn, J. R.; Dötz, F.; Kastler, M.; Facchetti, A. Nature 2009, 457, 679
9. Polander, L. E.; Tiwari, S. P.; Pandey, L.; Seifried, B. M.; Zhang, Q.; Barlow, S.; Risko, C.; Brédas, J.-L.; Kippelen, B.; Marder, S. R. Chem. Mater. 2011, 23, 3408
10. Gao, X.; Di, C.; Hu, Y.; Yang, X.; Fan, H.; Zhang, F.; Liu, Y.; Li, H.; Zhu, D. J. Am. Chem. Soc. 2010, 132, 3697
11. Hu, Y.; Gao, X.; Di, C.; Yang, X.; Zhang, F.; Liu, Y.; Li, H.; Zhu, D. Chem. Mater. 2011, 23, 1204
12. Zhao, Y.; Di, C.; Gao, X.; Hu, Y.; Guo, Y.; Zhang, L.; Liu, Y.; Wang, J.; Hu, W.; Zhu, D. Adv. Mater. 2011, 23, 2448
13. Langhals, H.; Demmig, S.; Huber, H. Spectrochim. Acta A 1988, 44A, 1189
14. Wicklein, A.; Lang, A.; Muth, M.; Thelakkat, M. J. Am. Chem. Soc. 2009, 131, 14442
15. Würthner, F. Chem. Commun. 2004, 1564
16. Huang, C.; Barlow, S.; Marder, S. R. J. Org. Chem. 2011, 76, 2386
17. Katz, H. E.; Lovinger, A. J.; Johnson, J.; Kloc, C.; Siegrist, T.; Li, W.; Lin, Y.-Y.; Dodabalapur, A. Nature 2000, 404, 478
18. Shukla, D.; Nelson, S. F.; Freeman, D. C.; Rajeswaran, M.; Ahearn, W. G.; Meyer, D. M.; Carey, J. T. Chem. Mater. 2008, 20, 7486
19. Molla, M. R.; Ghosh, S. Chem. Mater. 2011, 23, 95
20. Newman, C. R.; Frisbie, C. D.; da Silva Filho, D. A.; Brédas, J.-L.; Ewbank, P.C.; Mann, K. R. Chem. Mater. 2004, 16, 4436
21. Anthony, J. E.; Facchetti, A.; Heeney, M.; Marder, S. R.; Zhan, X. Adv. Mater. 2010, 22, 3876
22. Gao, X.; Qiu, W.; Yang, X.; Liu, Y.; Wang, Y.; Zhang, H.; Qi, T.; Liu, Y.; Lu, K.; Du, C.; Shuai, Z.; Yu, G.; Zhu, D. Org. Lett. 2007, 9, 3917
23. Röger, C.; Würthner, F. J. Org. Chem. 2007, 72, 8070
24. Hatchard, W. R. J. Org. Chem. 1964, 29, 660
25. Zheng, Q.; Huang, J.; Sarjeant, A.; Katz, H. E. J. Am. Chem. Soc. 2008, 130, 14410
26. Tambara, K.; Ponnuswamy, N.; Hennrich, G.; Pantos, G. D. J. Org. Chem. 2011, 76, 3338
27. Yuan, Z.; Li, J.; Xiao, Y.; Li, Z.; Qian, X. J. Org. Chem. 2010, 75, 3007
28. Jones, B. A.; Facchetti, A.; Wasielewski, M. R.; Marks, T. J. J. Am. Chem. Soc. 2007, 129, 15259
29. Usta, H.; Facchetti, A.; Marks, T. J. Acc. Chem. Res. 2011, 44, 501