Largely π-extended thienoacenes with internal thieno[3,2-b]thiophene substructures: Synthesis, characterization, and organic field-effect transistor applications

Organic Letters

Volumn 14, Issue 18, 2012, Pages 4914-4917

  Yamamoto, Tatsuya ^a   Nishimura, Takeshi ^a   Mori, Takamichi ^a   Miyazaki, Eigo ^a   Osaka, Itaru ^a   Takimiya, Kazuo ^a,b  

^a HIROSHIMA UNIVERSITY   (Japan)

^b RIKEN   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84868246665     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol302243t     Document Type: Article

References (26)

1. (a) Anthony, J. E. Chem. Rev. 2006, 106, 5028-5048.
2. (b) Anthony, J. E. Angew. Chem., Int. Ed. 2008, 47, 452-483.
3. (c) Takimiya, K.; Shinamura, S.; Osaka, I.; Miyazaki, E. Adv. Mater. 2011, 23, 4347-4370.
4. (d) Wang, C.; Dong, H.; Hu, W.; Liu, Y.; Zhu, D. Chem. Rev. 2012, 112, 2208-2267.
5. (a) Takimiya, K.; Kunugi, Y.; Konda, Y.; Ebata, H.; Toyoshima, Y.; Otsubo, T. J. Am. Chem. Soc. 2006, 128, 3044-3050.
6. (b) Takimiya, K.; Ebata, H.; Sakamoto, K.; Izawa, T.; Otsubo, T.; Kunugi, Y. J. Am. Chem. Soc. 2006, 128, 12604-12605.
7. (c) Ebata, H.; Izawa, T.; Miyazaki, E.; Takimiya, K.; Ikeda, M.; Kuwabara, H.; Yui, T. J. Am. Chem. Soc. 2007, 129, 15732-15733.
8. (d) Izawa, T.; Miyazaki, E.; Takimiya, K. Chem. Mater. 2009, 21, 903-912.
9. (a) Yamamoto, T.; Takimiya, K. J. Am. Chem. Soc. 2007, 129, 2224-2225.
10. (b) Yamamoto, T.; Shinamura, S.; Miyazaki, E.; Takimiya, K. Bull. Chem. Soc. Jpn. 2010, 83, 120-130.
11. (c) Kang, M. J.; Yamamoto, T.; Shinamura, S.; Miyazaki, E.; Takimiya, K. Chem. Sci. 2010, 1, 179-183.
12. (d) Kang, M. J.; Doi, I.; Mori, H.; Miyazaki, E.; Takimiya, K.; Ikeda, M.; Kuwabara, H. Adv. Mater. 2011, 23, 1222-1225.
13. (e) Niimi, K.; Kang, M. J.; Miyazaki, E.; Osaka, I.; Takimiya, K. Org. Lett. 2011, 13, 3430-3433.
14. Takimiya, K.; Yamamoto, T.; Ebata, H.; Izawa, T. Sci. Tech. Adv. Mater. 2007, 8, 273-276.
15. Huang, J.; Luo, H.; Wang, L.; Guo, Y.; Zhang, W.; Chen, H.; Zhu, M.; Liu, Y.; Yu, G. Org. Lett. 2012, 14, 3300-3303.
16. Niedermann, H.-P.; Eckes, H.-L.; Meier, H. Tetrahedron Lett. 1989, 30, 155-158.
17. MO calculations were carried out with the DFT/TD-DFT method at the B3LYP/6-31g(1) (d) level using the Gaussian 03 program package. Frisch, M. J. et al. Gaussian 03, revision C.02; Gaussian, Inc.:Wallingford, CT, 2004. See Supporting Information for full reference.
18. Usta, H.; Risko, C.; Wang, Z.; Huang, H.; Deliomeroglu, M. K.; Zhukhovitskiy, A.; Facchetti, A.; Marks, T. J. J. Am. Chem. Soc. 2009, 131, 5586-5608.
19. (a) Takimiya, K.; Kunugi, Y.; Konda, Y.; Niihara, N.; Otsubo, T. J. Am. Chem. Soc. 2004, 126, 5084-5085.
20. (b) Shinamura, S.; Osaka, I.; Miyazaki, E.; Nakao, A.; Yamagishi, M.; Takeya, J.; Takimiya, K. J. Am. Chem. Soc. 2011, 133, 5024-5035.
21. (a) ADF2008.01, SCM, Theoretical Chemistry, Vrije Universiteit, Amsterdam, TheNetherlands, http://www.scm.com.
22. (b) Senthilkumar, K.; Grozema, F. C.; Bickelhaupt, F. M.; Siebbeles, L. D. A. J. Chem. Phys. 2003, 119, 9809-9817.
23. (c) Prins, P.; Senthilkumar, K.; Grozema, F. C.; Jonkheijm, P.; Schenning, A. P. H. J.; Meijer, E. W.; Siebbeles, L. D. A. J. Chem. Phys. B 2005, 109, 18267-18274.
24. (a) Sirringhaus, H.; H. Friend, R.; Wang, C.; Leuninger, J.; Mullen, K. J. Mater. Chem. 1999, 9, 2095-2101.
25. (b) Niimi, K.; Shinamura, S.;Osaka, I.;Miyazaki, E.;Takimiya,K. J. Am.Chem. Soc. 2011, 133, 8732-8739.
26. Kuribara, K.; Wang, H.; Uchiyama, N.; Fukuda, K.; Yokota, T.; Zschieschang, U.; Jaye, C.; Fischer, D.; Klauk, H.; Yamamoto, T.; Takimiya, K.; Ikeda, M.; Kuwabara, H.; Sekitani, T.; Loo, Y.-L.; Someya, T. Nat. Commun. 2012, 3, 723-1-7.