Effect of the substitution pattern of alkyl side chain in a benzodithiophene core π-system on intra and inter-molecular charge carrier mobility

Journal of Physical Chemistry B

Volumn 115, Issue 26, 2011, Pages 8446-8452

  Kumagai, Jun ^a   Hirano, Koji ^a   Satoh, Tetsuya ^a   Seki, Shu ^a   Miura, Masahiro ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRONIC PROPERTIES; EMISSION SPECTROSCOPY; MESFET DEVICES; OLIGOMERS; PHOTOLYSIS;

ABSORPTION AND EMISSION SPECTRA; ALKYL SIDE CHAINS; BENZODITHIOPHENE; CHARGE-CARRIER MOBILITY; CONJUGATED OLIGOMER; FET PROPERTIES; INTERMOLECULAR PACKING; SUBSTITUTION PATTERNS; THERMAL-ANNEALING; TIME-RESOLVED MICROWAVE CONDUCTIVITIES; TOP CONTACT; TRANSLATIONAL MOTIONS;

HOLE MOBILITY;

EID: 79960022118     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp2036668     Document Type: Article

References (29)

1. Recent reviews: Katz, H. E.; Bao, Z.; Gilat, S. L. Acc. Chem. Res. 2001, 34, 359
2. Takimiya, K.; Kunugi, Y.; Otsubo, T. Chem. Lett. 2007, 36, 578
3. Murphy, A. R.; Fréchet, J. M. J. Chem. Rev. 2007, 107, 1066
4. Ong, B. S.; Wu, Y.; Li, Y.; Liu, P.; Pan, H. Chem.-Eur. J. 2008, 14, 4766
5. Allard, S.; Forster, M.; Souharce, B.; Thiem, H.; Schert, U. Angew. Chem., Int. Ed. 2008, 120, 4138
6. Chen, J.; Cao, A. Y. Acc. Chem. Res. 2009, 42, 1709
7. For a recent example of β,β′-dialkylthiophene derivatives with high charge carrier mobility and conductivity: Prasanthkumar, S.; Saeki, A.; Seki, S.; Ajyayaghosh, A. J. Am. Chem. Soc. 2010, 132, 8866
8. Prasanthkumar, S.; Gopal, A.; Ajayaghosh, A. J. Am. Chem. Soc. 2010, 132, 13206
9. Pan, H.; Li, Y.; Wu, Y.; Liu, P.; Ong, B. S.; Zhu, S.; Xu, G. Chem. Mater. 2006, 18, 3237
10. Pan, H.; Wu, Y.; Li, Y.; Liu, P.; Ong, B. S.; Zhu, S.; Xu, G. Adv. Funct. Mater. 2007, 17, 3574
11. Pan, H.; Li, Y.; Wu, Y.; Liu, P.; Ong, B. S.; Zhu, S.; Xu, G. J. Am. Chem. Soc. 2007, 129, 4112
12. Higa, T.; Krubsack, A. J. J. Org. Chem. 1975, 40, 3037
13. Ried, W.; Oremek, G.; Ocakcioglu, B. Liebigs Ann. Chem. 1980, 1424
14. Malešević, M.; Karminsky-Zamola, G.; Bajić, M.; Boykin, D. W. Heterocycles 1995, 41, 2691
15. Gelman, D.; Buchwald, S. L. Angew. Chem., Int. Ed. 2003, 42, 5993
16. Yamamoto, T.; Komarudin, D.; Arai, M.; Lee, B. L.; Suganuma, H.; Asakawa, N.; Inoue, Y.; Kubota, K.; Sasaki, S.; Fukuda, T.; Matsuda, H. J. Am. Chem. Soc. 1998, 120, 2047
17. Ong, B. S.; Wu, Y.; Liu, P.; Gardner, S. J. Am. Chem. Soc. 2004, 126, 3378
18. Wu, Y.; Liu, P.; Gardner, S.; Ong, B. S. Chem. Mater. 2005, 17, 221
19. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03; Gaussian, Inc., Wallingford CT, 2004.
20. Saeki, A.; Seki, S.; Tagawa, S. J. Appl. Phys. 2006, 100, 023703
21. Microwave measurement of mobility with ESR method: Marumoto, K.; Arai, N.; Goto, H.; Kijima, M.; Murakami, K.; Tominari, Y.; Takeya, J.; Shimoi, Y.; Tanaka, H.; Kuroda, S.; Kaji, T.; Nishikawa, T.; Takenobu, T.; Iwasa, Y. Phys. Rev. B 2011, 83, 075302-1
22. Funston, A. M.; Silverman, E. E.; Miller, J. R.; Schanze, K. S. J. Phys. Chem. B 2004, 108, 1544
23. Levin, E. I.; Shklovskii, B. I. Solid State Commun. 1988, 67, 233
24. Kunimi, Y.; Seki, S.; Tagawa, S. Solid State Commun. 2000, 114, 469
25. Umeda, N.; Tsurugi, H.; Satoh, T.; Miura, M. Angew. Chem., Int. Ed. 2008, 47, 4019
26. Horita, A.; Tsurugi, H.; Funayama, A.; Satoh, T.; Miura, M. Org. Lett. 2007, 9, 2231
27. Pelter, A.; Jenkins, I.; Jones, D. E. Tetrahedron 1997, 53, 10357
28. Seki, S.; Yoshida, Y.; Tagawa, S.; Asai, K.; Ishigure, K.; Furukawa, K.; Fujiki, M.; Matsumoto, N. Phil. Mag. B 1999, 79, 1631
29. Acharya, A.; Seki, S.; Koizumi, Y.; Saeki, A.; Tagawa, S. J. Phys. Chem. B 2005, 109, 20174