Linear- and angular-shaped naphthodithiophenes: Selective synthesis, properties, and application to organic field-effect transistors

Journal of the American Chemical Society

Volumn 133, Issue 13, 2011, Pages 5024-5035

  Shinamura, Shoji ^a   Osaka, Itaru ^a   Miyazaki, Eigo ^a   Nakao, Akiko ^b   Yamagishi, Masakazu ^c   Takeya, Jun ^c   Takimiya, Kazuo ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

^b HIGH ENERGY ACCELERATOR RESEARCH ORGANIZATION KEK   (Japan)

^c OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION BAND; AXISYMMETRIC; BUILDING BLOCKES; CENTROSYMMETRIC; CHEMOSELECTIVE; CHRYSENE; CORE STRUCTURE; NAPHTHACENE; OPTICAL MEASUREMENT; ORBITAL OVERLAP; ORGANIC SEMICONDUCTING MATERIALS; ORGANIC SEMICONDUCTOR; OXIDATION POTENTIALS; RED-SHIFTED; RING-CLOSING REACTIONS; SELECTIVE FORMATION; SELECTIVE SYNTHESIS; SONOGASHIRA COUPLING REACTIONS; SYNTHETIC APPROACH; SYNTHETIC PROCEDURES; THIOPHENE RING;

BROMINE; ELECTRONIC STRUCTURE; FIELD EFFECT TRANSISTORS; MOLECULES; NAPHTHALENE; O RINGS; OPTICAL DATA PROCESSING; ORGANIC POLYMERS; SYNTHESIS (CHEMICAL); THIOPHENE;

ORGANIC FIELD EFFECT TRANSISTORS;

BENZENE DERIVATIVE; BIPHENYL; BROMINE; CHRYSENE; NAPHTHALENE; NAPHTHALENE DERIVATIVE; NAPHTHO[ 2,1 B:6,5 B']DITHIOPHENE; NAPHTHO[ 2,3 B:6,7 B']DITHIOPHENE; NAPHTHO[ 2,3 B:7,6 B']DITHIOPHENE; OCTANE; ORGANIC COMPOUND; ORTHO BROMOETHYNYLBENZENE; THIOPHENE; THIOPHENE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; ELECTROCHEMICAL ANALYSIS; ELECTRONICS; ENERGY TRANSFER; FIELD EFFECT TRANSISTOR; FILM; IONIZATION; ISOMER; ISOMERIZATION; MOLECULE; OPTICS; PARTICLE SIZE; RING CLOSING METATHESIS; SOLID STATE; SONOGASHIRA REACTION; STEREOCHEMISTRY;

CHEMISTRY, PHYSICAL; CRYSTALLOGRAPHY, X-RAY; MEMBRANES, ARTIFICIAL; MODELS, MOLECULAR; MOLECULAR STRUCTURE; QUANTUM THEORY; SEMICONDUCTORS; STEREOISOMERISM; THIOPHENES;

EID: 79953840273     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja110973m     Document Type: Article

References (74)

1. Laquindanum, J. G.; Katz, H. E.; Lovinger, A. J.; Dodabalapur, A. Adv. Mater. 1997, 8, 36-39
2. Takimiya, K.; Kunugi, Y.; Konda, Y.; Niihara, N.; Otsubo, T. J. Am. Chem. Soc. 2004, 126, 5084-5085
3. Takimiya, K.; Kunugi, Y.; Ebata, H.; Otsubo, T. Chem. Lett. 2006, 35, 1200-1201
4. Kashiki, T.; Miyazaki, E.; Takimiya, K. Chem. Lett. 2008, 37, 284-285
5. Kashiki, T.; Miyazaki, E.; Takimiya, K. Chem. Lett. 2009, 38, 568-569
6. Laquindanum, J. G.; Katz, H. E.; Lovinger, A. J. J. Am. Chem. Soc. 1998, 120, 664-672
7. Payne, M. M.; Parkin, S. R.; Anthony, J. E.; Kuo, C.-C.; Jackson, T. N. J. Am. Chem. Soc. 2005, 127, 4986-4987
8. Dickey, K. C.; Anthony, J. E.; Loo, Y. L. Adv. Mater. 2006, 18, 1721-1726
9. Chen, M.-C.; Kim, C.; Chen, S.-Y.; Chiang, Y.-J.; Chung, M.-C.; Facchetti, A.; Marks, T. J. J. Mater. Chem. 2008, 18, 1029-1036
10. Li, X. -C.; Sirringhaus, H.; Garnier, F.; Holmes, A. B.; Moratti, S. C.; Feeder, N.; Clegg, W.; Teat, S. J.; Friend, R. H. J. Am. Chem. Soc. 1998, 120, 2206-2207
11. Sirringhaus, H.; Friend, R. H.; Wang, C.; Leuninger, J.; Mullen, K. J. Mater. Chem. 1999, 9, 2095-2101
12. Anthony, J. E. Chem. Rev. 2006, 106, 5028-5048
13. Takimiya, K.; Ebata, H.; Sakamoto, K.; Izawa, T.; Otsubo, T.; Kunugi, Y. J. Am. Chem. Soc. 2006, 128, 12604-12605
14. Takimiya, K.; Kunugi, Y.; Konda, Y.; Ebata, H.; Toyoshima, Y.; Otsubo, T. J. Am. Chem. Soc. 2006, 128, 3044-3050
15. Yamamoto, T.; Takimiya, K. J. Am. Chem. Soc. 2007, 129, 2224-2225
16. Ebata, H.; Izawa, T.; Miyazaki, E.; Takimiya, K.; Ikeda, M.; Kuwabara, H.; Yui, T. J. Am. Chem. Soc. 2007, 129, 15732-15733
17. Takimiya, K.; Kunugi, Y.; Otsubo, T. Chem. Lett. 2007, 36, 578-583
18. Gao, J.; Li, R.; Li, L.; Meng, Q.; Jiang, H.; Li, H.; Hu, W. Adv. Mater. 2007, 19, 3008-3011
19. Anthony, J. E. Angew. Chem., Int. Ed. 2008, 47, 452-483
20. Izawa, T.; Miyazaki, E.; Takimiya, K. Adv. Mater. 2008, 20, 3388-3392
21. Gao, P.; Beckmann, D.; Tsao, H. N.; Feng, X.; Enkelmann, V.; Baumgarten, M.; Pisula, W.; Müllen, K. Adv. Mater. 2009, 21, 213-216
22. Pan, H.; Li, Y.; Wu, Y.; Liu, P.; Ong, B. S.; Zhu, S.; Xu, G. Chem. Mater. 2006, 18, 3237-3241
23. Pan, H.; Li, Y.; Wu, Y.; Liu, P.; Ong, B. S.; Zhu, S.; Xu, G. J. Am. Chem. Soc. 2007, 129, 4112-4113
24. Pan, H.; Wu, Y.; Li, Y.; Liu, P.; Ong, B. S.; Zhu, S.; Xu, G. Adv. Funct. Mater. 2007, 17, 3574-3579
25. Liang, Y.; Wu, Y.; Feng, D.; Tsai, S.-T.; Son, H.-J.; Li, G.; Yu, L. J. Am. Chem. Soc. 2009, 131, 56-57
26. Liang, Y.; Feng, D.; Wu, Y.; Tsai, S.-T.; Li, G.; Ray, C.; Yu, L. J. Am. Chem. Soc. 2009, 131, 7792-7799
27. Huo, L.; Hou, J.; Zhang, S.; Chen, H. Y.; Yang, Y. Angew. Chem. Inter. Ed. 2010, 49, 1500-1503
28. Liang, Y.; Xu, Z.; Xia, J.; Tsai, S.-T.; Wu, Y.; Li, G.; Ray, C.; Yu, L. Adv. Mater. 2010, 22, E135-E138
29. Piliego, C.; Holcombe, T. W.; Douglas, J. D.; Woo, C. H.; Beaujuge, P. M.; Fréchet, J. M. J. Am. Chem. Soc. 2010, 132, 7595-7597
30. Zhang, Y.; Hau, S. K.; Yip, H.-L.; Sun, Y.; Acton, O.; Jen, A. K. Y. Chem. Mater. 2010, 22, 2696-2698
31. Zou, Y.; Najari, A.; Berrouard, P.; Beaupré, S.; Aïch, B. R.; Tao, Y.; Leclerc, M. J., M. J. Am. Chem. Soc. 2010, 132, 5330-5331
32. Lloyd, M. T.; Mayer, A. C.; Subramanian, S.; Mourey, D. A.; Herman, D. J.; Bapat, A. V.; Anthony, J. E.; Malliaras, G. G. J. Am. Chem. Soc. 2007, 129, 9144-9149
33. Mühlbacher, D.; Scharber, M.; Morana, M.; Zhu, Z.; Waller, D.; Gaudiana, R.; Brabec, C. Adv. Mater. 2006, 18, 2884-2889
34. Hou, J.; Chen, H.-Y.; Zhang, S.; Li, G.; Yang, Y. J. Am. Chem. Soc. 2008, 130, 16144-16145
35. Wang, C.-H.; Hu, R.-R.; Liang, S.; Chen, J.-H.; Yang, Z.; Pei, J. Tetrahedron Lett. 2005, 46, 8153-8157
36. Ebata, H.; Miyazaki, E.; Yamamoto, T.; Takimiya, K. Org. Lett. 2007, 9, 4499-4502
37. Zhou, Y.; Liu, W.-J.; Ma, Y.; Wang, H.; Qi, L.; Cao, Y.; Wang, J.; Pei, J. J. Am. Chem. Soc. 2007, 129, 12386-12387
38. Beimling, P.; Kömehl, G. Chem. Ber. 1986, 119, 3198-3203
39. Takimiya, K.; Konda, Y.; Ebata, H.; Niihara, N.; Otsubo, T. J. Org. Chem. 2005, 70, 10569-10571
40. Kashiki, T.; Shinamura, S.; Kohara, M.; Miyazaki, E.; Takimiya, K.; Ikeda, M.; Kuwabara, H. Org. Lett. 2009, 11, 2473-2475
41. Coropceanu, V.; Kwon, O.; Wex, B.; Kaafarani, B. R.; Gruhn, N. E.; Durivage, J. C.; Neckers, D. C.; Bredas, J.-L. Chem.-Eur. J. 2006, 12, 2073-2080
42. Umeda, R.; Fukuda, H.; Miki, K.; Rahman, S. M. A.; Sonoda, M.; Tobe, Y. C. R. Chimie 2009, 12, 378 - 384. see also
43. Tilak, B. D. Proc. Indian Acad. Sci. Sect. A 1951, 33A, 71-77
44. Shinamura, S.; Miyazaki, E.; Takimiya, K. J. Org. Chem. 2010, 75, 1228-1234
45. Osaka, I.; Abe, T.; Shinamura, S.; Miyazaki, E.; Takimiya, K. J. Am. Chem. Soc. 2010, 132, 5000-5001
46. Mataka, S.; Takahashi, K.; Ikezaki, Y.; Hatta, T.; Tori-i, A.; Tashiro, M. Bull. Chem. Soc. Jpn. 1991, 64, 68-73
47. Cooke, R. G.; Johnson, B. L.; Owen, W. R. Aust. J. Chem. 1960, 13, 256-260
48. Kitamura, C.; Ohara, T.; Kawatsuki, N.; Yoneda, A.; Kobayashi, T.; Naito, H.; Komatsu, T.; Kitamura, T. CrystEngComm 2007, 9, 644-647
49. Wheeler, A. S.; Ergle, D. R. J. Am. Chem. Soc. 1930, 52, 4872-4880
50. Wheeler, A. S.; Mattox, W. J. J. Am. Chem. Soc. 1933, 55, 686-690
51. Takimiya, K.; Yamamoto, T.; Ebata, H.; Izawa, T. Sci. Tech. Adv. Mater. 2007, 8, 273-276
52. Suresh, C. H.; Gadre, S. R. J. Org. Chem. 1999, 64, 2505-2512
53. Poater, J.; Visser, R.; Sola, M.; Bickelhaupt, F. M. J. Org. Chem. 2007, 72, 1134-1142
54. MO calculations were carried out with the DFT/TD-DFT method at the B3LYP/6-31g(d) level using Gaussian 03 program package. Frisch, M. J. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
55. Maliakal, A.; Raghavachari, K.; Katz, H.; Chandross, E.; Siegrist, T. Chem. Mater. 2004, 16, 4980-4986
56. Tang, M. L.; Okamoto, T.; Bao, Z. J. Am. Chem. Soc. 2006, 128, 16002-16003
57. Valiyev, F.; Hu, W.-S.; Chen, H.-Y.; Kuo, M.-Y.; Chao, I.; Tao, Y.-T. Chem. Mater. 2007, 19, 3018-3026
58. Tang, M. L.; Mannsfeld, S. C. B.; Sun, Y.-S.; Becerril, H. t. A.; Bao, Z. J. Am. Chem. Soc. 2009, 131, 882-883
59. Takimiya, K.; Kunugi, Y.; Toyoshima, Y.; Otsubo, T. J. Am. Chem. Soc. 2005, 127, 3605-3612
60. ADF2008.01. SCM Theoretical Chemistry; Vrije Universiteit: Amsterdam, The Netherlands, http://www.scm.com.
61. Senthilkumar, K.; Grozema, F. C.; Bickelhaupt, F. M.; Siebbeles, L. D. A. J. Chem. Phys. 2003, 119, 9809-9817
62. 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
63. Valiyev, F.; Hu, W.-S.; Chen, H.-Y.; Kuo, M.-Y.; Chao, I.; Tao, Y.-T. Chem. Mater. 2007, 19, 3018-3026
64. Kim, E.-G.; Coropceanu, V.; Gruhn, N. E.; Sanchez-Carrera, R. S.; Snoeberger, R.; Matzger, A. J.; Bredas, J.-L. J. Am. Chem. Soc. 2007, 129, 13072-13081
65. These transfer integrals are also larger than those calculated for 3c (∼25 meV) and 4c (∼11 meV) using the bulk single crystal structures. See Supporting Information.
66. Sanchez-Carrera, R. S.; Atahan, S.; Schrier, J.; Aspuru-Guzik, A. J. Phys. Chem. C 2010, 114, 2334-2340
67. Bredas, J.-L.; Beljonne, D.; Coropceanu, V.; Cornil, J. Chem. Rev. 2004, 104, 4971-5004
68. Sakanoue, K.; Motoda, M.; Sugimoto, M.; Sakaki, S. J. Chem. Phys. A 1999, 103, 5551-5556
69. hs for 2a - 4a are 100, 266, and 245 meV, respectively, reflecting their electronic structures.
70. Kano, M.; Minari, T.; Tsukagoshi, K. Appl. Phys. Lett. 2009, 94, 143304
71. Kobayashi, N.; Sasaki, M.; Nomoto, K. Chem. Mater. 2009, 21, 552-556
72. Meng, H.; Bao, Z.; Lovinger, A. J.; Wang, B.-C.; Mujsce, A. M. J. Am. Chem. Soc. 2001, 123, 9214-9215
73. Sheldrick, G. M. SHELXL (SHELX97). Programs for the refinement of crystal structures. University of Goettingen: Germany, 1997.
74. t eXsan: Single Crystal Structure Analysis Software, Version 1.19; Molecular Structure Corporation and Rigaku Corporation: 2000.