Bis(methylthio)tetracenes: Synthesis, crystal-packing structures, and OFET properties

Journal of Organic Chemistry

Volumn 76, Issue 12, 2011, Pages 5018-5025

  Kimoto, Takakazu ^a   Tanaka, Kenro ^a   Kawahata, Masatoshi ^b   Yamaguchi, Kentaro ^b   Otsubo, Saika ^c   Sakai, Yoshimasa ^c   Ono, Yuuki ^c   Ohno, Akira ^c   Kobayashi, Kenji ^a  

^a SHIZUOKA UNIVERSITY   (Japan)

^b TOKUSHIMA BUNRI UNIVERSITY   (Japan)

^c MITSUBISHI CHEMICAL CORPORATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BOTTOM-CONTACT; CRYSTALLOGRAPHIC DATA; DEVICE CONFIGURATIONS; DFT CALCULATION; HOMO-LUMO ENERGY GAP; LUMO ENERGY LEVELS; ON/OFF RATIO; PENTACENES; SPIN-COATED FILMS; TETRACENE;

X RAY CRYSTALLOGRAPHY;

SULFUR COMPOUNDS;

BENZENE DERIVATIVE; BIS(METHYLTHIO)TETRACENE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL; DEVICE; FILM; ORGANIC FIELD EFFECT TRANSISTOR; SOLUBILITY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; METHYLATION; MICROSCOPY, ATOMIC FORCE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NAPHTHACENES; SULFHYDRYL COMPOUNDS;

EID: 79958773844     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200696a     Document Type: Article

References (69)

1. Anthony, J. E. Chem. Rev. 2006, 106, 5028-5048
2. Würthner, F.; Schmidt, R. ChemPhysChem 2006, 7, 793-797
3. Murphy, A. R.; Fréchet, J. M. J. Chem. Rev. 2007, 107, 1066-1096
4. Anthony, J. E. Angew. Chem., Int. Ed. 2008, 47, 452-483
5. Allard, S.; Forster, M.; Souharce, B.; Thiem, H.; Scherf, U. Angew. Chem., Int. Ed. 2008, 47, 4070-4098
6. Jurchescu, O. D.; Baas, J.; Palstra, T. T. M. Appl. Phys. Lett. 2004, 84, 3061-3063
7. Sundar., V. C.; Zaumseil, J.; Podzorov, V.; Menard, E.; Willet, R. L.; Someya, T.; Gershenson, M. E.; Rogers, J. A. Science 2004, 303, 1644-1646
8. Takeya, J.; Yamagishi, M.; Tominari, Y.; Hirahara, R.; Nakazawa, Y.; Nishikawa, T.; Kawase, T.; Shimoda, T.; Ogawa, S. Appl. Phys. Lett. 2007, 90, 102120-1-3
9. Klauk, H.; Halik, M.; Zschieschang, U.; Schmid, G.; Radlik, W.; Weber, W. J. Appl. Phys. 2002, 92, 5259-5263
10. Desiraju, G. R.; Gavezzotti, A. Acta Crystallogr. Sect. B 1989, 45, 473-482
11. Desiraju, G. R. Crystal Engineering: The Design of Organic Solids; Elsevier: Amsterdam, 1989; Chapter 4.
12. Cornil, J.; Calbert, J. P.; Brédas, J. L. J. Am. Chem. Soc. 2001, 123, 1250-1251
13. Fritz, S. E.; Martin, S. M.; Frisbie, C. D.; Ward, M. D.; Toney, M. F. J. Am. Chem. Soc. 2004, 126, 4084-4085
14. Brédas, J.-L.; Calbert, J. P.; da Silva Filho, D. A.; Cornil., J. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5804-5809
15. Haddon, R. C.; Chi, X.; Itkis, M. E.; Anthony, J. E.; Eaton, D. L.; Siegrist, T.; Mattheus, C. C.; Palstra, T. T. M. J. Phys. Chem. B 2002, 106, 8288-8292
16. Curtis, M. D.; Cao, J.; Kampf, J. W. J. Am. Chem. Soc. 2004, 126, 4318-4328
17. Brédas, J.-L.; Beljonne, D.; Coropceanu, V.; Cornil, J. Chem. Rev. 2004, 104, 4971-5003
18. Deng, W.-Q.; Goddard, W. A., III. J. Phys. Chem. B 2004, 108, 8614-8621
19. da Silva Filho, D. A.; Kim, E.-G.; Brédas, J.-L. Adv. Mater. 2005, 17, 1072-1076
20. Silvestri, F.; Marrocchi, A.; Seri, M.; Kim, C.; Marks, T. J.; Facchetti, A.; Taticchi, A. J. Am. Chem. Soc. 2010, 132, 6108-6123
21. Anthony, J. E.; Brooks, J. S.; Eaton, D. L.; Parkin, S. R. J. Am. Chem. Soc. 2001, 123, 9482-9483
22. Anthony, J. E.; Eaton, D. L.; Parkin, S. R. Org. Lett. 2002, 4, 15-18
23. Payne, M. M.; Parkin, S. R.; Anthony, J. E.; Kuo, C.-C.; Jackson, T. N. J. Am. Chem. Soc. 2005, 127, 4986-4987
24. Subramanian, S.; Park, S. K.; Parkin, S. R.; Podzorov, V.; Jackson, T. N.; Anthony, J. E. J. Am. Chem. Soc. 2008, 130, 2706-2707
25. Kobayashi, K.; Masu, H.; Shuto, A.; Yamaguchi, K. Chem. Mater. 2005, 17, 6666-6673
26. Sasaki, H.; Wakayama, Y.; Chikyow, T.; Barrena, E.; Dosch, H.; Kobayashi, K. Appl. Phys. Lett. 2006, 88, 081907-1-3
27. Kobayashi, K.; Shimaoka, R.; Kawahata, M.; Yamanaka, M.; Yamaguchi, K. Org. Lett. 2006, 8, 2385-2388
28. Wakayama, Y.; Hayakawa, R.; Chikyow, T.; Machida, S.; Nakayama, T.; Egger, S.; de Oteyza, D. G.; Dosch, H.; Kobayashi, K. Nano Lett. 2008, 8, 3273-3277
29. For S-S interactions for molecular ordering, see also: Werz, D. B.; Gleiter, R.; Rominger, F. J. Am. Chem. Soc. 2002, 124, 10638-10639
30. Gleiter, R.; Werz, D. B. Chem. Lett. 2005, 34, 126-131
31. Bleiholder, C.; Werz, D. B.; Köppel, H.; Gleiter, R. J. Am. Chem. Soc. 2006, 128, 2666-2674
32. Kaur, I.; Jia, W.; Kopreski, R. P.; Selvarasah, S.; Dokmeci, M. R.; Pramanik, C.; McGruer, N. E.; Miller, G. P. J. Am. Chem. Soc. 2008, 130, 16274-16286
33. Kaur, I.; Stein, N. N.; Kopreski, R. P.; Miller, G. P. J. Am. Chem. Soc. 2009, 131, 3424-3425
34. Kaur, I.; Jazdzyk, M.; Stein, N. N.; Prusevich, P.; Miller, G. P. J. Am. Chem. Soc. 2010, 132, 1261-1263
35. For selected examples of sulfur-containing heretoacenes, see ref 8c,8d and: Laquindanum, J. G.; Katz, H. E.; Lovinger, A. J. J. Am. Chem. Soc. 1998, 120, 664-672
36. 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
37. Mas-Torrent, M.; Durkut, M.; Hadley, P.; Ribas, X.; Rovira, C. J. Am. Chem. Soc. 2004, 126, 984-985
38. Takimiya, K.; Kunugi, Y.; Konda, Y.; Niihara, N.; Otsubo, T. J. Am. Chem. Soc. 2004, 126, 5084-5085
39. Meng, H.; Sun, F.; Goldfinger, M. B.; Jaycox, G. D.; Li, Z.; Marshall, W. J.; Blackman, G. S. J. Am. Chem. Soc. 2005, 127, 2406-2407
40. Xiao, K.; Liu, Y.; Qi, T.; Zhang, W.; Wang, F.; Gao, J.; Qiu, W.; Ma, Y.; Cui, G.; Chen, S.; Zhan, X.; Yu, G.; Qin, J.; Hu, W.; Zhu, D. J. Am. Chem. Soc. 2005, 127, 13281-13286
41. Naraso; Nishida, J.; Kumaki, D.; Tokito, S.; Yamashita, Y. J. Am. Chem. Soc. 2006, 128, 9598-9599
42. Takimiya, K.; Ebata, H.; Sakamoto, K.; Izawa, T.; Otsubo, T.; Kunugi, Y. J. Am. Chem. Soc. 2006, 128, 12604-12605
43. Briseno, A.; Miao, Q.; Ling, M.-M.; Reese, C.; Meng, H.; Bao, Z.; Wudl, F. J. Am. Chem. Soc. 2006, 128, 15576-15577
44. Tang, M. L.; Okamoto, T.; Bao, Z. J. Am. Chem. Soc. 2006, 128, 16002-16003
45. Yamamoto, T.; Takimiya, K. J. Am. Chem. Soc. 2007, 129, 2224-2225
46. Yamada, K.; Okamoto, T.; Kudoh, K.; Wakamiya, A.; Yamaguchi, S.; Takeya, J. Appl. Phys. Lett. 2007, 90, 072102-1-3
47. Tang, M. L.; Reichardt, A. D.; Miyaki, N.; Stoltenberg, R. M.; Bao, Z. J. Am. Chem. Soc. 2008, 130, 6064-6065
48. Didane, Y.; Mehl, G. H.; Kumagai, A.; Yoshimoto, N.; Videlot-Ackermann, C.; Brisset, H. J. Am. Chem. Soc. 2008, 130, 17681-17683
49. For selected examples of OFET properties of functionalized tetracenes, see ref 3 and: Tulevski, G. S.; Miao, Q.; Fukuto, M.; Abram, R.; Ocko, B.; Pindak, R.; Steigerwald, M. L.; Kagan, C. R.; Nuckolls, C. J. Am. Chem. Soc. 2004, 126, 15048-15050
50. Moon, H.; Zeis, R.; Borkent, E.-J.; Besnard, C.; Lovinger, A. J.; Siegrist, T.; Kloc, C.; Bao, Z. J. Am. Chem. Soc. 2004, 126, 15322-15323
51. Merlo, J. A.; Newman, C. R.; Gerlach, C. P.; Kelley, T. W.; Muyres, D. V.; Fritz, S. E.; Toney, M. F.; Frisbie, C. D. J. Am. Chem. Soc. 2005, 127, 3997-4009
52. Schmidt, R.; Göttling, S.; Leusser, D.; Stalke, D.; Krause, A.-M.; Würthner, F. J. Mater. Chem. 2006, 16, 3708-3714
53. Paraskar, A. S.; Reddy, A. R.; Patra, A.; Wijsboom, Y. H.; Gidron, O.; Shimon, L. J. W.; Leitus, G.; Bendikov, M. Chem.-Eur. J. 2008, 14, 10639-10647
54. Kimoto, T.; Tanaka, K.; Sakai, Y.; Ohno, A.; Yoza, K.; Kobayashi, K. Org. Lett. 2009, 11, 3658-3661
55. For selected examples of other functionalized tetracenes, see: Odom, S. A.; Parkin, S. R.; Anthony, J. E. Org. Lett. 2003, 5, 4245-4248
56. Del Guerzo, A.; Olive, A. G. L.; Reichwagen, J.; Hopf, H.; Desvergne, J.-P. J. Am. Chem. Soc. 2005, 127, 17984-17985
57. Kyushin, S.; Ishikita, Y.; Matsumoto, H.; Horiuchi, H.; Hiratsuka, H. Chem. Lett. 2006, 35, 64-65
58. Chen, Z.; Muller, P.; Swager, T. M. Org. Lett. 2006, 8, 273-276
59. Liang, Z.; Zhao, W.; Wang, S.; Tang, Q.; Lam, S.-C.; Miao, Q. Org. Lett. 2008, 10, 2007-2010
60. Kitamura, C.; Abe, Y.; Ohara, T.; Yoneda, A.; Kawase, T.; Kobayashi, T.; Naito, H.; Komatsu, T. Chem.-Eur. J. 2010, 16, 890-898
61. Guindon, Y.; Frenette, R.; Fortin, R.; Rokach, J. J. Org. Chem. 1983, 48, 1357-1359
62. See the Supporting Information.
63. s = 3.69 ns). Thus, one reason why 1 is more resistant to photooxidation than 2 and 3 may be a consequence of a shorter excited state lifetime of 1 relative to those of 2 and 3.
64. b Å. Elemental Radii in the Cambridge Structural Database, Cambridge Crystallographic Data Centre, Cambridge.
65. Pauling, L. The Nature of the Chemical Bond, 3 rd ed.; Cornell University Press: Ithaca, NY, 1973.
66. Maitland, G. C.; Rigby, M.; Smith, E. B.; Wakeham, W. A. Intermolecular Forces; Clarendon Press: Oxford, 1981.
67. The TFT devices were fabricated in yellow light and were measured in the dark. The devices measured two structures (bottom electrode contact and top electrode contact). These values were the average of more than three samples.
68. Minakata, T.; Natsume, Y. Synth. Met. 2005, 153, 1-4
69. Sheldrick, G. M. SHELXS-97 and SHELXL-97, University of Göttingen, Göttingen, Germany, 1997.