Dibenzo[a,e]pentalene-embedded dicyanomethylene-substituted thienoquinoidals for n-channel organic semiconductors: Synthesis, properties, and device characteristics

Journal of Materials Chemistry C

Volumn 3, Issue 2, 2015, Pages 283-290

  Nakano, Masahiro ^a   Osaka, Itaru ^a   Takimiya, Kazuo ^a,b  

^a RIKEN Center for Emergent Matter Science   (Japan)

^b HIROSHIMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BOND LENGTH; CRYSTAL STRUCTURE; CYCLIC VOLTAMMETRY; MOLECULES; ORGANIC POLYMERS; SINGLE CRYSTALS; THIN FILMS; X RAY ANALYSIS;

AMBIPOLAR CHARACTERISTICS; BOND LENGTH ALTERNATION; DEVICE CHARACTERISTICS; EXTENDED STRUCTURES; INTERMOLECULAR INTERACTIONS; N-CHANNEL ORGANIC SEMICONDUCTORS; N-TYPE ORGANIC SEMICONDUCTOR; SINGLE CRYSTAL X-RAY ANALYSIS;

FIELD EFFECT TRANSISTORS;

EID: 84918558778     PISSN: 20507534     EISSN: 20507526     Source Type: Journal    
DOI: 10.1039/c4tc02164a     Document Type: Article

References (63)

1. (a) Organic Electronics, Manufacturing and Applications, ed. H. Klauk, Wiley-VCH, Weinheim, 2006;
2. (b) Organic Electronics II, More Materials and Applications, ed. H. Klauk, Wiley-VCH, Weinheim, 2012;
3. (c) A. Facchetti, Mater. Today, 2007, 10, 28-37.
4. Organic Field-effect Transistors, ed. Z. Bao and J. Locklin, CRC Press, Boca Raton, FL, 2007.
5. (a) X. Gao and Y. Hu, J. Mater. Chem. C, 2014, 2, 3099-3117;
6. (b) J. E. Anthony, A. Faccheti, M. Heeney, S. R. Marder and X. Zhan, Adv. Mater., 2010, 22, 3876-3892;
7. (c) H. Usta, A. Facchetti and T. J. Marks, Acc. Chem. Res., 2011, 501-510.
8. (a) F. Würthner and M. Stolte, Chem. Commun., 2011, 47, 5109-5115;
9. (b) S.-L. Suraru and F. Würthner, Angew. Chem., Int. Ed., 2014, 53, 7428-7448;
10. (c) X. Zhan, A. Facchetti, S. Barlow, T. J. Marks, M. A. Ratner, M. R. Wasielewski and S. R. Marder, Adv. Mater., 2011, 23, 268-284;
11. (d) M. Sommer, J. Mater. Chem. C., 2014, (2), 3088-3098;
12. (e) Z. Liu, G. Zhang, Z. Cai, X. Chen, H. Luo, Y. Li, J. Wang and D. Zhang, Adv. Mater., 2014, 26, 6965-6977;
13. (f) X. Guo, A. Facchetti and T. J. Marks, Chem. Rev., 2014, 114, 8943-9021.
14. (a) R. C. Haddon, A. S. Perel, R. C. Morris, T. T. M. Palstra, A. F. Hebard and R. M. Fleming, Appl. Phys. Lett., 1995, 67, 121-123;
15. (b) C. Waldauf, P. Schilinsky, M. Perisutti, J. Hauch and C. J. Brabec, Adv. Mater., 2003, 15, 2084-2088;
16. (c) T. B. Singh, N. Marjanoviæ, P. Stadler, M. Auinger, G. J. Matt, S. Günes and N. S. Saricifici, J. Appl. Phys., 2005, 97, 083714.
17. (a) Z. Bao, A. J. Lovinger and J. Brown, J. Am. Chem. Soc., 1998, 120, 207-208;
18. (b) Y. Sakamoto, T. Suzuki, M. Kobayashi, Y. Gao, Y. Fukai, Y. Inoue, F. Sato and S. Tokito, J. Am. Chem. Soc., 2004, 126, 8138-8140.
19. (a) J. Ferraris, D. O. Cowan, V. Walatka and J. H. Perlstein, J. Am. Chem. Soc., 1973, 95, 948-949;
20. (b) N. Martin, J. L. Segura and C. Seoane, J. Mater. Chem., 1997, 7, 1661-1676.
21. (a) J. Casado, R. Ponce Ortiz and J. T. Lopez Navarrete, Chem. Soc. Rev., 2012, 41, 5672-5686;
22. (b) S. Gronowitz and B. Uppström, Acta Chem. Scand., Ser. B, 1974, 28, 981-985;
23. (c) K. Yui, Y. Aso, T. Otsubo and F. Ogura, J. Chem. Soc., Chem. Commun., 1987, 1816-1817;
24. (d) K. Yui, H. Ishida, Y. Aso, T. Otsubo and F. Ogura, Chem. Lett., 1987, 2339-2342;
25. (e) K. Yui, Y. Aso, T. Otsubo and F. Ogura, Bull. Chem. Soc. Jpn., 1989, 62, 1539-1546;
26. (f) K. Yui, H. Ishida, Y. Aso, T. Otsubo, F. Ogura, A. Kawamoto and J. Tanaka, Bull. Chem. Soc. Jpn., 1989, 62, 1547-1555.
27. (a) A. R. Brown, D. M. de Leeuw, E. J. Lous and E. E. Havinga, Synth. Met., 1994, 66, 257-261;
28. (b) J. G. Laquindanum, H. E. Katz, A. Dodabalapur and A. J. Lovinger, J. Am. Chem. Soc., 1996, 118, 11331-11332;
29. (c) D. M. de Leeuw, M. M. J. Simenon, A. R. Brown and R. E. F. Einerhand, Synth. Met., 1997, 87, 53-59;
30. (d) E. Menard, V. Podzorov, S.-H. Hur, A. Gaur, M. E. Gershenson and J. A. Rogers, Adv. Mater., 2004, 16, 2097-2101;
31. (e) N. Yanai, T. Mori, S. Shinamura, I. Osaka and K. Takimiya, Org. Lett., 2014, 16, 240-243.
32. (a) T. M. Pappenfus, R. J. Chesterfield, C. D. Frisbie, K. R. Mann, J. Casado, J. D. Raff and L. L. Miller, J. Am. Chem. Soc., 2002, 124, 4184-4185;
33. (b) J. Casado, L. L. Miller, K. R. Mann, T. M. Pappenfus, H. Higuchi, E. Orti, B. Milian, R. Pou-Amerigo, V. Hernandez and J. T. Lopez Navarrete, J. Am. Chem. Soc., 2002, 124, 12380-12388;
34. (c) R. J. Chesterfield, C. R. Newman, T. M. Pappenfus, P. C. Ewbank, M. H. Haukaas, K. R. Mann, L. L. Miller and C. D. Frisbie, Adv. Mater., 2003, 15, 1278-1282;
35. (d) A. Berlin, S. Grimoldi, G. Zotti, R. M. Osuna, M. C. Ruiz Delgado, R. P. Ortiz, J. Casado, V. Hernandez and J. T. Lopez Navarrete, J. Phys. Chem. B, 2005, 109, 22308-22318;
36. (e) Y. Kunugi, K. Takimiya, Y. Toyoshima, K. Yamashita, Y. Aso and T. Otsubo, J. Mater. Chem., 2004, 14, 1367-1369;
37. (f) S. Handa, E. Miyazaki, K. Takimiya and Y. Kunugi, J. Am. Chem. Soc., 2007, 129, 11684-11685;
38. (g) S. Handa, E. Miyazaki and K. Takimiya, Chem. Commun., 2009, 3919-3921;
39. (h) J. C. Ribierre, T. Fujihara, S. Watanabe, M. Matsumoto, T. Muto, A. Nakao and T. Aoyama, Adv. Mater., 2010, 22, 1722-1726;
40. (i) Y. Suzuki, E. Miyazaki and K. Takimiya, J. Am. Chem. Soc., 2010, 132, 10453-10466;
41. (j) Y. Suzuki, M. Shimawaki, E. Miyazaki, I. Osaka and K. Takimiya, Chem. Mater., 2011, 23, 795-804;
42. (k) J. C. Ribierre, S. Watanabe, M. Matsumoto, T. Muto, D. Hashizume and T. Aoyama, J. Phys. Chem. C, 2011, 115, 20703-20709.
43. (a) T. Kashiki, E. Miyazaki and K. Takimiya, Chem. Lett., 2009, 38, 568-569;
44. (b) Q. Wu, R. Li, W. Hong, H. Li, X. Gao and D. Zhu, Chem. Mater., 2011, 23, 3138-3140;
45. (c) T. Mori, N. Yanai, I. Osaka and K. Takimiya, Org. Lett., 2014, 16, 1334-1337;
46. (d) G. E. Rudebusch, A. G. Fix, H. A. Henthorn, C. L. Vonnegut, L. N. Zakharov and M. M. Haley, Chem. Sci., 2014, 5, 3627-3633.
47. (a) H. Zhong, J. Smith, S. Rossbauer, A. J. P. White, T. D. Anthopoulos and M. Heeney, Adv. Mater., 2012, 24, 3205-3211;
48. (b) Y. Qiao, Y. Guo, C. Yu, F. Zhang, W. Xu, Y. Liu and D. Zhu, J. Am. Chem. Soc., 2012, 134, 4084-4087;
49. (c) Q. Wu, S. Ren, M. Wang, X. Qiao, H. Li, X. Gao, X. Yang and D. Zhu, Adv. Funct. Mater., 2013, 23, 2277-2284.
50. (a) J. Yang, M. V. Lakshmikantham, M. P. Cava, D. Lorcy and J. R. Bethelot, J. Org. Chem., 2000, 65, 6739-6742;
51. (b) M. Nakano, I. Osaka, K. Takimiya and T. Koganezawa, J. Mater. Chem. C, 2014, 2, 64-70.
52. M. Uno, K. Seto and S. Takahashi, J. Chem. Soc., Chem. Commun., 1984, 932-933.
53. A. Klapars and S. L. Buchwald, J. Am. Chem. Soc., 2002, 124, 14844-14845.
54. MO calculations were carried out with the DFT/TD-DFT method at the B3LYP/6-31G(d) level using Gaussian 03 program package, M. J. Frisch, et al., Gaussian 03, revision C.02, Gaussian, Inc., Wallingford, CT, 2004.
55. 2 substrate by drop-casting from hot o-dichlorobenzene solution. Comparison of the out-of-plane and in-plane XRD patterns of the film with the simulated powder pattern from the bulk 7a-crystal structure suggested that the packing structure and molecular orientation of 7a in the thin-film should be different from those in the bulk single crystal (Fig. S5†).
56. (a) H. Inokuchi, G. Saito, P. Wu, K. Seki, T. B. Tang, T. Mori, K. Imaeda, T. Enoki, Y. Higuchi, K. Inaka and N. Yasuoka, Chem. Lett., 1986, 15, 1263-1266;
57. (b) H. Ebata, T. Izawa, E. Miyazaki, K. Takimiya, M. Ikeda, H. Kuwabara and T. Yui, J. Am. Chem. Soc., 2007, 129, 15732-15733.
58. A. Mishra, R. K. Behera, P. K. Behera, B. K. Mishra and G. B. Behera, Chem. Rev., 2000, 100, 1973-2012.
59. (a) S.-L. Suraru, U. Zschieschang, H. Klauk and F. Würthner, Chem. Commun., 2011, 47, 11504-11506;
60. (b) Y. Fukutomi, M. Nakano, J.-Y. Hu, I. Osaka and K. Takimiya, J. Am. Chem. Soc., 2014, 135, 11445-11448.
61. M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, G. L. Cascarano, L. De Caro, C. Giacovazzo, G. Polidori, D. Siliqi and R. Spagna, J. Appl. Cryst., 2007, 40, 609-613.
62. Rigaku, CrystalStructure. Version 4.0, Rigaku Corporation, Tokyo, Japan, 2011.
63. B. S. Ong, Y. Wu, P. Liu and S. Gardner, J. Am. Chem. Soc., 2004, 126, 3378-3379.