Preparation, characterization, and FET properties of novel dicyanopyrazinoquinoxaline derivatives

Organic Letters

Volumn 6, Issue 12, 2004, Pages 2007-2010

  Nishida, Jun Ichi ^a   Naraso, ^a   Murai, Shio ^a   Fujiwara, Eiichi ^b   Tada, Hirokazu ^b   Tomura, Masaaki ^b   Yamashita, Yoshiro ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; NITRILE; PYRAZINE DERIVATIVE; QUINOXALINE DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; DEVICE; ELECTROCHEMICAL ANALYSIS; ELECTRON TRANSPORT; ENERGY; METHODOLOGY; OXIDATION REDUCTION REACTION; SEMICONDUCTOR; SYNTHESIS; X RAY ANALYSIS;

EID: 3042710760     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0494010     Document Type: Article

References (27)

1. (a) Katz, H. E. J. Mater. Chem. 1997, 7, 369-376.
2. (b) Horowitz, G. Adv. Mater. 1998, 10, 365-377.
3. (c) Voss, D. Nature 2000, 407, 442-444.
4. (a) Gundlach, D. J.; Lin, Y. Y.; Jackson, T. N.; Nelson, S. F.; Schlom, D. G. IEEE Electron Device Lett. 1997, 18, 87-89.
5. (b) Klauk, H.; Halik, M.; Zschieschang, U.; Schmid, G.; Radlik, W.; Weber, W. J. Appl. Phys. 2002, 92, 5259-5263.
6. (a) Dodabalapur, A.; Torsi, L.; Katz, H. E. Science 1995, 268, 270-271.
7. (b) Dimitrakopoulos, C. D.; Furman, B. K.; Graham T.; Hegde, S.; Purushothaman, S. Synth. Met. 1998, 92, 47-52.
8. (c) Katz, H. E.; Lovinger, A. J.; Laquindanum J. G. Chem. Mater. 1998, 10, 457-459.
9. (a) Crone, B.; Dodabalapur, A.; Lin, Y.-Y.; Filas, R. W.; Bao, Z.; Laduca, A.; Sarpeshkar, R.; Katz, H. E.; Li, W. Nature 2000, 403, 521-523.
10. (b) Dimitrakopoulos, C. D.; Malenfant, P. R. L. Adv. Mater. 2002, 14, 99-117.
11. (c) Würthner, F. Angew. Chem., Int. Ed. 2001, 40, 1037-1039.
12. Katz, H. E.; Lovinger, A. J.; Johnson, J.; Kloc, C.; Siegrist, T.; Li, W.; Lin, Y.-Y.; Dodabalapur, A. Nature 2000, 404, 478-481.
13. (a) Facchetti, A.; Deng, Y.; Wang, A.; Koide, Y.; Sirringhaus, H.; Marks, T. J.; Friend, R. H. Angew. Chem., Int. Ed. 2000, 39, 4547-4551.
14. (b) Facchetti, A.; Yoon, M.-H.; Stern, C. L.; Katz, H. E.; Marks, T. J. Angew. Chem., Int. Ed. 2003, 42, 3900-3903.
15. Bao, Z.; Lovinger, A. J.; Brown, J. J. Am. Chem. Soc. 1998, 120, 207-208.
16. Chesterfield, R. J.; Newman, C. R.; Pappenfus, T. M.; Ewbank, P. C.; Haukaas, M. H.; Mann, K. R.; Miller, L. L.; Frisbie, C. D. Adv. Mater. 2003, 15, 1278-1282.
17. (a) Siegrist, T.; Kloc, C.; Schön, J. H.; Batlogg, B.; Haddon, R. C.; Berg, S.; Thomas, G. A. Angew. Chem., Int. Ed. 2001, 40, 1732-1736.
18. (b) Mattheus, C. C.; Wijs, G. A.; Groot, R. A.; Palstra, T. T. M. J. Am. Chem. Soc. 2003, 125, 6323-6330.
19. (c) Brinkmann, M.; Graff, S.; Straupé, C.; Wittmann, J.-C.; Chaumont, C.; Nuesch, F.; Aziz, A.; Schaer, M.; Zuppiroli, L. J. Phys. Chem. B 2003, 107, 10531-10539.
20. (a) Laquindanum, J. G.; Katz, H. E.; Lovinger, A. J. J. Am. Chem. Soc. 1998, 120, 664-672.
21. (b) Miao, Q.; Nguyen, T.-Q.; Someya, T.; Blanchet, G. B.; Nuckolls, C. J. Am. Chem. Soc. 2003, 125, 10284-10287.
22. Ried, W.; Tsiotis, G. Liebigs Ann. Chem. 1988, 1197-1199.
23. Van der Tol, E. B.; Van Ramesdonk, H. J.; Verhoeven, J. W.; Streemers, F. J.; Kerver, E. G.; Verboom, W.; Reinhoudt, D. N. Chem. Eur. J. 1998, 4, 2315-2323.
24. (a) Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209-220.
25. (b) Stewart, J. J. P. J. Comput. Chem. 1989, 10, 221-264.
26. 2 = 0.153, S = 0.96.
27. The film of 1f did not show the FET property on a Au electrode. The film of 1a showed almost the same FET properties on Au and Al electrodes.