Synthesis and properties of hexyl end-capped thiophene oligomers containing anthracene moiety in the center

Bulletin of the Korean Chemical Society

Volumn 28, Issue 7, 2007, Pages 1175-1182

  Jung, Hei Choi ^a   Dae, Won Cho ^b   Jin, Sung Ho ^a   Ung, Chan Yoon ^a  

^a Pusan National University   (South Korea)

^b Chosun University   (South Korea)

Author keywords

Anthracene; Stille reaction; Thiophene oligomer; Thiophene anthracene oligomer

Indexed keywords

ANTHRACENE; REACTION KINETICS; SEMICONDUCTING ORGANIC COMPOUNDS; SYNTHESIS (CHEMICAL);

STILLE REACTION; THIOPHENE OLIGOMER; THIOPHENE-ANTHRACENE OLIGOMER;

OLIGOMERS;

EID: 34547488862     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2007.28.7.1175     Document Type: Article

References (36)

1. (a) Barbarella, G.; Favaretto, L.; Sotgiu, G.; Zambianchi, M.; Bongini, A.; Arbizzani, C.; Mastragostino, M.; Anni, M.; Gigli, G.; Cingolani, R. J. Am. Chem. Soc. 2000, 122, 11971.
2. (b) Ho, H. A.; Brisset, H.; Elandaloussi, E. H.; Frere, P.; Roncali, J. Adv. Mater. 1996, 8, 990.
3. (c) Hicks, R. G.; Nodwell, M. B. J. Am. Chem. Soc. 2000, 122, 6746.
4. (d) Lee, Y.-H.; Cho, Y. H.; Shin, H.; Kim, J.; Lee, J.; Lee, H.; Sung, M. M. Bull. Korean Chem. Soc. 2006, 27, 1633.
5. (a) Burroughes, J. H.; Bradley, D. D. C.; Brown, A. R.; Marks, R. N.; Mackay, K.; Friend, R. H.; Burn, P. L.; Holmes, A. B. Nature 1990, 347, 539.
6. (b) Lee, W. L.; An, J.-G.; Yoon, H.-K.; Jang, H.; Kim, N. G.; Do, Y. Bull. Korean Chem. Soc. 2005, 26, 1569.
7. (a) Horowitz, G. Adv. Mater. 1998, 10, 365.
8. (b) Katz, H. E.; Lovinger, A. J.; Johnson, J.; Kloc, C.; Siegrist, T.; Li, W.; Lin, Y. Y.; Dodabalapur, A. Nature 2000, 404, 478.
9. (a) Sariciftci, N. S.; Smilowitz, L.; Heeger, A. J.; Wudl, F. Science 1992, 258, 1474.
10. (b) Yu, G.; Gao, J.; Hummelen, J. C.; Wudl, F.; Heeger, A. J. Science 1995, 270, 1789.
11. (c) Kang, M. S.; Oh, J. B.; Roh, S. G.; Kim, M.-R.; Lee, J. K.; Jin, S.-H.; Kim, H. K. Bull. Korean Chem. Soc. 2007, 28, 33.
12. (a) Newman, C. R.; Frisbie, C. D.; da Silva Filho, D. A.; Bredas, J.-L.; Ewbank, P. C.; Mann, K. R. Chem. Mater. 2004, 16, 4436.
13. (b) Dimitrakopoulos, C. D.; Malenfant, P. R. L. Adv. Mater. 2002, 14, 99.
14. (c) Katz, H. E.; Bao, Z.; Gilat, S. L. Acc. Chem. Res. 2001, 34, 359.
15. (d) Facchetti, A.; Mushrush, M.; Katz, H. E.; Marks, T. J. Adv. Mater. 2003, 15, 33.
16. (e) Sheraw, C. D.; Jackson, T. N.; Eaton, D. L.; Anthony, J. E. Adv. Mater. 2003, 15, 2009.
17. (a) Klauk, H.; Halik, M.; Zshieschang, U.; Schmid, G.; Radlik, W.; Weber, W. J. Appl. Phys. 2002, 92, 5259.
18. (b) Sheraw, C. D.; Zhou, L.; Huang, J. R.; Gundlach, D. J.; Jackson, T. N.; Kane, M. G.; Hill, I. G.; Hammond, M. S.; Campi, J.; Greening, B. K.; Francl, J.; West, J. Appl. Phys. Lett. 2002, 80, 1088.
19. (a) Pope, M.; Swenberg, C. E. Electronic Processes in Organic Crystals and Polymers; Oxford University Press: New York, 1999; p 234.
20. (b) Karl, N.; Marktanner, J. Mol. Cryst. Liq. Cryst. 2001, 355, 149.
21. Ito, K.; Suzuki, T.; Sakamoto, Y.; Kubota, D.; Inoue, Y.; Sato, F.; Tokito, S. Angew. Chem. Int. Ed. 2003, 42, 1159.
22. (a) 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.
23. (b) Ando, S.; Nishida, J.-i.; Fujiwara, E.; Tada, H.; Inoue, Y.; Tokito, S.; Yamashita, Y. Chem. Mater. 2005, 17, 1261.
24. Garnier, F.; Yassar, A.; Hajlaoui, R.; Horowitz, G.; Deloffre, F.; Servet, B.; Ries, S.; Alnot, P. J. Am. Chem. Soc. 1993, 115, 8716.
25. Raposo, M. M. M.; Fonseca, A. M. C.; Kirsch, G. Tetrahedron 2004, 60, 4071.
26. Murov, S. L.; Carmichael, I.; Hug, G. L. Handbook of Photochemistry, 2nd ed; Marcel Dekker: New York, 1993.
27. Kotha, S.; Ghosh, A. K.; Deodhar, K. D. Synthesis 2004, 4, 549.
28. Facchetti, A.; Yoon, M.-H.; Stern, C. L.; Hutchison, G. R.; Ratner, M. A.; Marks, T. J. J. Am. Chem. Soc. 2004, 126, 13480.
29. Nessakh, B.; Horowitz, G.; Garnier, F.; Deloffre, F.; Srivastava, P.; Yassar, A. J. Electroanal. Chem. 1995, 399, 97.
30. (a) Lap, D. V.; Grebner, D.; Rentsch, S. J. Phys. Chem. A 1997, 101, 107.
31. (b) Chosrovian, H.; Rentsch, S.; Grebner, D.; Dahm, D. U.; Birckner, E.; Naarmann, H. Synth. Met. 1993, 60, 23.
32. (c) Garcia, P.; Pernaut, J. M.; Hapiot, P.; Wintgens, V.; Valat, P.; Garnier, F.; Delabouglise, D. J. Phys. Chem. 1993, 97, 513.
33. Becker, R. S.; Seixas de Melo, J.; Macanita, A. L.; Elisei, F. J. Phys. Chem. 1996, 100, 18683.
34. Wintgens, V.; Valat, P.; Garnier. F. J. Phys. Chem. 1994, 98, 228.
35. Facchetti, A.; Deng, H.; Wang, A. C.; Koide, Y.; Sirrinhaus, H.; Marks, T. J.; Friend, R. H. Angew. Chem. Int. Ed. 2000, 39, 4547.
36. Tian, H.; Wang, J.; Shi, J.; Yan, D.; Wang, L.; Geng, Y.; Wang, F. J. Mater. Chem. 2005, 15, 3026.