Synthesis and polymerization of 3,3″-di[(S)-(+)-2-methylbutyl]-2,2′:5′,2″-terthiophene: a new monomer precursor to chiral regioregular poly(thiophene)

Abstract

3,3″-Di[(S)-(+)-2-methylbutyl]-2,2′:5′,2″-terthiophene, having two equivalent reactive positions, allows the synthesis of the corresponding optically active poly(thiophene) with regioregular enchainment by using an aspecific oxidative polymerization method.

References

1. J. Roncali, Chem. Rev., 1992, 92, 711.
2. M. Lemaire, D. Delabouglise, R. Garreau, A. Guy and J. Roncali, J. Chem. Soc., Chem. Commun., 1988, 658.
3. D. Kotkar, V. Joshi and P. K. Ghosh, J. Chem. Soc., Chem. Commun., 1988, 917.
4. D. Kotkar, P. K. Ghosh and A. Ray, in Frontiers of Polymer Research, ed. P. N. Prasad and J. K. Nigam, Plenum, New York, 1991, p. 407.
5. M. M. Bouman and E. W. Meijer, Polym. Prepr., 1994, 35, 309.
6. M. M. Bouman and E. W. Meijer, Adv. Mater., 1995, 7, 385.
7. G. Bidan, S. Guillerez and V. Sorokin, Adv. Mater., 1996, 8, 157.
8. B. M. W. Langeveld-Voss, M. M. Bouman, M. P. T. Christiaans, R. A. J. Janssen and E. W. Meijer, Polym. Prepr., 1996, 37, 499.
9. R. D. McCullough and R. D. Lowe, J. Chem. Soc., Chem. Commun., 1992, 70.
10. R. D. McCullough, R. D. Lowe, M. Jayaraman and D. L. Anderson, J. Org. Chem., 1993, 58, 904.
11. T. A. Chen and R. D. Rieke, J. Am. Chem. Soc., 1992, 114, 10 087.
12. M. C. Gallazzi, L. Castellani, G. Zerbi and P. Sozzani, Synth. Met., 1991, 41–43, 495.
13. M. C. Gallazzi, L. Castellani, R. A. Marin and G. Zerbi, J. Polym. Sci., Part A: Polym. Chem., 1993, 31, 3339.
14. K. Faïd and M. Leclerc, J. Chem. Soc., Chem. Commun., 1993, 962.
15. C. Wang, M. E. Benz, E. LeGoff, J. L. Schindler, J. Allbritton-Thomas, C. R. Kannewurf and M. G. Kanatzidis, Chem. Mater., 1994, 6, 401.
16. P. T. Henderson and D. M. Collard, Chem. Mater., 1995, 7, 1879.
17. G. Zotti, M. C. Gallazzi, G. Zerbi and S. V. Meille, Synth. Met., 1995, 73, 217.
18. F. Andreani, E. Salatelli and M. Lanzi, Polymer, 1996, 37, 661.
19. H. Suzuki, K. Nakamura and R. Goto, Bull. Chem. Soc. Jpn., 1966, 39, 128.
20. M. Kobayashi, J. Chen, T. C. Chung, F. Moraes, A. J. Heeger and F. Wudl, Synth. Met., 1984, 9, 77.
21. M. Sato, S. Tanaka and K. Kaeriyama, Makromol. Chem., 1987, 188, 1763.
22. Y. Furakawa, M. Akimoto and I. Harada, Synth. Met., 1987, 18, 151.
23. S. Hotta, M. Soga and N. Sonoda, Synth. Met., 1988, 26, 267.
24. R. Sugimoto, S. Takeda, H. B. Gu and K. Yoshino, Chem. Express, 1986, 1, 635.