Inversion of optical activity of chiral polythiophene aggregates by a change of solvent

Macromolecules

Volumn 31, Issue 19, 1998, Pages 6702-6704

  Langeveld Voss, B M W ^a   Christiaans, M P T ^a   Janssen, R A J ^a   Meijer, E W ^a  

^a EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CONFORMATIONS; CRYSTALLINE MATERIALS; METHANOL; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC SOLVENTS; PLASTIC FILMS; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL); THERMAL EFFECTS; ULTRAVIOLET SPECTROSCOPY;

CHLOROFORM; CIRCULAR DICHROISM SPECTROSCOPY; DECANOL; NONANOL; POLYTHIOPHENES;

AROMATIC POLYMERS;

EID: 0032163173     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma980813w     Document Type: Article

References (25)

1. Green, M. M.; Andreola, C.; Muñoz, B.; Reidy, M. P.; Zero, K. J. Am. Chem. Soc. 1998, 110, 4063.
2. Ramos, E.; Bosch, J.; Serrano, J. L.; Sierra, T.; Veciana, J. J. Am. Chem. Soc. 1996, 118, 4703.
3. Janssen, H. M.; Meijer, E. W. Macromolecules 1997, 30, 8129.
4. (a) Pohl, F. M.; Jovin, T. M. J. Mol. Biol. 1972, 67, 375.
5. (b) Cosstick, R.; Eckstein, F. Biochemistry 1985, 24, 3630.
6. Okamoto, Y.; Nakano, T.; Ono, E.; Hatada, K. Chem. Lett. 1991, 525.
7. (a) Steinberg, I. Z.; Harrington, W. F.; Berger, A.; Sela, M.; Katchalski, E. J. Am. Chem. Soc. 1960, 82, 5263.
8. (b) Blout, E. R.; Carver, J. P.; Gross, J. J. Am. Chem. Soc. 1963, 85, 644.
9. (c) Gratzer, W. B.; Rhodes, W.; Fasman, G. D. Biopolymers 1963, 1, 319.
10. (a) Price, C. C.; Osgan, M. J. Am. Chem. Soc. 1956, 78, 4789.
11. (b) Furukawa J. In Optically Active Polymers; Sélégny, E., Ed.; D. Reidel Publishing Co.: Dordrecht, 1979.
12. For a recent review on optically active π-conjugated polymers see: Pu L. Acta Polym. 1997, 48, 116.
13. Bouman, M. M.; Meijer, E. W. Adv. Mater. 1995, 7, 385.
14. Bidan, G.; Guillerez, S.; Sorokin, V. Adv. Mater. 1996, 8 157.
15. McCullough, R. D.; Lowe, R, D.; Jayaraman, M.; Anderson, D. L. J. Org. Chem. 1993, 58, 904.
16. Rughooputh, S. D. D. V.; Hotta, S.; Heeger, A. J.; Wudl, F. J. Polym. Sci, Polym. Phys. Ed. 1987, 25, 1071.
17. (a) Langeveld-Voss, B. M. W.; Janssen, R. A. J.; Christiaans, M. P. T.; Meskers, S. C. J.; Dekkers, H. P. J. M.; Meijer, E. W. J. Am. Chem. Soc. 1996, 118, 4908.
18. (b) Langeveld-Voss, B. M. W.; Beljonne, D.; Shuai, Z.; Janssen, R. A. J.; Meskers, S. C. J.; Meijer, E. W.; Brédas, J. L. Adv. Mater., in press.
19. One of the reviewers suggested that the alcohols make a hydrogen bond with the ether oxygen of 1 and 2, affecting the aggregation and the sign of the CD effect. Although this seems a likely explanation based on our experiments, it does not explain similar inversions previously observed in poly-(3-alkylthiophenes) (ref 10).
20. 13C NMR. The lack of complete regioregularity in this case is probably related to the position of the oxygen in the side chain, as in the lithiated intermediate an energetically favored (chelating) complex is formed by exchange of bromine and lithium (See: McCullough, R. D.; Williams, S. P. J. Am. Chem. Soc. 1993, 115, 11608). As a result of the low regioregularity the aggregation of this polymer was very poor in 1-decanol (a small positive CD couplet was found with g = +0.003 at 510 nm) and further studies were abandoned.
21. (a) Prosa, T. J.; Winokur, M. J.; McCullough, R. D. Macromolecules 1996, 29, 3654.
22. (b) Bolognesi, A.; Pozio, W.; Zhuo, G.; Ezquerra, T. Eur. Polym. J. 1996, 32, 1097.
23. (a) Slaney, A. J.; Nishiyama, I.; Styring, P.; Goodby, J. W. J. Mater. Chem. 1992, 2, 805.
24. (b) Loubser, C.; Wessels, P. L.; Styring, P.; Goodby, J. W. J. Mater. Chem. 1994, 4, 71.
25. (c) Radley, K.; McLay, N. J. Phys. Chem. 1994, 98, 3071.