Synthesis and characterization of novel π-conjugated polymers with phosphole ring derivatives

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 45, Issue 14, 2007, Pages 2867-2875

  Na, Hai Sub ^a   Morisaki, Yasuhiro ^a   Aiki, Yasuhiro ^a   Chujo, Yoshiki ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Conjugated polymers; Heteroatom containing polymers; Phosphole; UV vis spectroscopy

Indexed keywords

CATALYST ACTIVITY; DERIVATIVES; FOURIER TRANSFORM INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PALLADIUM COMPOUNDS; SYNTHESIS (CHEMICAL); ULTRAVIOLET VISIBLE SPECTROSCOPY;

HETEROATOM-CONTAINING POLYMERS; PHOSPHOLE; PHOSPHOLE RING DERIVATIVES;

CONJUGATED POLYMERS;

EID: 34547399636     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.22043     Document Type: Article

References (39)

1. (a) Handbook of Conducting Polymers, 2nd ed.; Skotheim, T. A.; Elsenbaumer, R. L.; Reynolds, J., Eds.; Marcel Dekker: New York, 1998;
2. (b) Nonlinear Optical Effects in Organic Polymers; Messier, J.; Kajzar, F.; Prasad, P. N.; Ulrich, D. R., Eds.; Kluwer Academic: Dordrecht, 1989;
3. (c) Introduction to Nonlinear Optical Effects in Molecules and Polymers; Prasad, P. N.; Williams, D. J., Eds.; Wiley: New York, 1990;
4. (d) Materials for Nonlinear Optics; Marder, S. R.; Sohn, J. E.; Stucky, G. D., Eds.; ACS Symposium Series 455; American Chemical Society: Washington, DC, 1991;
5. (e) Molecular Nonlinear Optics: Materials, Physics, and Devices; Zyss, J., Ed.; Academic:Boston, 1994;
6. (f) Electronic Materials: The Oligomer Approach; Müllen, K.; Wegner, G., Eds.; Wiley-VCH: Weinheim, 1998;
7. (g) Kraft, A.; Grimsdale, A. C.; Holmes, A. B. Angew Chem Int Ed 1998, 37, 402;
8. (h) McQuade, D. T.; Pullen, A. E.; Swager, T. M. Chem Rev 2000, 100, 2537;
9. (i) Bredas, J. L.; Adant, C.; Tackx, P.; Persoons, A.; Pierce, B. M. Chem Rev 1994, 94, 243;
10. (j) Dimitrakopoulos, C. D.; Mascaro, D. J. IBM J Res Dev 2001, 45, 11.
11. (a) Quin, L. D.; Quin, G. S. In Phosphorus-Carbon Heterocyclic Chemistry: The Rise of a New Domain; Mathey, F., Ed.; Pergamon: Amsterdam, 2001;
12. (b) Nyulaszi, L. Chem Rev 2001, 101, 1229;
13. (c) Mathey, F. Chem Rev 1988, 88, 429;
14. (d) Bevière, M.-O.; Mercier, F.; Ricard, L.; Mathey, F. Angew Chem Int Ed 1990, 6, 655.
15. Norman, R. O. C.; Coxon, J. M. Principles of Organic Synthesis, 3rd ed.; Blackie: London, 1993.
16. For a report on the synthesis of a fused phosphole, see (a) Wittig, G.; Geissler, G. Justus Liebigs Ann Chem 1953, 580, 44. A reliable synthesis for phospholes has been reported by two independent groups;
17. see (b) Leavitt, F. C.; Manuel, T. A.; Johnson, F. J Am Chem Soc 1959, 81, 3163;
18. (c) Braye, E. H.; Hübel, W. Chem Ind (London) 1959, 1250.
19. (a) Dillon, K. B.; Mathy, F.; Nixon, J. F. Phosphorus: The Carbon Copy; Wiley: Chichester, England, 1998;
20. (b) Comprehensive Heterocyclic Chemistry; Quin, L. D.; Katritzky, A. R.; Ress, C. W.; Scriven, E. F. V., Eds.; Elsevier: Oxford, 1996; Vol. 2;
21. (c) Louis, D. Q. The Heterocyclic Chemistry of Phosphorus: Systems Based on the Phosphorus-Carbon Bond; Wiley: New York, 1981.
22. Mao, S. S. H.; Tilley, T. D. Macromolecules 1997, 30, 5566.
23. (a) Hay, C.; Fischmeister, C.; Hissler, M.; Toupet, L.; Réau, R. Angew Chem Int Ed 2000, 39, 1812;
24. (b) Hay, C.; Hissler, M.; Fischmeister, C.; Rault-Berthelot, J.; Toupet, L.; Nyulászi, L.; Réau, R. Chem - Eur J 2001, 7, 4222.
25. Morisaki, Y.; Aiki, Y.; Chujo, Y. Macromolecules 2003, 36, 2594.
26. (a) Dieck, H. A.; Heck, R. F. J Organomet Chem 1975, 93, 259;
27. (b) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett 1975, 16, 4467.
28. (a) Negishi, E.; Cederbaum, F. E.; Takahashi, T. Tetrahedron Lett 1986, 27, 2829;
29. (b) Negishi, E.; Takahashi, T. Acc Chem Res 1994, 27, 124.
30. (a) Doherty, S.; Robins, E. G.; Nieuwenhuyzen, M.; Knight, J. G.; Champkin, P. A.; Clegg, W. Organometallics 2002, 21, 1383;
31. (b) Doherty, S.; Knight, J. G.; Robins, E. G.; Scanlan, T. H.; Champkin, P. A.; Clegg, W. J Am Chem Soc 2001, 123, 5110;
32. (c) Takahashi, T.; Sun, W. H.; Nakajima, K. Chem Commun 1999, 1595.
33. Ogasawara, M.; Yoshida, K.; Hayashi, T. Organometallics 2001, 20, 1014.
34. (a) Coggon, P.; Engel, J. F.; McPhail, A. T.; Quin, L. D. J Am Chem Soc 1970, 92, 5773;
35. (b) Ozbrin, W. P.; Jacobson, R. A.; Clardy, J. C. Chem Commun 1971, 1062.
36. (a) Li, H.; Powell, D. R.; Hayashi, R. K.; West, R. Macromolecules 1998, 31, 52;
37. (b) Moroni, M.; Moigne, J. L. Macromolecules 1994, 27, 562.
38. unk are the absorbances of the standard and unknown samples, respectively; Fstd and Funk are the corresponding relative integrated fluorescence intensities; and nD is the refractive index [CH2Cl2 (nD = 1.424) and CHCl3 (nD = 1.446) were used].
39. Altomare, A.; Burla, M. C.; Camalli, G.; Cascarano, G.; Giacovazzo, C.; Gualiardi, A.; Polidori, G. J Appl Crystallogr 1994, 27, 435.