Cationic dithieno[3,2-b:2′,3′-d]phospholes: A new building block for luminescent, conjugated polyelectrolytes

Organic Letters

Volumn 8, Issue 25, 2006, Pages 5893-5896

  Durben, Stefan ^a   Dienes, Yvonne ^b   Baumgartner, Thomas ^a  

^a UNIVERSITY OF CALGARY   (Canada)

^b RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33846280127     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062580w     Document Type: Article

References (33)

1. See, e.g.: (a) Handbook of Conducting Polymers, 2nd ed.; Skotheim, T. A., Elsenbaumer, R. L., Reynolds, J. R., Eds.; Marcel Dekker: New York, 1998.
2. (b) Achyuthan, K. E.; Bergstedt, T. S.; Chen, L.; Jones, R. M.; Kumaraswamy, S.; Kushon, S. A.; Ley, K. D.; Lu, L.; McBranch, D.; Mukundan, H.; Rininsland, F.; Shi, X.; Xia, W.; Whitten, D. G. J. Mater. Chem. 2005, 15, 2648.
3. (c) Ramey, M. B.; Hiller, J.; Rubner, M. F.; Tan, C.; Schanze, K. S.; Reynolds, J. R. Macromolecules 2005, 38, 234.
4. (d) Nilsson, K. P. R.; Herland, A.; Hammarstroem, P.; Inganaes, O. Biochemistry 2005, 44, 3718.
5. (e) Nguyen, B. T.; Gautrot, J. E.; Ji, C.; Brunner, P.-L.; Nguyen, M. T.; Zhu, X. X. Langmuir 2006, 22, 4799.
6. (f) Jiang, H.; Zhao, X.; Schanze, K. S. Langmuir 2006, 22, 5541.
7. (a) Huang, F.; Wu, H.; Wang, D.; Yang, W.; Cao, Y. Chem. Mater. 2004, 16, 708.
8. (b) Kim, S.; Jackiw, J.; Robinson, E.; Schanze, K. S.; Reynolds, J. R.; Baur, J.; Rubner, M. F.; Boils, D. Macromolecules 1998, 31, 964.
9. (a) Mathey, F. Angew. Chem., Int. Ed. 2003, 42, 1578.
10. (b) Hissler, M.; Lescop, C.; Réau, R. J. Organomet. Chem. 2005, 690, 2482.
11. (c) Gates, D. P. Top. Curr. Chem. 2005, 250, 107.
12. (d) Hissler, M.; Dyer, P. W.; Réau, R. Top. Curr. Chem. 2005, 250, 127.
13. Mathey, F. Chem. Rev. 1988, 88, 429.
14. (a) Hay, C.; Hissler, M.; Fischmeister, C.; Rault-Berthelot, J.; Toupet, L.; Nyulászi, L.; Réau, R. Chem.-Eur. J. 2001, 7, 4222.
15. (b) Fave, C.; Hissler, M.; Kárpáti, T.; Rault-Berthelot, J.; Déborde, V.; Toupet, L.; Nyulászi, L.; Réau, R. J. Am. Chem. Soc. 2004, 126, 6058.
16. (c) Su, H.-C.; Fadhel, O.; Yang, C.-J.; Cho, T.-Y.; Fave, C.; Hissler, M.; Wu, C.-C.; Réau, R. J. Am. Chem. Soc. 2006, 128, 983.
17. (a) Baumgartner, T.; Neumann, T.; Wirges, B. Angew. Chem., Int. Ed. 2004, 43, 6197.
18. (b) Baumgartner, T.; Bergmans, W.; Kárpáti, T.; Neumann, T.; Nieger, M.; Nyulászi, L. Chem.-Eur. J. 2005, 11, 4687.
19. (c) Dienes, Y.; Eggenstein, M.; Neumann, T.; Englert, U.; Baumgartner, T. Dalton Trans. 2006, 1424.
20. (d) Neumann, T.; Dienes, Y.; Baumgartner, T. Org. Lett. 2006, 8, 495.
21. (e) Baumgartner, T.; Wilk, W. Org. Lett. 2006, 8, 503.
22. Crystallographic data for the structure of 2 have been deposited in the Cambridge Crystallographic Data Centre (deposition number: CCDC 622319). Copies of these data can be obtained free of charge via the Internet at www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, U.K.; fax (+44) 1223-336-033; or deposit@ccdc.cam.ac.uk).
23. Adkine, P.; Cantat, T.; Deschamps, E.; Ricard, L.; Mezailles, N.; Le Floch, P.; Geoffroy, M. Phys. Chem. Chem. Phys. 2006, 8, 862.
24. Demas, N. J.; Crosby, G. A. J. Chem. Phys. 1971, 75, 991.
25. Karstens, T.; Kobs, K. J. Phys. Chem. 1980, 84, 1871.
26. The fluorescence emission is too weak to provide an accurate quantum yield efficiency.
27. Becker, R. S.; de Melo, J. S.; Macanita, A. L.; Elisei, F. J. Phys. Chem. 1996, 100, 18683.
28. Sotgiu, G.; Zambianchi, M.; Barbarella, G.; Aruffo, F.; Cipriani, F.; Ventola, A. J. Org. Chem. 2003, 68, 1512.
29. Metal-Catalyzed Cross-Coupling Reactions, 2nd ed.; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004.
30. Handbook of Oligo- and Polythiophenes; Fichou, D., Ed.; Wiley-VCH: Weinheim, 1998.
31. (a) Klaerner, G.; Miller, R. D. Macromolecules 1998, 31, 2007.
32. (b) Liu, B.; Yu, W.-L.; Lai, Y.-H.; Huang, W. Macromolecules 2000, 33, 8945.
33. (c) Liu, M. S.; Luo, J.; Jen, A. K.-Y. Chem. Mater. 2003, 15, 3496.