New low-gap polymers from 3,4-ethylenedioxythiophene-bis-substituted electron-poor thiophenes. The roles of thiophene, donor-acceptor alternation, and copolymerization in intrinsic conductivity

Chemistry of Materials

Volumn 16, Issue 19, 2004, Pages 3667-3676

  Berlin, Anna ^a   Zotti, Gianni ^a   Zecchin, Sandro ^a   Schiavon, Gilberto ^a   Vercelli, Barbara ^a   Zanelli, Alberto ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

COPOLYMERIZATION; FOURIER TRANSFORM INFRARED SPECTROSCOPY; QUARTZ; REDOX REACTIONS; ULTRAVIOLET SPECTROSCOPY;

ELECTROCHEMICAL GAPS; HOMOPOLYMERS; LOW-GAP POLYMERS;

ORGANIC POLYMERS;

4 DICYANOMETHYLENE 4H CYCLOPENTA[2,1 B:3,4 B']DITHIOPHENE; ALKENE DERIVATIVE; CYCLOPENTA[2,1 B:3,4 B']DITHIOPHEN 4 ONE; ETHYLENE DERIVATIVE; KETONE DERIVATIVE; POLYMER; PYRAZINE DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION; ARTICLE; CONDUCTANCE; CYCLIC POTENTIOMETRY; ELECTROCHEMISTRY; ELECTRON; FRACTIONATION; INFRARED SPECTROSCOPY; OXIDATION REDUCTION REACTION; POLYMERIZATION; ULTRAVIOLET SPECTROSCOPY;

EID: 4544288719     PISSN: 08974756     EISSN: None     Source Type: Journal    
DOI: 10.1021/cm049572z     Document Type: Article

References (46)

1. Roncali, J. Chem. Rev. 1997, 97, 173.
2. (a) Meng, H.; Tucker, D.; Chaffins, S.; Chen, Y.; Helgeson, R.; Dunn, B.; Wudl, F. Adv. Mater. 2003, 15, 146.
3. (b) Sonmeyz, G.; Meng, H.; Wudl, F. Chem. Mater. 2003, 15, 4923.
4. Wudl, F.; Kobayashi, M.; Heeger, A. J. J. Org. Chem. 1984, 49, 3382.
5. Lambert, T. L.; Ferraris, J. P. J. Chem. Soc., Chem. Commun. 1991, 752.
6. Ferraris, J. P.; Lambert, T. L. J. Chem. Soc., Chem. Commun. 1991, 1268.
7. Havinga, E. E.; ten Hoeve, W.; Wynberg, H. Polym. Bull. 1992, 29, 119.
8. Loganathan, K.; Cammisa, E. G.; Myron, B. D.; Pickup, P. G. Chem. Mater. 2003, 15, 1918.
9. Brisset, H.; Thobie-Gauthier, C.; Gorgues, A.; Jubault, M.; Roncali, J. J. Chem. Soc., Chem. Commun. 1994, 1305.
10. Kurti, J.; Surian, P. R.; Kertesz, M. J. Am. Chem. Soc. 1991, 113, 9865.
11. Pomerantz, M.; Chaloner-Gill, B.; Harding, L. O.; Tseng, J. J.; Pomerantz, W. J. J. Chem. Soc., Chem. Commun. 1992, 1672.
12. McCullough, R. D.; Lowe, R. D.; Jayaraman, M.; Anderson, D. L. J. Org. Chem. 1993, 58, 904.
13. Zotti, G.; Schiavon, G.; Berlin, A.; Fontana, G.; Pagani, G. Macromolecules 1994, 27, 1938.
14. Huang, H.; Pickup, P. G. Acta Polym. 1997, 48, 455.
15. Kozaki, M.; Yonezawa, Y.; Igarashi, H.; Okada, K. Synth. Met. 2003, 135-136, 107.
16. Akoudad, S.; Roncali, J. J. Chem. Soc., Chem. Commun. 1998, 2081.
17. Huang, H.; Pickup, P. G. Chem. Mater. 1998, 10, 2212.
18. Salzner, U.; Erkan Kose, M. J. Phys. Chem. B 2002, 106, 9221.
19. Kenning, D. D.; Mitchell, K. A.; Calhoun, T. R.; Funfar, M. R.; Sattler, D. J.; Rasmussen, S. C. J. Org. Chem. 2002, 9073.
20. (a) Lucas, P.; Mehdi, N. E.; Ho, H. A.; Belanger, D.; Breau, L. Synthesis 2000, 9, 1253.
21. (b) Jordens, P.; Rawson, G.; Winberg, H. J. Chem. Soc. C 1970, 273.
22. Zhu, S. S.; Swager, T. M. J. Am. Chem. Soc. 1997, 119, 12568.
23. Sankaran, B.; Reynolds, J. R. Macromolecules 1997, 30, 2582.
24. Sotzing, G. A.; Reynolds, J. R.; Steel, P. J. Adv. Mater. 1997, 9, 795.
25. Zotti, G.; Schiavon, G. Synth. Met. 1994, 63, 53.
26. Schiavon, G.; Sitran, S.; Zotti, G. Synth. Met. 1989, 32, 209.
27. Aubert, P. H.; Groenendaal, L.; Louwet, F.; Lutsen, L.; Vanderzande, D.; Zotti, G. Synth. Met. 2002, 126, 193.
28. Kitamura, C.; Tanaka, S.; Yamashita, Y. Chem. Mater. 1996, 8, 570.
29. Chidsey, C. E. D.; Murray, R. W. J. Phys. Chem. 1986, 90, 1479.
30. Zotti, G.; Zecchin, S.; Berlin, A.; Schiavon, G.; Giro, G. Chem. Mater. 2001, 13, 43.
31. Zotti, G.; Zecchin, S.; Schiavon, G.; Vercelli, B.; Berlin, A.; Dalcanale, E.; Groenendaal, L. Chem. Mater. 2003, 15, 4642.
32. Groenendaal, L.; Zotti, G.; Jonas, F. Synth. Met. 2001, 118, 105.
33. Kvarnstrom, C.; Neugebauer, H.; Blomquist, S.; Ahonen, H. J.; Kankare, J.; Ivaska, A. Electrochim. Acta 1999, 44, 2739.
34. Dietrich, M.; Heinze, J.; Heywang, G.; Jonas, F. J. Electroanal. Chem. 1994, 369, 87.
35. Catellani, M.; Arbizani, C.; Mastragostino, M.; Zanetti, A. Synth. Met. 1995, 69, 373.
36. Catellani, M.; Botta, C.; Stein, P.C.; Luzzati, S.; Consonni, R. Synth. Met. 1995, 69, 375.
37. McDiarmid A. G.; Heeger, A. J. Synth. Met. 1979, 1, 101.
38. Kaneto, K.; Ura, S.; Yoshino K.; Inuishi, Y. Jpn. J. Appl. Phys. 1984, 23, L109
39. Crooks, R. M.; Chyan, O. M. R.; Wrighton, M. S. Chem. Mater. 1989, 1, 2.
40. Bakhshi, A. K.; Ladik, J.; Seel, M. Phys. Rev. B 1987, 35, 704.
41. Alberti, A.; Favaretto, L.; Seconi, G. J. Chem. Soc.. Perkin Trans. 2 1990, 931.
42. Kaneto, K.; Hayashi, S.; Ura, S.; Yoshino, K. J. Phys. Soc. Jpn. 1985, 54, 1146.
43. Bauerle, P.; Segelbacher, U.; Gaudl, K. U.; Huttenlocher, D.; Mehring, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 76.
44. Miller, L. L.; Mann, K. R. Acc. Chem. Res. 1996, 29, 417 and references therein.
45. Kenning, D. D.; Funfar, M. R.; Rasmussen, S. C. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 2001, 42, 506.
46. Zecchin, S.; Casalbore, G.; Gallazzi, M. C. Manuscript in preparation.