Low-cost synthesis and physical characterization of thieno[3,4-c]pyrrole-4, 6-dione-based polymers

Journal of Organic Chemistry

Volumn 77, Issue 18, 2012, Pages 8167-8173

  Berrouard, Philippe ^a   Dufresne, Stéphane ^a   Pron, Agnieszka ^a   Veilleux, Justine ^a   Leclerc, Mario ^a  

^a UNIVERSITÉ LAVAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL CHAIN; HETEROARYLATION; OPTOELECTRONIC PROPERTIES; PHYSICAL CHARACTERIZATION; POWDER X RAY DIFFRACTION; THIOPHENE RING; UV-VISIBLE ABSORPTION;

CONDENSATION REACTIONS; SYNTHESIS (CHEMICAL); THIOPHENE; X RAY DIFFRACTION;

POLYMERS;

AMINE; MONOMER; POLYMER; THIENO [3,4 C] PYRROLE 4,6 DIONE; THIOPHENE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; ARYLATION; CHEMICAL STRUCTURE; ELECTROCHEMISTRY; PHYSICAL CHEMISTRY; POLYMERIZATION; SANDMEYER REACTION; SEMICONDUCTOR; SOLID STATE; SYNTHESIS; ULTRAVIOLET RADIATION; X RAY DIFFRACTION;

EID: 84868113311     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301512e     Document Type: Article

References (35)

1. Gendron, D.; Leclerc, M. Energy Environ. Sci. 2011, 4, 1225.
2. Thompson, B. C.; Fréchet, J. M. J. Angew. Chem., Int. Ed. 2008, 47, 58.
3. Mayer, A. C.; Scully, S. R.; Hardin, B. E.; Rowell, M. W.; McGehee, M. D. Mater. Today 2007, 10, 28.
4. Kim, J. Y.; Lee, K.; Coates, N. E.; Moses, D.; Nguyen, T.-Q.; Dante, M.; Heeger, A. J. Science 2007, 317, 222.
5. Chen, H.-Y.; Hou, J.; Zhang, S.; Liang, Y.; Yang, G.; Yang, Y.; Yu, L.; Wu, Y.; Li, G. Nature Photon. 2009, 3, 649.
6. Liang, Y.; Xu, Z.; Xia, J.; Tsai, S.-T.; Wu, Y.; Li, G.; Ray, C.; Yu, L. Adv. Mater. 2010, 22, E135.
7. Zou, Y.; Najari, A.; Berrouard, P.; Beaupré, S.; Réda Aïch, B.; Tao, Y.; Leclerc, M. J. Am. Chem. Soc. 2010, 132, 5330.
8. Chu, T.-Y.; Lu, J.; Beaupré, S.; Zhang, Y.; Pouliot, J.-R.; Wakim, S.; Zhou, J.; Leclerc, M.; Li, Z.; Ding, J.; Tao, Y. J. Am. Chem. Soc. 2011, 133, 4250.
9. Amb, C. M.; Chen, S.; Graham, K. R.; Subbiah, J.; Small, C. E.; So, F.; Reynolds, J. R. J. Am. Chem. Soc. 2011, 133, 10062.
10. Small, C. E.; Chen, S.; Subbiah, J.; Amb, C. M.; Tsang, S.-W.; Lai, T.-H.; Reynolds, J. R.; So, F. Nature Photon. 2012, 6, 115.
11. Zhang, Y.; Hau, S. K.; Yip, H.-L.; Sun, Y.; Acton, O.; Jen, A. K. Y. Chem. Mater. 2010, 22, 2696.
12. Lin, Z.; Bjorgaard, J.; Gul Yavuz, A.; Iyer, A.; Kose, M. E. RSC Adv. 2012, 2, 642.
13. Najari, A.; Berrouard, P.; Ottone, C.; Boivin, M.; Zou, Y.; Gendron, D.; Caron, W.-O.; Legros, P.; Allen, C. N.; Sadki, S.; Leclerc, M. Macromolecules 2012, 45, 1833.
14. Piliego, C.; Holcombe, T. W.; Douglas, J. D.; Woo, C. H.; Beaujuge, P. M.; Fréchet, J. M. J. J. Am. Chem. Soc. 2010, 132, 7595.
15. Zhang, G.; Fu, Y.; Zhang, Q.; Xie, Z. Chem. Commun. 2010, 46, 4997.
16. Guo, X.; Ortiz, R. P.; Zheng, Y.; Kim, M.-G.; Zhang, S.; Hu, Y.; Lu, G.; Facchetti, A.; Marks, T. J. J. Am. Chem. Soc. 2011, 133, 13685.
17. Pomerantz, M.; Amarasekara, A. S. Synth. Met. 2003, 135-136, 257.
18. Nielsen, C. B.; Bjørnholm, T. Org. Lett. 2004, 6, 3381.
19. Berrouard, P.; Najari, A.; Pron, A.; Gendron, D.; Morin, P.-O.; Pouliot, J.-R.; Veilleux, J.; Leclerc, M. Angew. Chem., Int. Ed. 2012, 51, 2068.
20. Fujinami, Y.; Kuwabara, J.; Lu, W.; Hayashi, H.; Kanbara, T. ACS Macro Lett. 2011, 1, 67.
21. Lu, W.; Kuwabara, J.; Kanbara, T. Macromolecules 2011, 44, 1252.
22. Cornelis, D.; Peeters, H.; Zrig, S.; Andrioletti, B.; Rose, E.; Verbiest, T.; Koeckelberghs, G. Chem. Mater. 2008, 20, 2133.
23. Najari, A.; Beaupré, S.; Berrouard, P.; Zou, Y.; Pouliot, J.-R.; Lepage-Pérusse, C.; Leclerc, M. Adv. Funct. Mater. 2011, 21, 718.
24. Dufresne, S.; Bourgeaux, M.; Skene, W. G. J. Mater. Chem. 2007, 17, 1166.
25. Wang, K.; Kim, D.; Dömling, A. J. Comb.Chem. 2009, 12, 111.
26. Dong, Y.; Bolduc, A.; McGregor, N.; Skene, W. G. Org. Lett. 2011, 13, 1844.
27. Berrouard, P.; Grenier, F.; Pouliot, J.-R.; Gagnon, E.; Tessier, C.; Leclerc, M. Org. Lett. 2011, 13, 38.
28. Cadogan, J. I. G.; Molina, G. A. J. Chem. Soc., Perkin Trans. 1 1973, 541.
29. Phillips; Fevig, T. L.; Lau, P. H.; Klemm, G. H.; Mao, M. K.; Ma, C.; Gloeckner, J. A.; Clark, A. S. Org. Process Res. Dev. 2002, 6, 357.
30. Kowalski, S.; Allard, S.; Scherf, U. ACS Macro Lett. 2012, 1, 465.
31. Facchetti, A.; Vaccaro, L.; Marrocchi, A. Angew. Chem., Int. Ed. 2012, 51, 3520.
32. Campeau, L.-C.; Parisien, M.; Jean, A.; Fagnou, K. J. Am. Chem. Soc. 2005, 128, 581.
33. René, O.; Fagnou, K. Adv. Synth. Catal. 2010, 352, 2116.
34. Herrmann, W. A.; Brossmer, C.; Reisinger, C.-P.; Riermeier, T. H.; Öfele, K.; Beller, M. Chem. Eur. J. 1997, 3, 1357.
35. Burkhart, B.; Khlyabich, P. P.; Thompson, B. C. Macromolecules 2012, 45, 3740.