The effect of a solvent on direct arylation polycondensation of substituted thiophenes

Polymer Chemistry

Volumn 6, Issue 6, 2015, Pages 891-895

  Kuwabara, Junpei ^a   Yamazaki, Kohtaro ^a   Yamagata, Takuya ^a   Tsuchida, Wataru ^a   Kanbara, Takaki ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CHEMICAL REACTIONS; ORGANIC SOLVENTS; POLYCONDENSATION; POLYMERIZATION;

DIMETHYLACETAMIDE; DIRECT ARYLATION POLYCONDENSATION; ELECTRON-DEFICIENT; ELECTRON-RICH; SUBSTITUTED THIOPHENE; THIOPHENE DERIVATIVES;

THIOPHENE;

EID: 84922041789     PISSN: 17599954     EISSN: 17599962     Source Type: Journal    
DOI: 10.1039/c4py01387e     Document Type: Article

References (48)

1. (a) T. Satoh and M. Miura, Chem. Lett., 2007, 36, 200;
2. (b) L. Ackermann, R. Vicente and A. R. Kapdi, Angew. Chem., Int. Ed., 2009, 48, 9792;
3. (c) B. Liégault, D. Lapointe, L. Caron, A. Vlassova and K. Fagnou, J. Org. Chem., 2009, 74, 1826;
4. (d) D. Lapointe and K. Fagnou, Chem. Lett., 2010, 39, 1118;
5. (e) R. Rossi, F. Bellina, M. Lessi and C. Manzini, Adv. Synth. Catal., 2014, 356, 17.
6. (a) S. Kowalski, S. Allard, K. Zilberberg, T. Riedl and U. Scherf, Prog. Polym. Sci., 2013, 38, 1805;
7. (b) L. G. Mercier and M. Leclerc, Acc. Chem. Res., 2013, 46, 1597;
8. (c) P. P. Khlyabich, B. Burkhart, A. E. Rudenko and B. C. Thompson, Polymer, 2013, 54, 5267;
9. (d) K. Okamoto, J. Zhang, J. B. Housekeeper, S. R. Marder and C. K. Luscombe, Macromolecules, 2013, 46, 8059;
10. (e) A. E. Rudenko and B. C. Thompson, J. Polym. Sci., Part A: Polym. Chem., 2014, 52, DOI: 10.1002/pola.27279;
11. (f) J. Kuwabara and T. Kanbara, J. Synth. Org. Chem., Jpn., 2014, 72, 1271.
12. M. Sévignon, J. Papillon, E. Schulz and M. Lemaire, Tetrahedron Lett., 1999, 40, 5873.
13. Q. Wang, R. Takita, Y. Kikuzaki and F. Ozawa, J. Am. Chem. Soc., 2010, 132, 11420.
14. (a) M. Wakioka, Y. Kitano and F. Ozawa, Macromolecules, 2013, 46, 370;
15. (b) M. Wakioka, M. Ichihara, Y. Kitano and F. Ozawa, Macromolecules, 2014, 47, 626.
16. (a) P. Berrouard, A. Najari, A. Pron, D. Gendron, P.-O. Morin, J.-R. Pouliot, J. Veilleux and M. Leclerc, Angew. Chem., Int. Ed., 2012, 51, 2068;
17. (b) J. Jo, A. Pron, P. Berrouard, W. L. Leong, J. D. Yuen, J. S. Moon, M. Leclerc and A. J. Heeger, Adv. Energy Mater., 2012, 2, 1397;
18. (c) D. H. Wang, A. Pron, M. Leclerc and A. J. Heeger, Adv. Funct. Mater., 2013, 23, 1297.
19. (a) S. Beaupré, A. Pron, S. H. Drouin, A. Najari, L. G. Mercier, A. Robitaille and M. Leclerc, Macromolecules, 2012, 45, 6906;
20. (b) J.-R. Pouliot, L. G. Mercier, S. Caron and M. Leclerc, Macromol. Chem. Phys., 2013, 214, 453.
21. (a) W. Lu, J. Kuwabara and T. Kanbara, Macromolecules, 2011, 44, 1252;
22. (b) Y. Fujinami, J. Kuwabara, W. Lu, H. Hayashi and T. Kanbara, ACS Macro Lett., 2012, 1, 67;
23. (c) W. Lu, J. Kuwabara and T. Kanbara, Polym. Chem., 2012, 3, 3217;
24. (d) K. Yamazaki, J. Kuwabara and T. Kanbara, Macromol. Rapid Commun., 2013, 34, 69;
25. (e) J. Kuwabara, Y. Nohara, S. J. Choi, Y. Fujinami, W. Lu, K. Yoshimura, J. Oguma, K. Suenobu and T. Kanbara, Polym. Chem., 2013, 4, 947;
26. (f) S. J. Choi, J. Kuwabara and T. Kanbara, ACS Sustainable Chem. Eng., 2013, 1, 878;
27. (g) W. Lu, J. Kuwabara and T. Kanbara, Macromol. Rapid Commun., 2013, 34, 1151;
28. (h) M. Kuramochi, J. Kuwabara, W. Lu and T. Kanbara, Macromolecules, 2014, 47, 7378.
29. J. Kuwabara, T. Yasuda, S. J. Choi, W. Lu, K. Yamazaki, S. Kagaya, L. Han and T. Kanbara, Adv. Funct. Mater., 2014, 24, 3226.
30. (a) S. Kowalski, S. Allard and U. Scherf, ACS Macro Lett., 2012, 1, 465;
31. (b) A. E. Rudenko, C. A. Wiley, S. M. Stone, J. F. Tannaci and B. C. Thompson, J. Polym. Sci., Part A: Polym. Chem., 2012, 50, 3691;
32. (c) S.-W. Chang, H. Waters, J. Kettle, Z.-R. Kuo, C.-H. Li, C.-Y. Yu and M. Horie, Macromol. Rapid Commun., 2012, 33, 1927;
33. (d) L. A. Estrada, J. J. Deininger, G. D. Kamenov and J. R. Reynolds, ACS Macro Lett., 2013, 2, 869;
34. (e) K. Nakabayashi and H. Mori, Chem. Lett., 2013, 42, 717;
35. (f) X. Zhang, Y. Gao, S. Li, X. Shi, Y. Geng and F. Wang, J. Polym. Sci., Part A: Polym. Chem., 2014, 52, 2367;
36. (g) X. Wang and M. Wang, Polym. Chem., 2014, 5, 5784.
37. (a) T. Yamamoto, Macromol. Rapid Commun., 2002, 23, 583;
38. (b) J. Roncali, Macromol. Rapid Commun., 2007, 28, 1761;
39. (c) J. Sakamoto, M. Rehahn, G. Wegner and A. D. Schlüter, Macromol. Rapid Commun., 2009, 30, 653;
40. (d) B. Carsten, F. He, H. J. Son, T. Xu and L. Yu, Chem. Rev., 2011, 111, 1493;
41. (e) K. Okamoto and C. K. Luscombe, Polym. Chem., 2011, 2, 2424;
42. (f) T. Yokozawa, Y. Nanashima and Y. Ohta, ACS Macro Lett., 2012, 1, 862;
43. (g) T. Koizumi and T. Kanbara, in Organometallic Reactions and Polymerization, ed. K. Osakada, Springer, Heiderberg, Lecture Notes in Chemistry, 2014, vol. 85, ch. 8, pp. 271-301.
44. D. J. Schipper and K. Fagnou, Chem. Mater., 2011, 23, 1594.
45. A. Yokooji, T. Satoh, M. Miura and M. Nomura, Tetrahedron Lett., 2004, 60, 6575.
46. S.-Y. Chang, P.-H. Lin and C.-Y. Liu, RSC Adv., 2014, 4, 35868.
47. (a) M. Wakioka, Y. Nakamura, Y. Hihara, F. Ozawa and S. Sakaki, Organometallics, 2013, 32, 4423;
48. (b) M. Wakioka, Y. Nakamura, Y. Hihara, F. Ozawa and S. Sakaki, Organometallics, 2014, 33, 6247.