Paper
Journal of Materials Chemistry A
to remove bromo and trimethystannyl end groups. The mixture
was then poured into methanol. The precipitated material was
collected and extracted with ethanol, acetone, hexane, and
toluene in a Soxhlet extractor. The solution of the copolymer in
toluene was condensed to 20 mL and then poured into methanol
8 F. Huang, K.-S. Chen, H.-L. Yip, S. K. Hau, O. Acton,
Y. Zhang, J. Luo and A. K.-Y. Jen, J. Am. Chem. Soc., 2009,
131, 13886–13887.
9 N. Blouin, A. Michaud and M. Leclerc, Adv. Mater., 2007, 19,
2295–2300.
(500 mL). The precipitate was collected and dried under vacuum 10 E. Wang, L. Wang, L. Lan, C. Luo, W. Zhuang, J. Peng and
overnight (yield: 75%). Mn ¼ 9650 g molꢀ1 with a polydisperse
Y. Cao, Appl. Phys. Lett., 2008, 92, 033307.
index (PDI) of 1.58. 1H NMR (CDCl3, 400 MHz), d (ppm): 9.01 (br, 11 C. Duan, W. Cai, F. Huang, J. Zhang, M. Wang, T. Yang,
2H), 7.40 (br, 2H), 7.01 (br, 2H), 4.22 (br, 2H), 3.97 (br, 2H), 2.03–
0.84 (m, br, 124).
C. Zhong, X. Gong and Y. Cao, Macromolecules, 2010, 43,
5262–5268.
ˇ ´
Synthesis of PBT-T-DPP-C12. PBT-T-DPP-C12 was synthesized 12 W.-Y. Wong, X.-Z. Wang, Z. He, A. B. DjuriSiC, C.-T. Yip,
using the procedure of PBT-HD-DPP-C16, except that the poly-
merization was carried out with IV (406.0 mg, 0.3 mmol) and 3,6-
bis(5-bromothineno-2-yl)-N,N0-bis(2-butyloctyl)-1,4-dioxopyrrolo
[3,4-c]pyrrole (237.7 mg, 0.30 mmol). Yield: 85%. Mn ¼ 20 600 g
K.-Y. Cheung, H. Wang, C. S. K. Mak and W.-K. Chan, Nat.
Mater., 2007, 6, 521–527.
13 R. C. Coffin, J. Peet, J. Rogers and G. C. Bazan, Nat. Chem.,
2009, 1, 657–661.
molꢀ1 with PDI of 1.67. 1H NMR (CDCl3, 400 MHz),d (ppm): 9.00 14 Y. Xia, Y. Li, Y. Zhu, J. Li, P. Zhang, J. Tong, C. Yang, H. Li
(br, 2H), 7.25 (br, 2H), 7.00 (br, 2H), 6.91 (br, 2H), 3.99 (br, 2H),
2.90 (br, 2H), 2.64 (br, 2H), 1.56–0.81 (m, br, 122).
and D. Fan, J. Mater. Chem. C, 2014, 2, 1601–1604.
15 Y. Xia, Y. Gao, Y. Zhang, J. Tong, J. Li, H. Li, D. Chen and
D. Fan, Polymer, 2013, 54, 607–613.
Synthesis of PBT-TIPS-DPP-C16. The PBT-TIPS-DPP-C16 was
synthesized using the procedure of PBT-HD-DPP-C16, except 16 Z. Ma, D. Dang, Z. Tang, D. Gedefaw, J. Bergqvist, W. Zhu,
¨
that the polymerization was carried out with V (296.6 mg, 0.3
mmol) and 3,6-bis(5-bromothineno-2-yl)-N,N0-bis(2-hexyldecyl)-
1,4-dioxopyrrolo[3,4-c]pyrrole (271.3 mg, 0.3 mmol). Yield: 85%.
W. Mammo, M. R. Andersson, O. Inganas, F. Zhang and
E. Wang, Adv. Energy Mater., 2013, DOI: 0.1002/
aenm.201301455.
Mn ¼ 16 150 g molꢀ1 with PDI of 1.71. H NMR (CDCl3, 400 17 J. Peet, M. L. Senatore, A. J. Heeger and G. C. Banzan, Adv.
MHz), d (ppm): 9.11 (br, 2H), 7.00 (br, 2H), 6.71 (br, 2H), 4.32
(br, 2H), 1.67–0.78 (m, br, 104).
Mater., 2009, 21, 1521–1527.
18 J. Peet, J. Y. Kim, N. E. Coates, W. L. Ma, D. Mose, A. J. Heeger
and G. C. Banzan, Nat. Mater., 2007, 6, 497–500.
19 L. Ye, S. Zhang, W. Ma, B. Fan, X. Guo, Y. Huang, H. Ade and
J. Hou, Adv. Mater., 2012, 24, 6335–6341.
Acknowledgements
´
20 T.-Y. Chu, J. Lu, S. Beaupre, Y. Zhang, J.-R. Pouliot,
The authors are deeply grateful to the Major State Basic
Research Development Program (Grant no. 2013CB922302), the
Program for New Century Excellent Talents in University (NCET-
13-0840), the National Science Foundation of China (61166002,
61264002, 91333206), the Gansu Province Natural Foundation
(#1107RJZA154, 1111RJDA009), and the Open Fund of the State
Key Llaboratory of Infrared Physics (Z201302) for nancial
support.
S. Wakim, J. Zhou, M. Leclerc, Z. Li, J. Ding and Y. Tao, J.
Am. Chem. Soc., 2011, 133, 4250–4253.
21 J. Hou, H.-Y. Chen, S. Zhang, G. Li and Y. Yang, J. Am. Chem.
Soc., 2008, 130, 16144–16145.
22 Y. Liang, D. Feng, Y. Wu, S.-T. Tsai, G. Li, C. Ray and L. Yu, J.
Am. Chem. Soc., 2009, 131, 7792–7799.
23 Y. Liang, Z. Xu, J. Xia, S.-T. Tsai, Y. Wu, G. Li, C. Ray and
L. Yu, Adv. Mater., 2010, 22, E135–E138.
24 Z. He, C. Zhong, S. Su, M. Xu, H. Wu and Y. Cao, Nat.
Photonics, 2012, 6, 591–595.
25 M. Wang, X. Hu, P. Liu, W. Li, X. Gong, F. Huang and Y. Cao,
J. Am. Chem. Soc., 2011, 133, 9638–9641.
26 T. Yang, M. Wang, C. Duan, X. Hu, L. Huang, J. Peng, F. Huang
and X. Gong, Energy Environ. Sci., 2012, 5, 8208–8214.
27 L. Huo, S. Zhang, X. Guo, F. Xu, Y. Li and J. Hou, Angew.
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J. Mater. Chem. A