Citation: Jia Tao, Zheng Nannan, Cai Wanqing, Ying Lei, Huang Fei. Naphthalene Diimide-Based Polymers Consisting of Amino Alkyl Side Groups:Three-Component One-Pot Polymerization and Their Application in Polymer Solar Cells[J]. Acta Chimica Sinica, ;2017, 75(8): 808-818. doi: 10.6023/A17030114 shu

Naphthalene Diimide-Based Polymers Consisting of Amino Alkyl Side Groups:Three-Component One-Pot Polymerization and Their Application in Polymer Solar Cells

Institute of Polymer Optoelectronic Materials and Devices, State Key Laboratory of Luminescent Materials and Devices, South China University of Technology, Guangzhou 510640

Corresponding author: Huang Fei, msfhuang@scut.edu.cn
Received Date: 22 March 2017
Available Online: 11 August 2017
Fund Project: Project supported by the National Natural Science Foundation of China (No.21490573)Project supported by the National Natural Science Foundation of China 21490573

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In this work, we demonstrate the microwave-assisted synthesis of naphthalene diimide-based polymers via three-component polymerization (TCP) of diynes, dialdehydes and dibenzylamine, and the applications of such polymers as cathode interfacial layers for polymer solar cells. The TCP of diynes (1a~1c), dialdehydes (2a~2b) and dibenzylamine catalyzed by InCl₃ could be performed smoothly under microwave irradiation in very short reaction time, yielding soluble polymers P1~P4 with high molecular weights. The chemical structures of these resulting polymers were confirmed by nuclear magnetic resonance spectroscopy. The thermal stability, photophysical and electrochemical properties of the resulting polymers were also investigated. Besides, the effects of chemical environment of amine groups on the resulting polymers' electrode modification capability and self-doping behavior were explored by conducting scanning Kelvin probe microscopy and electron paramagnetic resonance (EPR) spectroscopy studies, respectively. It was found that the chemical environment variation of amine groups, including the decreasing electron density of the nitrogen atoms in alkylamine and the enhancing steric hindrance around the nitrogen atoms from substituent groups, can substantially influence the electrode modification capability and self-doping behavior of the resulting polymers. Moreover, quantum chemistry calculation was also conducted to qualitatively illuminate the essential distinction in chemical environment of different amine groups. It was found that the negative atomic dipole moment corrected Hirshfeld (ADCH) charge of nitrogen atoms in side chains was significantly larger than the ADCH charges of nitrogen atoms in main chains. Among all the resulting polymers, P1 can be easily dissolved in alcohol due to its amino functionalized side chain groups and thus was utilized as the cathode interlayer for polymer solar cells. The device with P1 as the cathode interlayer and PTB7-Th:PC₇₁BM as the photoactive layer exhibits a high power conversion efficiency of 9.34%, which is much better than that of the control device without such cathode interlayer. All these results provide a guideline for the material design of amino-functionalized polymers for the optoelectronic devices. And it was also shown that the multicomponent polymerization (MCP) is an effective strategy for the synthesis of functional polymers, and may trigger broad research interests in developing effective polymerization approaches toward multi-functional polymer materials.
- three-component polymerization,
- polymer solar cells,
- cathode interlayer
1. [1]
  Domling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168. doi: 10.1002/(ISSN)1521-3773
2. [2]
  Kakuchi, R. Angew. Chem., Int. Ed. 2014, 53, 46. doi: 10.1002/anie.v53.1
3. [3]
  Balme, G.; Bossharth, E.; Monteiro, N. Eur. J. Org. Chem. 2003, 2003, 4101. doi: 10.1002/(ISSN)1099-0690
4. [4]
  Andreana, P. R.; Liu, C. C.; Schreiber, S. L. Org. Lett. 2004, 6, 4231. doi: 10.1021/ol0482893
5. [5]
  D'Souza, D. M.; Mueller, T. J. J. Chem. Soc. Rev. 2007, 36, 1095. doi: 10.1039/B608235C
6. [6]
  Biggs-Houck, J. E.; Younai, A.; Shaw, J. T. Curr. Opin. Chem. Biol. 2010, 14, 371. doi: 10.1016/j.cbpa.2010.03.003
7. [7]
  Siamaki, A. R.; Sakalauskas, M.; Arndtsen, B. A. Angew. Chem., Int. Ed. 2011, 50, 6552. doi: 10.1002/anie.v50.29
8. [8]
  Thanh Binh, N.; Minh Quan, T.; Ermolenko, L.; Al-Mourabit, A. Org. Lett. 2014, 16, 310. doi: 10.1021/ol403345e
9. [9]
  Rotstein, B. H.; Zaretsky, S.; Rai, V.; Yudin, A. K. Chem. Rev. 2014, 114, 8323. doi: 10.1021/cr400615v
10. [10]
  Levi, L.; Muller, T. J. J. Chem. Soc. Rev. 2016, 45, 2825. doi: 10.1039/C5CS00805K
11. [11]
  Teimouri, M. B.; Abbasi, T.; Mivehchi, H. Tetrahedron 2008, 64, 10425. doi: 10.1016/j.tet.2008.08.039
12. [12]
  Yu, J.; Shi, F.; Gong, L.-Z. Acc. Chem. Res. 2011, 44, 1156. doi: 10.1021/ar2000343
13. [13]
  Ruijter, E.; Scheffelaar, R.; Orru, R. V. A. Angew. Chem., Int. Ed. 2011, 50, 6234. doi: 10.1002/anie.201006515
14. [14]
  Hossaini, Z.; Seyfi, S.; Rostami-Charati, F.; Ghambarian, M. Comb. Chem. High Throughput Screen 2013, 16, 788. doi: 10.2174/13862073113169990046
15. [15]
  Pagadala, R.; Kommidi, D. R.; Kankala, S.; Maddila, S.; Singh, P.; Moodley, B.; Koorbanally, N. A.; Jonnalagadda, S. B. Org. Biomol. Chem. 2015, 13, 1800. doi: 10.1039/C4OB02229G
16. [16]
  Theato, P., Multi-Component and Sequential Reactions in Polymer Synthesis, Springer, 2015, Vol. 269.
17. [17]
  Leitch, D. C.; Kayser, L. V.; Han, Z.-Y.; Siamaki, A. R.; Keyzer, E. N.; Gefen, A.; Arndtsen, B. A. Nature Commun. 2015, 6, 7411. doi: 10.1038/ncomms8411
18. [18]
  Hu, R. R.; Li, W. Z.; Tang, B. Z. Macromol. Chem. Phys. 2016, 217, 213. doi: 10.1002/macp.201500291
19. [19]
  Kreye, O.; Toth, T.; Meier, M. A. R. J. Am. Chem. Soc. 2011, 133, 1790. doi: 10.1021/ja1113003
20. [20]
  Lee, I.-H.; Kim, H.; Choi, T.-L. J. Am. Chem. Soc. 2013, 135, 3760. doi: 10.1021/ja312592e
21. [21]
  Chan, C. Y. K.; Tseng, N.-W.; Lam, J. W. Y.; Liu, J. Z.; Kwok, R. T. K.; Tang, B. Z. Macromolecules 2013, 46, 3246. doi: 10.1021/ma4005346
22. [22]
  Liu, Y. J.; Gao, M.; Lam, J. W. Y.; Hu, R. R.; Tang, B. Z. Macromolecules 2014, 47, 4908. doi: 10.1021/ma501477w
23. [23]
  Deng, H. Q.; Hu, R. R.; Zhao, E. G.; Chan, C. Y. K.; Lam, J. W. Y.; Tang, B. Z. Macromolecules 2014, 47, 4920. doi: 10.1021/ma501190g
24. [24]
  Li, W. Z.; Wu, X. Y.; Zhao, Z. J.; Qin, A. J.; Hu, R. R.; Tang, B. Z. Macromolecules 2015, 48, 7747. doi: 10.1021/acs.macromol.5b02193
25. [25]
  Zheng, C.; Deng, H. Q.; Zhao, Z. J.; Qin, A. J.; Hu, R. R.; Tang, B. Z. Macromolecules 2015, 48, 1941. doi: 10.1021/acs.macromol.5b00175
26. [26]
  Deng, H. Q.; Hu, R. R.; Leung, A. C. S.; Zhao, E. G.; Lam, J. W. Y.; Tang, B. Z. Polym. Chem. 2015, 6, 4436. doi: 10.1039/C5PY00477B
27. [27]
  Yu, G.; Gao, J.; Hummelen, J. C.; Wudl, F.; Heeger, A. J. Science 1995, 270, 1789. doi: 10.1126/science.270.5243.1789
28. [28]
  Heeger, A. J. Chem. Soc. Rev. 2010, 39, 2354. doi: 10.1039/b914956m
29. [29]
  Hains, A. W.; Liang, Z.; Woodhouse, M. A.; Gregg, B. A. Chem. Rev. 2010, 110, 6689. doi: 10.1021/cr9002984
30. [30]
  Huang, Y.; Kramer, E. J.; Heeger, A. J.; Bazan, G. C. Chem. Rev. 2014, 114, 7006. doi: 10.1021/cr400353v
31. [31]
  Lu, L. Y.; Zheng, T. Y.; Wu, Q. H.; Schneider, A. M.; Zhao, D. L.; Yu, L. P. Chem. Rev. 2015, 115, 12666. doi: 10.1021/acs.chemrev.5b00098
32. [32]
  Zhang, X.; Wang, Z. L.; Chen, S. Y.; Zhao, Z.; Yuan, W.; Wang, H. P.; Gao, X. K. Chin. J. Chem. 2014, 32, 1057.
33. [33]
  Zhao, C. B.; Wang, Z. L.; Zhou, K.; Ge, H. G.; Zhang, Q.; Jin, L. X.; Wang, W. L.; Yin, S. W. Acta Chim. Sinica 2015, 74, 251. doi: 10.3969/j.issn.0253-2409.2015.02.017
34. [34]
  Liu, L. Q.; Zhang, G. C.; He, B. T.; Huang, F. Chin. J. Chem. 2015, 33, 902.
35. [35]
  Zhang, Z.-G.; Qi, B.; Jin, Z.; Chi, D.; Qi, Z.; Li, Y.; Wang, J. Energy Environ. Sci. 2014, 7, 1966. doi: 10.1039/c4ee00022f
36. [36]
  Wu, Z. H.; Sun, C.; Dong, S.; Jiang, X.-F.; Wu, S. P.; Wu, H. B.; Yip, H.-L.; Huang, F.; Cao, Y. J. Am. Chem. Soc. 2016, 138, 2004. doi: 10.1021/jacs.5b12664
37. [37]
  Zhang, K.; Guan, X.; Huang, F.; Cao, Y. Acta Chim. Sinica 2012, 70, 2489.
38. [38]
  Duan, C. H.; Zhang, K.; Zhong, C. M.; Huang, F.; Cao, Y. Chem. Soc. Rev. 2013, 42, 9071. doi: 10.1039/c3cs60200a
39. [39]
  Hu, Z. C.; Zhang, K.; Huang, F.; Cao, Y. Chem. Commun. 2015, 51, 5572. doi: 10.1039/C4CC09433F
40. [40]
  Yip, H.-L.; Jen, A. K. Y. Energy Environ. Sci. 2012, 5, 5994. doi: 10.1039/c2ee02806a
41. [41]
  Lu, J. M.; Cai, W. Q.; Zhang, G. C.; Liu, S. J.; Ying, L.; Huang, F. Acta Chim. Sinica 2015, 73, 1153. doi: 10.3866/PKU.WHXB201504145
42. [42]
  Zhang, K.; Hu, Z. C.; Sun, C.; Wu, Z. H.; Huang, F.; Cao, Y. Chem. Mater. 2017, 29, 141. doi: 10.1021/acs.chemmater.6b02802
43. [43]
  van Reenen, S.; Kouijzer, S.; Janssen, R. A. J.; Wienk, M. M.; Kemerink, M. Adv. Mater. Inter. 2014, 1, 1400189. doi: 10.1002/admi.201400189
44. [44]
  Hu, Z. H.; Zhong, Z. M.; Chen, Y. W.; Sun, C.; Huang, F.; Peng, J. B.; Wang, J.; Cao, Y. Adv. Funct. Mater. 2016, 26, 129. doi: 10.1002/adfm.201503420
45. [45]
  Liu, S. J.; Zhang, K.; Lu, J. M.; Zhang, J.; Yip, H. L.; Huang, F.; Cao, Y. J. Am. Chem. Soc. 2013, 135, 15326. doi: 10.1021/ja408363c
46. [46]
  Liu, X.; Xu, R. G.; Duan, C.; Huang, F.; Cao, Y. J. Mater. Chem. C 2016, 4, 4288.
47. [47]
  Guan, X.; Zhang, K.; Huang, F.; Bazan, G. C.; Cao, Y. Adv. Funct. Mater. 2012, 22, 2846. doi: 10.1002/adfm.v22.13
48. [48]
  Kan, Y. Y.; Zhu, Y. X.; Liu, Z. L.; Zhang, L. J.; Chen, J. W.; Cao, Y. Macromol. Rapid Commun. 2015, 36, 1393. doi: 10.1002/marc.v36.15
49. [49]
  Jia, T.; Zheng, N. N.; Cai, W. Q.; Zhang, J.; Ying, L.; Huang, F.; Cao, Y. Chin. J. Polym. Sci. 2017, 35, 269.
50. [50]
  Yan, H.; Chen, Z. H.; Zheng, Y.; Newman, C.; Quinn, J. R.; Dötz, F.; Kastler, M.; Facchetti, A. Nature 2009, 457, 679. doi: 10.1038/nature07727
51. [51]
  Bucella, S. G.; Luzio, A.; Gann, E.; Thomsen, L.; McNeill, C. R.; Pace, G.; Perinot, A.; Chen, Z. H.; Facchetti, A.; Caironi, M. Nature Commun. 2015, 6, 8394. doi: 10.1038/ncomms9394
52. [52]
  Facchetti, A. Mater. Today 2013, 16, 123. doi: 10.1016/j.mattod.2013.04.005
53. [53]
  Mu, C.; Liu, P.; Ma, W.; Jiang, K.; Zhao, J.; Zhang, K.; Chen, Z. H.; Wei, Z. H.; Yi, Y.; Wang, J. N.; Yang, S. H.; Huang, F.; Facchetti, A.; Ade, H.; Yan, H. Adv. Mater. 2014, 26, 7224. doi: 10.1002/adma.v26.42
54. [54]
  Fabiano, S.; Himmelberger, S.; Drees, M.; Chen, Z.; Altamimi, R. M.; Salleo, A.; Loi, M. A.; Facchetti, A. Adv. Energy Mater. 2014, 4, 1301409. doi: 10.1002/aenm.201301409
55. [55]
  Sun, C.; Wu, Z. H.; Yip, H.-L.; Zhang, H.; Jiang, X.-F.; Xue, Q.; Hu, Z. C.; Hu, Z.; Shen, Y.; Wang, M.; Huang, F.; Cao, Y. Adv. Energy Mater. 2016, 6, 15011534.
56. [56]
  Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650.
57. [57]
  McLean, A.; Chandler, G. J. Chem. Phys. 1980, 72, 5639.
58. [58]
  Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
59. [59]
  Lu, T.; Chen, F. W. J. Comput. Chem. 2012, 33, 580. doi: 10.1002/jcc.v33.5
60. [60]
  Lu, T.; Chen, F. W. J. Theor. Comput. Chem. 2012, 11, 163. doi: 10.1142/S0219633612500113
61. [61]
  Bhosale, S. V.; Jani, C. H.; Langford, S. J. Chem. Soc. Rev. 2008, 37, 331. doi: 10.1039/B615857A
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