Citation: Tao Jia, Nan-nan Zheng, Wan-qing Cai, Jie Zhang, Lei Ying, Fei Huang, Yong Cao. Microwave-assisted One-pot Three-component Polymerization of Alkynes, Aldehydes and Amines toward Amino-functionalized Optoelectronic Polymers[J]. Chinese Journal of Polymer Science, ;2017, 35(2): 269-281. doi: 10.1007/s10118-017-1890-0 shu

Microwave-assisted One-pot Three-component Polymerization of Alkynes, Aldehydes and Amines toward Amino-functionalized Optoelectronic Polymers

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

Corresponding author: Fei Huang, msfhuang@scut.edu.cn
Received Date: 30 September 2016
Revised Date: 2 November 2016
Accepted Date: 3 November 2016

Fund Project: the National Natural Science Foundation of China 21490573

We present a microwave-assisted one-pot polymerization with three-components of alkynes, aldehydes and amines for the synthesis of new amino-functionalized optoelectronic polymers. The polymerization of diynes (1a-1c), dialdehydes (2a and 2b) and dibenzylamine catalyzed by InCl₃ was carried out smoothly within 1 h under microwave radiation, yielding four soluble polymers with high molecular weights. The resulting polymers P1 and P2 could be easily dissolved in alcohol and thus utilized as the cathode interlayer for polymer solar cells (PSCs). Compared with the control device, the PSCs with P1 and P2 as the cathode interlayer and PTB7-Th:PC₇₁BM as the photoactive layer exhibited significantly higher power conversion efficiencies (PCEs) of 9.49% and 9.16%, respectively. These results suggest that this polycoupling reaction is an efficient approach to construct three-component polymers for the practical applications.
- One-pot three-component polymerization,
- Polymer solar cells,
- Cathode interlayer
1. [1]
  Ruijter, E., Scheffelaar, R. and Orru, R.V.A., Angew. Chem., Int. Ed., 2011, 50:6234 doi: 10.1002/anie.201006515
2. [2]
  Domling, A. and Ugi, I., Angew. Chem., Int. Ed., 2000, 39:3168
3. [3]
  Kakuchi, R., Angew. Chem., Int. Ed., 2014, 53:46 doi: 10.1002/anie.v53.1
4. [4]
  Rotstein, B.H., Zaretsky, S., Rai, V. and Yudin, A.K., Chem. Rev., 2014, 114:8323 doi: 10.1021/cr400615v
5. [5]
  D'Souza, D.M. and Mueller, T.J.J., Chem. Soc. Rev., 2007, 36:1095 doi: 10.1039/B608235C
6. [6]
  Siamaki, A.R., Sakalauskas, M. and Arndtsen, B.A., Angew. Chem., Int. Ed., 2011, 50:6552 doi: 10.1002/anie.v50.29
7. [7]
  Toure, B.B. and Hall, D.G., Chem. Rev., 2009, 109:4439 doi: 10.1021/cr800296p
8. [8]
  Teiber, M. and Mueller, T.J.J., Chem. Commun., 2012, 48:2080 doi: 10.1039/c2cc17548g
9. [9]
  Zhang, Y., Li, P., Wang, M. and Wang, L., J. Org. Chem., 2009, 74:4364 doi: 10.1021/jo900507v
10. [10]
  Thanh Binh, N., Minh Quan, T., Ermolenko, L. and Al-Mourabit, A., Org. Lett., 2014, 16:310 doi: 10.1021/ol403345e
11. [11]
  Dhawan, R., Dghaym, R.D. and Arndtsen, B.A., J. Am. Chem. Soc., 2003, 125:1474 doi: 10.1021/ja027474d
12. [12]
  Rudick, J.G., J. Polym. Sci., Part A:Polym. Chem., 2013, 51:3985 doi: 10.1002/pola.26808
13. [13]
  Frapper, G., Bachmann, C., Gu, Y., de Sousa, R.C. and Jerome, F., Phys. Chem. Chem. Phys., 2011, 13:628 doi: 10.1039/B927015A
14. [14]
  Kakuchi, R. and Theato, P., ACS Macro Lett., 2013, 2:419 doi: 10.1021/mz400144q
15. [15]
  Kim, H. and Choi, T.L., ACS Macro Lett., 2014, 3:791 doi: 10.1021/mz5003239
16. [16]
  Ihara, E., Hara, Y., Itoh, T. and Inoue, K., Macromolecules, 2011, 44:5955 doi: 10.1021/ma201037p
17. [17]
  Li, W., Wu, X., Zhao, Z., Qin, A., Hu, R. and Tang, B.Z., Macromolecules, 2015, 48:7747 doi: 10.1021/acs.macromol.5b02193
18. [18]
  Liu, Y., Gao, M., Lam, J.W.Y., Hu, R. and Tang, B.Z., Macromolecules, 2014, 47:4908 doi: 10.1021/ma501477w
19. [19]
  Zhang, Z., You, Y.Z., Wu, D.C. and Hong, C.Y., Macromolecules, 2015, 48:3414 doi: 10.1021/acs.macromol.5b00463
20. [20]
  Zheng, C., Deng, H., Zhao, Z., Qin, A., Hu, R. and Tang, B.Z., Macromolecules, 2015, 48:1941 doi: 10.1021/acs.macromol.5b00175
21. [21]
  Kreye, O., Trefzger, C., Sehlinger, A. and Meier, M.A.R., Macromol. Chem. Phys., 2014, 215:2207 doi: 10.1002/macp.v215.22
22. [22]
  Yang, L., Zhang, Z., Cheng, B., You, Y., Wu, D. and Hong, C., Sci. China Chem., 2015, 58:1734 doi: 10.1007/s11426-015-5448-0
23. [23]
  Kreye, O., Toth, T. and Meier, M.A.R., J. Am. Chem. Soc., 2011, 133:1790 doi: 10.1021/ja1113003
24. [24]
  Lee, I.H., Kim, H. and Choi, T.L., J. Am. Chem. Soc., 2013, 135:3760 doi: 10.1021/ja312592e
25. [25]
  Deng, H., Hu, R., Zhao, E., Chan, C.Y.K., Lam, J.W.Y. and Tang, B.Z., Macromolecules, 2014, 47:4920 doi: 10.1021/ma501190g
26. [26]
  Li, C.J. and Wei, C., Chem. Commun., 2002:268
27. [27]
  Chan, C.Y.K., Tseng, N.W., Lam, J.W.Y., Liu, J., Kwok, R.T.K. and Tang, B.Z., Macromolecules, 2013, 46:3246 doi: 10.1021/ma4005346
28. [28]
  Chauveau, E., Marestin, C. and Mercier, R., Polymer, 2014, 55:6435 doi: 10.1016/j.polymer.2014.10.042
29. [29]
  Hugel, H.M., Molecules, 2009, 14:4936 doi: 10.3390/molecules14124936
30. [30]
  Huang, F., Wu, H.B., Wang, D., Yang, W. and Cao, Y., Chem. Mater., 2004, 16:708 doi: 10.1021/cm034650o
31. [31]
  Wang, J., Lin, K., Zhang, K., Jiang, X.F., Mahmood, K., Ying, L., Huang, F. and Cao, Y., Adv. Energy Mater., 2016, 6
32. [32]
  Lu, J., Cai, W., Zhang, G., Liu, S., Ying, L. and Huang, F., Acta Chimica Sinica (in Chinese), 2015, 73:1153 doi: 10.6023/A15080546
33. [33]
  Zhu, Y., Guang, S., Xu, H., Su, X. and Liu, X., J. Mater. Chem. C, 2013, 1:5277 doi: 10.1039/c3tc30597j
34. [34]
  Xu, Q., An, L., Yu, M. and Wang, S., Macromol. Rapid Commun., 2008, 29:390 doi: 10.1002/(ISSN)1521-3927
35. [35]
  Bura, T. and Ziessel, R., Tetrahedron Lett., 2010, 51:2875 doi: 10.1016/j.tetlet.2010.03.095
36. [36]
  Sommer, J.R., Shelton, A.H., Parthasarathy, A., Ghiviriga, I., Reynolds, J.R. and Schanze, K.S., Chem. Mater., 2011, 23:5296 doi: 10.1021/cm202241e
37. [37]
  Fang, J., Wallikewitz, B.H., Gao, F., Tu, G., Muller, C., Pace, G., Friend, R.H. and Huck, W.T., J. Am. Chem. Soc., 2011, 133:683 doi: 10.1021/ja108541z
38. [38]
  Xing, Y., Sun, C., Yip, H.L., Bazan, G.C., Huang, F. and Cao, Y., Nano Energy, 2016, 26:7 doi: 10.1016/j.nanoen.2016.04.057
39. [39]
  Wu, Z.H., Sun, C., Dong, S., Jiang, X.F., Wu, S.P., Wu, H.B., Yip, H.L., Huang, F. and Cao, Y., J. Am. Chem. Soc., 2016, 138:2004 doi: 10.1021/jacs.5b12664
1. [1]
  Yaohua Li , Qi Cao , Xuanhua Li . Tailoring the configuration of polymer passivators in perovskite solar cells. Chinese Journal of Structural Chemistry, 2025, 44(2): 100413-100413. doi: 10.1016/j.cjsc.2024.100413
2. [2]
  Qingyan JIANG , Yanyong SHA , Chen CHEN , Xiaojuan CHEN , Wenlong LIU , Hao HUANG , Hongjiang LIU , Qi LIU . Constructing a one-dimensional Cu-coordination polymer-based cathode material for Li-ion batteries. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 657-668. doi: 10.11862/CJIC.20240004
3. [3]
  Yikun Wang , Qiaomei Chen , Shijie Liang , Dongdong Xia , Chaowei Zhao , Christopher R. McNeill , Weiwei Li . Near-infrared double-cable conjugated polymers based on alkyl linkers with tunable length for single-component organic solar cells. Chinese Chemical Letters, 2024, 35(4): 109164-. doi: 10.1016/j.cclet.2023.109164
4. [4]
  Chengcheng Xie , Chengyi Xiao , Hongshuo Niu , Guitao Feng , Weiwei Li . Mesoporous organic solar cells. Chinese Chemical Letters, 2024, 35(11): 109849-. doi: 10.1016/j.cclet.2024.109849
5. [5]
  Bowen Wang , Longwu Sun , Qianqian Cao , Xinzhi Li , Jianai Chen , Shizhao Wang , Miaolin Ke , Fener Chen . Cu-catalyzed three-component CSP coupling for the synthesis of trisubstituted allenyl phosphorothioates. Chinese Chemical Letters, 2024, 35(12): 109617-. doi: 10.1016/j.cclet.2024.109617
6. [6]
  Ren Shen , Yanmei Fang , Chunxiao Yang , Quande Wei , Pui-In Mak , Rui P. Martins , Yanwei Jia . UV-assisted ratiometric fluorescence sensor for one-pot visual detection of Salmonella. Chinese Chemical Letters, 2025, 36(4): 110143-. doi: 10.1016/j.cclet.2024.110143
7. [7]
  Mengxing Liu , Jing Liu , Hongxing Zhang , Jianan Tao , Peiwen Fan , Xin Lv , Wei Guo . One-pot accessing of meso–aryl heptamethine indocyanine NIR fluorophores and potential application in developing dye-antibody conjugate for imaging tumor. Chinese Chemical Letters, 2025, 36(4): 109994-. doi: 10.1016/j.cclet.2024.109994
8. [8]
  Yaxin Sun , Huiyu Li , Shiquan Guo , Congju Li . Metal-based cathode catalysts for electrocatalytic ORR in microbial fuel cells: A review. Chinese Chemical Letters, 2024, 35(5): 109418-. doi: 10.1016/j.cclet.2023.109418
9. [9]
  Pingping HAO , Fangfang LI , Yawen WANG , Houfen LI , Xiao ZHANG , Rui LI , Lei WANG , Jianxin LIU . Hydrogen production performance of the non-platinum-based MoS₂/CuS cathode in microbial electrolytic cells. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1811-1824. doi: 10.11862/CJIC.20240054
10. [10]
  Yu Pang , Min Wang , Ning-Hua Yang , Min Xue , Yong Yang . One-pot synthesis of a giant twisted double-layer chiral macrocycle via [4 + 8] imine condensation and its X-ray structure. Chinese Chemical Letters, 2024, 35(10): 109575-. doi: 10.1016/j.cclet.2024.109575
11. [11]
  Chen Lu , Zefeng Yu , Jing Cao . Advancement in porphyrin/phthalocyanine compounds-based perovskite solar cells. Chinese Journal of Structural Chemistry, 2024, 43(3): 100240-100240. doi: 10.1016/j.cjsc.2024.100240
12. [12]
  Chi Li , Peng Gao . Is dipole the only thing that matters for inverted perovskite solar cells?. Chinese Journal of Structural Chemistry, 2024, 43(6): 100324-100324. doi: 10.1016/j.cjsc.2024.100324
13. [13]
  Yuqing Wang , Zhemin Li , Qingjun Lu , Qizhao Li , Jiaxin Luo , Chengjie Li , Yongshu Xie . Solar cells based on doubly concerted companion dyes with the efficiencies modulated by inserting an ethynyl group at different positions. Chinese Chemical Letters, 2024, 35(5): 109093-. doi: 10.1016/j.cclet.2023.109093
14. [14]
  Kangrong Yan , Ziqiu Shen , Yanchun Huang , Benfang Niu , Hongzheng Chen , Chang-Zhi Li . Curing the vulnerable heterointerface via organic-inorganic hybrid hole transporting bilayers for efficient inverted perovskite solar cells. Chinese Chemical Letters, 2024, 35(6): 109516-. doi: 10.1016/j.cclet.2024.109516
15. [15]
  Bo Yang , Pu-An Lin , Tingwei Zhou , Xiaojia Zheng , Bing Cai , Wen-Hua Zhang . Facile surface regulation for highly efficient and thermally stable perovskite solar cells via chlormequat chloride. Chinese Chemical Letters, 2024, 35(10): 109425-. doi: 10.1016/j.cclet.2023.109425
16. [16]
  Yingfen Li , Zhiqi Wang , Yunhai Zhao , Dajun Luo , Xueliang Zhang , Jun Zhao , Zhenghua Su , Shuo Chen , Guangxing Liang . Potassium doping for grain boundary passivation and defect suppression enables highly-efficient kesterite solar cells. Chinese Chemical Letters, 2024, 35(11): 109468-. doi: 10.1016/j.cclet.2023.109468
17. [17]
  Zhiyang Zhang , Yi Chen , Yingnan Zhang , Chuanlang Zhan . Deuterated chloroform replaces ultra-dry chloroform to achieve high-efficient organic solar cells. Chinese Chemical Letters, 2025, 36(1): 110083-. doi: 10.1016/j.cclet.2024.110083
18. [18]
  Rongjun Zhao , Tai Wu , Yong Hua , Yude Wang . Improving performance of perovskite solar cells enabled by defects passivation and carrier transport dynamics regulation via organic additive. Chinese Chemical Letters, 2025, 36(2): 109587-. doi: 10.1016/j.cclet.2024.109587
19. [19]
  Shaonan Liu , Shuixing Dai , Minghua Huang . The impact of ester groups on 1,8-naphthalimide electron transport material in organic solar cells. Chinese Journal of Structural Chemistry, 2024, 43(6): 100277-100277. doi: 10.1016/j.cjsc.2024.100277
20. [20]
  Wenbiao Zhang , Bolong Yang , Zhonghua Xiang . Atomically dispersed Cu-based metal-organic framework directly for alkaline polymer electrolyte fuel cells. Chinese Chemical Letters, 2025, 36(2): 109630-. doi: 10.1016/j.cclet.2024.109630

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(897)
HTML views(39)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142