Naphthalene Diimide-Based Polymers Consisting of Amino Alkyl Side Groups:Three-Component One-Pot Polymerization and Their Application in Polymer Solar Cells
- Corresponding author: Huang Fei, msfhuang@scut.edu.cn
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
Domling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168.
doi: 10.1002/(ISSN)1521-3773
Kakuchi, R. Angew. Chem., Int. Ed. 2014, 53, 46.
doi: 10.1002/anie.v53.1
Balme, G.; Bossharth, E.; Monteiro, N. Eur. J. Org. Chem. 2003, 2003, 4101.
doi: 10.1002/(ISSN)1099-0690
Andreana, P. R.; Liu, C. C.; Schreiber, S. L. Org. Lett. 2004, 6, 4231.
doi: 10.1021/ol0482893
D'Souza, D. M.; Mueller, T. J. J. Chem. Soc. Rev. 2007, 36, 1095.
doi: 10.1039/B608235C
Biggs-Houck, J. E.; Younai, A.; Shaw, J. T. Curr. Opin. Chem. Biol. 2010, 14, 371.
doi: 10.1016/j.cbpa.2010.03.003
Siamaki, A. R.; Sakalauskas, M.; Arndtsen, B. A. Angew. Chem., Int. Ed. 2011, 50, 6552.
doi: 10.1002/anie.v50.29
Thanh Binh, N.; Minh Quan, T.; Ermolenko, L.; Al-Mourabit, A. Org. Lett. 2014, 16, 310.
doi: 10.1021/ol403345e
Rotstein, B. H.; Zaretsky, S.; Rai, V.; Yudin, A. K. Chem. Rev. 2014, 114, 8323.
doi: 10.1021/cr400615v
Levi, L.; Muller, T. J. J. Chem. Soc. Rev. 2016, 45, 2825.
doi: 10.1039/C5CS00805K
Teimouri, M. B.; Abbasi, T.; Mivehchi, H. Tetrahedron 2008, 64, 10425.
doi: 10.1016/j.tet.2008.08.039
Yu, J.; Shi, F.; Gong, L.-Z. Acc. Chem. Res. 2011, 44, 1156.
doi: 10.1021/ar2000343
Ruijter, E.; Scheffelaar, R.; Orru, R. V. A. Angew. Chem., Int. Ed. 2011, 50, 6234.
doi: 10.1002/anie.201006515
Hossaini, Z.; Seyfi, S.; Rostami-Charati, F.; Ghambarian, M. Comb. Chem. High Throughput Screen 2013, 16, 788.
doi: 10.2174/13862073113169990046
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
Theato, P., Multi-Component and Sequential Reactions in Polymer Synthesis, Springer, 2015, Vol. 269.
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
Hu, R. R.; Li, W. Z.; Tang, B. Z. Macromol. Chem. Phys. 2016, 217, 213.
doi: 10.1002/macp.201500291
Kreye, O.; Toth, T.; Meier, M. A. R. J. Am. Chem. Soc. 2011, 133, 1790.
doi: 10.1021/ja1113003
Lee, I.-H.; Kim, H.; Choi, T.-L. J. Am. Chem. Soc. 2013, 135, 3760.
doi: 10.1021/ja312592e
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
Liu, Y. J.; Gao, M.; Lam, J. W. Y.; Hu, R. R.; Tang, B. Z. Macromolecules 2014, 47, 4908.
doi: 10.1021/ma501477w
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
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
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
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
Yu, G.; Gao, J.; Hummelen, J. C.; Wudl, F.; Heeger, A. J. Science 1995, 270, 1789.
doi: 10.1126/science.270.5243.1789
Heeger, A. J. Chem. Soc. Rev. 2010, 39, 2354.
doi: 10.1039/b914956m
Hains, A. W.; Liang, Z.; Woodhouse, M. A.; Gregg, B. A. Chem. Rev. 2010, 110, 6689.
doi: 10.1021/cr9002984
Huang, Y.; Kramer, E. J.; Heeger, A. J.; Bazan, G. C. Chem. Rev. 2014, 114, 7006.
doi: 10.1021/cr400353v
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
Zhang, X.; Wang, Z. L.; Chen, S. Y.; Zhao, Z.; Yuan, W.; Wang, H. P.; Gao, X. K. Chin. J. Chem. 2014, 32, 1057.
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
Liu, L. Q.; Zhang, G. C.; He, B. T.; Huang, F. Chin. J. Chem. 2015, 33, 902.
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
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
Zhang, K.; Guan, X.; Huang, F.; Cao, Y. Acta Chim. Sinica 2012, 70, 2489.
Duan, C. H.; Zhang, K.; Zhong, C. M.; Huang, F.; Cao, Y. Chem. Soc. Rev. 2013, 42, 9071.
doi: 10.1039/c3cs60200a
Hu, Z. C.; Zhang, K.; Huang, F.; Cao, Y. Chem. Commun. 2015, 51, 5572.
doi: 10.1039/C4CC09433F
Yip, H.-L.; Jen, A. K. Y. Energy Environ. Sci. 2012, 5, 5994.
doi: 10.1039/c2ee02806a
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
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
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
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
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
Liu, X.; Xu, R. G.; Duan, C.; Huang, F.; Cao, Y. J. Mater. Chem. C 2016, 4, 4288.
Guan, X.; Zhang, K.; Huang, F.; Bazan, G. C.; Cao, Y. Adv. Funct. Mater. 2012, 22, 2846.
doi: 10.1002/adfm.v22.13
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
Jia, T.; Zheng, N. N.; Cai, W. Q.; Zhang, J.; Ying, L.; Huang, F.; Cao, Y. Chin. J. Polym. Sci. 2017, 35, 269.
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
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
Facchetti, A. Mater. Today 2013, 16, 123.
doi: 10.1016/j.mattod.2013.04.005
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
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
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.
Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650.
McLean, A.; Chandler, G. J. Chem. Phys. 1980, 72, 5639.
Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
Lu, T.; Chen, F. W. J. Comput. Chem. 2012, 33, 580.
doi: 10.1002/jcc.v33.5
Lu, T.; Chen, F. W. J. Theor. Comput. Chem. 2012, 11, 163.
doi: 10.1142/S0219633612500113
Bhosale, S. V.; Jani, C. H.; Langford, S. J. Chem. Soc. Rev. 2008, 37, 331.
doi: 10.1039/B615857A
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