1, 2, 5, 6-Naphthalenediimide-based Conjugated Copolymers Linked by Ethynyl Units
- Corresponding author: Jian-min Dou, jmdou@lcu.edu.cn Da-cheng Li, lidacheng62@lcu.edu.cn Xi-ke Gao, gaoxk@sioc.ac.cn
Citation:
Bing-yong Liu, Xiao-chun Yang, Cong-wu Ge, Jian-min Dou, Da-cheng Li, Xi-ke Gao. 1, 2, 5, 6-Naphthalenediimide-based Conjugated Copolymers Linked by Ethynyl Units[J]. Chinese Journal of Polymer Science,
;2017, 35(11): 1342-1351.
doi:
10.1007/s10118-017-1988-4
Jung, B.J., Tremblay, N.J., Yeh, M.L. and Katz, H.E., Chem. Mater., 2011, 23:568
doi: 10.1021/cm102296d
Anthony, J.E., Facchetti, A., Heeney, M., Marder, S.R. and Zhan, X., Adv. Mater., 2011, 22:3876
Zhan, X., Facchetti, A., Barlow, S., Marks, T.J., Ratner, M.A., Wasielewski, M.R. and Marder S.R., Adv. Mater., 2011, 23:268
doi: 10.1002/adma.v23.2
Huang, C., Barlow, S. and Marder, S.R., J. Org. Chem., 2011, 76:2386
doi: 10.1021/jo2001963
Wang, C.L., Hu, W.P., Liu, Y.Q. and Zhu, D.B., Chem. Rev., 2012, 112:2208
doi: 10.1021/cr100380z
Katz, H.E., Lovinger, A.J., Johnson, J., Kloc, C., Siegrist, T., Li, W., Lin, Y. and Dodabalapur, A., Nature, 2000, 404:478
doi: 10.1038/35006603
Gao, X., Di, C., Hu, Y., Yang, X., Fan, H., Zhang, F., Liu, Y., Li, H. and Zhu, D., J. Am. Chem. Soc., 2010, 132:3697
doi: 10.1021/ja910667y
Piliego, C., Jarzab, D., Gigli, G., Chen, Z., Facchetti, A. and Loi, M.A., Adv. Mater., 2009, 21:1573
doi: 10.1002/adma.v21:16
Ortiz, R.P., Herrera, H., Blanco, R., Huang, H., Facchetti, A., Marks, T.J., Zheng, Y. and Segura, J.L., J. Am. Chem. Soc., 2010, 132:8440
doi: 10.1021/ja1018783
Yan, H., Chen, Z., Zheng, Y., Newman, C., Quinn, J.R., Dotz, F., Kastler, M. and Facchetti, A., Nature, 2009, 457:679
doi: 10.1038/nature07727
Chopin, S., Chaignon, F., Blart, E. and Odobel, F., J. Mater. Chem., 2007, 17:4139
doi: 10.1039/b704489e
Chaignon, F., Falkenstrom, M., Karlsson, S., Blart, E., Odobel, F. and Hammarstrom, L., Chem. Commun., 2007, 42:64
Thalacker, C., Röger, C. and Würthner, F., J. Org. Chem., 2006, 71:8098
doi: 10.1021/jo0612269
Zhan, X., Tan, Z., Domercq, B., An, Z., Zhang, X., Barlow, S., Li, Y., Zhu, D., Kippelen, B. and Marder, S.R., J. Am. Chem. Soc., 2007, 129:7246
doi: 10.1021/ja071760d
Chen, Z., Zheng, Y., Yan, H. and Facchetti, A., J. Am. Chem. Soc., 2009, 131:8
doi: 10.1021/ja805407g
Durban, M.M., Kazarinoff, P.D. and Luscombe, C.K., Macromolecules, 2010, 43:6348
doi: 10.1021/ma100997g
Kudla, C.J., Dolfen, D., Schottler, K.J., Koenen, J.M., Breusov, D., Allard S. and Scherf, U., Macromolecules, 2010, 43:7864
doi: 10.1021/ma1014885
Zhou, E., Cong, J., Wei, Q., Tajima, K., Yang, C. and Hashimoto, K., Angew. Chem. Int. Ed., 2010, 50:2799
Monika, M.S., Eliot, H.G., Christopher, R.M., Vincent, L., Yoann, O., Lars, T., Yana, V., Michael, S. and Henning, S., Chem. Mater., 2014, 26:6796
doi: 10.1021/cm5033578
Takimiya, K. and Nakano, I.O.M., Chem. Mater., 2014, 26:587
doi: 10.1021/cm4021063
Dou, C., Long, X., Ding, Z., Xie, Z., Liu, J. and Wang, L., Angew. Chem. Int. Ed., 2016, 55:1436
doi: 10.1002/anie.201508482
Long, X., Ding, Z., Dou, C., Zhang, J., Liu, J. and Wang, L., Adv. Mater., 2016, 28:6504
doi: 10.1002/adma.201601205
Ding, Z., Long, X., Dou, C., Liu, J. and Wang, L., Chem. Sci., 2016, 7:6197
doi: 10.1039/C6SC01756H
Jung, J.W., Jo, J.W., Chueh, C.C., Liu, F., Jo, W.H., Russell, T.P. and Jen, A.K.Y., Adv. Mater., 2015, 27:3310
doi: 10.1002/adma.v27.21
Hwang, Y.J., Courtright, B.A., Ferreira, A.S., Tolbert, S.H. and Jenekhe, S.A., Adv. Mater., 2015, 27:4578
doi: 10.1002/adma.v27.31
Gao, L., Zhang, Z.G., Xue, L., Min. J., Zhang, J., Wei, Z. and Li, Y., Adv. Mater., 2016, 28:1884
doi: 10.1002/adma.201504629
Shi, S., Yuan, J., Ding, G., Ford, M., Lu, K., Shi, G., Sun, J., Ling, X., Li, Y. and Ma, W., Adv. Funct. Mater., 2016, 26:5669
doi: 10.1002/adfm.v26.31
Zhou, E., Cong, J., Hashimoto, K. and Tajima, K., Adv. Mater., 2013, 25:6991
doi: 10.1002/adma.v25.48
Hwang, T.J., Ren, G., Murari, N.M. and Jenekhe, S.A., Macromolecules, 2012, 45:9056
doi: 10.1021/ma3020239
Mu, C., Liu, P., Ma, W., Jiang, K., Zhao, J., Zhang, K., Chen, Z., Wei, Z., Yi, Y., Wang, J., Yang, S., Huang, F., Facchetti, A., Ade, H. and Yan, H., Adv. Mater., 2014, 26:7224
doi: 10.1002/adma.v26.42
Kim, T., Kim, J.H., Kang, T.E., Lee, C., Kang, H., Shin, M., Wang, C., Ma, B., Jeong, U., Kim, T.S. and Kim, B.J., Nat. Commun., 2015, 6:8547
doi: 10.1038/ncomms9547
Li, Z., Xu, X., Zhang, W., Meng, X., Ma, W., Yartsev, A., Inganas, O., Andersson, M.R., Janssen, R.A. and Wang, E., J. Am. Chem. Soc., 2016, 138:10935
doi: 10.1021/jacs.6b04822
Chen, S.C., Zhang, Q.K., Zheng, Q.D., Tang, C.Q. and Lu, C.Z., Chem. Commun., 2012, 48:1254
doi: 10.1039/C2CC15733K
Zhao, Z., Zhang, F.J., Zhang, X., Yang, X.D., Li, H.X., Gao, X.K., Di, C.A. and Zhu, D.B., Macromolecules, 2013, 46:7705
doi: 10.1021/ma4013994
Zhao, Z., Wang, Z.L., Ge, C.W., Zhang, X., Yang, X.D. and Gao, X.K., Polym. Chem., 2016, 7:573
doi: 10.1039/C5PY01709B
Li, Z.J., Feng, K., Liu, J., Mei, J., Li, Y. and Peng, Q., J. Mater. Chem. A, 2016, 4:7372
doi: 10.1039/C6TA01766E
Chen, S.C., Zheng, Q.D., Zhang, Q.K., Cai, D.D., Wang, J.Y. and Tang, C.Q., J. Polym. Sci., Part A:Polym. Chem., 2013, 51:1999
doi: 10.1002/pola.26580
Zhang, S., Liu, J., Han, Y.C. and Wang, L.X., Macromol. Chem. Phys., 2017, DOI:10.1002/macp. 201600606
doi: 10.1002/macp.201600606
Bunz, U.H.F., Chem. Rev., 2000, 100:1605
doi: 10.1021/cr990257j
Bunz, U.H.F., Acc. Chem. Res., 2001, 34:998
doi: 10.1021/ar010092c
Thomas, S.W., Joly, G.D. and Swager, T.M., Chem. Rev., 2007, 107:1339
doi: 10.1021/cr0501339
VanVeller, B., Miki, K. and Swager, T.M., Org. Lett., 2010, 12:1292
doi: 10.1021/ol1001768
Esser, B. and Swager, T.M., Angew. Chem. Int. Ed., 2010, 49:8872
doi: 10.1002/anie.v49.47
Bajaj, A., Miranda, O.R., Phillips, R., Kim, I.B., Jerry, D.J., Bunz, U.H.F. and Rotello, V.M., J. Am. Chem. Soc., 2009, 132:1018
Bumm, L.A., Arnold, J.J., Cygan, M.T., Dunbar, T.D., Burgin, T.P., Jones, L., Allara, D.L., Tour, J.M. and Weiss, P.S., Science, 1996, 271:1705
doi: 10.1126/science.271.5256.1705
Samori, P., Francke, V., Müllen, K. and Rabe, J.P., Chem. Eur. J., 1999, 5:2312
doi: 10.1002/(SICI)1521-3765(19990802)5:8<>1.0.CO;2-B
Samori, P., Sikharulidze, I., Francke, V., Muüllen, K. and Rabe, J.P., Nanotechnology, 1999, 10:77
doi: 10.1088/0957-4484/10/1/015
Lu, S.L., Yang, M.J., Luo, J., Cao, Y. and Bai, F.L., Synthetic Met., 2004, 146:175
doi: 10.1016/j.synthmet.2004.06.015
Chu, Q.H. and Pang, Y., Macromolecules, 2003, 36:3848
doi: 10.1021/ma034028h
Intemann, J.J., Emily, S., Tlach, E.S., Ewan, B.C., Barnes, M.D., Bhuwalka, C.A., Cai, A., Shinar, M., Shinar, J.R. and Jeffries, E.L., Macromolecules, 2012, 45:6888
doi: 10.1021/ma300821m
Woody, K.B., Henry, E.M., Jagtap, S. and Collard, D.M., Macromolecules, 2011, 44:9118
doi: 10.1021/ma201347z
Popere, B.C., Pelle, A.M.D. and Thayumanavan, S., Macromolecules, 2011, 44:4767
doi: 10.1021/ma200839q
Kola, S., Kim, J.H., Ireland, R., Yeh, M.L., Smith, K., Guo, W.M. and Katz, H.E., ACS Macro Lett., 2013, 2:664
doi: 10.1021/mz400164s
Dong, H.L., Wang, E.J., Yan, S.K., Zhang, J.M., Yang, C.M., Hiroshi, N., Keiichi, T. and Hu, W.P., J. Phys. Chem. B, 2009, 113:4176
doi: 10.1021/jp811374h
Kokil, A., Shiyanovskaya, I., Singer, K.D. and Weder, C., Synthetic Met., 2003, 138:513
doi: 10.1016/S0379-6779(02)01241-9
Hou, Y.H., Yin, S.G., Chen, Y.S., Yua, A., Liu, Q., Yang, M. and Wan, X.J., Macromolecules, 2008, 41:3114
doi: 10.1021/ma702864c
Du, C., Li, W., Li, C. and Bo, Z., J. Polym. Sci., Part A:Polym. Chem., 2013, 51:383
doi: 10.1002/pola.26396
Kim, B.S., Ma, B.W., Donuru, V.R., Liu, H.Y. and Fréchet, J.M.J., Chem. Commun., 2010, 46:4148
doi: 10.1039/b927350f
Voskerician, G. and Weder, C., Adv. Polym. Sci., 2005, 177:209
doi: 10.1007/b101353
Debnath, S., Singh, S., Bedi, A., Krishnamoorthy, K. and Zade, S.S., J. Polym. Sci., Part A:Polym. Chem., 2016, 54:1978
doi: 10.1002/pola.v54.13
Anna, L.P., Yoosaf, K., Traboulsi, H., Mohanraj, J., Seldrum, T., Dumont, J., Minoia, A., Lazzaroni, R., Armaroli, N. and Bonifazi, D., J. Am. Chem. Soc., 2011, 133:15412
doi: 10.1021/ja2011516
Hu, Y.B., Qin, Y.K., Gao, X.K., Zhang, F.J., Di, C.A., Zhao, Z., Li, H.X. and Zhu, D.B., Org. Lett., 2012, 14:292
doi: 10.1021/ol203059r
Peng, X.J., Song, F.L., Lu, E.H., Wang, Y.N., Zhou, W., Fan, J.L. and Gao, Y.L., J. Am. Chem. Soc., 2005, 127:4170
doi: 10.1021/ja043413z
Benniston, A.C., Harriman, A., Lawrie, D. J. and Mayeux, A., Phys. Chem. Chem. Phys., 2004, 6:51
doi: 10.1039/B312286G
Kaneda, K. and Arai, T., Photochem. Photobiol. Sci., 2003, 2:402
doi: 10.1039/B211834N
Jenekhe, S.A. and Osaheni, J.A., Science, 1994, 265:765
doi: 10.1126/science.265.5173.765
Min Chen , Boyu Peng , Xuyun Guo , Ye Zhu , Hanying Li . Polyethylene interfacial dielectric layer for organic semiconductor single crystal based field-effect transistors. Chinese Chemical Letters, 2024, 35(4): 109051-. doi: 10.1016/j.cclet.2023.109051
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
Tong Tong , Lezong Chen , Siying Wu , Zhong Cao , Yuanbin Song , Jun Wu . Establishment of a leucine-based poly(ester amide)s library with self-anticancer effect as nano-drug carrier for colorectal cancer treatment. Chinese Chemical Letters, 2024, 35(12): 109689-. doi: 10.1016/j.cclet.2024.109689
Qianqian Liu , Xing Du , Wanfei Li , Wei-Lin Dai , Bo Liu . Synergistic Effects of Internal Electric and Dipole Fields in SnNb2O6/Nitrogen-Enriched C3N5 S-Scheme Heterojunction for Boosting Photocatalytic Performance. Acta Physico-Chimica Sinica, 2024, 40(10): 2311016-. doi: 10.3866/PKU.WHXB202311016
Jaeyong Ahn , Zhenping Li , Zhiwei Wang , Ke Gao , Huagui Zhuo , Wanuk Choi , Gang Chang , Xiaobo Shang , Joon Hak Oh . Surface doping effect on the optoelectronic performance of 2D organic crystals based on cyano-substituted perylene diimides. Chinese Chemical Letters, 2024, 35(9): 109777-. doi: 10.1016/j.cclet.2024.109777
Weiping Guo , Ying Zhu , Hong-Hua Cui , Lingyun Li , Yan Yu , Zhong-Zhen Luo , Zhigang Zou . β-Pb3P2S8: A new optical crystal with exceptional birefringence effect. Chinese Chemical Letters, 2025, 36(2): 110256-. doi: 10.1016/j.cclet.2024.110256
Jinge Zhu , Ailing Tang , Leyi Tang , Peiqing Cong , Chao Li , Qing Guo , Zongtao Wang , Xiaoru Xu , Jiang Wu , Erjun Zhou . Chlorination of benzyl group on the terminal unit of A2-A1-D-A1-A2 type nonfullerene acceptor for high-voltage organic solar cells. Chinese Chemical Letters, 2025, 36(1): 110233-. doi: 10.1016/j.cclet.2024.110233
Xiutao Xu , Chunfeng Shao , Jinfeng Zhang , Zhongliao Wang , Kai Dai . Rational Design of S-Scheme CeO2/Bi2MoO6 Microsphere Heterojunction for Efficient Photocatalytic CO2 Reduction. Acta Physico-Chimica Sinica, 2024, 40(10): 2309031-. doi: 10.3866/PKU.WHXB202309031
Bicheng Zhu , Jingsan Xu . S-scheme heterojunction photocatalyst for H2 evolution coupled with organic oxidation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100327-100327. doi: 10.1016/j.cjsc.2024.100327
Shuai Liu , Wen Wu , Peili Zhang , Yunxuan Ding , Chang Liu , Yu Shan , Ke Fan , Fusheng Li . Mechanistic insights into acidic water oxidation by Mn(2,2′-bipyridine-6,6′-dicarboxylate)-based hydrogen-bonded organic frameworks. Chinese Journal of Structural Chemistry, 2025, 44(3): 100535-100535. doi: 10.1016/j.cjsc.2025.100535
Weihong Ding , Kaiyue Song , Xianglong Li , Xiaoxia Sun . High-temperature-stable RRAMs with well-defined thermal effect mechanisms enable by engineering of robust 2D <100>-oriented organic-inorganic hybrid perovskites. Chinese Chemical Letters, 2025, 36(4): 110495-. doi: 10.1016/j.cclet.2024.110495
Yuanyuan Zeng , Fang Liu , Jun Wang , Bianfei Shao , Tao He , Zhongzheng Xiang , Yan Wang , Shunyao Zhu , Tian Yang , Siting Yu , Changyang Gong , Lei Liu . Fisetin micelles precisely exhibit a radiosensitization effect by inhibiting PDGFRβ/STAT1/STAT3/Bcl-2 signaling pathway in tumor. Chinese Chemical Letters, 2025, 36(2): 109734-. doi: 10.1016/j.cclet.2024.109734
Zhili Li , Qijun Wo , Dongdong Huang , Dezhong Zhou , Lei Guo , Yeqing Mao . Improving gene transfection efficiency of highly branched poly(β-amino ester)s through the in-situ conversion of inactive terminal groups. Chinese Chemical Letters, 2024, 35(8): 109737-. doi: 10.1016/j.cclet.2024.109737
Ping Lu , Baoyin Du , Ke Liu , Ze Luo , Abiduweili Sikandaier , Lipeng Diao , Jin Sun , Luhua Jiang , Yukun Zhu . Heterostructured In2O3/In2S3 hollow fibers enable efficient visible-light driven photocatalytic hydrogen production and 5-hydroxymethylfurfural oxidation. Chinese Journal of Structural Chemistry, 2024, 43(8): 100361-100361. doi: 10.1016/j.cjsc.2024.100361
Xinghong Cai , Qiang Yang , Yao Tong , Lanyin Liu , Wutang Zhang , Sam Zhang , Min Wang . AlO2: A novel two-dimensional material with a high negative Poisson's ratio for the adsorption of volatile organic compounds. Chinese Chemical Letters, 2025, 36(2): 109586-. doi: 10.1016/j.cclet.2024.109586
Dong-Xue Jiao , Hui-Li Zhang , Chao He , Si-Yu Chen , Ke Wang , Xiao-Han Zhang , Li Wei , Qi Wei . Layered (C5H6ON)2[Sb2O(C2O4)3] with a large birefringence derived from the uniform arrangement of π-conjugated units. Chinese Journal of Structural Chemistry, 2024, 43(6): 100304-100304. doi: 10.1016/j.cjsc.2024.100304
Gangsheng Li , Xiang Yuan , Fu Liu , Zhihua Liu , Xujie Wang , Yuanyuan Liu , Yanmin Chen , Tingting Wang , Yanan Yang , Peicheng Zhang . Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade. Chinese Chemical Letters, 2025, 36(2): 109880-. doi: 10.1016/j.cclet.2024.109880
Bairu Meng , Zongji Zhuo , Han Yu , Sining Tao , Zixuan Chen , Erik De Clercq , Christophe Pannecouque , Dongwei Kang , Peng Zhan , Xinyong Liu . Design, synthesis, and biological evaluation of benzo[4,5]thieno[2,3-d]pyrimidine derivatives as novel HIV-1 NNRTIs. Chinese Chemical Letters, 2024, 35(6): 108827-. doi: 10.1016/j.cclet.2023.108827
Ke-Ai Zhou , Lian Huang , Xing-Ping Fu , Li-Ling Zhang , Yu-Ling Wang , Qing-Yan Liu . Fluorinated metal-organic framework for methane purification from a ternary CH4/C2H6/C3H8 mixture. Chinese Journal of Structural Chemistry, 2023, 42(11): 100172-100172. doi: 10.1016/j.cjsc.2023.100172
Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533