Citation: Wang Heng, Zhang Yukun, Zou Sheng, Cao Jinxin, Huang Qingfei, Wang Qiwei, Zhu Jin. Design and Synthesis of a Class of Aromatic Polyamide Foldamer[J]. Chinese Journal of Organic Chemistry, ;2018, 38(8): 2060-2066. doi: 10.6023/cjoc201712043 shu

Design and Synthesis of a Class of Aromatic Polyamide Foldamer

Wang Heng ^a,b ,
Zhang Yukun ^a,b ,
Zou Sheng ^a ,
Cao Jinxin ^a ,
Huang Qingfei ^a,, ,
Wang Qiwei ^a ,
Zhu Jin ^a,,

a.
Chengdu Institute of Organic Chemistry, Chinese Academy of Science, Chengdu 610041
b.
Universtiy of Chinese Academy of Sciense, Beijing 100049

Corresponding author: Huang Qingfei, qfhuang@cioc.ac.cn Zhu Jin, jinzhu@cioc.ac.cn
Received Date: 29 December 2017
Revised Date: 14 February 2018
Available Online: 16 August 2018
Fund Project: the National Natural Science Foundation of China 20772123Project supported by the National Natural Science Foundation of China (No. 20772123)

Figures(5)

Long aromatic polymer chains which based on 3, 5-diaminobenzoic acid derivatives and 4, 6-dihydroxyisophthalic acid derivatives are designed and synthesized. The results of solubility, NMR, UV-Vis spectrum and circular dichroism (CD) experments indicate that the polymer adopts a hollow helical conformation that is stablized by intramolecular H-bonding interaction between side chains.
- aromatic polyamide,
- foldamer,
- helice
1. [1]
  Gellman, S. H. Acc. Chem. Res. 1998, 31, 173. doi: 10.1021/ar960298r
2. [2]
  David, J. H.; Matthew J. M.; Ryan, B. P.; Thomas, S. H.; Moore, J. S. Chem. Rev. 2001, 101, 3893. doi: 10.1021/cr990120t
3. [3]
  Gong, B. Chem.-Eur. J. 2001, 7, 4336. doi: 10.1002/(ISSN)1521-3765
4. [4]
  Huc, I. Eur. J. Org. Chem. 2004, 17.
5. [5]
  Li, Z. T.; Hou, J. L.; Li, C.; Yi, H.-P. Chem.-Asian J. 2006, 1, 766. doi: 10.1002/(ISSN)1861-471X
6. [6]
  Goodman, C. M.; Choi, S.; Shandler, S.; Degrado, W. F. Nat. Chem. Biol. 2007, 3, 252. doi: 10.1038/nchembio876
7. [7]
  Guichard, G.; Huc, I. Chem. Commun. 2011, 47, 5933. doi: 10.1039/c1cc11137j
8. [8]
  Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 13071. doi: 10.1021/ja963290l
9. [9]
  Yang, D.; Li, W.; Qu, J.; Luo, S.-W.; Wu, Y. D. J. Am. Chem. Soc. 2003, 125, 13018. doi: 10.1021/ja036136p
10. [10]
  Nelson, J. C.; Saven, J. G.; Moore, J. S.; Wolynes, P G. Science 1997, 277, 1793. doi: 10.1126/science.277.5333.1793
11. [11]
  Seebach, D.; Overh, M.; Kiihnle, F. N. M.; Martinoni, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913.
12. [12]
  Hamuro, Y.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Soc. 1997, 119, 10587. doi: 10.1021/ja963449u
13. [13]
  Zhu, J.; Parra, R. N. D.; Zeng, H.; Skrzypczak-Jankun, E.; Zeng, X C.; Gong, B. J. Am. Chem. Soc, 2000, 122, 4219. doi: 10.1021/ja994433h
14. [14]
  Jiang, H.; LéGer, J.-M.; Huc, I. J. Am. Chem. Soc. 2003, 125, 3448. doi: 10.1021/ja029887k
15. [15]
  Hou, J. L.; Shao, X. B.; Chen, G. J.; Zhou, Y. X.; Jiang, X. K.; Li, Z. T. J. Am. Chem. Soc. 2004, 126, 12386. doi: 10.1021/ja047436p
16. [16]
  Wang, Y.; Wang, H.; Zhang, D.-W.; Li, Z.-T. Chin. J. Org. Chem. 2016, 36, 1580(in Chinese).
17. [17]
  Sun, G.; Nie, C.; Zhao, X.; Li, Z. Chin. J. Org. Chem. 2017, 37, 1757(in Chinese).
18. [18]
  Yang, L.; Zhao, W.; Che, Y. K.; Wang, Y.; Jiang, H. Chin. Chem. Lett. 2017, 28, 1659. doi: 10.1016/j.cclet.2017.06.006
19. [19]
  Van Gorp, J J.; Vekemans, J. A. J. M.; Meijer, E. W. Chem. Commun. 2004, 60.
20. [20]
  Sinkeldam, R. W.; Van Houtem, M. H. C. J.; Pieterse, K.; Vekemans, J. A. J. M.; Meijer, E. W. Chem.-Eur. J. 2006, 12, 6129. doi: 10.1002/(ISSN)1521-3765
21. [21]
  Lu, Y. X.; Shi, Z. M.; Li, Z. T.; Guan, Z. Chem. Commun. 2010, 46, 9019. doi: 10.1039/c0cc03689g
22. [22]
  Cao, J.; Kline, M.; Chen, Z.; Luan, B.; Lv, M.; Zhang, W.; Lian, C.; Wang, Q.; Huang, Q.; Wei, X.; Deng, J.; Zhu, J.; Gong, B. Chem. Commun. 2012, 48, 11112. doi: 10.1039/c2cc35886g
23. [23]
  Zhang, Y.-C.; Chen, L.; Wang, H.; Zhou, Y.-M.; Zhang, D.-W.; Li, Z.-T. Chin. Chem. Lett. 2016, 27, 817. doi: 10.1016/j.cclet.2016.03.041
24. [24]
  Zhang, P.; Wang, Z.; Zhang, L.; Wang, H.; Zhang, D.; Hou, J.; Li, Z. Chin. J. Chem. 2016, 34, 678. doi: 10.1002/cjoc.v34.7
25. [25]
  Gong, B. Acc. Chem. Res. 2008, 41, 1376. doi: 10.1021/ar700266f
26. [26]
  Parra, R. D.; Zeng, H.; Zhu, J.; Zheng, C.; Zeng, X. C.; Gong, B. Chem.-Eur. J. 2001, 7, 4352. doi: 10.1002/(ISSN)1521-3765
27. [27]
  Feng, W.; Yamato, K.; Yang, L.; Ferguson, J. S.; Zhong, L.; Zou, S.; Yuan, L.; Zeng, X. C.; Gong, B. J. Am. Chem. Soc. 2009, 131, 2629. doi: 10.1021/ja807935y
28. [28]
  Aimin, Z.; Joseph S, F.; Kazuhiro, Y.; Chong, Z.; Gong, B. Org. Lett. 2006, 8, 5117. doi: 10.1021/ol062103d
29. [29]
  Wei, X.; Zhang, G.; Shen, Y.; Zhong, Y.; Liu, R.; Yang, N.; Al-Mkhaizim, F Y.; Kline, M A.; He, L.; Li, M.; Lu, Z. L.; Shao, Z.; Gong, B. J. Am. Chem. Soc. 2016, 138, 2749. doi: 10.1021/jacs.5b12698
30. [30]
  García, J. M.; García, F. C.; Serna, F.; de la Peña, J. L. Prog. Polym. Sci. 2010, 35, 623. doi: 10.1016/j.progpolymsci.2009.09.002
31. [31]
  Sakurai, K.; Mizu, M.; Shinkai, S. Biomacromolecules, 2001, 2, 641. doi: 10.1021/bm000121r
32. [32]
  Creighton, T. E. Proteins:Structures and Molecular Properties, 2nd ed., W. H. Freeman, New York, 1993.
33. [33]
  Vicente, A. I.; Caio, J. M.; Sardinha, J.; Moiteiro, C.; Delgado, R.; Félix, V. Tetrahedron 2012, 68, 670. doi: 10.1016/j.tet.2011.10.090
1. [1]
  Zhongxin YU , Wei SONG , Yang LIU , Yuxue DING , Fanhao MENG , Shuju WANG , Lixin YOU . Fluorescence sensing on chlortetracycline of a Zn-coordination polymer based on mixed ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2415-2421. doi: 10.11862/CJIC.20240304
2. [2]
  Bao Jia , Yunzhe Ke , Shiyue Sun , Dongxue Yu , Ying Liu , Shuaishuai Ding . Innovative Experimental Teaching for the Preparation and Modification of Conductive Organic Polymer Thin Films in Undergraduate Courses. University Chemistry, 2024, 39(10): 271-282. doi: 10.12461/PKU.DXHX202404121
3. [3]
  Xiao SANG , Qi LIU , Jianping LANG . Synthesis, structure, and fluorescence properties of Zn(Ⅱ) coordination polymers containing tetra-alkenylpyridine ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2124-2132. doi: 10.11862/CJIC.20240158
4. [4]
  Xuefei Leng , Yanshai Wang , Hai Wang , Shengyang Tao . The In-Depth integration of “Industry-University-Research” in the Exploration and Practice of “Comprehensive Training in Polymer Engineering”. University Chemistry, 2025, 40(4): 66-71. doi: 10.12461/PKU.DXHX202405105
5. [5]
  Ruiying WANG , Hui WANG , Fenglan CHAI , Zhinan ZUO , Benlai WU . Three-dimensional homochiral Eu(Ⅲ) coordination polymer and its amino acid configuration recognition. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 877-884. doi: 10.11862/CJIC.20250052
6. [6]
  Junjie Zhang , Yue Wang , Qiuhan Wu , Ruquan Shen , Han Liu , Xinhua Duan . Preparation and Selective Separation of Lightweight Magnetic Molecularly Imprinted Polymers for Trace Tetracycline Detection in Milk. University Chemistry, 2024, 39(5): 251-257. doi: 10.3866/PKU.DXHX202311084
7. [7]
  Xingchao Zhao , Xiaoming Li , Ming Liu , Zijin Zhao , Kaixuan Yang , Pengtian Liu , Haolan Zhang , Jintai Li , Xiaoling Ma , Qi Yao , Yanming Sun , Fujun Zhang . 倍增型全聚合物光电探测器及其在光电容积描记传感器上的应用. Acta Physico-Chimica Sinica, 2025, 41(1): 2311021-. doi: 10.3866/PKU.WHXB202311021
8. [8]
  Fanpeng Meng , Fei Zhao , Jingkai Lin , Jinsheng Zhao , Huayang Zhang , Shaobin Wang . 优化氮化碳纳米片/球形共轭聚合物S型异质结界面电场以促进析氢反应. Acta Physico-Chimica Sinica, 2025, 41(8): 100095-. doi: 10.1016/j.actphy.2025.100095
9. [9]
  Caixia Lin , Ting Liu , Zhaojiang Shi , Hong Yan , Keyin Ye , Yaofeng Yuan . Innovative Experiment of Electrochemical Dearomative Spirocyclization of N-Acyl Sulfonamides. University Chemistry, 2025, 40(4): 359-366. doi: 10.12461/PKU.DXHX202406107
10. [10]
  Dongdong Yao , JunweiGu , Yi Yan , Junliang Zhang , Yaping Zheng . Teaching Phase Separation Mechanism in Polymer Blends Using Process Representation Teaching Method: A Teaching Design for Challenging Theoretical Concepts in “Polymer Structure and Properties” Course. University Chemistry, 2025, 40(4): 131-137. doi: 10.12461/PKU.DXHX202408125
11. [11]
  You Wu , Chang Cheng , Kezhen Qi , Bei Cheng , Jianjun Zhang , Jiaguo Yu , Liuyang Zhang . ZnO/D-A共轭聚合物S型异质结高效光催化产H₂O₂及其电荷转移动力学研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2406027-. doi: 10.3866/PKU.WHXB202406027
12. [12]
  .
  南开大学师唯/华北电力大学（保定）刘景维：二维配位聚合物中有序的亲锂冠醚位点用于无枝晶锂沉积
  . CCS Chemistry, 2025, 7(0): -.
13. [13]
  Liang TANG , Jingfei NI , Kang XIAO , Xiangmei LIU . Synthesis and X-ray imaging application of lanthanide-organic complex-based scintillators. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1892-1902. doi: 10.11862/CJIC.20240139
14. [14]
  Hao Wu , Zhen Liu , Dachang Bai . ¹H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020
15. [15]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
16. [16]
  Hong Zheng , Xin Peng , Chunwang Yi . The Tale of Caprolactam Cyclic Oligomers: The Ever-changing Life of “Princess Cyclo”. University Chemistry, 2024, 39(9): 40-47. doi: 10.12461/PKU.DXHX202403058
17. [17]
  Min LIU , Huapeng RUAN , Zhongtao FENG , Xue DONG , Haiyan CUI , Xinping WANG . Neutral boron-containing radical dimers. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 123-130. doi: 10.11862/CJIC.20240362
18. [18]
  Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095
19. [19]
  Gonglan Ye , Xia Yin , Feng Xu , Peng Yang , Yingpeng Wu , Huilong Fei . Innovations in “Four-in-One” Inorganic Chemistry Education. University Chemistry, 2024, 39(8): 136-141. doi: 10.3866/PKU.DXHX202401071
20. [20]
  Xingyuan Lu , Yutao Yao , Junjing Gu , Peifeng Su . Energy Decomposition Analysis and Its Application in the Many-Body Effect of Water Clusters. University Chemistry, 2025, 40(3): 100-107. doi: 10.12461/PKU.DXHX202405074

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(1217)
HTML views(123)

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

Design and Synthesis of a Class of Aromatic Polyamide Foldamer

南开大学师唯/华北电力大学（保定）刘景维：二维配位聚合物中有序的亲锂冠醚位点用于无枝晶锂沉积

Metrics

通讯作者: 陈斌, bchen63@163.com