Citation: Bian Song, Ye Jia-Hai, Fan Zheng, Zhang Wenchao, Wang Leyong. Assembly of Tetraphenylethene Containing Amine and Crown Ether Units and Aggregation-Induced Emission Properties[J]. Chinese Journal of Organic Chemistry, ;2016, 36(4): 855-861. doi: 10.6023/cjoc201510030 shu

Assembly of Tetraphenylethene Containing Amine and Crown Ether Units and Aggregation-Induced Emission Properties

Bian Song ^a ,
Ye Jia-Hai ^a,, ,
Fan Zheng ^a ,
Zhang Wenchao ^a ,
Wang Leyong ^b,,

a.
a. School of Chemical Engineering, Nanjing Univesity of Science and Technology, Nanjing 210094;
b.
b. Laboratory for Supramolecular Chemistry and Dynamic. Materials, School of Chemistry and Chemical Engineering, Nanjing Universty, Nanjing 210093

Corresponding author: Ye Jia-Hai, Wang Leyong,
Received Date: 26 October 2015
Available Online: 9 December 2015

Dibenzo-24-crown-8 (DB24C8) and dibenzylammonium (DBA) are always utilized for the construction of supramolecular assemblies. We reported a new kind supramolecular assembly polymer constructed by M1 which was synthesized from tetraphenylethene (TPE) linked with DB24C8 and DBA through click reaction. The chemical structures of all the compounds were fully characterized by ¹H NMR, ¹³C NMR, and MS. The ¹H NMR titration showed that the supramolecular assembly was successfully constructed in acidic condition. The fluorescent results showed that the assemblies displayed ratio-metric properties with the changes of aggregation-induced emission and monomer-emission, and fluorescence quenching with addition of Pd²⁺.
- tetraphenylethene,
- DB24C8,
- secondary ammonium ion,
- supramolecular polymer,
- aggregations-induced emission
1. [1]
  [1] (a) Yan, X.; Wang, F.; Zheng, B.; Huang, F. Chem. Soc. Rev. 2012, 41, 6042.
2. [2]
  (b) Li, S. L.; Xiao, T.; Lin, C.; Wang, L. Chem. Soc. Rev. 2012, 41, 5950.
3. [3]
  [2] (a) Brinkmann, J.; Cavatorta, E.; Sankaran, S.; Schmidt, B.; van Weerd, J.; Jonkheijm, P. Chem. Soc. Rev. 2014, 43, 4449.
4. [4]
  (b) Pescitelli, G.; Di Bari, L.; Berova, N. Chem. Soc. Rev. 2014, 43, 5211.
5. [5]
  (c) Monti, S.; Manet, I. Chem. Soc. Rev. 2014, 43, 4051.
6. [6]
  (d) Liu, Y.; Wang, Z.; Zhang, X. Chem. Soc. Rev. 2012, 41, 5922.
7. [7]
  (e) Appel, E. A.; del Barrio, J.; Loh, X. J.; Scherman, O. A. Chem. Soc. Rev. 2012, 41, 6195.
8. [8]
  (f) Dong, S.; Zheng, B.; Wang, F.; Huang, F. Acc. Chem. Res. 2014, 47, 1982.
9. [9]
  (g) Li, C. Chem. Commun. 2014, 50, 12420.
10. [10]
  (h) Yi, J.; Xiao, X.; Zhang, Y.; Xue, S.; Tao, Z.; Zhang, J. Acta Chim. Sinica 2014, 72, 949 (in Chinese). (易君明, 肖欣, 张云黔, 薛赛凤, 陶朱, 张建新, 化学学报, 2014, 72, 949.)
11. [11]
  [3] Gokel, G. W.; Leevy, W. M.; Weber, M. E. Chem. Rev. 2004, 104, 2723.
12. [12]
  [4] (a) Ji, X.; Yao, Y.; Li, J.; Yan, X.; Huang, F. J. Am. Chem. Soc. 2013, 135, 74.
13. [13]
  (b) Dong, S.; Zheng, B.; Xu, D.; Yan, X.; Zhang, M.; Huang, F. Adv. Mater. 2012, 24, 3191.
14. [14]
  (c) Dong, S.; Luo, Y.; Yan, X.; Zheng, B.; Ding, X.; Yu, Y.; Ma, Z.; Zhao, Q.; Huang, F. Angew. Chem., Int. Ed. 2011, 50, 1905.
15. [15]
  (d) Yan, X.; Cook, T. R.; Pollock, J. B.; Wei, P.; Zhang, Y.; Yu, Y.; Huang, F., Stang, P. J. J. Am. Chem. Soc. 2014, 136, 4460.
16. [16]
  [5] (a) Hong, Y.; Lam, J. W.; Tang, B. Z. Chem. Soc. Rev. 2011, 40, 5361.
17. [17]
  (b) Qiu, S.; Xu, S.; Zhou, G.; Shui, L.; Zhu, X. Chin. J. Org. Chem. 2015, 35, 1746 (in Chinese). (邱淑海, 许胜杰, 周国富, 水玲玲, 朱晓张, 有机化学, 2015, 35, 1746.)
18. [18]
  (c) Guan, C.; Qian, Y. Chin. J. Org. Chem. 2014, 34, 537 (in Chinese). (管成飞, 钱鹰, 有机化学, 2014, 34, 537.)
19. [19]
  (d) Han, X.; Lü, X.; Chen, Z.; Yu, G.; Yin, J.; Liu, S. Chin. J. Chem. 2015, 33, 1064.
20. [20]
  (e) Xun, Z.; Tang, H.; Zeng, Y.; Chen, J.; Yu, T.; Zhang, X.; Li, Y. Acta Chim. Sinica 2015, 73, 819 (in Chinese). (寻知庆, 唐海云, 曾毅, 陈金平, 于天君, 张小辉, 李嫕, 化学学报, 2015, 73, 819.)
21. [21]
  [6] Hu, R.; Leung, N. L.; Tang, B. Z. Chem. Soc. Rev. 2014, 43, 4494.
22. [22]
  [7] (a) Song, N.; Chen, D. X.; Qiu, Y. C.; Yang, X. Y.; Xu, B.; Tian, W.; Yang, Y. W. Chem. Commun. 2014, 50, 8231.
23. [23]
  (b) Wang, P.; Yan, X., Huang, F. Chem. Commun. 2014, 50, 5017.
24. [24]
  (c) Ogoshi, T.; YamafuJi, D.; Yamagishi, T. A.; Brouwer, A. M. Chem. Commun. (Camb.) 2013, 49, 5468.
25. [25]
  (d) Bai, W.; Wang, Z.; Tong, J.; Mei, J.; Qin, A.; Sun, J. Z.; Tang, B. Z. Chem. Commun. (Camb.) 2015, 51, 1089.
26. [26]
  (e) Wu, J.; Sun, S.; Feng, X.; Shi, J.; Hu, X. Y.; Wang, L. Chem. Commun. (Camb.) 2014, 50, 9122.
27. [27]
  (f) Chen, R.; Jiang, H.; Gu, H.; Zhou, Q.; Wu, J.; Chen, D.; Zhang, J. Chem. Commun. (Camb.) 2015, 51, 12220.
28. [28]
  (g) Yao, X. Y.; Ma, X.; Tian, H. J. Mater. Chem C 2014, 2, 5155.
29. [29]
  [8] Yan, X.; Xu, D.; Chi, X.; Chen, J.; Dong, S.; Ding, X.; Yu, Y.; Huang, F. Adv. Mater. 2012, 24, 362.
30. [30]
  [9] Ye, J.-H.; Duan, L.; Yan, C.; Zhang, W.; He, W. Tetrahedron Lett. 2012, 53, 593.
31. [31]
  [10] Zong, Q.; Wu, J. Chin. J. Org. Chem. 2013, 33, 568 (in Chinese). (宗乾收, 吴建一, 有机化学, 2013, 33, 568.)
32. [32]
  [11] Cheng, H.-B.; Zhang, H.-Y.; Liu, Y. J. Am. Chem. Soc. 2013, 135, 10190.
33. [33]
  [12] Liu, D.; Wang, D.; Wang, M.; Zheng, Y.; Koynov, K.; Auernhammer, G. K.; Butt, H.-J.; Ikeda, T. Macromolecules 2013, 46, 4617.
34. [34]
  [13] (a) Aoki, D.; Uchida, S.; Takata, T. ACS Macro Lett. 2014, 3, 324.
35. [35]
  (b) Chen, D.; Zhan, J.; Zhang, M.; Zhang, J.; Tao, J.;Tang, D.; Shen, A.; Qiu, H.; Yin, S. Polym. Chem. 2015, 6, 25.
36. [36]
  [14] Ge, Z.; Hu, J.; Huang, F.; Liu, S. Angew. Chem., Int. Ed. 2009, 48, 1798.
1. [1]
  Chengqian Mao , Yanghan Chen , Haotong Bai , Junru Huang , Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014
2. [2]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  .
  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): -.
6. [6]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
7. [7]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-. doi: 10.3866/PKU.WHXB202309027
8. [8]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
9. [9]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
10. [10]
  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
11. [11]
  Tao Cao , Fang Fang , Nianguang Li , Yinan Zhang , Qichen Zhan . Green Synthesis of p-Hydroxybenzonitrile Catalyzed by Spinach Extracts under Red-Light Irradiation: Research and Exploration of Innovative Experiments for Pharmacy Undergraduates. University Chemistry, 2024, 39(5): 63-69. doi: 10.3866/PKU.DXHX202309098
12. [12]
  Xiuyun Wang , Jiashuo Cheng , Yiming Wang , Haoyu Wu , Yan Su , Yuzhuo Gao , Xiaoyu Liu , Mingyu Zhao , Chunyan Wang , Miao Cui , Wenfeng Jiang . Improvement of Sodium Ferric Ethylenediaminetetraacetate (NaFeEDTA) Iron Supplement Preparation Experiment. University Chemistry, 2024, 39(2): 340-346. doi: 10.3866/PKU.DXHX202308067
13. [13]
  Yanyang Li , Zongpei Zhang , Kai Li , Shuangquan Zang . Ideological and Political Design for the Comprehensive Experiment of the Synthesis and Aggregation-Induced Emission (AIE) Performance Study of Salicylaldehyde Schiff-Base. University Chemistry, 2024, 39(2): 105-109. doi: 10.3866/PKU.DXHX202307020
14. [14]
  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
15. [15]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
16. [16]
  Yanhui Zhong , Ran Wang , Zian Lin . Analysis of Halogenated Quinone Compounds in Environmental Water by Dispersive Solid-Phase Extraction with Liquid Chromatography-Triple Quadrupole Mass Spectrometry. University Chemistry, 2024, 39(11): 296-303. doi: 10.12461/PKU.DXHX202402017
17. [17]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
18. [18]
  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
19. [19]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
20. [20]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(747)
HTML views(77)

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

Assembly of Tetraphenylethene Containing Amine and Crown Ether Units and Aggregation-Induced Emission Properties

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