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

  • 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+.
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    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.

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