Citation: Zhang Liang, Li Meng, Gao Qingyu, Chen Chuanfeng. Synthesis and Properties of New Organic Luminescent Materials Based on Halogen-Substituted Phthalimides[J]. Chinese Journal of Organic Chemistry, ;2020, 40(2): 516-520. doi: 10.6023/cjoc201909012 shu

Synthesis and Properties of New Organic Luminescent Materials Based on Halogen-Substituted Phthalimides

  • Corresponding author: Gao Qingyu, gaoqy@cumt.edu.cn Chen Chuanfeng, cchen@iccas.ac.cn
  • Received Date: 9 September 2019
    Revised Date: 13 October 2019
    Available Online: 1 February 2019

    Fund Project: the National Natural Science Foundation of China 21572233Project supported by the National Natural Science Foundation of China (Nos. 21572233, 21871272)the National Natural Science Foundation of China 21871272

Figures(7)

  • A new kind of organic luminescent materials containing halogen-substituted phthalimide group and carbazole subunit have been conveniently synthesized. They not only showed strong aggregation-induced emission (AIE) effect, but also exhibited thermally activated delayed fluorescence (TADF) in films and crystallization-induced room-temperature phosphorescence (RTP) properties. Especially, RTP with marked afterglow for Br-AI-Cz was observed by naked eye, which could be used as the promising smart materials for the encryption application.
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    1. [1]

      (a) Baldo, M. A.; O'Brien, D. F.; You, Y.; Shoustikow, A.; Sibley, S.; Thompson, M. E.; Forrest, S. R. Nature 1998, 395, 151.
      (b) Fermi, A.; Bergamini, G.; Roy, M.; Gingras, M.; Ceroni, P. J. Am. Chem. Soc. 2014, 136, 6395.

    2. [2]

      (a) Zhang, G.; Palmer, M. G.; Dewhirst, M. W.; Fraser, C. L. Nat. Mater. 2009, 8, 747.
      (b) Fateminia, S. M. A.; Mao, A.; Xu, S.; Yang, Z.; Chi, Z.; Liu, B. Angew. Chem., Int. Ed. 2017, 56, 12160.
      (c) Fang, Lei.; Lin, W.; Shen, Y.; Chen C. Chin. J. Org. Chem. 2018, 38, 541 (in Chinese).
      (房蕾, 林伟彬, 沈赟, 陈传峰, 有机化学, 2018, 38, 541.)

    3. [3]

      Xia, Z.; Meijerink, A. Chem. Soc. Rev. 2017, 46, 275.  doi: 10.1039/C6CS00551A

    4. [4]

      (a) Xu, S.; Chen, R.; Zheng, C.; Huang, W. Adv. Mater. 2016, 28, 9920.
      (b) Wu, Q.; Ma, H.; Ling, K.; Gan, N.; Cheng, Z.; Gu, L.; Cai, S.; An, Z.; Shi, H.; Huang, W. ACS Appl. Mater. Inter. 2018, 10, 33730.
      (c) Gong, Y.; Zhao, L.; Peng, Q.; Fan, D.; Yuan, W. Z.; Zhang, Y.; Tang, B. Z. Chem. Sci. 2015, 6, 4438.

    5. [5]

      (a) Xu, S.; Chen, R.; Zheng, C.; Huang, W. Adv. Mater. 2016, 28, 9920.
      (b) Wu, Q.; Ma, H.; Ling, K.; Gan, N.; Cheng, Z.; Gu, L.; Cai, S.; An, Z.; Shi, H.; Huang, W. ACS Appl. Mater. Inter. 2018, 10, 33730.
      (c) Gong, Y.; Zhao, L.; Peng, Q.; Fan, D.; Yuan, W. Z.; Zhang, Y.; Tang, B. Z. Chem. Sci. 2015, 6, 4438.

    6. [6]

      Yang, J.; Gao, X.; Xie, Z.; Gong, Y.; Fang, M.; Peng, Q.; Chi, Z.; Li, Z. Angew. Chem., Int. Ed. 2017, 56, 15299.  doi: 10.1002/anie.201708119

    7. [7]

      Zhang, Z.-Y.; Chen, Y.; Liu, Y. Angew. Chem., Int. Ed. 2019, 58, 6028.  doi: 10.1002/anie.201901882

    8. [8]

      Giachino, G. G.; Kearns D. R. J. Chem. Phys. 1970, 52, 2964.  doi: 10.1063/1.1673425

    9. [9]

      Ma, X.; Xu, C.; Wang, J.; Tian, H. Angew. Chem., Int. Ed. 2018, 57, 10854.  doi: 10.1002/anie.201803947

    10. [10]

      (a) Chen, X.; Xu, C.; Wang, T.; Zhou, C.; Du, J.; Wang, Z.; Xu, H.; Xie, T.; Bi, G.; Jiang, J.; Zhang, X.; Demas, J. N.; Trindle, C. O.; Luo, Y.; Zhang, G. Angew. Chem., Int. Ed. 2016, 55, 9872.
      (b) Bolton, O.; Lee, K. Kim, H. J.; Lin, K. Y.; Kim, J. Nat. Chem. 2011, 3, 205.
      (c) Xue, P.; Sun, J.; Chen, P.; Wang, P.; Yao, B.; Gong, P.; Zhang, Z.; Lu, R. Chem. Commun. 2015, 51, 10381.

    11. [11]

      (a) Gong, Y.; Chen, G.; Peng, Q.; Yuan, W. Z.; Xie, Y.; Li, S.; Zhang, Y.; Tang, B. Z. Adv. Mater. 2015, 27, 6195.
      (b) Cheng, Z.; Shi, H.; Ma, H.; Bian, L.; Wu, Q.; Gu, L.; Cai, S.; Wang, X.; Xiong, W. W.; An, Z.; Huang, W. Angew. Chem., Int. Ed. 2018, 57, 678.
      (c) Xiong, Q.; Xu, C.; Jiao, N.; Ma, X.; Zhang, Y.; Zhang, S. Chin. Chem. Lett. 2019, 30, 1387.

    12. [12]

      (a) Yang, Z.; Mao, Z.; Xie, Z.; Zhang, Y.; Liu, S.; Zhao, J.; Xu, J.; Chi, Z.; Aldred, M. P. Chem. Soc. Rev. 2017, 46, 91.
      (b) Zhang, Q.; Xu, S.; Li, M.; Wang, Y.; Zhang, N.; Guan, Y.; Chen, M.; Chen, C.-F.; Hu, H.-Y. Chem. Commun. 2019, 55, 5639.
      (c) Zheng, Y.; Xie, Q.; Wang, B. Chin. J. Org. Chem. 2016, 36, 803 (in Chinese).
      (郑月游, 谢琼琳, 王炳喜, 有机化学, 2016, 36, 803.)
      (d) Lin, D.; Song, S.; Chen, Z.; Guo, P.; Chen, J.; Shi, H.; Mai, Y.; Song, H. Chin. J. Org. Chem. 2018, 38, 103 (in Chinese).
      (林丹燕, 宋森川, 陈智勇, 郭鹏然, 陈江韩, 史华红, 麦裕良, 宋化灿, 有机化学, 2018, 38, 103.)
      (e) Tan, J.; Huo, Y.; Cai N.; Ji, S.; Li, Z.; Zhang, L. Chin. J. Org. Chem. 2017, 37, 2457 (in Chinese).
      (谭继华, 霍延平, 蔡宁, 籍少敏, 李宗植, 张力, 有机化学, 2017, 37, 2457.)

    13. [13]

      (a) Tao, Y.; Yuan, K.; Chen, T.; Xu, P.; Li, H.; Chen, R.; Zheng, C.; Zhang, L.; Huang, W. Adv. Mater. 2014, 26, 7931.
      (b) Li, M.; Liu, Y.; Duan, R.; Wei, X.; Yi, Y.; Wang, Y.; Chen, C.-F. Angew. Chem., Int. Ed. 2017, 56, 8818.
      (c) Li, M.; Li, S.-H.; Zhang, D.; Cai, M.; Duan, L.; Fung, M.-K.; Chen, C.-F. Angew. Chem., Int. Ed. 2018, 57, 2889.
      (d) Chen, C.; Lu, H.-Y.; Wang, Y.-F.; Li, M.; Shen, Y.-F.; Chen, C.-F. J. Mater. Chem. C, 2019, 7, 4673.
      (e) Wang, Y.-F.; Lu, H.-Y.; Chen, C.; Li, M.; Chen, C.-F. Org. Electron 2019, 70, 71.

    14. [14]

      (a) Hu, Y.; Wang, Z.; Jiang, X.; Cai, X.; Su, S.-J.; Huang, F.; Cao, Y. Chem. Commun. 2018, 54, 7850.
      (b) Pashazadeh, R.; Pander, P.; Bucinskas, A.; Skabara, P. J.; Dias, F. B.; Grazulevicius, J. V. Chem. Commun. 2018, 54, 13857.
      (c) Yu, L.; Wu, Z.; Zhong, C.; Xie, G.; Zhu, Z.; Ma, D.; Yang, C. Adv. Optic. Mater. 2017, 5, 1700588.
      (d) Ni, F.; Zhu, Z.; Tong, Xiao; Xie, M.; Zhao, Q.; Zhong, C.; Zou, Y.; Yang, C. Chem. Sci. 2018, 9, 6150.
      (e) Takeda, Y.; Kaihara, T.; Okazaki, M.; Higginbotham, H.; Data, P.; Tohnai, N.; Minakata, S. Chem. Commun. 2018, 54, 6847.
      (f) Pander, P.; Swist, A.; Motyka, R.; Oloducho, J.; Dias, S. F. B.; Data, P. J. Mater. Chem. C 2018, 6, 5434.
      (g) Zhang, L.; Li, M.; Hu T.-P.; Wang Y.-F.; Shen, Y.-F.; Yi, Y.-P.; Lu, H.-Y.; Gao Q.-Y.; Chen, C.-F. Chem. Commun. 2019, 55, 12172.

    15. [15]

      (a) Mei, J.; Leung, N. L. C.; Kwok, R. T. K.; Lam, J. W. Y.; Tang, B. Z. Chem. Rev. 2015, 115, 11718.
      (b) Liu, R.; Zeng, J. Chin. J. Org. Chem. 2017, 37, 3274 (in Chinese).
      (刘瑞姣, 曾竟, 有机化学, 2017, 37, 3274.)
      (c) Wang, Z.; Yang, J.; Yang, Y.; Xu, X.; Li, M.; Zhang, Y.; Fang, H.; Xu, H.; Wang, S. Chin. J. Org. Chem. 2018, 38, 1401 (in Chinese).
      (王忠龙, 杨金来, 杨益琴, 徐徐, 李明新, 张燕, 方华, 徐海军, 王石发, 有机化学, 2018, 38, 1401.)

    16. [16]

      Forni, A.; Lucenti, E.; Botta, C.; Cariati, E. J. Mater. Chem. C 2018, 6, 4603.  doi: 10.1039/C8TC01007B

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