研究简报

基于卤素取代邻苯二甲酰亚胺新型有机发光材料的合成及其性能研究

  • 张亮 ,
  • 李猛 ,
  • 高庆宇 ,
  • 陈传峰
展开
  • a 中国矿业大学化工学院 江苏徐州 221116;
    b 中国科学院化学研究所 分子识别与功能院重点实验室 北京 100190;
    c 中国科学院大学 北京 100049

收稿日期: 2019-09-09

  修回日期: 2019-10-13

  网络出版日期: 2019-11-01

基金资助

国家自然科学基金(Nos.21572233,21871272)资助项目.

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

  • Zhang Liang ,
  • Li Meng ,
  • Gao Qingyu ,
  • Chen Chuanfeng
Expand
  • a College of Chemical Engineering, China University of Mining and Technology, Xuzhou, Jangsu 221116;
    bCAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190;
    c University of Chinese Academy of Sciences, Beijing 100049

Received date: 2019-09-09

  Revised date: 2019-10-13

  Online published: 2019-11-01

Supported by

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

摘要

方便地合成了三个含有卤素取代邻苯二甲酰亚胺与咔唑基团的新型有机发光材料Br-Al-CzCl-Al-CzF-AI-Cz,发现它们不仅具有强的聚集诱导发光效应,而且显示膜态下热激活延迟荧光以及晶态诱导的室温磷光性质.尤其是化合物Br-Al-Cz表现出肉眼可见的长余辉室温磷光现象,因此在数据加密等中具有潜在用途.

本文引用格式

张亮 , 李猛 , 高庆宇 , 陈传峰 . 基于卤素取代邻苯二甲酰亚胺新型有机发光材料的合成及其性能研究[J]. 有机化学, 2020 , 40(2) : 516 -520 . DOI: 10.6023/cjoc201909012

Abstract

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.

参考文献

[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] (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] Xia, Z.; Meijerink, A. Chem. Soc. Rev. 2017, 46, 275.
[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] (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] Yang, J.; Gao, X.; Xie, Z.; Gong, Y.; Fang, M.; Peng, Q.; Chi, Z.; Li, Z. Angew. Chem., Int. Ed. 2017, 56, 15299.
[7] Zhang, Z.-Y.; Chen, Y.; Liu, Y. Angew. Chem., Int. Ed. 2019, 58, 6028.
[8] Giachino, G. G.; Kearns D. R. J. Chem. Phys. 1970, 52, 2964.
[9] Ma, X.; Xu, C.; Wang, J.; Tian, H. Angew. Chem., Int. Ed. 2018, 57, 10854.
[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] (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] (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] (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] (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] (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] Forni, A.; Lucenti, E.; Botta, C.; Cariati, E. J. Mater. Chem. C 2018, 6, 4603.
文章导航

/