Citation: Zhang Liang, Zhao Wen-Long, Li Meng, Lu Hai-Yan, Chen Chuan-Feng. Recent Progress on Room-Temperature Phosphorescent Materials of Organic Small Molecules[J]. Acta Chimica Sinica, ;2020, 78(10): 1030-1040. doi: 10.6023/A20060243 shu

Recent Progress on Room-Temperature Phosphorescent Materials of Organic Small Molecules

Zhang Liang ^a,b ,
Zhao Wen-Long ^c ,
Li Meng ^a ,
Lu Hai-Yan ^c,, ,
Chen Chuan-Feng ^a,c,,

a.
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
b.
College of Chemical Engineering, China University of Mining and Technology, Xuzhou 221116, China
c.
University of Chinese Academy of Sciences, Beijing 100049, China

Corresponding author: Lu Hai-Yan, haiyanlu@ucas.ac.cn Chen Chuan-Feng, cchen@iccas.ac.cn
Received Date: 17 June 2020
Available Online: 13 July 2020
Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 91956119, 21971235, 21871272)the National Natural Science Foundation of China 21971235the National Natural Science Foundation of China 91956119the National Natural Science Foundation of China 21871272

Figures(23)

Room-temperature phosphorescence (RTP) can not only intuitively reflect the excited state transition process of the phosphorescent luminescence, but also has wide potential applications in optoelectronics, sensing, bioimaging and security devices. Consequently, more and more attention and interests on RTP materials have been attracted, which turned it to be one of hot topics in luminescence materials, especially, organic luminescence materials in recent years. The halogen bonds and hydrogen bonds between the molecules can fix the phosphor to suppress non-radiative transitions. A twisted donor-acceptor skeleton can promot efficient thermally activated delayed fluorescence (TADF) and also benefit to the RTP. Moreover, circularly polarized room-temperature phosphorescence (CP-RTP) also remains a daunting challenge to implant circularly polarized luminescence (CPL) in metal-free RTP materials. This review summarizes recent research progress on RTP of small organic molecules, mainly focusing on RTP materials based on hydrogen bonds, RTP materials containing halogens, RTP materials based on D-A structures and RTP materials with CPL properties.
- room-temperature phosphorescence,
- organic small molecule,
- circularly polarized luminescence
1. [1]
  Wang, H.; Meng, L. Q.; Shen, X. X.; Wei, X.; Zheng, X.; Lv, X.; Yi, Y.; Wang, Y.; Wang, P. Adv. Mater. 2015, 27, 4041. doi: 10.1002/adma.201501373
2. [2]
  Yang, J.; Zhen, X.; Wang, B.; Gao, X.; Ren, Z.; Wang, J.; Xie, Y.; Li, J.; Peng, Q.; Pu, K.; Li, Z. Nat. Commun. 2018, 9, 840. doi: 10.1038/s41467-018-03236-6
3. [3]
  Li, J.; Jiang, Y.; Cheng, J.; Su, H.; Lam, J. W. Y.; Sung, H. H. Y.; Wong, K. S.; Kwok, H. S.; Tang, B. Z. Phys. Chem. Chem. Phys. 2015, 17, 1134. doi: 10.1039/C4CP04052J
4. [4]
  Miao, Q.; Xie, C.; Zhen, X.; Lyu, Y.; Duan, H.; Liu, X.; Jokerst, J. V.; Pu, K. Nat. Biotechnol. 2017, 35, 1102. doi: 10.1038/nbt.3987
5. [5]
  Wang, F.; Tao, Y.; Huang, W. Acta Chim. Sinica 2015, 73, 9 (in Chinese).
6. [6]
  Ma, Y.; Chen, K.; Guo, Z.; Liu, S.; Zhao, Q.; Wong, W. Y. Acta Chim. Sinica 2020, 78, 23 (in Chinese).
7. [7]
  Zhou, Y.; Chen, Y. Z.; Cao, J. H.; Yang, Q. Z.; Wu, L. Z.; Tung, C. H.; Wu, D. Y. Dyes Pigm. 2015, 112, 162. doi: 10.1016/j.dyepig.2014.07.001
8. [8]
  Mukherjee, S.; Thilagar, P. Chem. Commun. 2015, 51, 10988. doi: 10.1039/C5CC03114A
9. [9]
  Ma, H.; Peng, Q.; An, Z.; Huang, W.; Shuai, Z. J. Am. Chem. Soc. 2019, 141, 1010. doi: 10.1021/jacs.8b11224
10. [10]
  Xiao, L.; Fu, H. Chem. Eur. J. 2019, 25, 714. doi: 10.1002/chem.201802819
11. [11]
  Hirata, S. Adv. Opt. Mater. 2017, 5, 1700116. doi: 10.1002/adom.201700116
12. [12]
  Forni, A.; Lucenti, E.; Botta, C.; Cariati, E. J. Mater. Chem. C 2018, 6, 4603. doi: 10.1039/C8TC01007B
13. [13]
  Xu, S.; Chen, R.; Zheng, C.; Huang, W. Adv. Mater. 2016, 28, 9920. doi: 10.1002/adma.201602604
14. [14]
  Zhang, T.; Ma, X.; Wu, H.; Zhu, L.; Zhao, Y.; Tian, H. Angew. Chem., Int. Ed. 2020, 59, 2. doi: 10.1002/anie.201914768
15. [15]
  Gan, N.; Shi, H.; An, Z.; Huang, W. Adv. Funct. Mater. 2018, 28, 1802657. doi: 10.1002/adfm.201802657
16. [16]
  Ma, X.; Wang, J.; Tian, H. Acc. Chem. Res. 2019, 52, 738. doi: 10.1021/acs.accounts.8b00620
17. [17]
  Li, Q.; Li, Z. Acc. Chem. Res. 2020, 53, 962. doi: 10.1021/acs.accounts.0c00060
18. [18]
  Cai, S.; Shi, H.; Li, J.; Gu, L.; Ni, Y.; Cheng, Z.; Wang, S.; Xiong, W. W.; Li, L.; An, Z.; Huang, W. Adv. Mater. 2017, 29, 1701244. doi: 10.1002/adma.201701244
19. [19]
  An, Z.; Zheng, C.; Tao, Y.; Chen, R.; Shi, H.; Chen, T.; Wang, Z.; Li, H.; Deng, R.; Liu, X.; Huang, W. Nat. Mater. 2015, 14, 685. doi: 10.1038/nmat4259
20. [20]
  Zhao, W.; He, Z.; Lam, J. W. Y.; Peng, Q.; Ma, H.; Shuai, Z.; Bai, G.; Hao, J.; Tang, B. Z. Chem. 2016, 1, 592. doi: 10.1016/j.chempr.2016.08.010
21. [21]
  Gu, L.; Shi, H.; Bian, L.; Gu, M.; Ling, K.; Wang, X.; Ma, H.; Cai, S.; Ning, W.; Fu, L.; Wang, H.; Wang, S.; Gao, Y.; Yao, W.; Huo, F.; Tao, Y.; An, Z.; Liu, X.; Huang, W. Nat. Photonics 2019, 13, 406. doi: 10.1038/s41566-019-0408-4
22. [22]
  Kwon, M. S.; Lee, D.; Seo, S.; Jung, J.; Kim, J. Angew. Chem., Int Ed. 2014, 53, 11177. doi: 10.1002/anie.201404490
23. [23]
  Gong, Y.; Zhao, L.; Peng, Q.; Fan, D.; Yuan, W. Z.; Zhang, Y.; Tang, B. Z. Chem. Sci. 2015, 6, 4438. doi: 10.1039/C5SC00253B
24. [24]
  Chai, Z.; Wang, C.; Wang, J.; Fan, Liu.; Xie, Y.; Zhang, Y. Z.; Li, J. R.; Li, Q.; Li, Z. Chem. Sci. 2017, 8, 8336. doi: 10.1039/C7SC04098A
25. [25]
  Fang, M.; Yang, J.; Xiang, X.; Xie, Y.; Dong, Y.; Peng, Q.; Li, Q.; Li, Z. Mater. Chem. Front. 2018, 2, 2124. doi: 10.1039/C8QM00396C
26. [26]
  Li, D.; Lu, F.; Wang, J.; Hu, W.; Cao, X. M.; Ma, X.; Tian, H. J. Am. Chem. Soc. 2018, 140, 1916. doi: 10.1021/jacs.7b12800
27. [27]
  Chen, J.; Yu, T.; Ubba, E.; Yang, Z.; Zhang, Y.; Liu, S.; Xu, J.; Aldred, M. P.; Chi, Z. Adv. Opt. Mater. 2019, 7, 1801593. doi: 10.1002/adom.201801593
28. [28]
  Chen, X.; Liu, Z. F.; Jin, W. J. J. Phys. Chem. A. 2020, 124, 2746. doi: 10.1021/acs.jpca.9b11943
29. [29]
  Bolton, O.; Lee, K.; Kim, H. J.; Lin, K. Y.; Kim, J. Nat. Chem. 2011, 3, 205. doi: 10.1038/nchem.984
30. [30]
  Xiao, L.; Wu, Y.; Yu, Z.; Xu, Z.; Li, J.; Liu, Y.; Yao, J.; Fu, H. Chem. Eur. J. 2018, 24, 1801. doi: 10.1002/chem.201705391
31. [31]
  Li, B.; Gong, Y.; Wang, L.; Lin, H.; Li, Q.; Guo, F.; Li, Z.; Peng, Q.; Shuai, Z.; Zhao, L.; Zhang, Y. J. Phys. Chem. Lett. 2019, 10, 7141. doi: 10.1021/acs.jpclett.9b02885
32. [32]
  Goudappagouda; Manthanath, A.; Wakchaure, V. C.; Ranjeesh, K. C.; Das T.; Vanka, K.; Nakanishi, T.; Babu, S. S. Angew. Chem., Int. Ed. 2019, 58, 2284. doi: 10.1002/anie.201811834
33. [33]
  Zhang, L.; Li, M.; Gao, Q.; Chen, C. F. Chin. J. Org. Chem. 2020, 40, 516 (in Chinese).
34. [34]
  She, P.; Yu, Y.; Qin, Y.; Zhang, Y.; Li, F.; Ma, Y.; Liu, S.; Huang, W.; Zhao, Q. Adv. Opt. Mater. 2020, 8, 1901437. doi: 10.1002/adom.201901437
35. [35]
  Yu, L.; Wu, Z.; Zhong, C.; Xie, G.; Zhu, Z.; Ma D.; Yang, C. Adv. Opt. Mater. 2017, 5, 1700588. doi: 10.1002/adom.201700588
36. [36]
  Xiong, Y.; Zhao, Z.; Zhao, W.; Ma, H.; Peng, Q.; He, Z.; Zhang, X.; Chen, Y.; He, X.; Lam, J. W. Y.; Tang, B. Z. Angew. Chem., Int. Ed. 2018, 57, 7997. doi: 10.1002/anie.201800834
37. [37]
  Zhou, Y.; Qin, W.; Du, C.; Gao, H.; Zhu, F.; Liang, G. Angew. Chem., Int. Ed. 2019, 58, 12102. doi: 10.1002/anie.201906312
38. [38]
  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. doi: 10.1039/C9CC06384F
39. [39]
  Zhang, L.; Li, M.; Gao, Q. Y.; Chen, C. F. Chem. Commun. 2020, 56, 4296. doi: 10.1039/C9CC09636A
40. [40]
  Hirata, S.; Vacha, M. J. Phys. Chem. Lett. 2016, 7, 1539. doi: 10.1021/acs.jpclett.6b00554
41. [41]
  Chen, W.; Tian, Z.; Li, Y.; Jiang, Y.; Liu, M.; Duan, P. Chem. Eur. J. 2018, 24, 17444. doi: 10.1002/chem.201804342
42. [42]
  Liang, X.; Liu, T. T.; Yan, Z. P.; Zhou, Y.; Su, J.; Luo, X. F.; Wu, Z. G.; Wang, Y.; Zheng, Y. X.; Zuo, J. L. Angew. Chem., Int. Ed. 2019, 58, 17220. doi: 10.1002/anie.201909076
43. [43]
  Li, H.; Li, H.; Wang, W.; Wang, S.; Yang, Q.; Jiang, Y.; Zheng, C.; Huang, W.; Chen, R. Angew. Chem., Int. Ed. 2020, 59, 4756. doi: 10.1002/anie.201915164
44. [44]
  Li, M.; Lin, W. B.; Fang, L.; Chen, C. F. Acta Chim. Sinica 2017, 75, 1150 (in Chinese).
45. [45]
  Zhang, D. W.; Li, M.; Chen, C. F. Chem. Soc. Rev. 2020, 49, 1331. doi: 10.1039/C9CS00680J
1. [1]
  Wenxiu Yang , Jinfeng Zhang , Quanlong Xu , Yun Yang , Lijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-. doi: 10.3866/PKU.WHXB202312014
2. [2]
  Peiran ZHAO , Yuqian LIU , Cheng HE , Chunying DUAN . A functionalized Eu³⁺ metal-organic framework for selective fluorescent detection of pyrene. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 713-724. doi: 10.11862/CJIC.20230355
3. [3]
  Tiantian MA , Sumei LI , Chengyu ZHANG , Lu XU , Yiyan BAI , Yunlong FU , Wenjuan JI , Haiying YANG . Methyl-functionalized Cd-based metal-organic framework for highly sensitive electrochemical sensing of dopamine. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 725-735. doi: 10.11862/CJIC.20230351
4. [4]
  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
5. [5]
  Wendian XIE , Yuehua LONG , Jianyang XIE , Liqun XING , Shixiong SHE , Yan YANG , Zhihao HUANG . Preparation and ion separation performance of oligoether chains enriched covalent organic framework membrane. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1528-1536. doi: 10.11862/CJIC.20240050
6. [6]
  Yang YANG , Pengcheng LI , Zhan SHU , Nengrong TU , Zonghua WANG . Plasmon-enhanced upconversion luminescence and application of molecular detection. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 877-884. doi: 10.11862/CJIC.20230440
7. [7]
  Lu XU , Chengyu ZHANG , Wenjuan JI , Haiying YANG , Yunlong FU . Zinc metal-organic framework with high-density free carboxyl oxygen functionalized pore walls for targeted electrochemical sensing of paracetamol. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 907-918. doi: 10.11862/CJIC.20230431
8. [8]
  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
9. [9]
  Qiuyang LUO , Xiaoning TANG , Shu XIA , Junnan LIU , Xingfu YANG , Jie LEI . Application of a densely hydrophobic copper metal layer in-situ prepared with organic solvents for protecting zinc anodes. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1243-1253. doi: 10.11862/CJIC.20240110
10. [10]
  Jing SU , Bingrong LI , Yiyan BAI , Wenjuan JI , Haiying YANG , Zhefeng Fan . Highly sensitive electrochemical dopamine sensor based on a highly stable In-based metal-organic framework with amino-enriched pores. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1337-1346. doi: 10.11862/CJIC.20230414
11. [11]
  Youlin SI , Shuquan SUN , Junsong YANG , Zijun BIE , Yan CHEN , Li LUO . Synthesis and adsorption properties of Zn(Ⅱ) metal-organic framework based on 3, 3', 5, 5'-tetraimidazolyl biphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1755-1762. doi: 10.11862/CJIC.20240061
12. [12]
  Yuanpei ZHANG , Jiahong WANG , Jinming HUANG , Zhi HU . Preparation of magnetic mesoporous carbon loaded nano zero-valent iron for removal of Cr(Ⅲ) organic complexes from high-salt wastewater. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1731-1742. doi: 10.11862/CJIC.20240077
13. [13]
  Fan JIA , Wenbao XU , Fangbin LIU , Haihua ZHANG , Hongbing FU . Synthesis and electroluminescence properties of Mn²⁺ doped quasi-two-dimensional perovskites (PEA)₂Pb_yMn_1-yBr₄. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1114-1122. doi: 10.11862/CJIC.20230473
14. [14]
  Ming ZHENG , Yixiao ZHANG , Jian YANG , Pengfei GUAN , Xiudong LI . Energy storage and photoluminescence properties of Sm³⁺-doped Ba_0.85Ca_0.15Ti_0.90Zr_0.10O₃ lead-free multifunctional ferroelectric ceramics. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 686-692. doi: 10.11862/CJIC.20230388
15. [15]
  Yuhao SUN , Qingzhe DONG , Lei ZHAO , Xiaodan JIANG , Hailing GUO , Xianglong MENG , Yongmei GUO . Synthesis and antibacterial properties of silver-loaded sod-based zeolite. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 761-770. doi: 10.11862/CJIC.20230169
16. [16]
  Yufang GAO , Nan HOU , Yaning LIANG , Ning LI , Yanting ZHANG , Zelong LI , Xiaofeng LI . Nano-thin layer MCM-22 zeolite: Synthesis and catalytic properties of trimethylbenzene isomerization reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1079-1087. doi: 10.11862/CJIC.20240036
17. [17]
  Liang MA , Honghua ZHANG , Weilu ZHENG , Aoqi YOU , Zhiyong OUYANG , Junjiang CAO . Construction of highly ordered ZIF-8/Au nanocomposite structure arrays and application of surface-enhanced Raman spectroscopy. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1743-1754. doi: 10.11862/CJIC.20240075

Get Citation

PDF

XML

Metrics

PDF Downloads(141)
Abstract views(3655)
HTML views(1416)

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