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]
  Wenkai Chen , Yunjia Shen , Xiangmeng Kong , Yanli Zeng . Quantum Chemistry Calculation of Key Physical Quantity in Circularly Polarized Luminescence: Introducing an Exploratory Computational Chemistry Experiment. University Chemistry, 2025, 40(3): 83-91. doi: 10.12461/PKU.DXHX202405018
2. [2]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
3. [3]
  Yi DING , Peiyu LIAO , Jianhua JIA , Mingliang TONG . Structure and photoluminescence modulation of silver(Ⅰ)-tetra(pyridin-4-yl)ethene metal-organic frameworks by substituted benzoates. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 141-148. doi: 10.11862/CJIC.20240393
4. [4]
  Shicheng Yan . Experimental Teaching Design for the Integration of Scientific Research and Teaching: A Case Study on Organic Electrooxidation. University Chemistry, 2024, 39(11): 350-358. doi: 10.12461/PKU.DXHX202408036
5. [5]
  Qianlang Wang , Jijun Sun , Qian Chen , Quanqin Zhao , Baojuan Xi . The Appeal of Organophosphorus Compounds: Clearing Their Name. University Chemistry, 2025, 40(4): 299-306. doi: 10.12461/PKU.DXHX202405205
6. [6]
  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
7. [7]
  Aiai WANG , Lu ZHAO , Yunfeng BAI , Feng FENG . Research progress of bimetallic organic framework in tumor diagnosis and treatment. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1825-1839. doi: 10.11862/CJIC.20240225
8. [8]
  Feng Sha , Xinyan Wu , Ping Hu , Wenqing Zhang , Xiaoyang Luan , Yunfei Ma . Design of Course Ideology and Politics for the Comprehensive Organic Synthesis Experiment of Benzocaine. University Chemistry, 2024, 39(2): 110-115. doi: 10.3866/PKU.DXHX202307082
9. [9]
  Xinyu Zhu , Meili Pang . Application of Functional Group Addition Strategy in Organic Synthesis. University Chemistry, 2024, 39(3): 218-230. doi: 10.3866/PKU.DXHX202308106
10. [10]
  Yong Wang , Yingying Zhao , Boshun Wan . Analysis of Organic Questions in the 37th Chinese Chemistry Olympiad (Preliminary). University Chemistry, 2024, 39(11): 406-416. doi: 10.12461/PKU.DXHX202403009
11. [11]
  Ran HUO , Zhaohui ZHANG , Xi SU , Long CHEN . Research progress on multivariate two dimensional conjugated metal organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2063-2074. doi: 10.11862/CJIC.20240195
12. [12]
  Bin HE , Hao ZHANG , Lin XU , Yanghe LIU , Feifan LANG , Jiandong PANG . Recent progress in multicomponent zirconium?based metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2041-2062. doi: 10.11862/CJIC.20240161
13. [13]
  Xiaofang DONG , Yue YANG , Shen WANG , Xiaofang HAO , Yuxia WANG , Peng CHENG . Research progress of conductive metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 14-34. doi: 10.11862/CJIC.20240388
14. [14]
  Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . 碳基催化剂催化有机液体氢载体脱氢研究进展. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-. doi: 10.1016/j.actphy.2024.100044
15. [15]
  Lina Feng , Guoyu Jiang , Xiaoxia Jian , Jianguo Wang . Application of Organic Radical Materials in Biomedicine. University Chemistry, 2025, 40(4): 253-260. doi: 10.12461/PKU.DXHX202405171
16. [16]
  Jiajie Li , Xiaocong Ma , Jufang Zheng , Qiang Wan , Xiaoshun Zhou , Yahao Wang . Recent Advances in In-Situ Raman Spectroscopy for Investigating Electrocatalytic Organic Reaction Mechanisms. University Chemistry, 2025, 40(4): 261-276. doi: 10.12461/PKU.DXHX202406117
17. [17]
  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
18. [18]
  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
19. [19]
  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
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(207)
Abstract views(5845)
HTML views(2134)

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