Citation: Kejia Ling, Shunjie Li, Yuefei Wang, Huanyu Yang, Zhicheng Song, Xian Li, Suzhi Cai, Xiao Wang, Zhongfu An. Highly efficient and ultralong organic phosphorescence by doping crown ether derivatives into polymer[J]. Chinese Chemical Letters, ;2026, 37(6): 112110. doi: 10.1016/j.cclet.2025.112110 shu

Highly efficient and ultralong organic phosphorescence by doping crown ether derivatives into polymer

Kejia Ling ^{a, 1} ,
Shunjie Li ^{a, 1} ,
Yuefei Wang ^a ,
Huanyu Yang ^a ,
Zhicheng Song ^b ,
Xian Li ^a ,
Suzhi Cai ^{a, *,} ,
Xiao Wang ^{c, *,} ,
Zhongfu An ^{b, *,}

a.
Strait Institute of Flexible Electronics (SIFE, Future Technologies), Fujian Key Laboratory of Flexible Electronics, Fujian Normal University and Strait Laboratory of Flexible Electronics (SLoFE), Fuzhou 350117, China
b.
State Key Laboratory of Flexible Electronics (LoFE) & Institute of Advanced Materials (IAM), School of Flexible Electronics (Future Technologies), Nanjing Tech University (NanjingTech), Nanjing 211816, China
c.
Institute of Flexible Electronics (IFE, Future Technologies), Xiang’an Campus, Xiamen University, Xiamen 361102, China

ifeszhcai@fjnu.edu.cn

ifexwang@xmu.edu.cn

iamzfan@njtech.edu.cn

Received Date: 24 June 2025
Revised Date: 9 November 2025
Accepted Date: 11 November 2025
Available Online: 13 November 2025

Figures(4)

Ultralong organic phosphorescence (UOP) materials have attracted increasing attention due to its potential applications in opto-electronics, bioelectronics, and security protection. However, it is still a formidable challenge to develop a material with simultaneous efficiency and lifetime enhancement under ambient conditions. Here, highly efficient UOP is achieved by doping crown ether derivatives into rigid poly(vinyl alcohol) (PVA) matrix. Two crown ether derivatives exhibited weak yellow UOP. Impressively, after doped into PVA films, the resultant PVA films demonstrated bright blue UOP with a long lifetime of 595.9 ms and high phosphorescence efficiency of 13.3%. The sharp enhancement of efficiency and lifetime can be ascribed to abundant hydrogen bonding between the crown ether derivatives and PVA polymer chains. This work provides a new avenue for developing highly efficient UOP materials.
- Ultralong organic phosphorescence,
- Crown ether,
- Host-guest system,
- Hydrogen bonding,
- Afterglow decorations
1. [1]
  M. Wang, W. Yin, Y. Zhai, et al., Nat. Commun. 16 (2025) 2455. doi: 10.3390/microorganisms13112455
2. [2]
  W. Zhao, Z. He, B. Tang, Nat. Rev. Mater. 5 (2020) 869–885. doi: 10.1038/s41578-020-0223-z
3. [3]
  X. Li, Y. Wang, Z. Zhang, et al., Adv. Mater. 36 (2024) 2308290. doi: 10.1002/adma.202308290
4. [4]
  G. Zhang, G.M. Palmer, M.W. Dewhirst, C.L. Fraser, Nat. Mater. 8 (2009) 747–751. doi: 10.1038/nmat2509
5. [5]
  P. Jiang, B. Ding, J. Yao, et al., Angew. Chem. Int. Ed. 64 (2025) e202421036. doi: 10.1002/anie.202421036
6. [6]
  Z. He, H. Gao, S. Zhang, et al., Adv. Mater. 31 (2019) 1807222. doi: 10.1002/adma.201807222
7. [7]
  L. Zhang, J. Li, Y. Zhang, et al., Nat. Commun. 16 (2025) 3970. doi: 10.1038/s41467-025-59367-0
8. [8]
  R. Huang, Y. He, J. Wang, et al., Nat. Commun. 15 (2024) 1596. doi: 10.1038/s41467-024-45497-4
9. [9]
  H. Deng, G. Li, H. Xie, et al., Angew. Chem. Int. Ed. 63 (2024) e202317631. doi: 10.1002/anie.202317631
10. [10]
  G. Lu, J. Tan, H. Wang, et al., Nat. Commun. 15 (2024) 3705. doi: 10.1038/s41467-024-47888-z
11. [11]
  J. Deng, D. Liu, H. Liu, et al., Adv. Funct. Mater. 34 (2024) 2408821. doi: 10.1002/adfm.202408821
12. [12]
  S. Xiong, Y. Xiong, D. Wang, et al., Adv. Mater. 35 (2023) e2301874. doi: 10.1002/adma.202301874
13. [13]
  T. Zhu, T. Yang, Q. Zhang, W.Z. Yuan, Nat. Commun. 13 (2022) 2658. doi: 10.1038/s41467-022-30368-7
14. [14]
  L. Ma, S. Sun, B. Ding, X. Ma, H. Tian, Adv. Funct. Mater. 31 (2021) 2010659. doi: 10.1002/adfm.202010659
15. [15]
  Z. Wang, X. Cheng, Y. Xie, et al., CCS Chem. 5 (2023) 292–309. doi: 10.31635/ccschem.022.202202242
16. [16]
  K. Zhang, L. Peng, X. Liu, et al., Angew. Chem. Int. Ed. 62 (2023) e202300927. doi: 10.1002/anie.202300927
17. [17]
  A.J. Gillett, C. Tonnele, G. Londi, et al., Nat. Commun. 12 (2021) 6640. doi: 10.1038/s41467-021-26689-8
18. [18]
  E. Lucenti, A. Forni, C. Botta, et al., J. Phys. Chem. Lett. 8 (2017) 1894–1898. doi: 10.1021/acs.jpclett.7b00503
19. [19]
  Z. An, C. Zheng, Y. Tao, et al., Nat. Mater. 14 (2015) 685–690. doi: 10.1038/nmat4259
20. [20]
  Z. Chen, X. Chen, D. Ma, et al., J. Am. Chem. Soc. 145 (2023) 16748–16759. doi: 10.1021/jacs.3c04725
21. [21]
  J. Song, L. Ma, S. Sun, H. Tian, X. Ma, Angew. Chem. Int. Ed. 61 (2022) e202206157. doi: 10.1002/anie.202206157
22. [22]
  H. Hou, H. Wang, M. He, et al., Angew. Chem. Int. Ed. 63 (2024) e202411323. doi: 10.1002/anie.202411323
23. [23]
  C. Chen, W. Zhang, Z. Wang, et al., Angew. Chem. Int. Ed. 64 (2025) e202501448. doi: 10.1002/anie.202501448
24. [24]
  L. Wei, S. Guo, B. Zhang, et al., Adv. Funct. Mater. 34 (2024) 2409681. doi: 10.1002/adfm.202409681
25. [25]
  L. Jin, Z. Wang, W. Mo, et al., Angew. Chem. Int. Ed. 63 (2024) e202410974.
26. [26]
  L. Jiang, Z. Qian, Y. Chen, et al., Chin. Chem. Lett. 36 (2025) 110676. doi: 10.1016/j.cclet.2024.110676
27. [27]
  Z. Chen, J. Shi, Y. Zhou, P. Zhang, G. Liang, Chin. Chem. Lett. 36 (2025) 110629. doi: 10.1016/j.cclet.2024.110629
28. [28]
  J. Zhou, D. Liu, L. Li, et al., Chin. Chem. Lett. 35 (2024) 16300–16306. doi: 10.1021/acs.joc.3c02601
29. [29]
  H. Yao, F. Yang, J. Hu, et al., Chin. Chem. Lett. 36 (2025) 110375. doi: 10.1016/j.cclet.2024.110375
30. [30]
  F. Nie, D. Yan, Nat. Commun. 15 (2024) 9491. doi: 10.1038/s41467-024-53963-2
31. [31]
  Y. Xu, Z. Cheng, H. Wang, et al., Adv. Opt. Mater. 13 (2024) 2402607.
32. [32]
  Z. Chen, Z. Chen, Y. Zhu, et al., Adv. Funct. Mater. 34 (2024) 2408023. doi: 10.1002/adfm.202408023
33. [33]
  X. Fan, L. Gao, Y. Jin, et al., Adv. Opt. Mater. 13 (2024) 2402627.
34. [34]
  P. Chen, H. Qie, X. Yang, et al., Adv. Funct. Mater. 35 (2024) 2416430.
35. [35]
  Z. Wu, Z. Xu, D. Wang, et al., Adv. Funct. Mater. 35 (2024) 2415285.
36. [36]
  V. Kumar, G. Venugopal, A.B. Jadhav, et al., Angew. Chem. Int. Ed. 64 (2025) e202422125. doi: 10.1002/anie.202422125
37. [37]
  A. Huang, Y. Fan, K. Wang, et al., Adv. Mater. 35 (2023) 2209166. doi: 10.1002/adma.202209166
38. [38]
  Z. Yang, H. Liu, X. Zhang, et al., Adv. Mater. 36 (2023) 2306784.
39. [39]
  J. Wei, C. Chen, M. Xiao, et al., FlexMat 2 (2025) 180. doi: 10.1002/flm2.43
40. [40]
  Y. Lu, X. Chen, Y.D. Suh, et al., FlexMat 2 (2025) 107. doi: 10.1002/flm2.37
41. [41]
  C.J. Pedersen, J. Am. Chem. Soc. 89 (1967) 7017–7036. doi: 10.1021/ja01002a035
42. [42]
  P. Wei, X. Zhang, J. Liu, et al., Angew. Chem. Int. Ed. 59 (2020) 9293–9298. doi: 10.1002/anie.201912155
43. [43]
  W. Zhu, H. Xing, E. Li, H. Zhu, F. Huang, Macromolecules 55 (2022) 9802–9809. doi: 10.1021/acs.macromol.2c00680
44. [44]
  W. Zhu, B. Zhao, S. Fang, H. Zhu, F. Huang, Chem. Sci. 15 (2024) 16300–16306. doi: 10.1039/d4sc05077k
45. [45]
  Q. Zhou, T. Yang, Z. Zhong, et al., Chem. Sci. 11 (2020) 2926–2933. doi: 10.1039/c9sc06518k
46. [46]
  H. Wang, W. Xing, Z. Yu, et al., Adv. Opt. Mater. 10 (2022) 2201903. doi: 10.1002/adom.202201903
47. [47]
  H. Ju, H. Zhang, L. Hou, et al., J. Am. Chem. Soc. 145 (2023) 3763–3773. doi: 10.1021/jacs.2c13264
48. [48]
  Z. Wang, X. Zhang, J. Mo, C. Su, M. Pan, Adv. Opt. Mater. 11 (2023) 2203144. doi: 10.1002/adom.202203144
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1.
沈阳化工大学材料科学与工程学院沈阳 110142