Citation: Danman Guo, Yuyuan Wang, Jinzheng Chen, Yifeng Cao, Yiling Miao, Huahua Huang, Zhenguo Chi, Zhiyong Yang. Intrinsic persistent room temperature phosphorescence derived from 1H-benzo[f]indole itself as a guest[J]. Chinese Chemical Letters, ;2023, 34(7): 107882. doi: 10.1016/j.cclet.2022.107882 shu

Intrinsic persistent room temperature phosphorescence derived from 1H-benzo[f]indole itself as a guest

Danman Guo ^a ,
Yuyuan Wang ^a ,
Jinzheng Chen ^a ,
Yifeng Cao ^b ,
Yiling Miao ^a ,
Huahua Huang ^b, ,
Zhenguo Chi ^a, ,
Zhiyong Yang ^{a, c,}

a.
Key Laboratory for Polymeric Composite and Functional Materials of Ministry of Education, Guangdong Engineering Technology Research Center for High-performance Organic and Polymer Photoelectric Functional Films, School of Chemistry, Sun Yat-sen University, Guangzhou 510275, China
b.
School of Materials Science and Engineering, Sun Yat-sen University, Guangzhou 510275, China
c.
Guangdong Provincial Key Laboratory of Optical Chemicals, XinHuaYue Group, Maoming 525000, China

Received Date: 24 July 2022
Revised Date: 6 September 2022
Accepted Date: 4 October 2022
Available Online: 10 October 2022

Figures(3)

The influence of 1H-benzo[f]indole (Bd) and its derivatives on room temperature phosphorescence (RTP) has raised great concern since they were found to significantly affect RTP of the extensively studied carbazole (Cz) derivatives. However, the role of Bd itself existing in Cz-based or other doping systems was still unclear. In order to clarify its intrinsic phosphorescent property, Bd was introduced as a guest into different organic matrixes including substituted Cz derivatives and polymers. The phosphorescence located in 560–620 nm was confirmed to be derived from Bd itself, which can be detected whatever Bd was doped in the crystal or amorphous state of Cz derivatives. The suitable energy gap between Cz derivatives and Bd is the key to achieve ultralong RTP of Bd. Additionally, when doped in polymers with plenty of hydrogen bonds, RTP of Bd with lifetime over 280 ms was easily obtained. Among them, Bd@PHEMA (poly(hydroxyethyl methacrylate) exhibited superior phosphorescence, with yellow afterglow lasting for over 2.5 s. Therefore, this work demonstrated that a new organic RTP phosphor, Bd, is discovered, and ultralong RTP of Bd can be achieved not only doped in Cz derivatives but also in polymers as the hosts.
- Room temperature phosphorescence,
- Host-guest,
- 1H-benzo[f]indole,
- Amorphous,
- Hydrogen bonding
1. [1]
  C.A. DeRosa, S.A. Seaman, A.S. Mathew, et al., ACS Sens. 1 (2016) 1366–1373. doi: 10.1021/acssensors.6b00533
2. [2]
  S.M.A. Fateminia, Z. Mao, S. Xu, et al., Angew. Chem. Int. Ed. 56 (2017) 12160–12164. doi: 10.1002/anie.201705945
3. [3]
  L. Gu, H. Wu, H. Ma, et al., Nat. Commun. 11 (2020) 944. doi: 10.1038/s41467-020-14792-1
4. [4]
  F. Lin, H. Wang, Y. Cao, et al., Adv. Mater. 34 (2022) e2108333. doi: 10.1002/adma.202108333
5. [5]
  X.F. Wang, H. Xiao, P.Z. Chen, et al., J. Am. Chem. Soc. 141 (2019) 5045–5050. doi: 10.1021/jacs.9b00859
6. [6]
  S. Cai, Z. Sun, H. Wang, et al., J. Am. Chem. Soc. 143 (2021) 16256–16263. doi: 10.1021/jacs.1c07674
7. [7]
  Q. Liao, Q. Li, Z. Li, et al., ChemPhotoChem 5 (2021) 694–701. doi: 10.1002/cptc.202100016
8. [8]
  Y. Zhang, Y. Su, H. Wu, et al., J. Am. Chem. Soc. 143 (2021) 13675–13685. doi: 10.1021/jacs.1c05213
9. [9]
  J. Guo, C. Yang, Y. Zhao, et al., Acc. Chem. Res. 55 (2022) 1160–1170. doi: 10.1021/acs.accounts.2c00038
10. [10]
  H. Thomas, D.L. Pastoetter, M. Gmelch, et al., Adv. Mater. 32 (2020) e2000880. doi: 10.1002/adma.202000880
11. [11]
  X. Zhang, L. Du, W. Zhao, et al., Nat. Commun. 10 (2019) 5161. doi: 10.1038/s41467-019-13048-x
12. [12]
  Y. Gong, L. Zhao, Q. Peng, et al., Chem. Sci. 6 (2015) 4438–4444. doi: 10.1039/C5SC00253B
13. [13]
  H.E. Hackney, D.F. Perepichka, Aggregate. 3 (2022) e123. doi: 10.1002/agt2.123
14. [14]
  K. Narushima, Y. Kiyota, T. Mori, et al., Adv. Mater. 31 (2019) e1807268. doi: 10.1002/adma.201807268
15. [15]
  J.A. Li, J. Zhou, Z. Mao, et al., Angew. Chem. Int. Ed. 57 (2018) 6449–6453. doi: 10.1002/anie.201800762
16. [16]
  W. Zhao, T.S. Cheung, N. Jiang, et al., Nat. Commun. 10 (2019) 1595. doi: 10.1038/s41467-019-09561-8
17. [17]
  Z. Yang, Z. Mao, X. Zhang, et al., Angew. Chem. Int. Ed. 55 (2016) 2181–2185. doi: 10.1002/anie.201509224
18. [18]
  Z. An, C. Zheng, Y. Tao, et al., Nat. Mater. 14 (2015) 685–690. doi: 10.1038/nmat4259
19. [19]
  S. Chanmungkalakul, C. Wang, R. Miao, et al., Angew. Chem. Int. Ed. 61 (2022) e202200546. doi: 10.1002/anie.202200546
20. [20]
  B. Chen, W. Huang, X. Nie, et al., Angew. Chem. Int. Ed. 60 (2021) 16970–16973. doi: 10.1002/anie.202106204
21. [21]
  Y. Lei, W. Dai, J. Guan, et al., Angew. Chem. Int. Ed. 59 (2020) 16054–16060. doi: 10.1002/anie.202003585
22. [22]
  S. Sun, L. Ma, J. Wang, et al., Natl. Sci. Rev. 9 (2022) nwab085. doi: 10.1093/nsr/nwab085
23. [23]
  R. Tian, S. Xu, Q. Xu, et al., Sci. Adv. 6 (2020) eaaz6107. doi: 10.1126/sciadv.aaz6107
24. [24]
  Y. Gong, G. Chen, Q. Peng, et al., Adv. Mater. 27 (2015) 6195–6201. doi: 10.1002/adma.201502442
25. [25]
  Y. Tao, R. Chen, H. Li, et al., Adv. Mater. 30 (2018) e1803856. doi: 10.1002/adma.201803856
26. [26]
  W. Zhao, Z. He, Jacky W.Y. Lam, et al., Chem. 1 (2016) 592–602. doi: 10.1016/j.chempr.2016.08.010
27. [27]
  Z. He, W. Zhao, J.W.Y. Lam, et al., Nat. Commun. 8 (2017) 416. doi: 10.1038/s41467-017-00362-5
28. [28]
  Kenry, C. Chen, B. Liu, Nat. Commun. 10 (2019) 2111. doi: 10.1038/s41467-019-10033-2
29. [29]
  B. Xu, H. Wu, J. Chen, et al., Chem. Sci. 8 (2017) 1909–1914. doi: 10.1039/C6SC03038F
30. [30]
  Z. Mao, Z. Yang, Z. Fan, et al., Chem. Sci. 10 (2019) 179–184. doi: 10.1039/c8sc03019g
31. [31]
  Y. Xiong, Z. Zhao, W. Zhao, et al., Angew. Chem. Int. Ed. 57 (2018) 7997–8001. doi: 10.1002/anie.201800834
32. [32]
  C. Chen, Z. Chi, K.C. Chong, et al., Nat. Mater. 20 (2021) 175–180. doi: 10.1038/s41563-020-0797-2
33. [33]
  C. Qian, Z. Ma, B. Yang, et al., J. Mater. Chem. C 9 (2021) 14294–14302. doi: 10.1039/d1tc03020e
34. [34]
  C. Qian, Z. Ma, X. Fu, et al., Adv. Mater. 34 (2022) e2200544. doi: 10.1002/adma.202200544
35. [35]
  L. Tu, W. Che, S. Li, et al., J. Mater. Chem. C. 9 (2021) 12124–12132. doi: 10.1039/d1tc02742e
36. [36]
  X.F. Wang, W.J. Guo, H. Xiao, et al., Adv. Funct. Mater. 30 (2020) 1907282. doi: 10.1002/adfm.201907282
37. [37]
  Y. Su, Y. Zhang, Z. Wang, et al., Angew. Chem. Int. Ed. 59 (2020) 9967–9971. doi: 10.1002/anie.201912102
38. [38]
  H. Wang, H. Shi, W. Ye, et al., Angew. Chem. Int. Ed. 58 (2019) 18776–18782. doi: 10.1002/anie.201911331
39. [39]
  S. Xu, W. Wang, H. Li, et al., Nat. Commun. 11 (2020) 4802. doi: 10.1038/s41467-020-18572-9
40. [40]
  M.S. Kwon, D. Lee, S. Seo, J. Jung, et al., Angew. Chem. Int. Ed. 53 (2014) 11177–11181. doi: 10.1002/anie.201404490
41. [41]
  C. Maes, W. Luyten, G. Herremans, et al., Polym. Rev. 58 (2018) 209–246. doi: 10.1080/15583724.2017.1394323
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