Citation: Junying Zhang, Ruochen Li, Haihua Wang, Wenbing Kang, Xing-Dong Xu. Photo-induced tunable luminescence from an aggregated amphiphilic ethylene-pyrene derivative in aqueous media[J]. Chinese Chemical Letters, ;2024, 35(6): 109216. doi: 10.1016/j.cclet.2023.109216 shu

Photo-induced tunable luminescence from an aggregated amphiphilic ethylene-pyrene derivative in aqueous media

National Engineering Research Center for Colloidal Materials, Key Laboratory of Special Functional Aggregated Materials of Ministry of Education, Shandong Key Laboratory of Advanced Silicone Materials and Technology, School of Chemistry and Chemical Engineering, Shandong University, Ji’nan 250100, China

wbkang@sdu.edu.cn

xuxd@sdu.edu.cn

Received Date: 25 June 2023
Revised Date: 12 October 2023
Accepted Date: 15 October 2023
Available Online: 17 October 2023

Figures(7)

An amphiphilic derivative with a large Stokes shift by introducing flexible hydrophilic long chains into a rigid ethylene-pyrene compound have been successfully synthesized. The alkylated compound exhibited a notable change in charge distribution, facilitating cation-π interactions. Through the process of amphiphilic self-assembly, the formation of highly ordered aggregates enabled effective photo-dimerization under 449 nm LED irradiation. Notably, this photo-responsive technology not only exhibited advanced multi-color emission effects, including white light emission but also exhibited environmentally friendly behavior in the aqueous phase.
- Supramolecular chemistry,
- Amphiphilic assembly,
- Stimuli-responsive materials,
- Tunable luminescence,
- Pyrene derivative
1. [1]
  Y. Lee, W. Cho, J. Sung, et al., J. Am. Chem. Soc. 140 (2018) 974–983. doi: 10.1021/jacs.7b10433
2. [2]
  X. Jia, L. Zhu, Acc. Chem. Res. 56 (2023) 655–666. doi: 10.1021/acs.accounts.2c00818
3. [3]
  W. Qian, M. Zuo, P. Niu, X.Y. Hu, L. Wang, Chin. Chem. Lett. 33 (2022) 1975–1978. doi: 10.1016/j.cclet.2021.09.070
4. [4]
  T. Mori, Y. Yoshigoe, Y. Kuninobu, Angew. Chem. Int. Ed. 58 (2019) 14457–14461. doi: 10.1002/anie.201903408
5. [5]
  F. Lu, T. Nakanishi, Adv. Opt. Mater. 7 (2019) 1900176. doi: 10.1002/adom.201900176
6. [6]
  B.S. Santhosh, J. Aimi, H. Ozawa, et al., Angew. Chem. Int. Ed. 51 (2012) 3391–3395. doi: 10.1002/anie.201108853
7. [7]
  L. Duan, Q. Zheng, T. Tu, Adv. Mater. 34 (2022) e2202540. doi: 10.1002/adma.202202540
8. [8]
  D. Tu, P. Leong, S. Guo, et al., Angew. Chem. Int. Ed. 56 (2017) 11370–11374. doi: 10.1002/anie.201703862
9. [9]
  C. Chen, X. Jin, X. Zhou, et al., J. Mater. Chem. C 3 (2015) 4563–4569. doi: 10.1039/C4TC02771J
10. [10]
  H. Wu, Y. Chen, X. Dai, et al., J. Am. Chem. Soc. 141 (2019) 6583–6591. doi: 10.1021/jacs.8b13675
11. [11]
  H. Sun, L. Zhu, Aggregate 4 (2023) 253. doi: 10.1002/agt2.253
12. [12]
  Q. Xu, Z. Qin, Y. Bei, et al., Chin. Chem. Lett. 33 (2022) 4838–4841. doi: 10.1016/j.cclet.2022.01.079
13. [13]
  K. Diao, D.J. Whitaker, Z. Huang, et al., Chem. Commun. 58 (2022) 2343–2346. doi: 10.1039/d1cc06647a
14. [14]
  B.L. Zhang, X. Zhang, Chem. Commun. 58 (2022) 5261–5264. doi: 10.1039/D2CC01309F
15. [15]
  R. Taniguchi, T. Yamada, K. Sada, et al., Macromolecules 47 (2014) 6382–6388. doi: 10.1021/ma501198d
16. [16]
  N. Wang, L. Feng, X.D. Xu, et al., Macromol. Rapid Commun. 43 (2022) e2100885. doi: 10.1002/marc.202100885
17. [17]
  J.L. Zhu, L. Xu, Y.Y. Ren, et al., Nat. Commun. 10 (2019) 4285. doi: 10.1038/s41467-019-12204-7
18. [18]
  Q. Wang, Q. Zhang, Q.W. Zhang, et al., Nat. Commun. 11 (2020) 158. doi: 10.1038/s41467-019-13994-6
19. [19]
  X.L. Ni, S. Chen, Y. Yang, et al., J. Am. Chem. Soc. 138 (2016) 6177–6183. doi: 10.1021/jacs.6b01223
20. [20]
  X. Yan, F. Wang, B. Zheng, et al., Chem. Soc. Rev. 41 (2012) 6042–6065. doi: 10.1039/c2cs35091b
21. [21]
  R. Fu, L. Yu, J. Zhang, et al., Chin. Chem. Lett. 33 (2022) 1993–1996. doi: 10.1016/j.cclet.2021.10.018
22. [22]
  S. Chen, L.J. Chen, H.B. Yang, et al., J. Am. Chem. Soc. 134 (2012) 13596–13599. doi: 10.1021/ja306748k
23. [23]
  D.H. Qu, Q.C. Wang, Q.W. Zhang, et al., Chem. Rev. 115 (2015) 7543–7588. doi: 10.1021/cr5006342
24. [24]
  S. Chen, R. Costil, F.K. Leung, et al., Angew. Chem. Int. Ed. 60 (2021) 11604–11627. doi: 10.1002/anie.202007693
25. [25]
  D. Niu, Y. Jiang, L. Ji, et al., Angew. Chem. Int. Ed. 58 (2019) 5946–5950. doi: 10.1002/anie.201900607
26. [26]
  F. Camerel, L. Bonardi, M. Schmutz, et al., J. Am. Chem. Soc. 128 (2006) 4548–4549. doi: 10.1021/ja0606069
27. [27]
  K.M. Chan, D.K. Kolmel, S. Wang, et al., Angew. Chem. Int. Ed. 56 (2017) 6497–6501. doi: 10.1002/anie.201701235
28. [28]
  X. Chang, Z. Zhou, C. Shang, et al., J. Am. Chem. Soc. 141 (2019) 1757–1765. doi: 10.1021/jacs.8b12749
29. [29]
  Q. Chen, K. Cheng, W. Wang, et al., J. Pharm. Anal. 10 (2020) 490–497. doi: 10.1016/j.jpha.2020.07.003
30. [30]
  D. Kodura, L.L. Rodrigues, S.L. Walden, et al., J. Am. Chem. Soc. 144 (2022) 6343–6348. doi: 10.1021/jacs.2c00156
31. [31]
  J. Zhang, S.X. Tang, R. Fu, X.D. Xu, S. Feng, J. Mater. Chem. C 7 (2019) 13786–13793. doi: 10.1039/c9tc03786a
32. [32]
  M. Feng, J. Zhang, H. Ji, et al., Chem. Eng. J. 463 (2023) 142241. doi: 10.1016/j.cej.2023.142241
33. [33]
  N. Wang, H. Feng, X. Hao, et al., Polym. Chem. UK 14 (2023) 1396–1403. doi: 10.1039/d3py00140g
34. [34]
  N. Wang, J. Zhao, Q. Xu, et al., J. Mater. Chem. C: Mater. Opt. Electron. Devices 1 (2022) 1386–1387. doi: 10.3390/electronics11091386
35. [35]
  R. Fu, J. Zhang, S. Liu, et al., Chem. Commun. 56 (2020) 6719–6722. doi: 10.1039/d0cc02214d
36. [36]
  X.D. Xu, J. Zhang, X. Yu, et al., Chemistry 18 (2012) 16000–16013. doi: 10.1002/chem.201202902
37. [37]
  B. Jiang, W. Wang, Y. Zhang, et al., Angew. Chem. Int. Ed. 56 (2017) 14438–14442. doi: 10.1002/anie.201707209
38. [38]
  M.M. Gan, J.Q. Liu, L. Zhang, et al., Chem. Rev. 118 (2018) 9587–9641. doi: 10.1021/acs.chemrev.8b00119
39. [39]
  Y. Xue, S. Jiang, H. Zhong, et al., Angew. Chem. Int. Ed. 61 (2022) e202110766. doi: 10.1002/anie.202110766
40. [40]
  M. Van De Walle, K. De Bruycker, J.P. Blinco, et al., Angew. Chem. Int. Ed. 59 (2020) 14143–14147. doi: 10.1002/anie.202003130
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