Citation: Rong Fu, Longyue Yu, Junying Zhang, Huidong Yu, Shengyu Feng, Xing-Dong Xu. Facile construction of aggregation-induced emission molecular liquids via Piers-Rubinsztajn reaction for green fluorescent ink[J]. Chinese Chemical Letters, ;2022, 33(4): 1993-1996. doi: 10.1016/j.cclet.2021.10.018 shu

Facile construction of aggregation-induced emission molecular liquids via Piers-Rubinsztajn reaction for green fluorescent ink

Rong Fu ^a ,
Longyue Yu ^a ,
Junying Zhang ^a ,
Huidong Yu ^b ,
Shengyu Feng ^a ,
Xing-Dong Xu ^{a, *,}

a.
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, National Engineering Research Center for Colloidal Materials, Shandong University, Ji'nan 250100, China
b.
Shandong Qilu Zhonghe Technology Co., Ltd., Ji'nan 250100, China

xuxd@sdu.edu.cn

Received Date: 25 April 2021
Revised Date: 8 October 2021
Accepted Date: 11 October 2021
Available Online: 16 October 2021

Figures(5)

Solvent-free luminescent molecular liquids (LMLs), which exhibit nonvolatile fluidic nature and active optoelectronic properties, were widely used. For further development, we introduced siloxane units into AIE molecules, designed and synthesized TPE derivatives with siloxane side chains via facile Piers-Rubinsztajn reaction. The obtained AIE molecular liquids exhibit unique photophysical properties. Compared with the obtained alkyl TPE-solids, siloxane TPE show liquid state, which proves that the siloxane units have stronger liquefaction effect than alkyl. Viscosity test shows that siloxane TPE-liquids has far more lower viscosity and better fluidity than the long-chain alkyl molecular liquids in previous research. All those properties are attributed to the weak interaction between flexible molecular chains of siloxane. Besides, fluorescence test shows temperature responsiveness of siloxane TPE-liquids. We developed this low-viscosity nonvolatile AIE molecular liquid as green fluorescent ink.
- TPE derivatives,
- Piers-rubinsztajn reaction,
- Molecular liquids,
- Aggregation-induced emission,
- Green fluorescent ink
1. [1]
  P.F. Fulvio, S. Dai, Chem 6 (2020) 3263-3287. doi: 10.1016/j.chempr.2020.11.005
2. [2]
  R.G. Weiss, J. Am. Chem. Soc. 136 (2014) 7519-7530. doi: 10.1021/ja503363v
3. [3]
  K. Goossens, K. Lava, C.W. Bielawski, K. Binnemans, Chem. Rev. 116 (2016) 4643-4807. doi: 10.1021/cr400334b
4. [4]
  R. Hayes, G.G. Warr, R. Atkin, Chem. Rev. 115 (2015) 6357-6426. doi: 10.1021/cr500411q
5. [5]
  Q. Zhang, J. n. M. Shreeve, Chem. Rev. 114 (2014) 10527-10574. doi: 10.1021/cr500364t
6. [6]
  S.S. Babu, J. Aimi, H. Ozawa, et al., Angew. Chem. Int. Ed. 51 (2012) 3391-3395. doi: 10.1002/anie.201108853
7. [7]
  F. Lu, T. Nakanishi, Adv. Opt. Mater. 7 (2019) 1900176. doi: 10.1002/adom.201900176
8. [8]
  S.S. Babu, M.J. Hollamby, J. Aimi, et al., Nat. Commun. 4 (2013) 1969. doi: 10.1038/ncomms2969
9. [9]
  K. Okamoto, F. Lu, T. Nakanishi, Bull. Chem. Soc. Jpn. 91 (2018) 1258-1263. doi: 10.1246/bcsj.20180075
10. [10]
  A. Ghosh, T. Nakanishi, Chem. Commun. 53 (2017) 10344-10357. doi: 10.1039/C7CC05883G
11. [11]
  L.J. Chen, Y.Y. Ren, N.W. Wu, et al., J. Am. Chem. Soc. 137 (2015) 11725-11735. doi: 10.1021/jacs.5b06565
12. [12]
  Y. Hong, J.W.Y. Lam, B.Z. Tang, Chem. Commun. (2009) 4332-4353. doi: 10.1039/b904665h
13. [13]
  Y.X. Hu, X. Hao, L. Xu, et al., J. Am. Chem. Soc. 142 (2020) 6285-6294. doi: 10.1021/jacs.0c00698
14. [14]
  J. Liang, B.Z. Tang, B. Liu, Chem. Soc. Rev. 44 (2015) 2798-2811. doi: 10.1039/C4CS00444B
15. [15]
  R. Taniguchi, T. Yamada, K. Sada, K. Kokado, Macromolecules 47 (2014) 6382-6388. doi: 10.1021/ma501198d
16. [16]
  C. Zhao, T. Liu, M. Xu, H. Lin, C. Zhang, Chin. Chem. Lett. 32 (2021) 1925-1928. doi: 10.1016/j.cclet.2021.02.008
17. [17]
  L. Ma, C. Li, Q. Yan, et al., Chin. Chem. Lett. 31 (2020) 361-364. doi: 10.1016/j.cclet.2019.07.040
18. [18]
  X. Niu, T. Song, H. Xiong, Chin. Chem. Lett. 32 (2021) 1953-1956. doi: 10.1016/j.cclet.2021.01.006
19. [19]
  T. Machida, R. Taniguchi, T. Oura, K. Sada, K. Kokado, Chem. Commun. 53 (2017) 2378-2381. doi: 10.1039/C6CC09939D
20. [20]
  T. Takeda, S. Yamamoto, M. Mitsuishi, T. Akutagawa, J. Phys. Chem. C. 122 (2018) 9593-9598. doi: 10.1021/acs.jpcc.8b01131
21. [21]
  J. He, B. Xu, F. Chen, H. Xia, K. Li, L. Ye, W. Tian, J. Phys. Chem. C 113 (2009) 9892-9899. doi: 10.1021/jp900205k
22. [22]
  H. Imoto, K. Nohmi, K. Kizaki, et al., RSC Adv. 5 (2015) 94344-94350. doi: 10.1039/C5RA18690K
23. [23]
  S. Xue, X. Qiu, Q. Sun, W. Yang, J. Mater. Chem. C 4 (2016) 1568-1578. doi: 10.1039/C5TC04358A
24. [24]
  P. An, Z.F. Shi, W. Dou, X.P. Cao, H.L. Zhang, Org. Lett. 12 (2010) 4364-4367. doi: 10.1021/ol101847w
25. [25]
  S.S. Babu, M.J. Hollamby, J. Aimi, et al., Nat. Commun. 4 (2013) 1969-1969. doi: 10.1038/ncomms2969
26. [26]
  F. Lu, K. Hagiwara, M. Yoshizawa, et al., J. Mater. Chem. C 7 (2019) 2577-2582. doi: 10.1039/C8TC06254D
27. [27]
  F. Lu, K. Jang, I. Osica, et al., Chem. Sci. 9 (2018) 6774-6778. doi: 10.1039/C8SC02723D
28. [28]
  B.A. Kamino, J.B. Grande, M.A. Brook, T.P. Bender, Org. Lett. 13 (2011) 154-157. doi: 10.1021/ol102607v
29. [29]
  S. Gao, Y. Liu, S.Y. Feng, Z.J. Lu, J. Mater. Chem. A 7 (2019) 17498-17504. doi: 10.1039/C9TA04951G
30. [30]
  M. Guo, Y. Huang, J. Cao, Y. Xu, S. Lu, S. Feng, Macromol. Rapid Commun. 42 (2021) 2000606. doi: 10.1002/marc.202000606
31. [31]
  Y.Y. Liu, X. Wang, S.Y. Feng, Adv. Funct. Mater. 29 (2019) 12.
32. [32]
  B. Pang, J.Z. Zhang, M.L. Pang, et al., Polym. Chem. 9 (2018) 869-877. doi: 10.1039/C7PY01525A
33. [33]
  R. Sun, S. Feng, D. Wang, H. Liu, Chem. Mater. 30 (2018) 6370-6376. doi: 10.1021/acs.chemmater.8b02514
34. [34]
  D.B. Thompson, M.A. Brook, J. Am. Chem. Soc. 130 (2008) 32-33. doi: 10.1021/ja0778491
35. [35]
  M.A. Brook, Chem. Eur. J. 24 (2018) 8458-8469. doi: 10.1002/chem.201800123
36. [36]
  D.J. Keddie, J.B. Grande, F. Gonzaga, M.A. Brook, T.R. Dargaville, Org. Lett. 13 (2011) 6006-6009. doi: 10.1021/ol202051y
37. [37]
  C.F. Cao, P.H. Wang, J.W. Zhang, et al., Chem. Eng. J. 393 (2020) 124724. doi: 10.1016/j.cej.2020.124724
38. [38]
  H. Fang, M. Oestreich, Chem. Sci. 11 (2020) 12604-12615. doi: 10.1039/D0SC03712E
39. [39]
  B. Garg, T. Bisht, Y.C. Ling, Chem. Asian J. 15 (2020) 66-71. doi: 10.1002/asia.201901424
40. [40]
  G. Schwertz, A. Zanetti, M.N. de Oliveira, et al., J. Org. Chem. 85 (2020) 9607-9613. doi: 10.1021/acs.joc.0c00617
41. [41]
  X. Yang, B. Li, H. Xing, J. Qiu, T.P. Loh, P. Xie, Green Chem. 23 (2021) 1633-1637. doi: 10.1039/D1GC00191D
42. [42]
  R. Fu, J. Zhang, S. Liu, X.D. Xu, S. Feng, Chem. Commun. 56 (2020) 6719-6722. doi: 10.1039/D0CC02214D
43. [43]
  S.X. Tang, N. Wang, X.D. Xu, S. Feng, New J. Chem. 43 (2019) 6461-6464. doi: 10.1039/C8NJ06304D
44. [44]
  N. Wang, J. Zhang, X.D. Xu, S. Feng, Dalton Trans. 49 (2020) 1883-1890. doi: 10.1039/C9DT03985F
45. [45]
  J. Zhang, S.X. Tang, R. Fu, X.D. Xu, S. Feng, J. Mater. Chem. C 7 (2019) 13786-13793. doi: 10.1039/C9TC03786A
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