Citation: Ma Xiaoxie, Hu Linli, Han Xie, Yin Jun. Vinylpyridine- and vinylnitrobenzene-coating tetraphenylethenes: Aggregation-induced emission (AIE) behavior and mechanochromic property[J]. Chinese Chemical Letters, ;2018, 29(10): 1489-1492. doi: 10.1016/j.cclet.2018.06.022 shu

Vinylpyridine- and vinylnitrobenzene-coating tetraphenylethenes: Aggregation-induced emission (AIE) behavior and mechanochromic property

Ma Xiaoxie ^b ,
Hu Linli ^a,, ,
Han Xie ^b,, ,
Yin Jun ^b,,

a.
College of Chemistry and Environmental Engineering, Yangtze University, Jingzhou 434023, China
b.
Key Laboratory of Pesticide and Chemical Biology, Ministry of Education College of Chemistry, Central China Normal University, Wuhan 430079, China

Corresponding author: Hu Linli, hulinli@yangtzeu.edu.cn Han Xie, hanxie123321@163.com Yin Jun, yinj@mail.ccnu.edu.cn
Received Date: 5 May 2018
Revised Date: 20 June 2018
Accepted Date: 21 June 2018
Available Online: 22 October 2018

Figures(4)

Two functional tetraphenylethylene derivatives modified by vinylpyridine and vinylnitrobenzene, respectively, were synthesized by Heck coupling reaction. Their optical behaviors were investigated. The results showed they had AIE activity in solution. The property in solid state displayed that both of them had reversible mechanochromism. Upon grinding, their fluorescence spectra showed around 13-40 nm red-shift, and could return to the original state after solvent fuming. We believe that this work will be helpful for the design of stimuli-responsive materials in future.
- Aggregation-induced emission,
- Mechanochromism,
- Tetraphenylethylene
1. [1]
  (a) X.Q. Zhang, Z.G. Chi, Y. Zhang, S.W. Liu, J.R. Xu, J. Mater. Chem. C 1 (2013) 3376-3390;
  (b)R. Gao, Y.B. Zhao, X.G. Yang, D.P. Yan, RSC Adv. 5 (2015) 56470-56477.
2. [2]
  (a) S.F. Xue, X. Qiu, Q.K. Suna, W.J. Yang, J. Mater. Chem. C 4 (2016) 1568-1578;
  (b)L. Wang, K.Q. Ye, H.Y. Zhang, Chin. Chem. Lett. 27 (2016) 1367-1375.
3. [3]
  (a) P. Zhang, Z.Q. Guo, C.X. Yan, W.H. Zhu, Chin. Chem. Lett. 28 (2017) 1952-1956;
  (b)P.C. Xue, J.P. Ding, P.P. Wang, R. Lua, J. Mater. Chem. C 4 (2016) 6688-6706;
  (c)Y. Li, C. Xu, C. Shu, X. Hou, P. Wu, Chin. Chem. Lett. 28 (2017) 1961-1964;
  (d)C. Wang, Z. Li, Mater. Chem. Front. 1 (2017) 2174-2194.
4. [4]
  (a) D. Wu, Y. Shen, J. Chen, et al., Chin. Chem. Lett. 28 (2017) 1979-1982;
  (b)Z. Xu, J. Chen, L.L. Hu, et al., Chin. Chem. Lett. 28 (2017) 1935-1942.
5. [5]
  (a) F. Song, R. Liang, J. Deng, Z. Liu, X. Peng, Chin. Chem. Lett. 28 (2017) 1997-2000;
  (b)S.Z. Li, Y.J. Lin, D.P. Yan, J. Mater. Chem. C 4 (2016) 2527-2534;
  (c)G.L. Fan, D.Y. Peng, Adv.Opt. Mater. 4 (2016) 2139.
6. [6]
  (a) R. Zhang, Q. Wang, X. Zheng, J. Mater. Chem. C 6 (2018) 3182-3199;
  (b)D.P. Yan, H.J. Yang, Q.Y. Meng, H.Y. Lin, M. Wei, Adv. Funct. Mater. 24 (2014) 587.
7. [7]
  Y.J. Dong, B. Xu, J.B. Zhang, et al., Angew. Chem. Int. Ed. 51(2012) 10782-10785. doi: 10.1002/anie.v51.43
8. [8]
  (a) S. Leng, Q.L. Qiao, Y. Gao, et al., Chin. Chem. Lett. 28 (2017) 1911-1915;
  (b)Y. Chen, T. Wei, Z. Zhang, et al., Chin. Chem. Lett. 28 (2017) 1957-1960;
  (c)Z. Mao, Z.Y. Yang, Y.X. Mu, et al., Angew. Chem. Int. Ed. 54 (2015) 6270-6273.
9. [9]
  G.Q. Zhang, J.W. Lu, M. Sabat, C.L. Fraser, J. Am. Chem. Soc. 132(2010) 2160-2162. doi: 10.1021/ja9097719
10. [10]
  J.H. Liang, Z. Chen, L.J. Xu, et al., J. Mater. Chem. C 2(2014) 2243-2250. doi: 10.1039/c3tc31638f
11. [11]
  Z. Chen, J. Zhang, M. Song, et al., Chem. Commun. 51(2015) 326-329. doi: 10.1039/C4CC08087D
12. [12]
  Z. Chen, Z. Li, L. Yang, et al., Dyes Pigments 121(2015) 170-177. doi: 10.1016/j.dyepig.2015.05.021
13. [13]
  Z. Chen, J.H. Liang, Y.T. Nie, et al., Dalton Trans. 44(2015) 17473-17477. doi: 10.1039/C5DT02035B
14. [14]
  Z. Chen, L. Yang, Y.X. Hu, et al., RSC Adv. 5(2015) 93757-93764. doi: 10.1039/C5RA19378H
15. [15]
  Z. Chen, Z. Li, F. Hu, et al., Dyes Pigments 125(2016) 169-178. doi: 10.1016/j.dyepig.2015.10.038
16. [16]
  J. Zhang, Z. Chen, L. Yang, et al., Dyes Pigments 136(2017) 168-174. doi: 10.1016/j.dyepig.2016.08.051
17. [17]
  Y.B. Dong, Z. Chen, L. Yang, et al., Dyes Pigments 150(2018) 315-322. doi: 10.1016/j.dyepig.2017.12.030
18. [18]
  (a) X. Han, B.B. Zhang, J.H. Chen, et al., J. Mater. Chem. B 5 (2017) 5096-5100;
  (b)L. Wang, K.Q. Ye, H.Y. Zhang, Chin. Chem. Lett. 27 (2016) 1367-1375.
19. [19]
  J.H. Chen, D.Y. Li, W.J. Chi, et al., Chem.-Eur. J. 24(2018) 3671-3676. doi: 10.1002/chem.201705780
20. [20]
  J.B. Xiong, K. Wang, Z.Q. Yao, et al., ACS Appl. Mater. Interfaces 10(2018) 5819-5827. doi: 10.1021/acsami.7b18718
21. [21]
  X.F. Duan, J. Zeng, J.W. Lv, Z.B. Zhang, J. Org. Chem. 71(2006) 9873. doi: 10.1021/jo061644d
22. [22]
  Q.K. Qi, J.Y. Qian, X. Tan, et al., Adv. Funct. Mater. 25(2015) 4005-4010. doi: 10.1002/adfm.v25.26
23. [23]
  (a) D.P. Yan, D.G. Evans, Mater. Horiz. 1 (2014) 46-57;
  (b)Q.K. Qi, Y.F. Liu, X.F. Fang, et al., RSC Adv. 3 (2013) 7996-8002;
  (c)Q.K. Qi, J.B. Zhang, B. Xu, et al., J. Phys. Chem. C 117 (2013) 24997-25003.
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