Citation: Puhui Xie, Ying Zhou, Xiaochuan Li, Xiaojing Liu, Lijie Liu, Zhanqi Cao, Jianji Wang, Xin Zheng. Strong dual-state emission of unsymmetrical and symmetrical thiazolothiazole-bridged imidazolium salts[J]. Chinese Chemical Letters, ;2023, 34(3): 107582. doi: 10.1016/j.cclet.2022.06.005 shu

Strong dual-state emission of unsymmetrical and symmetrical thiazolothiazole-bridged imidazolium salts

Puhui Xie ^a ,
Ying Zhou ^b ,
Xiaochuan Li ^c ,
Xiaojing Liu ^a ,
Lijie Liu ^a ,
Zhanqi Cao ^a ,
Jianji Wang ^{c, *,} ,
Xin Zheng ^{a, *,}

a.
College of Sciences, Henan Agricultural University, Zhengzhou 450002, China
b.
Henan Institute of Advanced Technology, Zhengzhou University, Zhengzhou 450003, China
c.
Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China

jwang@htu.cn

zhengxin@henau.edu.cn

Received Date: 4 March 2022
Revised Date: 5 June 2022
Accepted Date: 6 June 2022
Available Online: 11 June 2022

Figures(6)

A novel thiazolothiazole-bridged imidazole derivative (1) was found to exhibit blue fluorescence in gaseous state or in methanol and yellow fluorescence in solid state. The N-alkylation of imidazole subunit(s) in 1 using n-propyl iodide generated unsymmetrically or symmetrically alkylated thiazolothiazole-bridged imidazolium salts with good water solubility and remarkably strong emission in solution. Furthermore, the replacement of iodide counter-anion by triflate or bis(trifluoromethane sulfonyl)imide achieved remarkably strong emission in solid state and in solution as well as good water solubility. The strong fluorescence of dicationic salts with triflate and NTf₂^– counter-anions in solid state can be ascribed to their twisted and rigid structures induced by interionic C−H···F hydrogen bonding.
- Dual-state fluorescence,
- Unsymmetrical TTz-bridged imidazolium,
- Water solubility,
- N-Alkylation of imidazole,
- Twisted and rigid structures
1. [1]
  Q. Peng, A. Obolda, M. Zhang, F. Li, Angew. Chem. Int. Ed. 54 (2015) 7091–7095. doi: 10.1002/anie.201500242
2. [2]
  A. Shao, Y. Xie, S. Zhu, et al., Angew. Chem. Int. Ed. 54 (2015) 7275-7280. doi: 10.1002/anie.201501478
3. [3]
  N. Wang, H. Yao, Q. Tao, et al. Chin. Chem. Lett. 33 (2022) 252–256. doi: 10.1016/j.cclet.2021.06.092
4. [4]
  J. Mei, N.L.C. Leung, R.T.K. Kwok, J.W.Y. Lam, B.Z. Tang, Chem. Rev. 115 (2015) 11718–11940. doi: 10.1021/acs.chemrev.5b00263
5. [5]
  Z. Zhao, H. Zhang, J.W.Y. Lam, B. Tang, Angew. Chem. Int. Ed. 59 (2020) 9888–9907. doi: 10.1002/anie.201916729
6. [6]
  Z. Guo, C. Yan, W.H. Zhu, Angew. Chem. Int. Ed. 59 (2020) 9812–9825. doi: 10.1002/anie.201913249
7. [7]
  Y.H. Cheng, J.G. Wang, Z.J. Qiu, et al., Adv. Mater. 29 (2017) 1703900. doi: 10.1002/adma.201703900
8. [8]
  Z. Li, T.Y. Wang, Y.W. Li, et al., Chin. Chem. Lett. 31 (2020) 783–786. doi: 10.1016/j.cclet.2019.05.021
9. [9]
  D. Saito, T. Ogawa, M. Yoshida, et al., Angew. Chem. Int. Ed. 59 (2020) 18723–18730. doi: 10.1002/anie.202008383
10. [10]
  X. Zheng, W. Zhu, C. Zhang, et al., J. Am. Chem. Soc. 141 (2019) 4704–4710. doi: 10.1021/jacs.8b13724
11. [11]
  Z. Zhuang, P. Shen, S. Ding, et al., Chem. Commun. 52 (2016) 10842–10845. doi: 10.1039/C6CC04233C
12. [12]
  J. Wang, X. Gu, H. Ma, et al., Nat. Commun. 9 (2018) 2963. doi: 10.1038/s41467-018-05298-y
13. [13]
  Z.B. Sun, J.K. Liu, D.F. Yuan, et al., Angew. Chem. Int. Ed. 58 (2019) 4840–4846. doi: 10.1002/anie.201813320
14. [14]
  A.J. Boydston, C.S. Pecinovsky, S.T. Chao, C.W. Bielawski, J. Am. Chem. Soc. 129 (2007) 14550–14551. doi: 10.1021/ja075963d
15. [15]
  K. Tanabe, Y. Suzui, M. Hasegawa, T. Kato, J. Am. Chem. Soc. 134 (2012) 5652–5661. doi: 10.1021/ja3001979
16. [16]
  K. Takagi, K. Kusafuka, Y. Ito, et al., J. Org. Chem. 80 (2015) 7172–7183. doi: 10.1021/acs.joc.5b01028
17. [17]
  K. Goossens, K. Lava, C.W. Bielawski, K. Binnemans, Chem. Rev. 116 (2016) 4643–4807. doi: 10.1021/cr400334b
18. [18]
  K. Leduskrasts, A. Kinens, E. Suna, Chem. Commun. 55 (2019) 12663–12666. doi: 10.1039/c9cc06829e
19. [19]
  A.N. Woodward, J.M. Kolesar, S.R. Hall, et al., J. Am. Chem. Soc. 139 (2017) 8467–8473. doi: 10.1021/jacs.7b01005
20. [20]
  T.J. Adams, A.R. Brotherton, J.A. Molai, et al., Adv. Funct. Mater. 31 (2021) 2103408. doi: 10.1002/adfm.202103408
21. [21]
  N.A. Sayresmith, A. Saminathan, J.K. Sailer, et al., J. Am. Chem. Soc. 141 (2019) 18780–18790. doi: 10.1021/jacs.9b08959
22. [22]
  Y. Yao, Y. Zhang, C. Yan, W.H. Zhu, Z. Guo, Chem. Sci. 12 (2021) 9885–9894. doi: 10.1039/d1sc02069b
23. [23]
  H. Liu, S. Zhang, L. Ding, Y. Fang, Chem. Commun. 57 (2021) 4011–4014. doi: 10.1039/d1cc00718a
24. [24]
  S. Ando, J. Nishida, H. Tada, et al., J. Am. Chem. Soc. 127 (2005) 5336–5337. doi: 10.1021/ja042219+
25. [25]
  Y. Lin, H. Fan, Y. Li, X. Zhan, Adv. Mater. 24 (2012) 3087–3106. doi: 10.1002/adma.201200721
26. [26]
  J.L. Anderson, R. Ding, A. Ellern, D.W. Armstrong, J. Am. Chem. Soc. 127 (2005) 593–604. doi: 10.1021/ja046521u
27. [27]
  K.J. Wallace, W.J. Belcher, D.R. Turner, K.F. Syed, J.W. Steed, J. Am. Chem. Soc. 125 (2003) 9699–9715. doi: 10.1021/ja034921w
28. [28]
  X. Zheng, X. Liu, L. Liu, et al, Angew. Chem. Int. Ed. 61 (2022) e202113073.
29. [29]
  I. Roy, S. Bobbala, J. Zhou, M.T. Nguyen, et al., J. Am. Chem. Soc. 140 (2018) 7206–7212. doi: 10.1021/jacs.8b03066
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