Citation: Xiao-Mei Sun, Juan Liu, Zhao-Hui Li, Yong-Peng Fu, Ting-Ting Huang, Zhong-Di Tang, Bingbing Shi, Hong Yao, Tai-Bao Wei, Qi Lin. Structure-property relationship on aggregation-induced emission properties of simple azine-based AIEgens and its application in metal ions detection[J]. Chinese Chemical Letters, ;2023, 34(5): 107792. doi: 10.1016/j.cclet.2022.107792 shu

Structure-property relationship on aggregation-induced emission properties of simple azine-based AIEgens and its application in metal ions detection

Xiao-Mei Sun ^a ,
Juan Liu ^b ,
Zhao-Hui Li ^c ,
Yong-Peng Fu ^d ,
Ting-Ting Huang ^a ,
Zhong-Di Tang ^a ,
Bingbing Shi ^a ,
Hong Yao ^a ,
Tai-Bao Wei ^a ,
Qi Lin ^{a, *,}

a.
College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, China
b.
Key Laboratory of Environment-Friendly Composite Materials of the State Ethnic Affairs Commission, College of Chemical Engineering, Northwest Minzu University, Lanzhou 730000 China
c.
Department of Pharmacy Jiangxi Medical College, Shangrao 334000, China
d.
Longnan Ecological and Environmental Monitoring Centre of Gansu Province, Longnan 746000, China

linqi2004@126.com

Received Date: 9 June 2022
Revised Date: 27 August 2022
Accepted Date: 29 August 2022
Available Online: 31 August 2022

Figures(4)

In recent twenty years, aggregation-induced emission (AIE), due to its excellent application prospect, has aroused widespread interests. The development of novel and easy to make AIE luminogens (AIEgens) is an attractive subject. For this purpose, it is very important to study the structure-property relationship of AIEgens. Because azine derivatives are easy to synthesis and some of them have nice AIE properties, herein, a series of azine derivatives (ADs) were employed as models to study the influence of different functional groups, electronic effects and structures on the AIE properties of azine derivatives. The AIE mechanism were studied by single crystal analysis, density functional theory (DFT) calculations and so on. The results indicated that the o-hydroxyl aryl substituted azine compounds could show good AIE properties. Meanwhile, the AIE properties of o-hydroxyl aryl substituted azine compounds were also influenced by the electronic effects of the aryl groups in the azine compounds. The o-hydroxyl groups could form intramolecular hydrogen bond with imine group, which play key role to restrict the intramolecular rotation of the aryl groups and act as base stone for the AIE process of this kind compounds. The HOMO-LUMO energy gaps of o-hydroxyl substituted azine are smaller than other homologous compounds, which is agree with the proposed AIE mechanism. Finally, thanks to the AIE properties, the o-hydroxy-substituted azines could be used as efficient Al³⁺ and Cu²⁺ fluorescent chemosensors in different conditions. In addition, test strips based on AD10 has been prepared, which can conveniently detect Cu²⁺ in industrial wastewater. This research supplied a way for the design of novel easy to make AIEgens through simple azine derivatives.
- AIEgens,
- Structure-property relationship,
- Fluorescent chemosensor,
- Azine derivatives,
- Calculations
1. [1]
  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
2. [2]
  Z.H. Zhang, Y.M. Zhang, T.B. Wei, et al., Chin. Chem. Lett. 34 (2023) 107085. doi: 10.1016/j.cclet.2021.12.077
3. [3]
  P. Wang, S.X. Cao, T. Yin, X.L. Ni, Chin. Chem. Lett. 32 (2021) 1679–1682. doi: 10.1016/j.cclet.2020.11.068
4. [4]
  L. Zhang, Y.F. Wang, M. Li, Q.Y. Gao, C.F. Chen, Chin. Chem. Lett. 32 (2021) 740–744. doi: 10.1016/j.cclet.2020.07.041
5. [5]
  H. Yao, Q. Zhou, Q. Lin, et al., Chin. Chem. Lett. 31 (2020) 1231–1234. doi: 10.1016/j.cclet.2019.09.046
6. [6]
  W.Q. Feng, Q. Su, B.Z. Tang, et al., J. Org. Chem. 85 (2020) 158–167. doi: 10.1021/acs.joc.9b02383
7. [7]
  J.B. Xiong, H.T. Feng, J.P. Sun, et al., J. Am. Chem. Soc. 138 (2016) 11469–11472. doi: 10.1021/jacs.6b07087
8. [8]
  J.Y. Gong, P.F. Wei, B.Z. Tang, et al., Chin. Chem. Lett. 29 (2018) 1493–1496. doi: 10.1016/j.cclet.2018.05.043
9. [9]
  P.F. Wei, J.X. Zhang, B.Z. Tang, et al., J. Am. Chem. Soc. 140 (2018) 1966–1975. doi: 10.1021/jacs.7b13364
10. [10]
  W.B. Dai, Z.X. Cai, Y.P. Dong, et al., ACS Mater. Lett. 3 (2021) 1767–1777. doi: 10.1021/acsmaterialslett.1c00528
11. [11]
  J.L. Tong, K.X. Zhang, B.Z. Tang, et al., J. Mater. Chem. C 8 (2020) 996–1001. doi: 10.1039/C9TC05822B
12. [12]
  G. Kumar, K. Paul, V. Luxami, Sens. Actuator. B: Chem. 263 (2018) 585–593. doi: 10.1016/j.snb.2018.02.078
13. [13]
  L. Peng, Z.J. Zhou, A.J. Tong, et al., Dye. Pigm. 108 (2014) 24–31. doi: 10.1016/j.dyepig.2014.04.020
14. [14]
  W.X. Tang, Y. Xiang, A.J. Tong, J. Org. Chem. 74 (2009) 2163–2166. doi: 10.1021/jo802631m
15. [15]
  Y. Y Xu, X.G. Gao, J.C. Leng, J.Z. Fan, CrystEngComm 23 (2021) 3582–3593. doi: 10.1039/D1CE00223F
16. [16]
  X.B. Haung, L.B. Qian, H.Y. Wu, et al., J. Mater. Chem. C 6 (2018) 5075–5096. doi: 10.1039/C8TC00043C
17. [17]
  Y.Z. Liu, X.B. Haung, H.Y. Wu, et al., Mater. Chem. C 4 (2016) 2862–2870. doi: 10.1039/C5TC02932E
18. [18]
  D. Magde, R. Wong, P. G Seybold, Photochem Photobiol 75 (2002) 327–334. doi: 10.1562/0031-8655(2002)075<0327:FQYATR>2.0.CO;2
19. [19]
  S. Tsuzuki, K. Honda, T. Uchimaru, M. Mikami, K. Tanabe, J. Am. Chem. Soc. 124 (2002) 104–112. doi: 10.1021/ja0105212
20. [20]
  T. Lu, F. Chen, Acta Phsy. Chim. Sin. 28 (2012) 1–18. doi: 10.3866/PKU.WHXB2012281
21. [21]
  B. Das, M. Dolai, A. Jana, et al., J. Phys. Chem. A 125 (2021) 1490–1504. doi: 10.1021/acs.jpca.0c10518
22. [22]
  H.R. Qin, J.B. Huang, H. Liang, J. Lu, ACS Appl. Mater. Interfaces 13 (2021) 5668–5677. doi: 10.1021/acsami.0c22698
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2. [2]
  Yu Zhou , Lin-Tao Jiang , Xiao-Ming Jiang , Bin-Wen Liu , Guo-Cong Guo . Mixed-anion square-pyramid [SbS₃I₂] units causing strong second-harmonic generation intensity and large birefringence. Chinese Chemical Letters, 2025, 36(4): 109740-. doi: 10.1016/j.cclet.2024.109740
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7. [7]
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9. [9]
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10. [10]
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11. [11]
  Yuan ZHU , Xiaoda ZHANG , Shasha WANG , Peng WEI , Tao YI . Conditionally restricted fluorescent probe for Fe³⁺ and Cu²⁺ based on the naphthalimide structure. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 183-192. doi: 10.11862/CJIC.20240232
12. [12]
  Jian Song , Shenghui Wang , Qiuge Liu , Xiao Wang , Shuo Yuan , Hongmin Liu , Saiyang Zhang . N-Benzyl arylamide derivatives as novel and potent tubulin polymerization inhibitors against gastric cancers: Design, structure–activity relationships and biological evaluations. Chinese Chemical Letters, 2025, 36(2): 109678-. doi: 10.1016/j.cclet.2024.109678
13. [13]
  Ziyi Liu , Xunying Liu , Lubing Qin , Haozheng Chen , Ruikai Li , Zhenghua Tang . Alkynyl ligand for preparing atomically precise metal nanoclusters: Structure enrichment, property regulation, and functionality enhancement. Chinese Journal of Structural Chemistry, 2024, 43(11): 100405-100405. doi: 10.1016/j.cjsc.2024.100405
14. [14]
  Xiaoling WANG , Hongwu ZHANG , Daofu LIU . Synthesis, structure, and magnetic property of a cobalt(Ⅱ) complex based on pyridyl-substituted imino nitroxide radical. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 407-412. doi: 10.11862/CJIC.20240214
15. [15]
  Ping Sun , Yuanqin Huang , Shunhong Chen , Xining Ma , Zhaokai Yang , Jian Wu . Indole derivatives as agrochemicals: An overview. Chinese Chemical Letters, 2024, 35(7): 109005-. doi: 10.1016/j.cclet.2023.109005
16. [16]
  Jiao Chen , Zihan Zhang , Guojin Sun , Yudi Cheng , Aihua Wu , Zefan Wang , Wenwen Jiang , Fulin Chen , Xiuying Xie , Jianli Li . Benzo[4,5]imidazo[1,2-a]pyrimidine-based structure-inherent targeting fluorescent sensor for imaging lysosomal viscosity and diagnosis of lysosomal storage disorders. Chinese Chemical Letters, 2024, 35(11): 110050-. doi: 10.1016/j.cclet.2024.110050
17. [17]
  Fangwen Peng , Zhen Luo , Yingjin Ma , Haibo Ma . Theoretical study of aromaticity reversal in dimethyldihydropyrene derivatives. Chinese Journal of Structural Chemistry, 2024, 43(5): 100273-100273. doi: 10.1016/j.cjsc.2024.100273
18. [18]
  Wei-Tao Dou , Qing-Wen Zeng , Yan Kang , Haidong Jia , Yulian Niu , Jinglong Wang , Lin Xu . Construction and application of multicomponent fluorescent droplets. Chinese Chemical Letters, 2025, 36(1): 109995-. doi: 10.1016/j.cclet.2024.109995
19. [19]
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20. [20]
  Yadan SUN , Xinfeng LI , Qiang LIU , Oshio Hiroki , Yinshan MENG . Structures and magnetism of dinuclear Co complexes based on imine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2212-2220. doi: 10.11862/CJIC.20240131

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