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
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