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
1. [1]
  Junjie Wang , Yan Wang , Zhengdong Li , Changqiang Xie , Musammir Khan , Xingzhou Peng , Fabiao Yu . Triphenylamine-AIEgens photoactive materials for cancer theranostics. Chinese Chemical Letters, 2024, 35(6): 108934-. doi: 10.1016/j.cclet.2023.108934
2. [2]
  Meng-Xin Liu , Xiao-Long Su , Pu Chen , Yan-Yan Liu , Jian-Peng Li , Li Zou , Ben Zhong Tang , Hai-Tao Feng . Sequential FRET system based on macrocyclic AIEgens for versatile photocatalysis. Chinese Chemical Letters, 2026, 37(4): 111516-. doi: 10.1016/j.cclet.2025.111516
3. [3]
  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
4. [4]
  Panpan Wang , Hongbao Fang , Mengmeng Wang , Guandong Zhang , Na Xu , Yan Su , Hongke Liu , Zhi Su . A mitochondria targeting Ir(III) complex triggers ferroptosis and autophagy for cancer therapy: A case of aggregation enhanced PDT strategy for metal complexes. Chinese Chemical Letters, 2025, 36(1): 110099-. doi: 10.1016/j.cclet.2024.110099
5. [5]
  Zhihao HE , Jiafu DING , Yunjie WANG , Xin SU . First-principles study on the structure-property relationship of AlX and InX (X=N, P, As, Sb). Chinese Journal of Inorganic Chemistry, 2025, 41(5): 1007-1019. doi: 10.11862/CJIC.20240390
6. [6]
  Yi Li , Zhaoxiang Cao , Peng Liu , Xia Wu , Dongju Zhang . Revealing the Coloration and Color Change Mechanisms of the Eriochrome Black T Indicator through Computational Chemistry and UV-Visible Absorption Spectroscopy. University Chemistry, 2025, 40(3): 132-139. doi: 10.12461/PKU.DXHX202405154
7. [7]
  Xuejie Wang , Guoqing Cui , Congkai Wang , Yang Yang , Guiyuan Jiang , Chunming Xu . Research Progress on Carbon-based Catalysts for Catalytic Dehydrogenation of Liquid Organic Hydrogen Carriers. Acta Physico-Chimica Sinica, 2025, 41(5): 100044-0. doi: 10.1016/j.actphy.2024.100044
8. [8]
  Youbo HU , Donggang LI , Changhua SUN , Zhenzhong LU , Songjun GU . Coordination polymers based on anthracene- and pyrene-derived ligands: Crystal structure, fluorescent property, and framework isomerization. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1681-1688. doi: 10.11862/CJIC.20250004
9. [9]
  Shaohua Zhang , Liyao Liu , Yingqiao Ma , Chong-an Di . Advances in theoretical calculations of organic thermoelectric materials. Chinese Chemical Letters, 2024, 35(8): 109749-. doi: 10.1016/j.cclet.2024.109749
10. [10]
  Hui Lei , Yingying Jiang , Jiayu Liu , Weifeng Zhang , Fanbo Meng , Jun Mou , Wenyi Liu , Pengcheng Lei , Rui Xiong , Zan Xu , Hang Zhang , Yanjun Wang , Guo-Bo Li , Lingling Yang , Hua-Li Wang . Structure-activity relationship studies of 3,4-disubstitued indole-2-ketone derivatives identify a potent glutaminyl cyclase inhibitor with antitumor activity against breast cancer. Chinese Chemical Letters, 2026, 37(6): 111511-. doi: 10.1016/j.cclet.2025.111511
11. [11]
  Bingwei Wang , Yihong Ding , Xiao Tian . Benchmarking model chemistry composite calculations for vertical ionization potential of molecular systems. Chinese Chemical Letters, 2025, 36(2): 109721-. doi: 10.1016/j.cclet.2024.109721
12. [12]
  Hanmei Zhang , Xiaoxu Liu , Tianyi Ji , Jianxin Ran , Yang Li , Zexiang Shen , Xiaofeng Wang . Applications of theoretical calculations in alkali metal-ion battery investigation. Chinese Chemical Letters, 2026, 37(4): 110790-. doi: 10.1016/j.cclet.2024.110790
13. [13]
  Wenyi Mei , Lijuan Xie , Xiaodong Zhang , Cunjian Shi , Fengzhi Wang , Qiqi Fu , Zhenjiang Zhao , Honglin Li , Yufang Xu , Zhuo Chen . Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells. Chinese Chemical Letters, 2024, 35(5): 108825-. doi: 10.1016/j.cclet.2023.108825
14. [14]
  Kun-Heng Li , Hong-Yang Zhao , Dan-Dan Wang , Ming-Hui Qi , Zi-Jian Xu , Jia-Mi Li , Zhi-Li Zhang , Shi-Wen Huang . Mitochondria-targeted nano-AIEgens as a powerful inducer for evoking immunogenic cell death. Chinese Chemical Letters, 2024, 35(5): 108882-. doi: 10.1016/j.cclet.2023.108882
15. [15]
  Meitong Wu , Ke Wu , Shumin Feng , Li Xu , Mi Lei , Jianmei Chen , Shuang Li , Mian Qin , Dahui Liu , Guoqiang Feng . A NIR and ratiometric fluorescent probe for quantitative detection of SO₂ derivatives in Chinese medicinal materials and bioimaging in vivo. Chinese Chemical Letters, 2026, 37(1): 110979-. doi: 10.1016/j.cclet.2025.110979
16. [16]
  Yumei Wu , Zhengjun Chen , Yuan Shen , Deying Tang , Huaiyu Mo , Zihan Chen , Hongyu Li , Zhe Zheng , Chunju Li , Jie Gao , Zeli Yuan . Water-soluble thiazolo[5,4-d]thiazole-based AIEgens for universal and Level 3 resolved latent fingerprint visualization. Chinese Chemical Letters, 2026, 37(9): 111889-. doi: 10.1016/j.cclet.2025.111889
17. [17]
  Lumin Zheng , Ying Bai , Chuan Wu . Multi-electron reaction and fast Al ion diffusion of δ-MnO₂ cathode materials in rechargeable aluminum batteries via first-principle calculations. Chinese Chemical Letters, 2024, 35(4): 108589-. doi: 10.1016/j.cclet.2023.108589
18. [18]
  Hanqi Zhang , Biao Gao , Yuanyuan Feng , Guijuan Zheng , Zhijun Liu , Lichun Kong , Junjun Liu , Haji Akber Aisa , Guangmin Yao . DFT calculations and dynamic NMR revealed the coalescent NMR phenomena of the 6/6/6/9 tetracyclic merosesquiterpenoids with an unprecedented 9,15-dioxatetracyclo[8.5.3.0^4,17.0^14,18]octadecane core skeleton. Chinese Chemical Letters, 2025, 36(9): 111234-. doi: 10.1016/j.cclet.2025.111234
19. [19]
  Si-Fu Gao , Qiang-Qiang Li , Xing Li , Zi-Qiang Zhang , Huanan Huang , Jun Xuan . Rational design of phenanthridine-based AIEgens for organelle-specific imaging: A dual-functional strategy via free amine modulation and carbon-insertion π-extension. Chinese Chemical Letters, 2026, 37(6): 111519-. doi: 10.1016/j.cclet.2025.111519
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(2656)
HTML views(115)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142