Synthesis of Triphenylamine Derivative and Its Recognition for Hg2+ with “OFF-ON” Fluorescence Response Based on Aggregation-Induced Emission (AIE) Mechanism

doi:10.6023/cjoc202206043

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (1): 320-325.DOI: 10.6023/cjoc202206043 Previous Articles Next Articles

NOTES

三苯胺衍生物的合成及其基于聚集诱导发光(AIE)机理对汞离子“OFF-ON”荧光识别

李阳阳^a, 孙小飞^a^,^*(), 胡晓玲^a, 任源远^b, 钟克利^a^,^*(), 燕小梅^c, 汤立军^a

a 渤海大学化学与材料工程学院食品科学与工程学院辽宁锦州 121013
b 中国水产科学研究院农业农村部水产品质量安全控制重点实验室北京 100141
c 大连医科大学检验医学院辽宁大连 116044

收稿日期:2022-06-22 修回日期:2022-08-01 发布日期:2022-09-01
通讯作者: 孙小飞, 钟克利
基金资助:
国家自然科学基金(22278038); 国家自然科学基金(32201948); 辽宁省自然科学基金(2020-MS-289); 辽宁省自然科学基金(20180551195); 农业农村部水产品质量安全控制重点实验室基金(2021C001); 辽宁省教育厅基本科研(LJKMZ20221480); 辽宁省教育厅基本科研(LJKQZ2021135)

Synthesis of Triphenylamine Derivative and Its Recognition for Hg²⁺ with “OFF-ON” Fluorescence Response Based on Aggregation-Induced Emission (AIE) Mechanism

Yangyang Li^a, Xiaofei Sun^a(), Xiaoling Hu^a, Yuanyuan Ren^b, Keli Zhong^a(), Xiaomei Yan^c, Lijun Tang^a

a College of Food Science and Technology, College of Chemistry and Materials Engineering, Bohai University, Jinzhou, Liaoning 121013
b Key Laboratory of Control of Quality and Safety for Aquatic Products, Ministry of Agriculture and Rural Affairs, hinese Academy of Fishery Sciences, Beijing 100141
c College of Laboratory Medicine, Dalian Medical University, Dalian, Liaoning 116044

Received:2022-06-22 Revised:2022-08-01 Published:2022-09-01
Contact: Xiaofei Sun, Keli Zhong
Supported by:
National Natural Science Foundation of China(22278038); National Natural Science Foundation of China(32201948); Natural Science Foundation of Liaoning Province(2020-MS-289); Natural Science Foundation of Liaoning Province(20180551195); Fund of Key Laboratory of Control of Quality and Safety for Aquatic Products, Ministry of Agriculture and Rural Affairs(2021C001); Scientific Research Fund of Liaoning Provincial Education Department(LJKMZ20221480); Scientific Research Fund of Liaoning Provincial Education Department(LJKQZ2021135)

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Abstract

As an environmental pollutant, mercury ion (Hg²⁺) cannot be biodegraded, and will accumulate through the food chain and cause damage to human body. Therefore, it is of great significance to develop a simple and effective method for detecting Hg²⁺. In this paper, a novel triphenylamine derivative Tbia was synthesized by a simple two-step reaction. Tbia can react with Hg²⁺ specifically in hydroxyethylpiperazine ethane sulfonic acid (HEPES) solution and release the precursor compound with aggregation-induced emission (AIE) properties, which realized recognition of Hg²⁺ with “off-on” response. Tbia has good selectivity and sensitivity for Hg²⁺, a wide range of pH, and the detection limit of 63 nmol/L. In addition, Tbia can be prepared into invisible ink and is expected to be used in packaging of anti-counterfeiting. The test paper loaded with Tbia can be used for qualitative or roughly quantitative detection of Hg²⁺, and Tbia can detect Hg²⁺in real water samples as well as image of Hg²⁺ in living cells.

Key words: fluorescent probe, aggregation-induced emission (AIE), recognition, mercury ion, multiple applications

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Yangyang Li, Xiaofei Sun, Xiaoling Hu, Yuanyuan Ren, Keli Zhong, Xiaomei Yan, Lijun Tang. Synthesis of Triphenylamine Derivative and Its Recognition for Hg²⁺ with “OFF-ON” Fluorescence Response Based on Aggregation-Induced Emission (AIE) Mechanism[J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 320-325.

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Fig. & Tab. 10

Scheme 1. Synthesis route and mechanism of Tbia sensing Hg2+

Figure 1. (a) Fluorescence spectrum of TCHO (10 μmol/L) in C2H5OH/HEPES (pH=7.4) with different water content (insert: the relationship between the fluorescence intensity (510 nm) of TCHO and the content of water); (b) Photograph of Tyndall phenomena of TCHO and Tbia in HEPES solution

Figure 2. Fluorescence change of Tbia (10 μmol/L) after adding various cations in HEPES solution (inset: The fluorescent color changes of Tbia without and with Hg2+)

Figure 3. Fluorescence emission change of Tbia with adding different concentrations of Hg2+ (0~22 μmol/L) in HEPES (pH=7.4) buffer (insert: the linear relationship between fluorescence intensity of Tbia and Hg2+ concentration)

Figure 4. Fluorescence intensity changes of Tbia and Tbia+Hg2+ at different pH

Figure 5. Application of Tbia as invisible ink, the imprints of the BHU letters collected on a silica gel plate under daylight (a) and UV light (b)

Figure 6. Fluorescent photographs of test strips loaded with Tbia with different concentrations of Hg2+ under portable UV light (365 nm)

Figure 7. Linear relation between fluorescence intensities of Tbia (10 μmol/L) and concentration of Hg2+ (4~8 μmol/L) in three real water samples

Sample	Added/ (μmol•L^–1)	Found/ (μmol•L^–1)	Recovery rate/%	CV (n=3)
Tap water	4	4.11	102.7	0.08
	5	4.94	98.9	0.05
	6	5.97	99.5	0.06
Lake water	4	3.98	99.5	0.02
	5	5.04	100.7	0.02
	6	5.95	99.2	0.01
River water	4	4.01	100.2	0.05
	5	4.90	98.0	0.09
	6	6.07	101.2	0.04

Table 1. Detection results of Hg2+ in water samples using Tbia

Figure 8. Images of bright channel (left), blue channel (middle) and merged channel (right) of MCF-7 cells pretreated with Tbia (10 μmol/L) and incubated with Hg2+ (0, 10, 30, 50, 100 μmol/L) for 30 min

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三苯胺衍生物的合成及其基于聚集诱导发光(AIE)机理对汞离子“OFF-ON”荧光识别

Synthesis of Triphenylamine Derivative and Its Recognition for Hg²⁺ with “OFF-ON” Fluorescence Response Based on Aggregation-Induced Emission (AIE) Mechanism

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