Progress in Design, Synthesis and Application of Triphenylamine-Based Fluorescent Probes

doi:10.6023/cjoc202009012

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (3): 919-933.DOI: 10.6023/cjoc202009012 Previous Articles Next Articles

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基于三苯胺的荧光探针设计、合成与应用研究进展

陈思鸿^a, 陈淇^a, 罗时荷^a^,^b^,^*(), 曹西颖^a, 杨国贤^a, 曾晓晴^a, 汪朝阳^a^,^b^,^*()

a 华南师范大学化学学院教育部环境理论化学重点实验室广州市生物医药分析化学重点实验室广州 510006
b 华南理工大学广东省功能分子工程重点实验室广州 510640

收稿日期:2020-09-05 修回日期:2020-09-29 发布日期:2020-10-22
通讯作者: 罗时荷, 汪朝阳
基金资助:
广州市科技计划科学研究专项(201607010251); 广东省科技计划(2017A010103016); 广东省功能分子工程重点实验室(2017kf01)

Progress in Design, Synthesis and Application of Triphenylamine-Based Fluorescent Probes

Sihong Chen^a, Qi Chen^a, Shihe Luo^a^,^b^,^*(), Xiying Cao^a, Guoxian Yang^a, Xiaoqing Zeng^a, Zhaoyang Wang^a^,^b^,^*()

a Key Laboratory of Theoretical Chemistry of Environment, Ministry of Education, Guangzhou Key Laboratory of Analytical Chemistry for Biomedicine, School of Chemistry, South China Normal University, Guangzhou 510006
b Key Lab of Functional Molecular Engineering of Guangdong Province in SCUT, Guangzhou 510640

Received:2020-09-05 Revised:2020-09-29 Published:2020-10-22
Contact: Shihe Luo, Zhaoyang Wang
About author:
* Corresponding authors. E-mail: wangzy@scnu.edu.cn;
pinky_r@163.com
Supported by:
Scientific Special Project of Guangzhou Science and Technology(201607010251); Science and Technology Project of Guangdong Province(2017A010103016); Open Fund of the Key Laboratory of Functional Molecular Engineering of Guangdong Province(2017kf01)

The triphenylamine fluorophore with propeller-structure can be used not only as a strong electron donor, but also as a potential aggregation-induced emission (AIE) framework. At the same time, triphenylamine derivatives with different substituted groups (e.g. formyl, amino, halogen, boronic acid group, alkynyl) can easily be modified for further functionalization by simple reactions, such as condensation and metal coupling reaction. Thus, the functional triphenylamine derivatives are widely applied in the molecular design of solar cells, fluorescent dyes, solid-state luminescent materials and fluorescent probes. According to the detected analytes, such as cations, anions, and neutral small molecules, the triphenylamine-based fluorescent probes reported in the past five years are divided into three types. And on the viewpoint of their structures and performances, the new progress on the molecular design, synthesis and detecting application is reviewed. The developing potential of triphenylamine-based fluorescent probes is also envisioned, and the AIE-type probes with the properties of near-infrared and high photoluminescence quantum yield should be highlighted in the future.

Key words: triphenylamine fluorophore, fluorescent probe, design strategy, synthetic route, sensing mechanism, detection application

Cite this article

Sihong Chen, Qi Chen, Shihe Luo, Xiying Cao, Guoxian Yang, Xiaoqing Zeng, Zhaoyang Wang. Progress in Design, Synthesis and Application of Triphenylamine-Based Fluorescent Probes[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 919-933.

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Fig. & Tab. 27

Scheme 1. Synthesis and sensing mechanism of probes 1 and 2

Scheme 2. Synthesis and sensing mechanism of probe 3

Scheme 3. Synthesis and sensing mechanism of probe 4

Figure 1. Molecular structures of blue fluorescent probes 5~8

Scheme 4. Synthesis and sensing mechanism of probe 9

Scheme 5. Sensing mechanism of probe 10

Scheme 6. Synthesis and sensing mechanism of probe 12

Scheme 7. Sensing mechanism of probe 13

Figure 2. Chemical structure of probe 14

Scheme 8. Synthesis and sensing mechanism of probe 15

Scheme 9. Synthesis and sensing mechanism of probe 16

Scheme 10. Synthesis and sensing mechanism of probe 17

Scheme 11. Synthesis and sensing mechanism of probe 18

Scheme 12. Sensing mechanism of probe 19

Scheme 13. Synthesis and sensing mechanism of probe 20

Scheme 14. Synthesis and sensing mechanism of probe 21

Scheme 15. Synthesis and sensing mechanism of probe 22

Figure 3. Molecular structures of probes 23 and 24

Scheme 16. Sensing mechanism of probes 25 and 26

Scheme 17. Synthesis route of probes 27 and 28

Figure 4. Molecular structures of probes 29~31

Scheme 18. Molecular structures and sensing mechanism of probes 36~39

Scheme 19. Synthesis and sensing mechanism of probe 40

Scheme 20. Synthesis and sensing mechanism of probe 41

Figure 5. Molecular structures of probes 42 and 43

Scheme 21. Synthesis and sensing mechanism of probe 44

Figure 6. Molecular structures of probes 45 and 46

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基于三苯胺的荧光探针设计、合成与应用研究进展

Progress in Design, Synthesis and Application of Triphenylamine-Based Fluorescent Probes

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