基于三苯胺的荧光探针设计、合成与应用研究进展

doi:10.6023/cjoc202009012

有机化学 ›› 2021, Vol. 41 ›› Issue (3): 919-933.DOI: 10.6023/cjoc202009012 上一篇下一篇

综述与进展

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)

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摘要/Abstract

螺旋桨结构的三苯胺荧光团既能作为强的电子供体, 又能作为潜在的聚集诱导发光(AIE)骨架. 同时, 三苯胺衍生物很容易通过简单的反应进行结构修饰, 如醛基、氨基、硼酸基、卤素、乙炔基等取代的三苯胺能够发生缩合反应或偶联反应等, 进一步功能化. 因此, 功能性三苯胺类化合物被广泛用于太阳能电池、荧光染料、固态发光材料和荧光探针的分子设计中. 根据三苯胺基荧光探针的检测对象, 将其分为阳离子、阴离子和中性小分子荧光探针三类, 并从分子的结构和性能出发, 重点综述了近五年来国内外三苯胺基荧光探针在分子设计、合成与检测应用方面的最新进展. 展望未来, 构建近红外发光和高量子效率的AIE荧光探针值得关注.

关键词: 三苯胺荧光团, 荧光探针, 设计策略, 合成路线, 传感机理, 检测应用

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

引用此文

陈思鸿, 陈淇, 罗时荷, 曹西颖, 杨国贤, 曾晓晴, 汪朝阳. 基于三苯胺的荧光探针设计、合成与应用研究进展[J]. 有机化学, 2021, 41(3): 919-933.

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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图/表 27

图式1. 探针1和2的合成与作用机理

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

图式2. 探针3的合成与作用机理

Scheme 2. Synthesis and sensing mechanism of probe 3

图式3. 探针4的合成与作用机理

Scheme 3. Synthesis and sensing mechanism of probe 4

图1. 蓝色荧光探针5~8的分子结构

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

图式4. 探针9的合成与作用机理

Scheme 4. Synthesis and sensing mechanism of probe 9

图式5. 探针10与Hg2+的作用机理

Scheme 5. Sensing mechanism of probe 10

图式6. 探针12的合成与作用机理

Scheme 6. Synthesis and sensing mechanism of probe 12

图式7. 探针13与Al3+和Cu2+的作用机理

Scheme 7. Sensing mechanism of probe 13

图2. 探针14的结构式

Figure 2. Chemical structure of probe 14

图式8. 探针15的合成与作用机理

Scheme 8. Synthesis and sensing mechanism of probe 15

图式9. 探针16的合成与作用机理

Scheme 9. Synthesis and sensing mechanism of probe 16

图式10. 探针17的合成与作用机理

Scheme 10. Synthesis and sensing mechanism of probe 17

图式11. 探针18的合成与作用机理

Scheme 11. Synthesis and sensing mechanism of probe 18

图式12. 探针19的作用机理

Scheme 12. Sensing mechanism of probe 19

图式13. 探针20的合成与作用机理

Scheme 13. Synthesis and sensing mechanism of probe 20

图式14. 探针21的合成与作用机理

Scheme 14. Synthesis and sensing mechanism of probe 21

图式15. 探针22的合成与作用机理

Scheme 15. Synthesis and sensing mechanism of probe 22

图3. 探针23和24的分子结构

Figure 3. Molecular structures of probes 23 and 24

图式16. 探针25和26的作用机理

Scheme 16. Sensing mechanism of probes 25 and 26

图式17. 探针27和28的合成路线

Scheme 17. Synthesis route of probes 27 and 28

图4. 探针29~31的分子结构

Figure 4. Molecular structures of probes 29~31

图式18. 探针36~39的分子结构和作用机理

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

图式19. 探针40的合成与作用机理

Scheme 19. Synthesis and sensing mechanism of probe 40

图式20. 探针41的合成与作用机理

Scheme 20. Synthesis and sensing mechanism of probe 41

图5. 探针42和43的分子结构

Figure 5. Molecular structures of probes 42 and 43

图式21. 探针44的合成与作用机理

Scheme 21. Synthesis and sensing mechanism of probe 44

图6. 探针45和46的分子结构

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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