Research Progress in Design, Synthesis and Application of Benzo Nitrogen-Containing Heterocyclic Fluorescent Probes

doi:10.6023/cjoc201904061

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (10): 2771-2785.DOI: 10.6023/cjoc201904061 Previous Articles Next Articles

Special Issue: 荧光探针-生物传感合辑；有机超分子化学合辑

REVIEW

苯并氮杂环类荧光探针的设计、合成与应用研究进展

王能^a, ManiArulkumar^a, 陈孝云^b^*(), 王柏文^a, 陈思鸿^a, 姚辰^a, 汪朝阳^a^*()

^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 江苏科技大学环境与化学工程学院镇江 212003

收稿日期:2019-04-25 修回日期:2019-05-14 发布日期:2019-06-03
通讯作者: 陈孝云,汪朝阳 E-mail:xiaoyun_chen12@163.com;wangzy@scnu.edu.cn
基金资助:
国家自然科学基金(21602085);广东省自然科学基金(2014A030313429);广州市科技计划科学研究专项(201607010251);江苏省自然科学基金(BK20160551);广东省科技计划(2017A010103016);华南师范大学大创计划资助项目(20191434)

Research Progress in Design, Synthesis and Application of Benzo Nitrogen-Containing Heterocyclic Fluorescent Probes

Wang Neng^a, Arulkumar Mani^a, Chen Xiaoyun^b^*(), Wang Bowen^a, Chen Sihong^a, Yao Chen^a, Wang Zhaoyang^a^*()

^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 School of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003

Received:2019-04-25 Revised:2019-05-14 Published:2019-06-03
Contact: Chen Xiaoyun,Wang Zhaoyang E-mail:xiaoyun_chen12@163.com;wangzy@scnu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China(21602085);The Natural Science Foundation of Guangdong Province(2014A030313429);The Guangzhou Science and Technology Project Scientific Special(201607010251);The Natural Science Foundation of Jiangsu Province(BK20160551);The Guangdong Provincial Science and Technology Project(2017A010103016);The Undergraduates Innovation Project of South China Normal University(20191434)

Benzo five-/six-membered nitrogen-containing heterocyclic compound with a rigid plane and a large conjugate structure can emit characteristic fluorescence in a variety of organic solvents and mixed solutions, and N, O, S heteroatoms in the structure can serve as binding sites for fluorescent probes. Therefore, in recent years, benzo nitrogen-containing heterocyclic compounds are increasingly becoming one of the research focuses in the field of fluorescent probes. From the perspective of starting materials, synthesis methods, molecular structure, interaction mechanism, benzo five- / six-membered nitrogen-containing heterocyclic fluorescent probes containing the structure of benzoxazole, benzothiazole, benzimidazole, indole, carbazole, quinoline, benzopyrazine and phenazine are introduced with emphasis. And their detection application for a variety of analytes, such small molecules, metal cations, anions and pH are reviewed. In the future, it is worthy of further attention to the research on the integration of multiple heterocyclic functional structures into a multifunctional fluorescent probe by simple and green synthesis.

Key words: benzo five-membered nitrogen heterocycle, benzo six-membered nitrogen heterocycle, fluorescent probe, design and synthesis, recognition mechanism, detection application, multifunctionalization

Cite this article

Wang Neng, Arulkumar Mani, Chen Xiaoyun, Wang Bowen, Chen Sihong, Yao Chen, Wang Zhaoyang. Research Progress in Design, Synthesis and Application of Benzo Nitrogen-Containing Heterocyclic Fluorescent Probes[J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2771-2785.

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Fig. & Tab. 24

Scheme 1. Synthesis of probe 2 and its interaction mechanism

Scheme 2. Synthesis of probe 3

Scheme 3. Synthesis of probe 6 and its interaction mechanism

Scheme 4. Synthesis of probe 8

Scheme 5. Synthesis of probe 10 and structure of isomer 11

Scheme 6. Synthesis of probe 12 and its interaction mechanism

Scheme 7. Synthesis of probe 13

Scheme 8. Synthesis of probe 14

Scheme 9. Synthesis of probe 16

Scheme 10. Synthesis of probe 20

Scheme 11. Synthesis of probe 21

Scheme 12. Synthesis of probe 22

Scheme 13. Synthesis of probe 25

Scheme 14. Synthesis of probe 26

Scheme 15. Synthesis of probe 28

Scheme 16. Synthesis of probe 29 and its interaction mechanism

Scheme 17. Synthesis of probe 30 and its interaction mechanism

Scheme 18. Synthesis of probes 42~44

Scheme 19. Synthesis of probes 49 and its interaction mechanism

Scheme 20. Synthesis of probe 52 and its interaction mechanism

Scheme 21. Synthesis of probes 53 and its interaction mechanism

Scheme 22. Synthesis of probe 55 and its interaction mechanism

Scheme 23. Synthesis of probe 66

Scheme 24. Synthesis of probes 67

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苯并氮杂环类荧光探针的设计、合成与应用研究进展

Research Progress in Design, Synthesis and Application of Benzo Nitrogen-Containing Heterocyclic Fluorescent Probes

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