聚集诱导发光(AIE)和激发态分子内质子转移(ESIPT)结构融合的反应型荧光探针的研究进展

doi:10.6023/cjoc202112009

摘要/Abstract

兼具激发态分子内质子转移(ESIPT)和聚集诱导发光(AIE)性质的反应型荧光探针, 因其具有较好的生物相容性、良好的传感性能、较大的斯托克斯位移以及较高的荧光量子效率等优点, 在近几年来被广泛应用于检测各种阴离子、金属阳离子和生物分子中. 简要总结了结构简单, 既是AIE结构模块又是ESIPT结构模块的苯并噻唑、水杨醛席夫碱、肼二腙、查尔酮荧光团等反应型荧光探针的研究进展, 并对相关研究进行了总结和展望.

关键词: 激发态分子内质子转移(ESIPT), 聚集诱导发光(AIE), 荧光探针, 反应型识别

Reactive fluorescent probes with the features of excited state intramolecular proton transfer (ESIPT) and aggregation-induced emission (AIE) have been widely used in the detection of various anions, metal cations and biomolecules in recent years, because they have some advantages including good biocompatibility, good sensing performance, a large Stokes shift, and as well high fluorescence quantum efficiency. The progress in reactive fluorescent probes that are structural simple and have the combined structures of AIE and ESIPT is briefly summarized, and the probes are divided into several types such as benzothiazole, salicylaldehyde Schiff base, hydrazine dihydrazone, chalcone fluorophore, etc. The related researches are discussed and prospected.

Key words: excited state intramolecular proton transfer (ESIPT), aggregation-induced emission (AIE), fluorescent probe, reaction-based recognition

引用此文

郭钺甜, 潘永鑫, 汤立军. 聚集诱导发光(AIE)和激发态分子内质子转移(ESIPT)结构融合的反应型荧光探针的研究进展[J]. 有机化学, 2022, 42(6): 1640-1650.

Yuetian Guo, Yongxin Pan, Lijun Tang. Progresses in Reactive Fluorescent Probes with Fused Aggregation- Induced Emission (AIE) and Excited State Intramolecular Proton Transfer (ESIPT) Structures[J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1640-1650.

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图/表 23

图1. ESIPT过程的四阶能量循环示意图

Figure 1. Schematic representation of the four-level energy cycle of the ESIPT process

图式1. 探针1与H2S的反应

Scheme 1. Reaction of probe 1 with H2S

图式2. 探针2与Hg2+的反应

Scheme 2. Reaction of probe 2 with Hg2+

图式3. 探针3与GUS的反应

Scheme 3. Reaction of probe 3 with GUS

图式4. 探针4的合成及4与Cys的反应机理

Scheme 4. Synthesis of probe 4 and its detection mechanism for Cys

图式5. 探针5与Cu2+和PPi的可逆反应

Scheme 5. Reversible reaction of probe 5 with Cu2+ and PPi

图式6. 探针6与Zn2+的反应

Scheme 6. Reaction of probe 6 with Zn2+

图式7. 探针7与H+的反应

Scheme 7. Reaction of probe 7 with H+

图式8. 探针8与Zn2+的反应

Scheme 8. Reaction of probe 8 with Zn2+

图式9. 探针9与酯酶的反应

Scheme 9. Reaction of probe 9 with esterase

图式10. 探针10与N2H4和ClO–的反应

Scheme 10. Reactions of probe 10 with N2H4 and ClO–

图式11. 探针11与Pd0的反应

Scheme 11. Reaction of probe 11 with Pd0

图式12. 探针12与Cys的反应机理

Scheme 12. Reaction mechanism of probe 12 and Cys

图式13. 探针13与Cys的反应机理

Scheme 13. Reaction mechanism of probe 13 and Cys

图式14. 探针15对β-内酰胺酶的检测机理

Scheme 14. The detection mechanism of probe 15 for β-lactamase

图式15. 探针16与ONOO–的反应

Scheme 15. Reaction of probe 16 with ONOO–

图式16. 探针17与ALP的反应

Scheme 16. Reaction of probe 17 with ALP

图式17. 探针18和19与H2O2的反应机理

Scheme 17. Reaction mechanism of probe 18 and 19 with H2O2

图式18. 探针20与NTR的反应

Scheme 18. Reaction of probe 20 with NTR

图式19. 探针21与Cys/GSH/Hcy的反应

Scheme 19. Reaction of probe 21 with Cys/GSH/Hcy

图式20. 探针22与H2O2的反应机理

Scheme 20. Reaction mechanism of probe 22 with H2O2

图式21. 探针23与超氧负离子的反应

Scheme 21. Reaction of probe 23 with superoxide anion

图式22. 探针24与Zn2+的反应机理

Scheme 22. Reaction mechanism of probe 24 with Zn2+

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