基于有机光致变色的聚集诱导发光分子的研究进展

doi:10.6023/cjoc202108046

摘要/Abstract

近年来, 有机聚集诱导发光(AIE)材料有效克服了传统荧光材料在固态或聚集态下荧光淬灭(ACQ)的主要缺陷,在生物探针、细胞成像、光学器件、防伪材料等方面得到了广泛研究与应用. 但是, 单功能的AIE材料往往满足不了科学技术发展和人们日益增长的物质生活需求. 为拓展AIE材料的应用范围, 多功能团组合的AIE分子的研究进一步成为当今材料领域的热点之一. 兼具有光致变色和AIE特性的多功能分子, 由于能够对外部刺激做出多重光响应和良好的可逆调控特性而受到了广泛关注. 根据分子中光致变色单元不同的异构化机制, 结合本课题组在这方面的研究实践, 综述了二十一世纪以来基于有机光致变色功能单元的AIE分子的主要研究进展和应用, 并对其未来发展进行了简要展望, 希望能为本领域的研究提供一些借鉴和思考.

关键词: 多功能材料, 聚集诱导发光, 光致变色, 异构化机制

In recent years, organic aggregation-induced emission (AIE) materials have effectively overcome the main shortcomings of traditional fluorescent materials in aggregation-caused quenching (ACQ) in solid or aggregate state, and have been widely studied and applied in cell imaging, biological probes, optical devices, anti-counterfeiting materials, etc. However, unifunctional AIE materials can’t meet the advancement of science and technology, and the increasing demands for material life. In order to expand the application range of AIE materials, the study of AIE molecules combined with multifunctional groups has further become one of the current focused topics in the field of materials. Multifunctional molecules with both photochromic and AIE properties have received extensive attention due to their promising performances in reversible control and multiple photoresponses upon external stimuli and good control properties. Based on the different isomerization mechanisms of the photochromic units in the multifunctional molecules, and combined with the research practice of our group in this topic, this presentation briefly reviews the main advances and application of AIE molecules based on the different photochromic functional units since the 21st century. It also looks forward to its future development, hoping to provide some reference and thinking for the research in this field.

Key words: multifunctional materials, aggregation-induced emission, photochromism, isomerization mechanism

引用此文

丁伟, 程勃雯, 王萌, 窦清玉, 李思颖, 张鹏, 罗千福. 基于有机光致变色的聚集诱导发光分子的研究进展[J]. 有机化学, 2022, 42(2): 363-383.

Wei Ding, Bowen Cheng, Meng Wang, Qingyu Dou, Siying Li, Peng Zhang, Qianfu Luo. Advances in Aggregation-Induced Emission Molecules Based on Organic Photochromism[J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 363-383.

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图/表 40

图1. DTE-TPE的光致变色过程及其在溶液和聚集态下的荧光行为

Figure 1. Photochromic process of DTE-TPE and its fluorescence behavior in solution and aggregate state

图2. 化合物DTE-1-DTE-5的分子结构

Figure 2. Molecular structures of compounds DTE-1-DTE-5

图3. 1a,2a的胶体悬浮液和1a, 2a在THF溶液中的荧光图片

Figure 3. Fluorescence pictures of 1a, 2a colloidal suspension and 1a, 2a in THF solution

图4. 二噻吩乙烯的分子结构

Figure 4. Molecular structure of dithiophenylethene

图5. BMBT的分子结构和光致变色过程

Figure 5. Molecular structure and photochromic process of BMBT

图6. DTE-QM在溶液中和聚集态时的光响应行为

Figure 6. Photoresponse behavior of DTE-QM in solution and in the aggregated state

图7. TPE-DASA的分子结构以及光致变色过程

Figure 7. Molecular structure and photochromic process of TPE-DASA

图8. 嵌入PMMA或PVDF后的DTE-BP在光环化反应前后的荧光变化

Figure 8. Fluorescence changes of DTE-BP embedded in PMMA or PVDF before and after photocyclization

图9. B2C在光环化反应前后的分子结构

Figure 9. Molecular structure of B2C before and after photocyclization

图10. 化合物的分子结构以及在移除紫外灯后的褪色情况(1p-h: 经研磨和加热处理后的产物; 1c: 单晶)

Figure 10. Molecular structure of the compound and discoloration after removal of the UV lamp (1p-h: the product after grinding and heating treatment; 1c: single crystal)

图11. TrPECl2在紫外光照射前后的化学结构转变

Figure 11. Chemical structure transition of TrPECl2 before and after UV light irradiation

图12. TrPEBCar的分子结构以及固态下按压或加热对光致变色行为的影响

Figure 12. Molecular structure of TrPEBCar and the effect of pressing or heating in the solid state on photochromic behavior

图13. BDPM-DHT的分子结构以及光致变色过程

Figure 13. Molecular structures and photochromic process of BDPM-DHT

图14. 杂合四芳烯及其衍生物的分子结构

Figure 14. Molecular structure of hybrid tetraarylethene and its derivatives

图15. TAE-1,2,3和TAE-1-O, 2-O, 3-O的分子结构

Figure 15. Molecular structures of TAE-1,2,3 and TAE-1-O, 2-O, 3-O

图16. DCS, DS, poly(DCS-BTE)的结构和poly(DCS-BTE)的光致变色过程

Figure 16. Structure of DCS, DS, poly(DCS-BTE) and photochromic process of poly(DCS-BTE)

图17. 组成LCNPs的各分子单元结构

Figure 17. Structure of each molecular unit constituting LCNPs

图18. 聚合物的分子结构

Figure 18. Molecular structure of polymer

图19. P-PHT的分子结构

Figure 19. Molecular structure of P-PHT

图20. 化合物G-C和H的分子结构

Figure 20. Molecular structure of G-C and H

图21. CN-TFMBE、SS-TFMBE和TFM-BTE的结构

Figure 21. Molecular structures of CN-TFMBE, SS-TFMBE and TFM-BTE

图22. CF3-BPDBTEO的光致变色响应和CN-TFMBE的热响应行为

Figure 22. Photochromic response of CF3-BPDBTEO and thermal response behavior of CN-TFMBE

图23. TPE-SP1和TPE-SP2在紫外/可见光和酸/碱作用下的异构化过程

Figure 23. Isomerization of TPE-SP1 and TPE-SP2 under UV/Vis and acid/base

图24. SP-TPE-SP在HCl/NH3和UV/Vis下的响应机制

Figure 24. Response mechanism of SP-TPE-SP under HCl/NH3 and UV/Vis

图25. SFX-2SP的光致变色和酸碱响应过程

Figure 25. Photochromism and acid-base response of SFX-2SP

图26. AIE纳米探针在检测过程中的荧光变化和成像机制

Figure 26. Fluorescence change and imaging mechanism of AIE nanoprobe during detection

图27. DSA-2SP的分子结构以及AIE调控机制

Figure 27. Molecular structure of DSA-2SP and AIE regulatory mechanism

图28. TPE-NP在溶液和聚集态下的光致变色、荧光变化机理

Figure 28. Mechanism of photochromism and fluorescence change of TPE-NP in solution and aggregate state

图29. RhTPE的分子结构以及酸/碱和紫外/可见照射下的异构化

Figure 29. Molecular structure of RhTPE and isomerization under acid/base and UV/Vis irradiation

图30. 聚合物中AIE单元与螺吡喃单元的结构式

Figure 30. Molecular structure of AIE units and spiropyran units in polymers

图31. 聚合物纳米粒子的结构片段

Figure 31. Structural fragments of polymer nanoparticles

图32. 各模块的分子结构以及模块间的自组装

Figure 32. Molecular structure of each building block and self-assembly between the building blocks

图33. 通过改变温度、聚集态、光照对由LMWG1, PI2, SP3组成的凝胶进行的多色发射调控

Figure 33. Multicolor emission tuning for organogels formed with the ensemble of LMWG1, PI2, SP3 by varying the temperature, concentration, and light irradiation

图34. 化合物TPASB在溶液以及聚集态下的ESIPT和PET过程

Figure 34. ESIPT and PET processes of compound TPASB in solution and aggregated state

图35. 化合物的ESIPT过程

Figure 35. ESIPT process of the compound

图36. 化合物的分子内质子转移过程

Figure 36. Intramolecular proton transfer of the compound

图37. 化合物通过ESIPT过程对AIE行为的调控机制

Figure 37. Regulatory mechanism of compounds on AIE behavior through ESIPT process

图38. 具有AIE特性的吡唑啉酮衍生物的质子转移过程

Figure 38. Proton transfer of pyrazolinone derivatives with AIE properties

图39. 3BuES和3BuAz的分子结构

Figure 39. Molecular structures of 3BuES and 3BuAz

图40. trans-Cn-Chol的分子结构

Figure 40. Molecular structures of trans-Cn-Chol

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