基于有机小分子的聚集诱导猝灭(ACQ)-聚集诱导发射(AIE)转换研究进展

doi:10.6023/cjoc202201007

摘要/Abstract

传统的有机荧光分子大多数具有不良的聚集诱导猝灭(ACQ)效应, 限制了他们在很多领域的应用. 因此, 如何保持传统共轭分子功能特性的同时实现ACQ向聚集诱导发射(AIE)的转变具有十分重要的意义. 近年来许多课题组在该领域做了大量的突破性工作, 根据聚集诱导发射发光分子(AIEgen)的构建方式和结构特点, 将其分为基于分子内运动受限(RIM)机理使用典型AIE基元(如四苯乙烯单元)修饰ACQ基元, 以及基于RIM机理引入三苯胺或氰基乙烯等功能性单元实现零起点构建AIE分子两大类. 在后者中, 一些涉及同分异构与激发态分子内质子转移(ESIPT)机制的其他AIEgen体系的构建在近年比较突出. 基于此分类, 从AIEgen的结构、性能、机制和应用四个方面, 重点综述了近5年国内外从ACQ分子出发合成AIE分子的构建策略.

关键词: 聚集诱导猝灭(ACQ), 聚集诱导发射(AIE), 分子内运动受限(RIM), 分子设计, 合成, 发光应用

Most of the traditional organic fluorescent molecules have notorious aggregation-induced quenching (ACQ) effect, which limits their application in many fields. Therefore, how to achieve the transition from ACQ to aggregation-induced emission (AIE) while maintaining the functional properties of traditional conjugated molecules is of great significance. In recent years, many research groups have done a lot of breakthrough works in this field. According to the construction method and structural characteristics of AIE luminogen (AIEgen), the ACQ to AIE transformation strategy can be divided into two types. Based on the restriction of intramolecular motion (RIM) mechanism, the first one is to decorate ACQphore with typical AIEgen (e.g. tetraphenylethene unit). As the second one, some functional units (e.g. triphenylamine and cyanoethylene moiety) are introduced to realize the construction of AIE molecules from zero starting point as the RIM mechanism. In the latter, the construction of other AIEgen systems involving isomerism and excited-state intramolecular proton transfer (ESIPT) mechanisms has also been prominent recently. Thus, according to these classifications, the new progress on the construction strategy of ACQ-to-AIE transformation in the past five years is summarized from the four aspects of AIEgens’ structure, performance, mechanism and application.

Key words: aggregation-caused quenching (ACQ), aggregation-induced emission (AIE), restriction of intramolecular motion (RIM), molecular design, synthesis, optical application

引用此文

陈思鸿, 许佳敏, 李月媚, 彭宝茹, 罗凌玉, 冯慧烨, 陈兆华, 汪朝阳. 基于有机小分子的聚集诱导猝灭(ACQ)-聚集诱导发射(AIE)转换研究进展[J]. 有机化学, 2022, 42(6): 1651-1666.

Sihong Chen, Jiamin Xu, Yuemei Li, Baoru Peng, Lingyu Luo, Huiye Feng, Zhaohua Chen, Zhaoyang Wang. Research Progress of Aggregation-Caused Quenching (ACQ) to Aggregation-Induced Emission (AIE) Transformation Based on Organic Small Molecules[J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1651-1666.

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图/表 27

图1. 常见的四苯乙烯原料的分子结构

Figure 1. Molecular structures of starting material for TPE derivatives

图2. AIE化合物2和3的分子结构

Figure 2. Molecular structures of AIE compounds 2 and 3

图式1. AIE化合物5~7的合成路线

Scheme 1. Synthetic route of AIE compounds 5~7

图3. AIE化合物8~10的分子结构式

Figure 3. Molecular structures of AIE compounds 8~10

图4. AIE化合物12和13的分子结构

Figure 4. Molecular structures of AIE compounds 12 and 13

图式2. AIE化合物14的合成路线

Scheme 2. Synthetic route of AIE compound 14

图式3. AIE化合物15的合成路线

Scheme 3. Synthetic route of AIE compound 15

图5. ACQ化合物16和AIE化合物17的分子结构

Figure 5. Molecular structures of ACQ compound 16 and AIE compound 17

图式4. AIE化合物18和19的合成路线

Scheme 4. Synthesis routes of AIE compounds 18 and 19

图6. AIE化合物21和22的分子结构

Figure 6. Molecular structures of AIE compounds 21 and 22

图式5. ACQ化合物23和AIE化合物24的合成路线

Scheme 5. Synthesis routes of ACQ compound 23 and AIE compound 24

图式6. AIE化合物25和26的合成路线

Scheme 6. Synthesis routes of AIE compounds 25 and 26

图式7. AIE化合物27的合成路线

Scheme 7. Synthesis route of AIE compound 27

图7. ACQ化合物30和AIE化合物31~34的分子结构

Figure 7. Molecular structures of ACQ compound 30 and AIE compounds 31~34

图8. AIE化合物35~38的分子结构

Figure 8. Molecular structure of AIE compounds 35~38

图式8. AIE化合物39~41的合成路线

Scheme 8. Synthesis routes of AIE compounds 39~41

图式9. AIE化合物42的合成路线

Scheme 9. Synthesis route to target compound 42

图式10. ACQ化合物43和AIE化合物44的合成路线

Scheme 10. Synthesis routes of ACQ compound 43 and AIE compound 44

图式11. ACQ化合物45和AIE化合物46的合成路线

Scheme 11. Synthesis routes of ACQ compound 45 and AIE compound 46

图式12. ACQ化合物47和AIE化合物48的合成路线

Scheme 12. Synthesis routes of ACQ compound 47 and AIE compound 48

图式13. ACQ化合物49和AIE化合物50的合成路线

Scheme 13. Synthesis routes of ACQ compound 49 and AIE compound 50

图式14. ACQ化合物51和AIE化合物52的合成路线

Scheme 14. Synthesis routes of ACQ compound 51 and AIE compound 52

图式15. ACQ化合物53与AIE化合物54、55的合成路线

Scheme 15. Synthesis routes of ACQ compound 53 and AIE compounds 54 & 55

图9. ACQ化合物56和57与AIE化合物58的分子结构

Figure 9. Molecular structures of ACQ compounds 56 & 57 and AIE compound 58

图10. AIE化合物59和60及相关探针分子的结构

Figure 10. Molecular structures of AIE compounds 59 and 60 and their corresponding probes

图式16. 化合物63~65与H+或OH–作用的机理图

Scheme 16. Interaction mechanism of compounds 63~65 added with H+ or OH–

图11. AIE化合物67~69的分子结构

Figure 11. Molecular structures of AIE compounds 67~69

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