高效聚集诱导发光光敏剂的合成策略

doi:10.6023/cjoc202503003

摘要/Abstract

聚集诱导发光(AIE)光敏剂即便处于高分子化或聚集态, 仍能维持强荧光特性且高效产生活性氧(ROS), 已成为新一代光动力治疗(PDT)候选材料. 围绕近年研究领域中分子电子结构与分子运动调控策略的相关进展, 重点梳理了构建供体-受体(D-A)框架的合成策略(如Suzuki-Miyaura偶联、Stille偶联、Buchwald-Hartwig偶联、Sonogashira偶联、Knoevenagel缩合), 调控π共轭骨架的合成策略(如Heck反应、Vilsmeier-Haac反应), 增强自旋轨道耦合(SOC)的合成策略(如Menshutkin反应、点击反应、金属配位反应), 以及分子运动限制策略(聚合物封装和纳米颗粒负载). 通过多维分子设计与材料工程协同, AIE光敏剂已在近红外成像与深部PDT疗效方面取得了显著进展. 展望未来, 可以借助机器学习辅助的分子筛选和多模态递送平台, 加速AIE光敏剂向临床深部实体瘤精准光疗的转化.

关键词: 聚集诱导发光, 光敏剂, 供体-受体框架, 近红外光疗, 活性氧

Aggregation-induced emission (AIE) photosensitizers have emerged as a new generation of candidates for photodynamic therapy (PDT) owing to their ability to maintain strong fluorescence and efficiently generate reactive oxygen species (ROS) in polymerized and aggregated states. Focusing on the recent research progress in molecular electronic structure and molecular motion regulation strategies, synthetic methodologies for constructing donor-acceptor (D-A) frameworks (such as Suzuki-Miyaura coupling, Stille coupling, Buchwald-Hartwig coupling, Sonogashira coupling, and Knoevenagel condensation), strategies for tuning π-conjugated backbones (such as the Heck reaction and Vilsmeier-Haack reaction), methods for enhancing spin-orbit coupling (SOC) including Menshutkin reactions, click chemistry, and metal coordination reaction, as well as motion-restricting strategies, including polymer encapsulation and nanoparticle loading, are mainly summarized. Through synergistic multidimensional molecular design and materials engineering, AIE photosensitizers have achieved significant improvements in near-infrared imaging and deep-tissue PDT efficacy. Looking forward, machine learning-assisted molecular screening and multimodal delivery platforms accelerate their clinical translation toward precision phototherapy of deep solid tumors.

Key words: aggregation-induced emission, photosensitizer, donor-acceptor framework, near-infrared phototherapy, reactive oxygen species

引用此文

代鸿宇, 孙红红, 魏培发, 管伟江. 高效聚集诱导发光光敏剂的合成策略[J]. 有机化学, 2025, 45(11): 4128-4142.

Hongyu Dai, Honghong Sun, Peifa Wei, Weijiang Guan. Strategies for the Synthesis of High-Efficiency Aggregation-Induced Emission Photosensitizers[J]. Chinese Journal of Organic Chemistry, 2025, 45(11): 4128-4142.

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图/表 15

图式1. 共轭聚合物3~5的合成

Scheme 1. Synthesis of conjugated polymers 3~5

图式2. 化合物6的合成

Scheme 2. Synthesis of compound 6

图式3. 化合物8的合成

Scheme 3. Synthesis of compound 8

图式4. 化合物9的合成和化合物10~12的结构

Scheme 4. Synthesis of compound 9 and chemical structures of compounds 10~12

图式5. 化合物13和14的合成

Scheme 5. Synthesis of compounds 13 and 14

图式6. 化合物20和21的合成

Scheme 6. Synthesis of compounds 20 and 21

图1. 化合物24的化学结构

Figure 1. Chemical structure of compound 24

图式7. 化合物27和28的合成

Scheme 7. Synthesis of compounds 27 and 28

图2. 化合物29~32的化学结构

Figure 2. Chemical structures of compounds 29~32

图3. 化合物33~36的化学结构

Figure 3. Chemical structures of compounds 33~36

图式8. 化合物37的合成和化合物38~43的化学结构

Scheme 8. Synthesis of compound 37, and chemical structures of compounds 38~43

图式9. 化合物45的合成

Scheme 9. Synthesis of compound 45

图4. 化合物47和48的化学结构

Figure 4. Chemical structures of compounds 47 and 48

图5. 不同肽合成AIE-NFs示意图

Figure 5. Schematic illustration of the synthesis of AIE-NFs with different peptides

图6. (A) QMC12的化学结构、(B) YNP-QMC的自组装及(C)核壳AD-Cu-DOX-HA的制备步骤

Figure 6. (A) Chemical structure of QMC12, (B) self-assembly of YNP-QMC, and (C) preparation procedure of core-shell AD-Cu- DOX-HA

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