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DOI: https://doi.org/10.6023/cjoc202503003

综述与进展

高效聚集诱导发光光敏剂的合成策略

  • 代鸿宇 ,
  • 孙红红 ,
  • 魏培发 ,
  • 管伟江
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  • a北京化工大学, 化工资源有效利用全国重点实验室 北京 100029;
    b安徽大学, 物质科学与信息技术研究院 合肥 230039

收稿日期: 2025-03-03

  修回日期: 2025-06-01

  网络出版日期: 2025-06-19

基金资助

国家自然科学基金 (No. 22422401, 22374007, 22375002) 和中央高校基本科研业务费专项资金资助 (JD2507) 资助项目.

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Strategies for the Synthesis of High-Efficiency Aggregation-Induced Emission Photosensitizers

  • Hongyu Dai ,
  • Honghong Sun ,
  • Peifa Wei ,
  • Weijiang Guan
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  • aState Key Laboratory of Chemical Resource Engineering, Beijing University of Chemical Technology ,Beijing, 100029;
    bInstitutes of Physical Science and Information Technology , Anhui University, Hefei, Anhui, 230039

Received date: 2025-03-03

  Revised date: 2025-06-01

  Online published: 2025-06-19

Supported by

National Natural Science Foundation of China (No. 22422401, 22374007, and 22375002) and the Fundamental Research Funds for the Central Universities (JD2507).

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摘要

聚集诱导发光 (AIE) 光敏剂因其在高分子化、聚集态仍能保持强荧光并高效产生活性氧 (ROS) 而成为新一代光动力治疗 (PDT) 候选材料. 本文围绕近年研究进展中的分子电子结构与分子运动调控策略, 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效能上实现显著提升. 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, 加速其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

本文引用格式

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, 0 : 202503003 -202503003 . DOI: 10.6023/cjoc202503003

Abstract

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. This review focuses on recent research progress about strategies for modulating molecular electronic structures and intramolecular motions. In particular, it summarizes 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. 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

参考文献

[1] Teng K. X.; Niu L. Y.; Yang Q. Z.J. Am. Chem. Soc. 2023, 145, 4081-4087.
[2] Huang Y.; Qiu F.; Chen R. J.; Yan D. Y.; Zhu X. Y.J. Mat. Chem. B 2020, 8, 3772-3788.
[3] Almeida A.; Faustino M. A.F.; Tomé, J. P. C. Future Med. Chem. 2015, 7, 1221-1224.
[4] Feng H. T.; Li Y. Y.; Duan X. C.; Wang X. X.; Qi C. X.; Lam J. W.Y.; Ding, D.; Tang, B. Z. J. Am. Chem. Soc. 2020, 142, 15966-15974.
[5] Fan W. P.; Huang P.; Chen X. Y. Chem. Soc. Rev. 2016, 45, 6488-6519.
[6] Liu S. S.; Feng G. X.; Tang B. Z.; Liu B. Chem.Sci. 2021, 12, 6488-6506.
[7] Piksa M.; Lian C.; Samuel I. C.; Pawlik K. J.; Samuel I. D.W.; Matczyszyn, K. Chem. Soc. Rev. 2023, 52, 1697-1722.
[8] Liu Y. H.; Chen X. Q.; Liu X. T.; Guan W. J.; Lu C. Chem. Soc. Rev. 2023, 52, 1456-1490.
[9] Pan J.; Li W. L.; Wang M. Y.; Peng C. P.; Dong J. H.; Zhou Q. T.; Xia F. Chem.Mater. 2024, 36, 11721-11737.
[10] Wang X. N.; Ramamurthy G.; Shirke A.; Walker E.; Mangadlao J.; Wang Z.; Wang Y.; Shan L. P.; Schluchter M.; Dong Z. P.; Brady-Kalnay, S. M.; Walker, N. K.; Gargesha, M.; MacLennan, G.; Luo, D.; Sun, R.; Scott, B.; Roy, D.; Li, J.; Basilion, J. P. Cancer Res. 2020, 80, 156-162.
[11] Pham T. C.; Nguyen V. N.; Choi Y.; Lee S.; Yoon J. Chem.Rev. 2021, 121, 13454-13619.
[12] Dang J. J.; He H.; Chen D. L.; Yin L. C. Biomater. Sci. 2017, 5, 1500-1511.
[13] Dichiara M.; Prezzavento O.; Marrazzo A.; Pittalà V.; Salerno L.; Rescifina A.; Amata E. Eur.J. Med. Chem. 2017, 142, 459-485.
[14] Nguyen V. N.; Yan Y. X.; Zhao J. Z.; Yoon J. Y.Accounts Chem. Res. 2021, 54, 207-220.
[15] Bonnett, R. Chem. Soc. Rev. 1995, 26, 19-33.
[16] Luo J.; Xie Z.; Lam J. W.Y.; Cheng, L.; Tang, B. Z.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhan, X.; Liu, Y.; Zhu, D. Chem. Commun. 2001, 18, 1740.
[17] Tang X. F.; Zhu Y. P.; Guan W. J.; Lu C. Aggregate 2023, 4, e348.
[18] Zhou C. C.; Ding Z. Y.; Guan W. J.; Tang B. Z. Aggregate 2023, 4, e366.
[19] Mei J.; Hong Y. N.; Lam J. W.Y.; Qin, A. J.; Tang, Y. H.; Tang, B. Z. Adv. Mater. 2014, 26, 5429-5479.
[20] Qi J.; Chen C.; Zhang X. Y.; Hu X. L.; Ji S. L.; Kwok R. T.K.; Lam, J. W. Y.; Ding, D.; Tang, B. Z. Nat. Commun. 2018, 9, 12.
[21] Wang H. P.; Chen X.; Qi Y. L.; Huang L. W.; Wang C. X.; Ding D.; Xue X. Adv.Drug Deliv. Rev. 2021, 179, 114028.
[22] Wang Y. B.; Shi L. L.; Wu W. B.; Qi G. B.; Zhu X. Y.; Liu B. Adv. Funct. Mater. 2021, 31, 2010241.
[23] Li L. Q.; Shao C.; Liu T.; Chao Z. C.; Chen H. L.; Xiao F.; He H. M.; Wei Z. X.; Zhu Y. L.; Wang H.; Zhang X. D.; Wen Y. T.; Yang B.; He F.; Tian L. L. Adv. Mater. 2020, 32, 2003471.
[24] Lu B. L.; Wang L. Y.; Tang H.; Cao D. R.J. Mat. Chem. B 2023, 11, 4600-4618.
[25] Maluenda I.; Navarro O. Molecules 2015, 20, 7528-7557.
[26] Li Y.; Zhang D.; Yu Y.; Zhang L.; Li L.; Shi L.; Feng G.; Tang B. Z. ACS Nano 2023, 17, 16993-17003.
[27] Xue B.; Hou A.; Du Y.; Qi Y.; Jiang H.; Zhou H.; Zhou Z.; Chen H. Surf. Interfaces 2023, 39, 102996.
[28] Li C. L.; Li J.; Pang Y. D.; Mei L. C.; Xu W. H.; Zhang Z. P.; Han C. P.; Sun Y. Chem. Eng. J. 2024, 498, 155471.
[29] Hu Y.; Yin S. Y.; Liu W.; Li Z.; Chen Y.; Li J. Aggregate 2023, 4, e256.
[30] Wu W. B.; Mao D.; Xu S. D.; Kenry; Hu, F.; Li, X. Q.; Kong, D. L.; Liu, B. Chem 2018, 4, 1937-1951.
[31] Chishiro A.; Konishi M.; Inaba R.; Yumura T.; Imoto H.; Naka K.Dalton Trans. 2021, 51, 95-103.
[32] Li D.; Chen X. H.; Wang D. L.; Wu H. Z.; Wen H. F.; Wang L.; Jin Q.; Wang D.; Ji J.; Tang B. Z. Biomaterials 2022, 283, 121476.
[33] Xiao Y.; Yuan Y.; Liang M.; Ni J.; Yu L.; Huang Z. S.; Du B.; Quan Y. Y.Dyes Pigm. 2023, 220, 111765.
[34] Heravi M. M.; Kheilkordi Z.; Zadsirjan V.; Heydari M.; Malmir M. J. Organomet. Chem. 2018, 861, 17-104.
[35] Wang Q.; Li C. B.; Song Y. C.; Shi Q. K.; Li H.; Zhong H.; Wang J. G.; Hu F. Chem.Sci. 2023, 14, 684-690.
[36] Zhang W. G.; Kang M. M.; Li X.; Pan Y. Z.; Li Z. R.; Zhang Y. B.; Liao C. R.; Xu G. X.; Zhang Z. J.; Tang B. Z.; Xu Z. R.; Wang D. Adv.Mater. 2024, 36, 2410142.
[37] Zhang Z. J.; Xu W. H.; Xiao P. H.; Kang M. M.; Yan D. Y.; Wen H. F.; Song N.; Wang D.; Tang B. Z. ACS Nano 2021, 15, 10689-10699
[38] Huang H. Y.; Xie W. S.; Wan Q.; Mao L. C.; Hu D. N.; Sun H.; Zhang X. Y.; Wei Y. Adv.Sci. 2022, 9, 2104101.
[39] Zhang Z. J.; Xu W. H.; Kang M. M.; Wen H. F.; Guo H.; Zhang P. F.; Xi L.; Li K.; Wang L.; Wang D.; Tang B. Adv.Mater. 2020, 32, 2003210.
[40] Liu L. Q.; Wang X.; Wang L. J.; Guo L. Q.; Li Y. B.; Bai B.; Fu F.; Lu H. G.; Zhao X. W. ACS Appl. Mater. Interfaces 2021, 13, 19668-19678.
[41] Zhuang J. B.; Wang B.; Chen H.; Zhang K. Y.; Zhao N.; Li N.; Tang B. Z. ACS Nano 2023, 17, 9110-9125.
[42] Hu Y. C.; Yin S. Y.; Deng T.; Li J. S. Chem. Commun. 2024, 60, 3047-3050.
[43] Bai H. Y.; Xiong Z.; Zhou F. F.; Qin J. M.; Wen S. L.; Li Z. M.; Chen Y.; Cao Q. Y.Dyes Pigm. 2022, 206,110652.
[44] Sun Z. C.; Wang J. X.; Xiao M. H.; Wu K. Y.; Wang C.; Fu H.; Lv S. Y.; Shi L. Q.; Zhu C. L. Chem. Eng. J. 2024, 499, 155782.
[45] Xue J.; Zhang Y. S.; Huan Z.; Yang J. D.; Cheng J. P.J. Org. Chem. 2022, 87, 15539-15546.
[46] Li Q. H.; Feng S. M.; Feng G. Q.Sens. Actuator B-Chem. 2025, 422, 136229.
[47] Shen C. J.; Xie M. T.; Pan L. Y.; Wu B. B.; Zhang W. X.; Yuan Y. Y.; Chen Y.; Quan Y. Y.; Ye X. X.; Huang Z. S. Mater. Des. 2023, 228, 111838.
[48] Liu S. S.; Wang B. N.; Yu Y. W.; Liu Y. B.; Zhuang Z. Y.; Zhao Z. J.; Feng G. X.; Qin A. J.; Tang B. Z. ACS Nano 2022, 16, 9130-9141.
[49] Wang J. J.; Zhu X. J.; Zhang J.; Wang H. Y.; Liu G.; Bu Y. C.; Yu J. H.; Tian Y. P.; Zhou H. P. ACS Appl. Mater. Interfaces 2020, 12, 1988-1996.
[50] Wang J. L.; Xia F. W.; Wang Y.; Shi H. Z.; Wang L. J.; Zhao Y.; Song J. X.; Wu M. Y.; Feng S. ACS Appl. Mater. Interfaces 2023, 15, 17433-17443.
[51] Ghosal K.; Bhattacharyya S. K.; Mishra V.; Zuilhof H. Chem.Rev. 2024, 124, 13216-13300.
[52] Li C. Y.; Liu J. K.; Hong Y. J.; Lin R. F.; Liu Z. C.; Chen M.; Lam J. W.Y.; Ning, G. H.; Zheng, X. L.; Qin, A. J.; Tang, B. Z. Angew. Chem. Int. Edit. 2022, 61, e202202005.
[53] Wang Y. B.; Xu S. D.; Shi L. L.; Teh C.; Qi G. B.; Liu B. Angew. Chem. Int. Edit. 2021, 60, 14945-14953.
[54] Zhang L. P.; Li Y. Y.; Che W. L.; Zhu D. X.; Li G. F.; Xie Z. G.; Song N.; Liu S.; Tang B. Z.; Liu X. M.; Su Z. M.; Bryce M. R. Adv. Sci. 2019, 6, 1802050.
[55] Liu L. L.; Zhu T.; Cai C. T.; Wang L. K.; Li S. L.; Lian X.; Feng Y.; Tian Y. P.; Zhang Q.Dalton Trans. 2022, 51, 16915-16920.
[56] Wei L.; He X. D.; Zhao D. M.; Kandawa-Shultz, M.; Shao, G. Q.; Wang, Y. H. Eur. J. Med. Chem. 2024, 264, 115985.
[57] Wang T.; He X.; Xu J.; Shen D.; Mei L.; Xu G.; Wei P.; Tang B. Z. CCS Chemistry 2025, 7, 105-115.
[58] Xiong X.; Liu J.; Wu L.; Xiong S.; Jiang W.; Wang P. Coord. Chem. Rev. 2024, 510, 215863.
[59] Mao L.; Huang H.; Hu D.; Ma H.; Tian M.; Zhang X.; Wei Y.Dyes Pigm. 2021, 194, 109521.
[60] Kamya E.; Yi S.; Hussain Z.; Lu Z.; Li W.; Yan J.; Ma F.; Ullah I.; Cao Y.; Pei R. ACS Macro Letters 2023, 12, 1549-1557.
[61] Zeng W.; Xu Y.; Yang W.; Liu K.; Bian K.; Zhang B. Adv. Healthcare Materials 2020, 9, 2000560.
[62] Wang H.; Wang Y.; Zheng Z.; Yang F.; Ding X.; Wu A. J. Mater. Chem. B 2022, 10, 1418-1426.
[63] Wu X.; Zhu Z.; Liu Z.; Li X.; Zhou T.; Zhao X.; Wang Y.; Shi Y.; Yu Q.; Zhu W.-H.; Wang Q. Molecules 2022, 27, 7981.
[64] Chen D.; Long Z.; Zhong C.; Chen L.; Dang Y.; Hu J.-J.; Lou X.; Xia F. ACS Appl.Bio Mater. 2021, 4, 5231-5239.
[65] Cao B.; Ma Y. F.; Zhang J.; Wang Y. N.; Wen Y.; Li Y.; Wang R.; Cao D. H.; Zhang R. P.Mater. Today Bio 2024, 26, 101091.
[66] Guo K.; Zhang M.; Cai J.; Ma Z.; Fang Z.; Zhou H.; Chen J.; Gao M.; Wang L. Small 2022, 18, 2108030.
[67] Song A.; Wang Y.; Xu J.; Wang X.; Wu Y.; Wang H.; Yao C.; Dai H.; Zhang Y.; Wang Q.; Wang C. Nano Today 2024, 54, 102109.
[68] Wang L.; Chen Y.; Han Z.; Wang E.; Zhang J.; Wang B.; Yang X. J. Anal. Test. 2023, 7, 215-226.
[69] Yan S.; Sun P.; Niu N.; Zhang Z.; Xu W.; Zhao S.; Wang L.; Wang D.; Tang B. Z. ACS Nano 2022, 16, 9785-9798.
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