高亮度近红外荧光染料研究进展

doi:10.6023/cjoc202303043

有机化学 ›› 2023, Vol. 43 ›› Issue (11): 3745-3760.DOI: 10.6023/cjoc202303043 上一篇下一篇

综述与进展

高亮度近红外荧光染料研究进展

邱建文^a, 刘梦^a, 熊新怡^a, 高勇^a^,^b^,^*(), 朱虎^a^,^c^,^*()

a 福建师范大学化学与材料学院福州 350117
b 福建师范大学福建省高分子材料重点实验室福建省先进材料化工基础重点实验室福州 350117
c 福建省师范大学生物医学材料与组织工程闽台科技合作基地工业生物催化福建省高校工程研究中心医学光电科学与技术教育部重点实验室福州 350117

收稿日期:2023-03-29 修回日期:2023-06-18 发布日期:2023-07-05
基金资助:
国家自然科学基金(U1805234); 福建省自然科学基金(2021J01147); 福建省高校创新团队培育计划、福建省百人计划、中央引导地方科技专项资金(2020L3008)

Research Progress in High Brightness Near Infrared Fluorescent Dyes

Jianwen Qiu^a, Meng Liu^a, Xinyi Xiong^a, Yong Gao^a^,^b(), Hu Zhu^a^,^c()

a College of Chemistry and Materials Science, Fujian Normal University, Fuzhou 350117
b Fujian Provincial Key Laboratory of Polymer Materials, Fujian Provincial Key Laboratory of Advanced Materials Oriented Chemical Engineering, Fujian Normal University, Fuzhou 350117
c Fujian-Taiwan Science and Technology Cooperation Base of Biomedical Materials and Tissue Engineering, Engineering Research Center of Industrial Biocatalysis, Key Laboratory of OptoElectronic Science and Technology for Medicine of Ministry of Education, Fujian Normal University, Fuzhou 350117

Received:2023-03-29 Revised:2023-06-18 Published:2023-07-05
Contact: * E-mail: gaoyong@fjnu.edu.cn; zhuhu@fjnu.edu.cn
Supported by:
National Natural Science Foundation of China(U1805234); Natural Science Foundation of Fujian Province(2021J01147); Program for Innovative Research Team in Science and Technology in Fujian Province University, the 100 Talents Program of Fujian Province and the Special Funds of the Central Government Guiding Local Science and Technology Development(2020L3008)

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摘要/Abstract

近红外光(650~1700 nm)在生物成像中具有组织穿透深度大、受生物体自身荧光干扰小和对生物体光损伤小等优点. 因此, 近红外染料已成为生物成像新的研究热点. 近红外荧光染料较窄的能量带隙使激发态非辐射跃迁几率增大, 导致荧光强度大幅降低. 同时较长的共轭疏水骨架及强大的分子电荷转移能力, 使他们容易与外部分子交互, 从而加剧非辐射能量损耗增加, 致使荧光强度降低. 为了获取高亮度近红外荧光染料, 研究人员针对近红外染料做了很多改进和修饰. 从荧光染料的结构-性质关系角度, 综述了目前主流的高亮度近红外染料的发展情况, 希望能为发展高亮度近红外荧光染料提供帮助和指导.

关键词: 高亮度, 近红外, 荧光, 染料

Abstract Due to the merits of near-infrared light (NIR) (650~1700 nm), such as deep tissue penetration, lower autofluore- scence interference in vivo, and little light damage to organisms, NIR dyes have been one of the research focuses in bioimaging. The narrow bandgaps of NIR dyes increase the probability of non-radiative transition of the excited state, resulting in a significant reduction of fluorescence intensity. Meanwhile, the longer conjugated hydrophobic skeleton and strong molecular charge transfer ability make NIR dyes easy to interact with external molecules, thus increasing the non-radiative energy loss and reducing the fluorescence intensity. To obtain NIR dyes with high brightness, researchers have made many improvements and modifications. From the perspective of the structure-property relationship of fluorescent dyes, the development of mainstream high-brightness near-infrared dyes is reviewed, hoping to provide assistance and guidance for the development of NIR fluorescent dyes with high-brightness.

Key words: high brightness, near infrared, fluorescence, dyes

引用此文

邱建文, 刘梦, 熊新怡, 高勇, 朱虎. 高亮度近红外荧光染料研究进展[J]. 有机化学, 2023, 43(11): 3745-3760.

Jianwen Qiu, Meng Liu, Xinyi Xiong, Yong Gao, Hu Zhu. Research Progress in High Brightness Near Infrared Fluorescent Dyes[J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3745-3760.

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图/表 22

图1. 小分子染料从可见光区域到近红外区域的设计策略

Figure 1. Design strategy for small molecular dyes from the visible region to the near-infrared region

图2. 有机小分子荧光染料光物理过程的雅布隆斯基图

Figure 2. Jablonski diagram of the photophysical processes of organic small molecule fluorophores Abs., IC, Fluo., ISC, and phos. represent absorption, internal conversion, fluorescence, intersystem crossing and phosphorescence, respectively

图3. 氧杂蒽(a)和罗丹明染料(b)的分子结构.

Figure 3. Molecular structures of xanthene (a) and rhodamine dyes (b)

图4. 氧杂蒽染料1的分子结构

Figure. Molecular structure of xanthene dye 1

图5. 氧杂蒽染料2~9的分子结构.

Figure 5. Molecular structures of xanthene dyes 2~9

图6. 氧杂蒽染料10~13的分子结构和基本光物理性质

Figure 6. Molecular structures and basic photophysical properties of xanthene dyes 10~13

图7. 氧杂蒽染料14~20的分子结构和基本光物理性质

Figure 7. Molecular structures and basic photophysical properties of xanthene dyes 14~20

图8. 氧杂蒽染料21~22的分子结构和基本光物理性质.

Figure 8. Molecular structures and basic photophysical properties of xanthene dyes 21~22

图9. BODIPY的分子结构

Figure 9. Molecular structure of BODIPY

图10. BODIPY染料23~30的分子结构和基本光物理性质

Figure 10. Molecular structures and basic photophysical properties of BODIPY dyes 23~30

图11. BODIPY染料31~38的分子结构和基本光物理性质

Figure 11. Molecular structures and basic photophysical properties of BODIPY dyes 31~38

图12. BODIPY染料39~42的分子结构和基本光物理性质

Figure 12. Molecular structures and basic photophysical properties of BODIPY dyes 39~42

图13. BODIPY染料43~46的分子结构和基本光物理性质.

Figure 13. Molecular structures and basic photophysical properties of BODIPY dyes 43~46

图14. 菁类染料的分子结构

Figure 14. Molecular structure of cyanine dye

图15. 菁类染料47~50的分子结构和基本光物理性质

Figure 15. Molecular structures and basic photophysical properties of cyanine dyes 47~50

图16. 菁类染料51~53的分子结构和基本光物理性质

Figure 16. Molecular structures and basic photophysical properties of cyanine dyes 51~53

图17. 菁类染料54~64的分子结构和基本光物理性质

Figure 17. Molecular structures and basic photophysical properties of cyanine dyes 54~64

图18. 菁类染料65~66的分子结构和基本光物理性质

Figure 18. Molecular structures and basic photophysical properties of cyanine dyes 65~66

图19. 噁嗪染料的分子结构

Figure 19. Molecular structure of oxazine dye

图20. 菁类染料67~72的分子结构和基本光物理性质.

Figure 20. Molecular structures and basic photophysical properties of cyanine dyes 67~72

图21. 菁类染料73~76的分子结构和基本光物理性质

Figure 21. Molecular structures and basic photophysical properties of cyanine dyes 73~76

图22. 杂交染料77~87的分子结构和基本光物理性质.

Figure 22. Molecular structures and basic photophysical properties of crossbreeding dyes 77~87

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高亮度近红外荧光染料研究进展

Research Progress in High Brightness Near Infrared Fluorescent Dyes

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