刚致荧光变色分子的研究进展

doi:10.6023/cjoc202503023

有机化学 ›› 2025, Vol. 45 ›› Issue (11): 3974-3997.DOI: 10.6023/cjoc202503023 上一篇下一篇

综述与进展

刚致荧光变色分子的研究进展

朱惠芬^a^,^b^,^c, 裴海洲^b^,^c, 刘杰^b^,^c^,^*(), 黄伟国^a^,^b^,^c^,^*()

^a 福建师范大学化学与材料学院福州 350117
^b 中国科学院福建物质结构研究所结构化学重点实验室福州 350002
^c 中国科学院大学福建学院福州 350002

收稿日期:2025-03-24 修回日期:2025-05-22 发布日期:2025-06-19
基金资助:
国家自然科学基金(52473201); 国家自然科学基金(22275193); 国家自然科学基金(22275189); 福建省科技厅(2023I0030); 中国科学院海西研究所自部署项目研究计划CXZX-2022- GH09(E255KF0101); 福建省光电子信息科技创新实验室(2021ZR115); 及中国科学院福建物质结构研究所(E055AJ01); 及中国科学院福建物质结构研究所(E355AJ01)

Research Progress in Rigidochromic Fluorophores

Huifen Zhu^a^,^b^,^c, Haizhou Pei^b^,^c, Jie Liu^b^,^c^,^*(), Weiguo Huang^a^,^b^,^c^,^*()

^a College of Chemistry and Materials, Fujian Normal University, Fuzhou 350117
^b State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002
^c Fujian College, University of Chinese Academy of Sciences, Fuzhou 350002

Received:2025-03-24 Revised:2025-05-22 Published:2025-06-19
Contact: *E-mail: whuang@fjirsm.ac.cn; liujie@fjirsm.ac.cn
Supported by:
National Natural Science Foundation of China(52473201); National Natural Science Foundation of China(22275193); National Natural Science Foundation of China(22275189); Fujian Provincial Department of Science and Technology(2023I0030); Self-Deployment Project Research Program of Haixi Institutes, Chinese Academy of Science, CXZX-2022-GH09(E255KF0101); Fujian Science & Technology Innovation Laboratory for Optoelectronic Information of China(2021ZR115); Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences(E055AJ01); Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences(E355AJ01)

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摘要/Abstract

聚合物作为一种重要的材料, 被广泛应用于工程和医疗等多个领域. 其中, 刚性是聚合物的重要力学性能之一, 其对结构强度、流变行为及玻璃化转变温度等具有关键影响. 因此, 准确测量和表征聚合物的刚性对于材料设计和性能调控至关重要. 传统刚致荧光变色分子在刚性增强时通常表现为轻微蓝移或仅强度发生变化, 导致其灵敏度低, 信号对比度差, 限制了其应用潜力. 近年来研究者们开发了一类新型刚致荧光变色分子, 它们在高刚性环境下呈现独特的刚致红移现象, 并表现出更高的检测灵敏度. 基于此, 系统介绍了几种经典的刚致荧光变色分子的工作机理, 并深入探讨了新型刚致荧光变色分子的设计策略、制备方法及其在各领域的应用前景.

关键词: 刚致荧光变色分子, 聚合物基质, 荧光红移, 强相互作用, 电荷转移

Polymers, as essential materials, have been widely utilized in multiple fields such as engineering and medicine. Among their properties, rigidity stands as a critical mechanical characteristic, which plays a decisive role in structural integrity, rheological behavior, and the glass transition temperature. Therefore, accurately measuring and characterizing polymer rigidity is crucial for material design and performance regulation. Conventional rigidochromic fluorophores typically exhibit either a slight blue-shifted emission or solely intensity variations upon rigidity enhancement, resulting in low sensitivity and poor signal contrast, which limits their application potential. However, in recent years, researchers have discovered a novel class of rigidochromic fluorophores that exhibit a unique rigidity-induced red shift in highly rigid environments, along with enhanced detection sensitivity. Based on this, the working mechanisms of several classical rigidochromic fluorophores are systematically introduced, the design strategies and preparation methods of novel rigidochromic fluorophores, and their potential applications in various fields are explored deeply.

Key words: rigidochromic fluorophore, polymer matrix, fluorescence redshift, strong interaction, charge transfer

引用此文

朱惠芬, 裴海洲, 刘杰, 黄伟国. 刚致荧光变色分子的研究进展[J]. 有机化学, 2025, 45(11): 3974-3997.

Huifen Zhu, Haizhou Pei, Jie Liu, Weiguo Huang. Research Progress in Rigidochromic Fluorophores[J]. Chinese Journal of Organic Chemistry, 2025, 45(11): 3974-3997.

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图/表 36

图1. ICT发射机制示意图

Figure 1. Schematic diagram of ICT launch mechanism

图2. 荧光探针DMANS以及各种树脂的结构

Figure 2. Fluorescence probe DMANS and the structure of various resins

图3. 与DA、TMPTA和TMPTA/DA混合物光聚合后的荧光探针的发射变化

Figure 3. Emission changes of fluorescent probe after photopolymerization with DA, TMPTA, and TMPTA/DA mixtures

图4. TICT发射机制示意图

Figure 4. Schematic diagram of TICT launch mechanism

图5. DMABN的TICT模型以及D-A的TICT激发态模型

Figure 5. TICT model of DMABN and model of TICT excited state for D-A

图6. DMABN及其衍生物的结构式

Figure 6. Structural formula of DMABN and its derivatives

图7. (a) DMABN及其相关化合物的结构式以及室温下(b) DMABN、(c) DEABN和(d) DMABEE在不同Mw的PMMA聚合物基质中的荧光光谱

Figure 7. (a) Structural formulas of DMABN and related compounds, and fluorescence spectrum of (b) DMABN, (c) DEABN and (d) DMABE in different Mw PMMA polymer matrix at room temperature

图8. 荧光比的增长率与重量法测定的聚合速率之间的相关关系

Figure 8. Correlation between the growth rate of the fluorescence ratio and the polymerization rate measured by gravimetric method

图9. FRET激发示意图

Figure 9. Schematic diagram of FRET excitation

图10. 利用FAK生物传感器的构象变化检测两个不同质膜微区DRM (Lyn-FAK)和非DRM (Kras-FAK)处的FAK信号的底层机制的示意图

Figure 10. Schematic diagram of the underlying mechanism detecting FAK signals at two different plasma membrane microregions DRM (Lyn-FAK) and non-DRM (Kras-FAK) through conformational change of the FAK biosensor

图11. 在不同刚度的基质上接种40 min后的细胞面积分析 (n=15, ***P<0.001)

Figure 11. Analysis of cell area after 40 min of seeding on substrates with different stiffness (n=15, ***P<0.001)

图12. 用于监测(光)聚合过程固化度的荧光探针

Figure 12. Fluorescence probe used to monitor the curing degree of the polymerization process

图13. PMMA/TMPTA光敏体系中fac-ClRe(CO)3(4,7-Ph2- phen)的发射光谱与紫外光照时间的关系

Figure 13. Relationship between the emission spectra of fac- ClRe(CO)₃(4,7-Ph₂phen) and UV irradiation time in a PMMA/ TMPTA photosensitive system (A) 0 s; (B) 5 s; (C) 10 s; (D) 20 s; (E) 30 s; (F) 60 s

图14. pPFPA的紫外-可见吸收光谱、荧光发射光谱和PTF1在不同溶剂中的荧光发射光谱

Figure 14. UV-Vis absorption spectrum, fluorescence emission spectrum of pPFPA and fluorescence emission spectrum of PTF1 in different solvents

	Component	Fluorescent intensity	Fluorescent color	Chemical structure	Mechanism
Anti-rigidochromism	Fluorophore＋non- conjugated polymer	NA^a	Red shift	Planar, rigid, conjugated fluorophore with various polymers	CTC and TSC^b
Rigidochromism	Fluorophore＋non- conjugated polymer	NA^a	Blue shift	Rotatable, conjugated, D-A structured fluorophores	TICT, ICT, Excimer, MLCT
AIE	Fluorophore	Increase	NA^a	Rotatable, vibrable, conjugated fluoro- phores	RIR^c, RIV^d
CTE	Non-conjugated polymer	Increase	NA^a	Polymer containing NH₂, OH, C=O, and other groups with n and π electrons	TSC^b
PIE	Non-conjugated polymer	Increase	Red shift	Specific monomers/functional groups (e.g., borane, aldehyde, dichlorobenzo- phenone)	TSC^b
SIE	Fluorophore guest＋ host	NA	Red shift	Well-defined fluorophores and specific hosts (e.g, macrocycles, molecular cages)	RIR, dimerization, ICT

表1. 新型刚致变色现象与聚集诱导发射(AIE)、簇发光(CTE)、聚合诱发发射(PIE)和超分子组装诱发发射(SIE)的主要区别

Table 1. Key differences of new-rigidochromism with respected to aggregation-induced emission (AIE), clusteringtriggered emission (CTE), polymerization induced emission (PIE), and supramolecularassembly induced emissions (SIE)

图15. (a) PTF1/pPFPA在甲苯/四氢呋喃(体积比1∶2)溶液中共组装过程的荧光图像以及相同条件下PTF1和pPFPA单独溶液48 h后的荧光图像(PTF1的浓度为7.5×10－6 mol/L, PTF1/PFPA物质的量之比为1∶5000); (b, c)沉淀前后四氢呋喃(THF)中PTF1/pPFPA共组装直径变化的DLS表征; (d)顶层溶液中PTF1/pPFPA共组装的平均直径随时间的分布

Figure 15. (a) Fluorescence images of PTF1/pPFPA during the co-assembly process in toluene/THF (volume ratio 1∶2) solution and after 48 h of PTF1 and pPFPA alone solution under the same conditions (molar concentration of PTF1 is 7.5×10－6 mol/L, and the molar ratio of PTF1/PFPA is 1∶5000); (b, c) DLS characterization of the variation of PTF1/pPFPA coassembly diameter in THF before and after precipitation; (d) distribution of the mean diameter of PTF1/pPFPA coassembled in the top solution with time

图16. PTF1/pPFPA (a,b)、pPFPA (c,d)和PTF1 (e,f)共组装膜的HRTEM

Figure 16. HRTEM of PTF1/pPFPA (a, b), pPFPA (c, d) and PTF1 (e, f) co-assembly film

图17. (a)电子从PTF1(蓝色虚线圈段1和含有3个菲啶单位的段2)到pPFPA(段3)的跃迁示意图以及(b)不同激发态下电子贡献率

Figure 17. (a) Electrons from PTF1 (blue dotted line segment 1 and contains three phenanthridine organism unit section 2) to pPFPA (segment 3) under different excited state transition diagram and (b) the electronic contribution

图18. 新型刚致荧光变色分子的结构式

Figure 18. Structural formula of a novel rigidochromic fluorophores

图19. (a) PTF2、 (b) PTF3随聚合物pPFPA浓度增加的发射(PFPA代表pPFPA的重复单元); (c) B1、PTF1和T1在甲苯中随pPF- PA浓度增加的荧光图像以及三种荧光团的发射波长和强度随甲苯中pPFPA浓度的增加而变化

Figure 19. Emission of (a) PTF2 and (b) PTF3 with increasing concentration of polymer pPFPA (PFPA stands for repeating unit of pPFPA); (c) Fluorescence images of B1, PTF1 and T1 with increasing pPFPA concentration in toluene, and emission wavelength and intensity of the three fluorophores changed with increasing pPFPA concentration in toluene

图20. (a) trans-D5、(b) cis-D5和(c) cyclo-D5的单晶结构(比例尺: 0.5 mm); (d) trans-D5、(e) cis-D5和(f) cyclo-D5在自然光和紫外光下的图像以及相应的UV-Vis和荧光发射光谱(图像的比例为1.5 cm×2 cm); (g) D5分子的化学结构和光转化

Figure 20. Single crystal structures of (a) trans-D5, (b) cis-D5 and (c) cyclo-D5 (scale: 0.5 mm); Images under natural light and UV light and corresponding UV-Vis and fluorescent emission spectra of (d) trans-D5, (e) cis-D5, and (f) cyclo-D5 (the scale of the images is 1.5 cm×2 cm); (g) Chemical structures and photo transformation of D5 molecules

图21. (a~c) trans-D5在甲苯中的图像、紫外-可见吸收和发射光谱; (d~f) cis-D5在甲苯中的图像、紫外-可见吸收和发射光谱; (g~i) cyclo-D5在甲苯中的图像、紫外-可见吸收和发射光谱(D5浓度: 2.5×10－5 mol/L)

Figure 21. (a~c) Image, UV-Vis absorption and emission spectra of trans-D5 in toluene; (d~f) Image, UV-vis absorption and emission spectra of cis-D5 in toluene; (g~i) Image, UV-vis absorption and emission spectra of cyclo-D5 in toluene (D5 concentration: 2.5×10－5 mol/L)

图22. PTF1/pPFPA 溶液的(a)荧光图像和(b)发射光谱; (c) PTF1/pPFPA溶液1931 CIE色度图(PTF1浓度为1.0×10－6 mol/L, pPFPA分别球磨0, 1和3 h); (d~g)不同浓度低Mw pPFPA和不同浓度高Mw pPFPA下的SE和F2的发射光谱; (h~k)不同浓度的低Mw PEtsOx和不同浓度的高Mw PEtsOx下SE和F2的发射光谱

Figure 22. (a) Fluorescence image and (b) emission spectrum of PTF1/pPFPA solution; (c) 1931 CIE chromaticity diagram of PTF1/pPFPA solution (PTF1 concentration was 1.0×10－6 mol/L and pPFPA was ball-milled for 0, 1, and 3 h, respectively); (d~g) Emission spectra of SE and F2 under different concentrations of low Mw pPFPA and different concentrations of high Mw pPFPA; (h~k) Emission spectra of SE and F2 under different concentrations of low Mw PEtsOx and high Mw PEtsOx

图23. (a) PTF1和PFPA单体共混物的发射光谱随溶液聚合时间的变化; (b) 1931 CIE色度坐标随pPFPA Mn的增加由蓝色变为黄色; (c) I590/I455对pPFPA Mn的曲线拟合图; (d) PTF1随pPFPA分子量变化的荧光发射图像

Figure 23. (a) Emission spectra evolution of PTF1and PFPA monomer blends over the solution polymerization time; (b) 1931 CIE chromaticity coordinate changed from blue to yellow as pPFPA Mn increases; (c) Plotting I590/I455 against pPFPA Mn; (d) Fluorescence emission images of PTF1 over molecular weight variation of pPFPA

图24. pPFPA、P1和P2对PF-B (a~c)和PF-N (d~f)的荧光响应(其中的摩尔比由荧光分子和聚合物的重复单元计算, 荧光分子的浓度为2.5×10－5 mol/L)

Figure 24. Fluorescence response of pPFPA, P1 and P2 to PF-B (a~c) and PF-N (d~f) (the molar ratio is calculated by the repeating unit of the fluorescent molecule and the polymer, concentration of the fluorescent molecule is 2.5×10－5 mol/L)

图25. SN、DN、SE、DE、F2和TF3分别在(a) PMMA、(b) pPFPA和(c) PEtsOx中随浓度增加的发射

Figure 25. Emission of SN, DN, SE, DE, F2 and TF3 in (a) PMMA, (b) pPFPA and (c) PEtsOx with increasing concentration, respectively

图26. 不同浓度线性pPFPA和不同浓度星形pPFPA下的SE和F2的发射光谱

Figure 26. Emission spectra of SE and F2 at different concentrations of linear pPFPA and star-shaped pPFPA

图27. (a~d)不同浓度PEtsOx-b-PEtOxSE和不同浓度PEtsOx-r-PEtOx下的SE和F2的发射光谱; (e) PEtsOx, (f) PEtsOx-b-PEtOx, (g) PEtsOx-r-PEtOx和(h) PEtOx的DSC表征; (i) SE, (j) SE/PEtsOx, (k) SE/PetsOx-b-PEtOx, (l) SE/PEtsOx-r-PEtOx共组装膜的HRTEM表征

Figure 27. (a~d) Emission spectra of SE and F2 under different concentrations of PEtsOx-b-PEtOxSE and PEtsOx-r-PEtOx; DSC characterization of (e) PEtsOx, (f) PEtsOx-b-PEtOx, (g) PEtsOx-r-PEtOx, and (h) PEtOx; HRTEM characterization of (i) SE, (j) SE/PEtsOx, (k) SE/PEtsOx-b-PEtOx, and (l) SE/PEtsOx-r-PEtOx co-assembly film

图28. (a) CLC薄膜制备工艺示意图、(b)紫外-可见CLC-1和CLC-2薄膜的透射光谱、(c) CLC-1和CLC-2薄膜的荧光发射光谱及(d) CLC-1和CLC-2薄膜的不对称因子值

Figure 28. (a) Schematic diagram of CLC film preparation process, (b) UV-Vis transmission spectra of CLC-1 and CLC-2 films, (c) fluorescence emission spectra of CLC-1 and CLC-2 films, and (d) asymmetry factor values for the CLC-1 and CLC-2 films

图29. (a) 纯PTF1和PTF1/pPFPA在甲苯中在77 K下的磷光图像、(b)不同温度下PTF1/pPFPA在甲苯中的荧光图像、(c) PTF1/pPFPA的磷光光谱和(d)不同温度下PTF1/pPFPA在甲苯中的发射光谱

Figure 29. (a) Phosphorescence images of pure PTF1 and PTF1/pPFPA in toluene at 77 K, (b) fluorescence images of PTF1/pPFPA in toluene at different temperatures, (c) phosphorescence spectra of PTF1/pPFPA film at different temperatures, and (d) emission spectra of PTF1/pPFPA in toluene at different temperatures

图30. 不同TFA浓度甲苯中(a) PF-B和(d) PF-N的荧光光谱和图像(荧光染料的浓度为2.5×10−5 mol/L)、(b) TFA-TEA处理循环后PF-B的可逆荧光光谱变化和(c)相应的I430/I384、(e) TFA-TEA处理循环后PF-N的可逆荧光光谱变化和(f)相应的I550/I431

Figure 30. Fluorescence spectra and images of (a) PF-B and (d) PF-N in toluene with different concentrations of TFA (concentration of the fluorescent dyes is 2.5×10−5 mol/L), (b) reversible fluorescence spectral change of PF-B upon cycles of TFA-TEA treatments and (c) the corresponding I430/I384, (e) reversible fluorescence spectral change of PF-N upon cycles of TFA-TEA treatments, and (f) the corresponding I550/I431

图31. 多米诺骨牌效应传感示意图

Figure 31. Schematic diagram of the domino effect sensing

图32. 薄膜数据写入示意图

Figure 32. Schematic diagram of film data writing

图33. 结合液晶薄膜实现多维防伪示意图

Figure 33. Schematic diagram of multi-dimensional anti-counterfeiting combined with liquid crystal film

图34. 嵌入式光化学打印示意图

Figure 34. Schematic diagram of embedded photochemical printing

图35. 使用DAPI、B1、F1和T1作为探针的活细胞成像

Figure 35. Live cell imaging using DAPI, B1, F1, and T1 as the probes The excitation wavelengths (λex) for DAPI, B1, F1, and T1 are 340, 350, 360, and 360 nm, respectively. The emission wavelengths (λem) of DAPI, B1, F1, and T1 are 450, 450, 550, and 500 nm, respectively. The scale bar is 20 μm.

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刚致荧光变色分子的研究进展

Research Progress in Rigidochromic Fluorophores

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