Research Progress in Rigidochromic Fluorophores

doi:10.6023/cjoc202503023

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (11): 3974-3997.DOI: 10.6023/cjoc202503023 Previous Articles Next Articles

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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)

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

Cite this article

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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Fig. & Tab. 36

Figure 1. Schematic diagram of ICT launch mechanism

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

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

Figure 4. Schematic diagram of TICT launch mechanism

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

Figure 6. Structural formula of DMABN and its derivatives

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

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

Figure 9. Schematic diagram of FRET excitation

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

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

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

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

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

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)

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

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

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

Figure 18. Structural formula of a novel rigidochromic fluorophores

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

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

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)

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

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

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)

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

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

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

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

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

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

Figure 31. Schematic diagram of the domino effect sensing

Figure 32. Schematic diagram of film data writing

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

Figure 34. Schematic diagram of embedded photochemical printing

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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