光刺激响应型聚集诱导发光材料的研究进展

doi:10.6023/cjoc202403027

摘要/Abstract

光作为一种清洁且安全可控的刺激响应信号, 具有非接触性、灵敏度高及可远程精准操控等优点. 近年来, 具有光刺激响应性质的聚集诱导发光(AIE)材料取得了飞速的发展, 其发光性质可以通过光刺激来精确调控, 在生物成像、防伪、光图案化和光学传感等领域展现出了极大的应用前景. 为了促进人们对光刺激响应型AIE材料的理解, 并推动相关领域的发展, 同时也因为缺少其在内在机理方面的系统性综述, 在此, 系统总结了近些年来光刺激响应型AIE材料的研究进展. 依据光刺激响应的内在机理(光化学和光物理), 介绍了近些年来光刺激响应型AIE材料的设计、性质调控以及应用实例, 并对该领域存在的挑战和未来发展方向进行了展望, 期望能对该领域未来的发展提供有益的指导.

关键词: 光刺激响应, 聚集诱导发光, 光化学, 光物理, 激发态

Light is regarded as a clean, safe and controllable stimulus-response signal due to its non-contact, highly sensitive, and precisely manipulated characteristics. In recent years, aggregation-induced emission (AIE) materials with photoresponsive behavior have achieved rapid development. Their luminescent properties can be precisely modulated by photostimulus, enabling them to be widely applied in bio-imaging, anticounterfeiting, light patterning, and optical sensing. In order to deepen the understanding of photostimulus-responsive AIE materials and promote the advance of the related fields, also there is a lack of systematic review of their intrinsic mechanisms, the recent research progress in this area is systematically reviewed. The design, property modulation, and applications of photostimulus-responsive AIE materials are summarized according to their intrinsic mechanism of photochemistry and photophysics. The existing challenges and the future development direction of this field are prospected, hoping to provide useful guidance for the future development of this field.

Key words: photostimulus-responsive, aggregation-induced emission, photochemistry, photophysics, excited state

引用此文

唐子然, 孙浩, 朱亮亮. 光刺激响应型聚集诱导发光材料的研究进展[J]. 有机化学, 2024, 44(8): 2393-2412.

Ziran Tang, Hao Sun, Liangliang Zhu. Research Progress of Photoresponsive Photoluminescent Materials with Aggregation-Induced Emission Characteristics[J]. Chinese Journal of Organic Chemistry, 2024, 44(8): 2393-2412.

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图/表 16

图1. (a) DSA-2SP的光异构化机制、(b) DSA-2SP和DSA-2MC在不同刺激下的可逆结构异构化以及DSA-2SP粉末和薄膜的可见和荧光照片、(c) DSA-2P粉末和薄膜状态下的紫外-可见光吸收光谱和PL光谱及(d) DSA-2SP对PSt-b-PEO共聚物自组装染色形成的圆柱形胶束的超分辨成像应用

Figure 1. (a) Photoisomerization mechanism of DSA-2SP, (b) reversible structural isomerization between DSA-2SP and DSA-2MC under different stimuli, and visible and fluorescent pictures of DSA-2SP powders and films, (c) UV-Vis absorption spectra and PL spectra of DSA-2P, and (d) super-resolution imaging of cylindrical micelles formed from PSt-b-PEO copolymer self-assembly staining by DSA-2SP

图2. (a) TPE-2DTE和OTPE-2DTE光异构化机制、(b) TPE-2DTE和OTPE-2DTE的AIE特性和(c)超分辨率成像应用

Figure 2. (a) Photoisomerization mechanism of TPE-2DTE and OTPE-2DTE, (b) AIE properties of TPE-2DTE and OTPE-2DTE, and (c) application of super-resolution fluorescent imaging

图3. (a) TPENOMe的合成路线、(b) TPENOMe-a和TPENOMe-b在紫外光照射前后的紫外-可见光吸收光谱、(c) TPENOMe-a和TPENOMe-b的PL光谱(激发波长: 365 nm)、(d) TPENOMe-a和TPENOMe-b在365nm紫外和可见光下的照片、(e) TPENOMe-a和TPENOMe-b的失活方式示意图、(f)作为可见光响应可复写纸的应用及(g)在数据加密中的应用

Figure 3. (a) Synthesis route of TPENOMe, (b) UV-Vis absorption spectra of TPENOMe-a and TPENOMe-b before and after UV irradiation, (c) PL spectra (excitation wavelength: 365 nm) of TPENOMe-a and TPENOMe-b, (d) photographs of TPENOMe-a and TPENOMe-b under 365 nm UV and visible light, (e) schematic representation of the inactivation way of TPENOMe-a and TPENOMe-b, (f) application as visible light responsive rewriteable paper, and (g) application in data encryption

图4. (a) TPE-DASA光异构化机制、(b) TPE-NH和开环TPE-DASA的光致发光光谱(其中90% 的水分含量在322 nm波长下激发)、(c)可见光(532 nm)照射前后TPE-DASA薄膜的光致发光光谱(在322 nm 波长下激发)、(d) DASA发色团在其开环的三烯和环戊烯酮形式之间的可逆异构化、(e) TPE-DASA薄膜的重复荧光切换、(f)开环TPE-DASA表面浮雕光栅的三维视图AFM光学显微镜地形图及(g)通过软光刻法制作了掺杂TPE-DASA的PMMA表面浮雕光栅

Figure 4. (a) Photoisomerization mechanism of TPE-DASA, (b) photoluminescence spectra of TPE-NH and TPE-DASA (open form, with 90% water fractions excited at 322 nm), (c) photoluminescence spectra of the TPE-DASA film before and after visible light (532 nm, irradiation exciting at 322 nm), (d) reversible isomerization of DASA chromophores between their open triene and cyclopentenone forms; (e) repeated fluorescence switching of TPE-DASA films, (f) 3D-view topographical AFM image of surface relief gratings of TPE-DASA (open form), and (g) fabricated surface relief gratings of TPE-DASA doped PMMA through the soft lithographic method

图5. (a) TPAHPy的光开关特性以及光异构化机制、(b) TPAHPy、TPAHB和TPAHPyMe的化学结构和单晶结构、(c) TPAHPy在不同含水量的THF/水混合物中的光致发光光谱、(d) Z-TPAHPy在450 nm波长照射下的紫外可见吸收光谱、(e) E-TPAHPy在365 nm波长照射下在甲苯中不同时间的紫外可见吸收光谱及(f) TPAHPy用于具有可变强度的荧光图像的应用

Figure 5. (a) Photoswitchable property and the photoisomerization mechanism of TPAHPy, (b) chemical and single-crystal structures of TPAHPy, TPAHB, and TPAHPyMe, (c) photoluminescence (PL) spectra of TPAHPy in THF/water mixtures with different water fractions, UV-Vis absorption spectra of (d) Z-TPAHPy under 450 nm irradiation and (e) E-TPAHPy under 365 nm irradiation in toluene for a different time, and (f) application of TPAHPy for fluorescent images with variable intensity

图6. (a)分子双AIE性质机制图、(b)立体阻碍光致变色系统中的双重AIE行为说明、(c)具有可旋转单元的开环异构体的立体应变依赖性AIE行为、(d)具有可振动核心的闭环异构体的二面角依赖性AIE行为及(e) PSt-b-PEO嵌段共聚物胶束的超分辨率中的荧光开关

Figure 6. (a) Mechanism diagram of molecular dual AIE behavior, (b) illustration of dual AIE behaviors in steric-hindrance photochromic system, (c) steric-strain-dependent AIE behavior of open isomers with rotatable units, (d) dihedral-angle-dependent AIE behavior of closed isomers with vibrable cores, and (e) turn-on fluorescent switching in super-resolution of PSt-b-PEO block copolymer micelles

图7. (a) DP-BTO的AIE和光环化作用机制图、(b) DTMOP-BTO的光学性质谱图、(c)白光照射不同时间后, DCFH (1 μmol/L)在1 μmol/L DTMOP-BTO或1 μmol/L PO-DTMOP-BTO存在下的相对PL强度图、(d)在白光照射前后, DMPO (25 mmol/L)在DMSO中含有1 mmol/L DTMOP-BTO的情况下的EPR光谱及(e)DTMOP-BTO的抗菌应用

Figure 7. (a) Diagram of the mechanism of action of AIE and photocyclization processes of DP-BTO, (b) optical property diagrams of DTMOP-BTO, (c) plots of relative PL intensity of DCFH (1 μmol/L) in the presence of 1 μmol/L DTMOP-BTO or 1 μmol/L PO- DTMOP-BTO upon white light irradiation for different times, (d) EPR spectra of DMPO (25 mmol/L) in the presence of 1 mmol/L DTMOP-BTO in DMSO before and after white light irradiation, and (e) antibacterial applications of DTMOP-BTO

图8. (a)通过光环化合成TBPIO的路线、(b)由对p-MOTPPIO光环合成对p-MOTBPIO的路线及其光物理性质比较和生物应用探索示意图(solv: 溶液; rt: 室温; FL: 荧光; PDT: 光动力疗法; ROS: 活性氧; LD: 脂滴)、(c) TBPIO衍生物的合成路线和分子结构、反应产率(在含有少量溶解氧的N2气氛下)以及推测的光环化机理、(d) p-MOTPPIO和p-MOTBPIO的性质差异及(e) ROS生成和体外光动力学疗法的应用

Figure 8. (a) Synthetic route of TBPIO by photocyclization, (b) synthetic route of p-MOTBPIO from p-MOTPPIO by photocyclization and the schematic diagram of their photophysical property comparison and biological application exploration (solv: solution; rt: room temperature; FL: fluorescence; PDT: photodynamic therapy; ROS: reactive oxygen species; LD: lipid droplet), (c) synthetic routes and molecular structures of TBPIO derivatives, indicated with reaction yields (under N2 atmosphere with a small amount of dissolved oxygen), and proposed photocyclization mechanism, (d) differences in the properties of p-MOTPPIO and p-MOTBPIO, and (e) application of ROS generation and PDT in vitro

图9. (a) P-BTO光二聚反应示意图和在DMSO-d6中用365 nm紫外光照射P-BTO粉末0、10、20、40、60、90和120 min前后的1H NMR图谱变化、(b) P-BTO的光学性质图谱及(c) P-BTO单晶在365 nm紫外光照射1 min后的荧光显微镜图像.

Figure 9. (a) Schematic of the P-BTO photodimerization reaction and change of 1H NMR spectra of P-BTO powders before and after UV irradiation at 365 nm from a hand-held UV lamp for 0, 10, 20, 40, 60, 90, and 120 min in DMSO-d6, (b) optical property diagrams of P-BTO, and (c) fluorescence microscopy images of P-BTO single crystals during irradiation with 365 nm UV light for 1 min

图10. (a)通过不同官能团的P-BTO-X单体分子间光二聚光激活固态荧光的示意图、(b) P-BTO-OH晶体在pH值切换时在蓝色和红色发射之间切换时的光激活固态荧光、(c)晶体中的P-BTO-Cl在连续紫外光照射下的随时间变化的PL光谱和图像、(d)固态2P-BTO、2P-BTO-F、2P-BTO-Cl、2P-BTO-Br和2P-BTO-OH的PL光谱和荧光图像、(e)稳定光打印应用及(f)可重复使用的高防伪应用

Figure 10. (a) Schematic illustration of photoactivation of solid-state fluorescence through intermolecular photodimerization of P-BTO-X monomers with different functionals, (b) photoactivated solid-state fluorescence of P-BTO-OH crystal under pH switching between blue and red emission, (c) time-dependent PL spectra and images of P-BTO-Cl in crystal under continuous UV irradiation, (d) PL spectra and fluorescence images of 2P-BTO, 2P-BTO-F, 2P-BTO-Cl, 2P-BTO-Br and 2P-BTO-OH in the solid state, (e) application of stable photoprinting, and (f) application of reusable high security anticounterfeiting

图11. (a)多重光反应示意图、(b)利用Z-MPPMNAN增强信噪比和锐边的二维荧光图案及(c) Z-MPPMNAN的合成及其在不同条件下的多重可控光反应

Figure 11. (a) Schematic diagram of multiple photoreactions, (b) two-dimensional fluorescent photopattern with enhanced signal-to- background ratio and sharp edges using Z-MPPMNAN, and (c) synthesis of Z-MPPMNAN and its multiple yet controllable photoreactions under different conditions

图12. (a)受保护的水杨醛肼衍生物的化学结构和光去除1~9生成10~12的方案(这些衍生物在不同波长的紫外光照射下可发出不同波长(颜色)的荧光)、(b) 1(绿色)、2(黄色)、3(橙色)、6(浅橙色)和8(从蓝色到白紫色)在固态和聚合体(胶体溶液)状态下, 在365或300 nm波长照射下的多色荧光增强或变化、(c) 6到12和8到11在300 nm选择性紫外照射下的转化以及6和8在300或365 nm紫外照射前后的荧光光谱、(d)多色和逐步光图案化应用及(e)光激活细胞成像应用

Figure 12. (a) Chemical structures of protected salicylaldehyde hydrazine derivatives and the scheme of photoremoval reaction from 1~9 to yield 10~12 (which are fluorescent at different wavelengths (colors) by UV irradiation at different wavelengths), (b) multiple-color fluorescence enhancement or change upon irradiation at 365 or 300 nm for 1 (green), 2 (yellow), 3 (orange), 6 (light orange), and 8 (from blue to white purple) in their solid and aggregate (colloid solution) states, (c) transformation of 6 to 12 and 8 to 11 by UV irradiation selectively at 300 nm, and the fluorescence spectra of 6 and 8 before and after UV irradiation at 300 or 365 nm, (d) application of multiple-color and stepwise photopatterning, and (e) application of photoactivatable cell imaging

图13. (a)光翻转反应机制图、(b)新型光翻转反应和原位生成炔聚合反应及(c)光刻高分辨率图案化应用

Figure 13. (a) Mechanism of photo ring-flipping reaction, (b) new photo ring-flipping reaction and in situ generation of alkyne polymerization, and (c) application of photolithography high-resolution patterning

图14. (a) TPE-4N的光致和热致机理图解、(b)晶体态和气体态的量子化学计算及(c) TPE-4N的应用

Figure 14. (a) Illustration of the photo- and thermo-responsive mechanism of TPE-4N, (b) quantum chemical calculation on crystalline and gas states, and (c) application of TPE-4N

图15. (a)光激发控制AIP的示意图、(b)化合物15构象变化的理论研究及(c)生物成像应用

Figure 15. (a) Schematic illustration of the photoexcitation-controlled AIP, (b) theoretical study of the conformational change of compound 15 upon photoexcitation, and (c) application of bioimaging

图16. (a)光激活S-CD磷光的推测机制、(b)多种刺激激活室温磷光策略及(c) S-CDs的应用

Figure 16. (a) Proposed mechanism for the photostimulus activated phosphorescence of S-CDs, (b) multiple stimulus-activated room-temperature phosphorescence strategies, and (c) application of S-CDs

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