Research Progress of Photoresponsive Photoluminescent Materials with Aggregation-Induced Emission Characteristics

doi:10.6023/cjoc202403027

Abstract

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

Cite this article

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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Fig. & Tab. 16

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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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