Advances in Aggregation-Induced Emission Molecules Based on Organic Photochromism

doi:10.6023/cjoc202108046

Abstract

In recent years, organic aggregation-induced emission (AIE) materials have effectively overcome the main shortcomings of traditional fluorescent materials in aggregation-caused quenching (ACQ) in solid or aggregate state, and have been widely studied and applied in cell imaging, biological probes, optical devices, anti-counterfeiting materials, etc. However, unifunctional AIE materials can’t meet the advancement of science and technology, and the increasing demands for material life. In order to expand the application range of AIE materials, the study of AIE molecules combined with multifunctional groups has further become one of the current focused topics in the field of materials. Multifunctional molecules with both photochromic and AIE properties have received extensive attention due to their promising performances in reversible control and multiple photoresponses upon external stimuli and good control properties. Based on the different isomerization mechanisms of the photochromic units in the multifunctional molecules, and combined with the research practice of our group in this topic, this presentation briefly reviews the main advances and application of AIE molecules based on the different photochromic functional units since the 21st century. It also looks forward to its future development, hoping to provide some reference and thinking for the research in this field.

Key words: multifunctional materials, aggregation-induced emission, photochromism, isomerization mechanism

Cite this article

Wei Ding, Bowen Cheng, Meng Wang, Qingyu Dou, Siying Li, Peng Zhang, Qianfu Luo. Advances in Aggregation-Induced Emission Molecules Based on Organic Photochromism[J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 363-383.

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Fig. & Tab. 40

Figure 1. Photochromic process of DTE-TPE and its fluorescence behavior in solution and aggregate state

Figure 2. Molecular structures of compounds DTE-1-DTE-5

Figure 3. Fluorescence pictures of 1a, 2a colloidal suspension and 1a, 2a in THF solution

Figure 4. Molecular structure of dithiophenylethene

Figure 5. Molecular structure and photochromic process of BMBT

Figure 6. Photoresponse behavior of DTE-QM in solution and in the aggregated state

Figure 7. Molecular structure and photochromic process of TPE-DASA

Figure 8. Fluorescence changes of DTE-BP embedded in PMMA or PVDF before and after photocyclization

Figure 9. Molecular structure of B2C before and after photocyclization

Figure 10. Molecular structure of the compound and discoloration after removal of the UV lamp (1p-h: the product after grinding and heating treatment; 1c: single crystal)

Figure 11. Chemical structure transition of TrPECl2 before and after UV light irradiation

Figure 12. Molecular structure of TrPEBCar and the effect of pressing or heating in the solid state on photochromic behavior

Figure 13. Molecular structures and photochromic process of BDPM-DHT

Figure 14. Molecular structure of hybrid tetraarylethene and its derivatives

Figure 15. Molecular structures of TAE-1,2,3 and TAE-1-O, 2-O, 3-O

Figure 16. Structure of DCS, DS, poly(DCS-BTE) and photochromic process of poly(DCS-BTE)

Figure 17. Structure of each molecular unit constituting LCNPs

Figure 18. Molecular structure of polymer

Figure 19. Molecular structure of P-PHT

Figure 20. Molecular structure of G-C and H

Figure 21. Molecular structures of CN-TFMBE, SS-TFMBE and TFM-BTE

Figure 22. Photochromic response of CF3-BPDBTEO and thermal response behavior of CN-TFMBE

Figure 23. Isomerization of TPE-SP1 and TPE-SP2 under UV/Vis and acid/base

Figure 24. Response mechanism of SP-TPE-SP under HCl/NH3 and UV/Vis

Figure 25. Photochromism and acid-base response of SFX-2SP

Figure 26. Fluorescence change and imaging mechanism of AIE nanoprobe during detection

Figure 27. Molecular structure of DSA-2SP and AIE regulatory mechanism

Figure 28. Mechanism of photochromism and fluorescence change of TPE-NP in solution and aggregate state

Figure 29. Molecular structure of RhTPE and isomerization under acid/base and UV/Vis irradiation

Figure 30. Molecular structure of AIE units and spiropyran units in polymers

Figure 31. Structural fragments of polymer nanoparticles

Figure 32. Molecular structure of each building block and self-assembly between the building blocks

Figure 33. Multicolor emission tuning for organogels formed with the ensemble of LMWG1, PI2, SP3 by varying the temperature, concentration, and light irradiation

Figure 34. ESIPT and PET processes of compound TPASB in solution and aggregated state

Figure 35. ESIPT process of the compound

Figure 36. Intramolecular proton transfer of the compound

Figure 37. Regulatory mechanism of compounds on AIE behavior through ESIPT process

Figure 38. Proton transfer of pyrazolinone derivatives with AIE properties

Figure 39. Molecular structures of 3BuES and 3BuAz

Figure 40. Molecular structures of trans-Cn-Chol

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