Aggregation-Induced Emission and Cell Imaging of Triphenylimidazole Derivatives

doi:10.6023/cjoc202212004

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (7): 2454-2461.DOI: 10.6023/cjoc202212004 Previous Articles Next Articles

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三苯基咪唑衍生物的聚集诱导发光性质及其细胞成像应用

赵洋, 陈盼盼, 韩立志^*(), 王恩举^*()

海南师范大学化学与化工学院热带药用资源化学教育部重点实验室热带药用植物化学海南省重点实验室海口 571158

收稿日期:2022-12-05 修回日期:2023-03-04 发布日期:2023-03-30
通讯作者: 韩立志, 王恩举
基金资助:
海南省自然科学基金(222MS059)

Aggregation-Induced Emission and Cell Imaging of Triphenylimidazole Derivatives

Yang Zhao, Panpan Chen, Lizhi Han(), Enju Wang()

Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, College of Chemistry & Chemical Engineering, Hainan Normal University, Haikou 571158

Received:2022-12-05 Revised:2023-03-04 Published:2023-03-30
Contact: Lizhi Han, Enju Wang
Supported by:
Natural Science Foundation of Hainan Province(222MS059)

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Abstract

Aggregation-induced emission (AIE)-active materials have great advantages in the biomedical field and open up a whole new world of opportunity for bioimaging. Herein, two butylidene-bridged bisimidazole derivatives and two butyl-sub- stituted monoimidazole derivatives were easily synthesized from dibromobutane/bromobutane and 2,4,5-triphenyl-1H-imida- zole derivatives. All the obtained imidazole derivatives showed excellent AIE properties, and the derivatives containing methoxy groups exhibited red-shifted emission. The research on AIE mechanism indicated that the restriction of twisted intramolecular charge transfer (TICT) mechanism was responsible for the AIE behaviors of these imidazole derivatives. Therefore, the strong electron-withdrawing nitro group is crucial for their AIE property. In addition, the steric effect of the substituent group at 1-position of imidazole ring is also indispensable for AIE, because it results in the twisted conformation and thus hampers the intermolecular π-π stacking interactions. Ultimately, the cell staining and bioimaging behaviour of butyl-substituted monoimidazole derivatives were investigated. Both of them displayed an excellent bioimaging performance in blue, green and red channels, but the different staining regions in cells were observed in different channels.

Key words: aggregation-induced emission (AIE), triphenylimidazole, twisted intramolecular charge transfer (TICT), twisted conformation

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Yang Zhao, Panpan Chen, Lizhi Han, Enju Wang. Aggregation-Induced Emission and Cell Imaging of Triphenylimidazole Derivatives[J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2454-2461.

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Fig. & Tab. 7

Scheme 1. Synthetic route to the triphenylimidazole derivatives

Figure 1. Absorption spectra of BTPI-H, BTPI-OMe, BBI-H and BBI-OMe in DMSO (solid line) and DMSO/H2O (V∶V=1∶9) (dashed line)

Figure 2. Fluorescence spectra of BBI-H (A), BBI-OMe (B), BTPI-H (C) and BTPI-OMe (D) in DMSO/H2O mixtures with different water fractions (fw), and photos (E) of them taken under 365 nm UV excitation 10 μmol/L, λex=377 nm for BBI-H and BTPI-H, and λex=394 nm for BBI-OMe and BTPI-OMes

Figure 3. Fluorescence spectra of BTPI-H in different solvents (A) and photographs taken under 365 nm UV excitation (B)

Figure 4. HOMO-LUMO distributions of BTPI-H and BTPI-OMe

Figure 5. Fluorescence spectra of TriPI-NO2 (A) and TetraPI-NO2 (B) in DMSO/H2O mixtures with different water fractions (λex=377 nm)

Figure 6. Confocal images of HeLa cells stained with the self-aggregation nanoparticles of BTPI-H (A, B, C, D) and BTPI-OMe (E, F, G, H) for 20 min (A and E) images in brightfield mode, (B and F) images in blue channel (λex=405 nm, λem=430~475 nm), (C and G) images in green channel (λex=488 nm, λem=500~550 nm), (D and H) images in red channel (λex=640 nm, λem=663~737 nm)

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三苯基咪唑衍生物的聚集诱导发光性质及其细胞成像应用

Aggregation-Induced Emission and Cell Imaging of Triphenylimidazole Derivatives

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