Tetraarylimidazole-Based Aggregation-Induced Emission Luminogens and Their Cell-Imaging Application

doi:10.6023/cjoc202210002

Abstract

1,2,4,5-Tetraphenylimidazole takes a highly twisted propeller-like conformation, which results in its potential to be developed into aggregation-induced emission (AIE)-active molecules. Herein, two tetraarylimidazole-based aggregation- induced emission luminogens (TAI-m and TAI-q) were easily synthesized through a one-pot, four-component reaction in high yields. Their structures were fully characterized by nuclear magnetic resonance (NMR) and high-resolution mass spectra (HRMS). Furthermore, the crystal structures of them confirmed their highly twisted conformation. Both TAI-m and TAI-q exhibited good AIE properties. The self-aggregation nanoparticles and the pluronic F-127 encapsulated nanoparticles of them were prepared for comparative study of their cell imaging performance. The findings indicated that they showed the distinct staining behaviors. The cells stained with the self-aggregates showed clear cell outlines but fuzzy cell interiors. By comparison, the pluronic F-127 encapsulated nanoparticles can be distributed in the whole cell.

Key words: aggregation-induced emission, tetraarylimidazole, self-aggregation nanoparticles, encapsulated nanoparticles, cell imaging

Cite this article

Yang Zhao, Panpan Chen, Gaonan Li, Zhigang Niu, Enju Wang. Tetraarylimidazole-Based Aggregation-Induced Emission Luminogens and Their Cell-Imaging Application[J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2156-2162.

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Fig. & Tab. 8

Scheme 1. Synthetic route to TAI-m and TAI-q

Figure 1. Fluorescence spectra of TAI-m (A) in CH3CN/H2O mixtures and TAI-q (B) in EtOH/H2O mixtures with different water fractions, and their images in dissolved state and in aggregation state taken under 365 nm UV excitation (10 μmol/L, λex=370 nm for TAI-m, λex=397 nm for TAI-q) Fluorescence spectra of TAI-m (A) in CH3CN/H2O mixtures and TAI-q (B) in EtOH/H2O mixtures with different water fractions, and their images in dissolved state and in aggregation state taken under 365 nm UV excitation (10 μmol/L, λex=370 nm for TAI-m, λex=397 nm for TAI-q)

Figure 2. Oak Ridge thermal ellipsoid plot (ORTEP) drawing of TAI-m (A) and TAI-q (C) with 50% probability ellipsoids The red letters were used to indicate the aromatic rings attached to imidazole. Crystal packing arrangement of TAI-m (B) viewed along the c-axis and TAI-q (D) viewed along the a-axis

Figure 3. Fluorescence spectra of TAI-m in CH3CN/glycerol mixtures (A) and TAI-q in EtOH/glycerol mixtures (B) with different glycerol fractions

Figure 4. Fluorescence spectra of TAI-m (A) and TAI-q (B) in different solvents and their images in different solvents taken under 365 nm

Figure 5. Viability of HeLa cells in the presence of different concentrations of TAI-m and TAI-q for 10 h

Figure 6. Confocal images of HeLa cells stained with the self-aggregation nanoparticles of TAI-m (A, B, C, D) and TAI-q (E, F, G, H) A and E images in brightfield mode, B and F images in blue channel, C and G images in green channel, and D and H images in red channel

Figure 7. Confocal images of HeLa cells stained with the pluronic F-127 encapsulated nanoparticles of TAI-m (A, B, C, D) and TAI-q (E, F, G, H)

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