Tetraphenylene-chalcone hybrid derivatives: Synthesis, structural, fluorescence properties and imaging in living cells

Chen, Hui; Fang, Shirong; Wang, Lihong; Liu, Xiang; Yan, Jiaying; Zhang, Nuonuo; Zheng, Kaibo

doi:10.1016/j.molliq.2020.114913

Cited by 26 publications

(11 citation statements)

References 48 publications

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“…They also exhibited AIEE characteristics [24,25]. In addition, chalcone-based AIEE molecules have been reported in several works [26][27][28], which further increases our interest and confidence in the study of the fluorescence characteristics of chalcone compounds. In this project, we tried to acquire smaller molecules through the same ideas and experiences.…”

Section: Introductionmentioning

confidence: 67%

Synthesis of New AIEE-Active Chalcones for Imaging of Mitochondria in Living Cells and Zebrafish In Vivo

Luo

Liu

et al. 2021

IJMS

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Fluorophores with aggregation-induced emission enhancement (AIEE) properties have attracted increasing interest in recent years. On the basis of our previous research, we successfully designed and synthesized eleven chalcones. Through an optical performance experiment, we confirmed that compounds 1–6 had obvious AIEE properties. As these AIEE molecules had excellent fluorescence properties and a large Stokes shift, we studied their application in living cell imaging, and the results showed that these compounds had low cytotoxicity and good biocompatibility at the experimental concentrations. More importantly, they could specifically label mitochondria. Subsequently, we selected zebrafish as experimental animals to explore the possibilities of these compounds in animal imaging. The fluorescence imaging of zebrafish showed that these AIEE molecules can enter the embryo and can be targeted to aggregate in the digestive tract, which provides a strong foundation for their practical application in the field of biological imaging. Compared with traditional fluorophores, these AIEE molecules have the advantages of possessing a small molecular weight and high flexibility. Therefore, they have excellent application prospects in the field of biological imaging. In addition, the findings of this study have very positive practical significance for the discovery of more AIEE molecules.

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Section: Introductionmentioning

confidence: 67%

Synthesis of New AIEE-Active Chalcones for Imaging of Mitochondria in Living Cells and Zebrafish In Vivo

Luo

Liu

et al. 2021

IJMS

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“…Overall, these results revealed that the SW emission efficiency of the ImDCN fluorophores is quenched, while their LW emission efficiency showed moderate AIE characteristics at a higher aggregation state. 59 2.5. Solid-State Properties.…”

Section: Aggregation-induced Emission (Aie) Investigationsmentioning

confidence: 99%

Impact of Electron-Donating Groups on Attaining Dual-Emitting Imidazole-Based Donor–Acceptor Materials

Ganesan

Zhang

et al. 2023

J. Org. Chem.

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Imidazole-based donor–acceptor materials are well known for their polarity-controlled trade-off phenomenon between the localized excitation-based short-wavelength (SW) emission in nonpolar solvents and charge transfer dominated long-wavelength (LW) emission in polar solvents. To attain concurrent SW- and LW-based dual-emission characteristics, a series of imidazole-based donor–acceptor fluorophores (CBImDCN, TPImDCN, PZImDCN) possessing different electron-donating groups such as carbazole, triphenylamine, and phenothiazine linked via the N-position of the imidazole core unit were synthesized and verified by NMR and mass spectroscopic techniques. As a result, the strong donating TPImDCN and PZImDCN exhibited dual emission in different solvents of varying polarity, covering the blue (SW) and green/orange (LW) regions. On the other hand, in contrast, only an SW emission band is observed with the weak donating CBImDCN. Moreover, PZImDCN shows panchromatic emission under 365 nm illumination, while only orange color emission is observed under visible light excitation, revealing two different origins of SW and LW emissions, as also evidenced from DFT calculations. Overall, this work reveals a new approach for attaining concurrent SW and LW emission characteristics from imidazole-based D–A materials and sheds light on the design and development of novel panchromatic emitters with intriguing properties for lighting and display applications.

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“…All complexes presented more than tenfold fluorescence emission intensity enhancement and the steric effect associated with bulkier halogens was responsible for J-aggregate formation. It is quite interesting to note that though heavy atoms trigger efficient spin orbit coupling and non-radiatively depopulate excited singlet species (Chen et al 2020), heavier halogens like Br and I did not quench the emission of these molecules. Instead, there was enhancement in the emission intensity in 7f and 7 g with Cl and Br atoms.…”

Section: Optoelectronic Applications Of Aie-active Chalconesmentioning

confidence: 99%

“…Hence four tetraphenylene-based chalcone hybrid derivatives (16a-d) as presented in Fig. 5b were synthesized (Chen et al 2020). Lower quantum yields (0.006-0.12) in these compounds in different organic solvents were due to the rotation and vibration of tetraphenylethene and benzothiazole derivatives.…”

Section: Biological Applications Of Aie-active Chalconesmentioning

confidence: 99%

“…Besides, the molecular design strategy to construct highly sensitive ratiometric fluorophores with red fluorescence emission in aggregated state utilizing natural products is Fig. 5 a Paper-based analytical tool that incorporates dual-state emissive chalcone for ratiometric determination of HSA in blood (Luo et al 2020) and b tetraphenylene-based AIE-active chalcone for live cell imaging (Chen et al 2020) yet another area that needs more investigations. Moreover, biocompatible materials with aggregation-induced emission that display ratiometric fluorescence signals with high selectivity and sensitivity are keenly sought after as potential bioimaging and bio probes.…”

Section: Conclusion and Future Prospectsmentioning

confidence: 99%

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Aggregation induced emission of chalcones

Kagatikar

Sunil

2021

Chem. Pap.

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There is always a need for efficient luminescent materials with simple synthesis and possible ease of hydrogen atom or functional group manipulation for use in different optoelectronic and biological applications. However, for certain real-world uses aggregation caused quenching effect of luminophores in their solid/aggregate state is undesirable, and is a cause of concern in areas, wherein the solid-state optical performance is more crucial. In this regard, chalcones have been explored for their ability to display aggregation-induced emission (AIE) or aggregation-induced enhanced emission (AIEE), which can be of practical use. This article is thus focused on an integrated evidence-based report on the AIE/AIEE-active chalcone systems for potential technological and biological applications. Graphic abstract

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Tetraphenylene-chalcone hybrid derivatives: Synthesis, structural, fluorescence properties and imaging in living cells

Cited by 26 publications

References 48 publications

Synthesis of New AIEE-Active Chalcones for Imaging of Mitochondria in Living Cells and Zebrafish In Vivo

Synthesis of New AIEE-Active Chalcones for Imaging of Mitochondria in Living Cells and Zebrafish In Vivo

Impact of Electron-Donating Groups on Attaining Dual-Emitting Imidazole-Based Donor–Acceptor Materials

Aggregation induced emission of chalcones

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