Identification of the donor-substitution effect of tetraphenylethylene AIEgen: Synthesis, photophysical property analysis, and bioimaging applications

Kim, Dokyoung

doi:10.1016/j.dyepig.2022.110098

Cited by 2 publications

(1 citation statement)

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“…In particular, fluorescence imaging and flow cytometry are considered as reliable and highly sensitive methods for determining the localization of pathogens in the human body [ 2 , 3 , 4 ]. The choice of a fluorescent probe with appropriate properties that allows identification and quantitative determination of biotargets in vivo using a non-destructive and non-invasive analysis is of crucial importance [ 5 , 6 , 7 , 8 ]. Therefore, the search for new chemical compounds as a basis for the development of useful fluorescent labels is considered an urgent task for chemists and biologists.…”

Section: Introductionmentioning

confidence: 99%

4,5-Bis(arylethynyl)-1,2,3-triazoles—A New Class of Fluorescent Labels: Synthesis and Applications

et al. 2022

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Cu-catalyzed 1,3-dipolar cycloaddition of ethyl 2-azidoacetate to iodobuta-1,3-diynes and subsequent Sonogashira cross-coupling were used to synthesize a large series of new triazole-based push–pull chromophores: 4,5-bis(arylethynyl)-1H-1,2,3-triazoles. The study of their optical properties revealed that all molecules have fluorescence properties, the Stokes shift values of which exceed 150 nm. The fluorescent properties of triazoles are easily adjustable depending on the nature of the substituents attached to aryl rings of the arylethynyl moieties at the C4 and C5 atoms of the triazole core. The possibility of 4,5-bis(arylethynyl)-1,2,3-triazoles’ application for labeling was demonstrated using proteins and the HEK293 cell line. The results of an MTT test on two distinct cell lines, HEK293 and HeLa, revealed the low cytotoxicity of 4,5-bis(arylethynyl)triazoles, which makes them promising fluorescent tags for labeling and tracking biomolecules.

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Section: Introductionmentioning

confidence: 99%

4,5-Bis(arylethynyl)-1,2,3-triazoles—A New Class of Fluorescent Labels: Synthesis and Applications

et al. 2022

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Synthesis of highly substituted alkenes by sulfur-mediated olefination of N-tosylhydrazones

Conen,

Nickisch,

Meier

2023

Commun Chem

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Tetraphenylethylenes (TPEs) are well-known for their aggregation-induced emission properties. The synthesis of TPE derivatives, as well as other highly substituted olefins, generally requires the use of hazardous reagents, such as metalorganic compounds, to overcome the high activation energies caused by the sterically congested double bond. Herein, we present an efficient and metal-free procedure for the synthesis of tetraarylethylenes via alkylidene-homocoupling of N-tosylhydrazones, derived from readily available benzophenones, in excellent yields. The method relies only on cheap and benign additives, i.e. elemental sulfur and potassium carbonate, and easily competes with other established procedures in terms of scope, yield and practicability. A mechanistic study revealed a diazo compound, a thioketone and a thiirane as key intermediates in the pathway of the reaction. Based on this, a modified method, which allows for selective alkylidene-cross-coupling, generating a broader scope of tri- and tetrasubstituted olefins in good yields, is showcased as well.

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Identification of the donor-substitution effect of tetraphenylethylene AIEgen: Synthesis, photophysical property analysis, and bioimaging applications

Cited by 2 publications

References 54 publications

4,5-Bis(arylethynyl)-1,2,3-triazoles—A New Class of Fluorescent Labels: Synthesis and Applications

4,5-Bis(arylethynyl)-1,2,3-triazoles—A New Class of Fluorescent Labels: Synthesis and Applications

Synthesis of highly substituted alkenes by sulfur-mediated olefination of N-tosylhydrazones

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