3-Aryl-2-(thiazol-2-yl)acrylonitriles assembled with aryl/hetaryl rings: Design of the optical properties and application prospects

Eltyshev, Alexander K.; Dzhumaniyazov, Timur H.; Suntsova, Polina O.; Minin, Artem S.; Поздина, Варвара А.; Dehaen, Wim; Benassi, Enrico; Belskaya, Nataliya P.

doi:10.1016/j.dyepig.2020.108836

Cited by 7 publications

(2 citation statements)

References 91 publications

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“…An asymmetric thiazole core exhibits fascinating behavior such as nonlinear optical properties and ferroelectricity with a lateral π-conjugated system [20]. Thiazole-based fluorophores are used as blue light-emitting polymers in organic light-emitting diodes (OLEDs); thiazoles are also used in dye synthesized solar cells [21]. Hydrazones and their derivatives are organic compounds with a wide range of applications.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, computational study, solvatochromism and biological studies of thiazole-owing hydrazone derivatives

2023

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In the present work, we have synthesized thiazole-hydrazone conjugates 5(a–h) and characterized them using various analytical techniques such as UV, IR, NMR, and mass spectrometry. Solvatochromic properties were evaluated in ten solvents with different polarity and quantum chemical parameters using a DFT study. The antibacterial activity results revealed that compounds 5c, 5d and 5g exhibited good efficacy and that the remaining compounds displayed significant activity. The synthesized compounds were screened for their cytotoxic activity against HepG2 and MCF-7 cell lines, and all the synthesized compounds exhibited significant potency towards the screened cancer cell lines. The anti-inflammatory efficacy of the synthesized thiazole derivatives was determined against MMP-2 and MMP-9, and some of the compounds showed significant activity. Furthermore, the in silico molecular docking was performed with the COX-2 receptor.

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Section: Introductionmentioning

confidence: 99%

Synthesis, computational study, solvatochromism and biological studies of thiazole-owing hydrazone derivatives

2023

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“…Thiazole core is a unique platform for the construction of new fluorophores with outstanding optical properties [16] . Thiazoles with arylidene fragment were shown to be efficient fluorophores and their properties can be easily tuned using substituents in aromatic rings [17a,b] . The electronic nature of this heterocycle creates opportunities for obtaining fluorophores with excellent photophysical characteristics that make them extremely sensitive to the microenvironment.…”

Section: Introductionmentioning

confidence: 99%

Photocaging of Carboxylic Function Bearing Biomolecules by New Thiazole Derived Fluorophore

Gagarin,

Minin,

Shevyrin

et al. 2023

Chemistry A European J

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The design and synthesis of a new fluorophore containing an arylidene thiazole scaffold resulted in a compound with good photophysical characteristics. Furthermore, the thiazole C5‐methyl group was easily modified into specific functional groups (CH2Br and CH2OH) for the formation of a series of photocourier molecules containing model compounds (benzoic acids), as well as prodrugs, including salicylic acid, caffeic acid, and chlorambucil via a “benzyl” linker. Spectral characteristics (1Н, 13С NMR, and high‐resolution mass spectra) corresponded to the proposed structures. The photocourier molecules demonstrated absorption with high values of coefficient of molar extinction, exhibited contrasting green emission, and showed good dark stability. The mechanism of the photorelease was investigated through spectral analysis, HPLV‐HRMS, and supported by TD‐DFT calculations. The photoheterolysis and elimination of carboxylic acids were proved to occur in the excited state, yielding a carbocation as an intermediate moiety. The fluorophore structure provided stability to the carbocation through the delocalization of the positive charge via resonance structures. Viability assessment of Vero cells using the MTT‐test confirmed the weak cytotoxicity of prodrugs without irradiation and it increase upon UV‐light.

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Asymmetric Dual‐State Emitters Featuring Thiazole Acceptors

et al. 2022

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This work describes a new approach to construct highly conjugated molecules with asymmetric donor-acceptor-donor' architectures (DÀ AÀ D'). Five new emissive compounds featuring thiazole, a scarcely used acceptor, were synthesized using a three-component Rh(II) catalytic reaction. The asymmetric fluorescent compounds show significant emission in solution (QY = 73 %-100 %) and the solid-state (QY = 14 %-59 %), and therefore considered Dual-State Emitters (DSE). We also evaluate the impact of O-alkyl chains with varying lengths in the photophysical properties in solution, aggregates, and solid-state. Computational studies indicate that the involved electronic transitions have a significant charge transfer character produced almost exclusively from the triphenylamine donors. According to the single crystal X-ray data of compounds 8 and 9, the conjugated structures have a twisted molecular conformation that contributes to the observed emission in the solid-state. These findings show a systematic approach to design DSE materials, which may help to stimulate their use in biological or optoelectronic applications.

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3-Aryl-2-(thiazol-2-yl)acrylonitriles assembled with aryl/hetaryl rings: Design of the optical properties and application prospects

Cited by 7 publications

References 91 publications

Synthesis, computational study, solvatochromism and biological studies of thiazole-owing hydrazone derivatives

Synthesis, computational study, solvatochromism and biological studies of thiazole-owing hydrazone derivatives

Photocaging of Carboxylic Function Bearing Biomolecules by New Thiazole Derived Fluorophore

Asymmetric Dual‐State Emitters Featuring Thiazole Acceptors

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