Pyrene-based chalcones as functional materials for organic electronics application

Kagatikar, Sneha; Sunil, Dhanya; Kekuda, Dhananjaya; Satyanarayana, M.; Kulkarni, Suresh D.; Sudhakar, Y.N.; Vatti, Anoop Kishore; Sadanala, Aditya

doi:10.1016/j.matchemphys.2022.126839

Cited by 17 publications

(5 citation statements)

References 47 publications

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“…On the other hand, chalcones are a class of organic compounds that contain a central α,β-unsaturated carbonyl system, which has attracted significant attention, due to their diverse applications in the fields of medicine, material science, and optics . Moreover, the chalcones due to the π-conjugated system and the two aromatic rings that act as donors and acceptors provide a reasonable fluorescence quantum yield, efficient stabilization of charge-transfer processes in the excited state, long-wavelength emission (λ em ), and large Stokes shifts, which means that they have potential applications in fluorescence microscopy or bioimaging applications as they can improve image sensitivity by reducing the interference caused by self-absorption or autofluorescence. − …”

Section: Introductionmentioning

confidence: 99%

Synthesis, Photophysical Properties, Theoretical Studies, and Living Cancer Cell Imaging Applications of New 7-(Diethylamino)quinolone Chalcones

Insuasty,

Mutis,

Trilleras

et al. 2024

ACS Omega

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In this article, three unsymmetrical 7-(diethylamino)quinolone chalcones with D-π–A-D and D-π–A-π-D type push–pull molecular arrangements were synthesized via a Claisen–Schmidt reaction. Using 7-(diethylamino)quinolone and vanillin as electron donor (D) moieties, these were linked together through the α,β-unsaturated carbonyl system acting as a linker and an electron acceptor (A). The photophysical properties were studied, revealing significant Stokes shifts and strong solvatofluorochromism caused by the ICT and TICT behavior produced by the push–pull effect. Moreover, quenching caused by the population of the TICT state in THF–H2O mixtures was observed, and the emission in the solid state evidenced a red shift compared to the emission in solution. These findings were corroborated by density functional theory (DFT) calculations employing the wb97xd/6-311G(d,p) method. The cytotoxic activity of the synthesized compounds was assessed on BHK-21, PC3, and LNCaP cell lines, revealing moderate activity across all compounds. Notably, compound 5b exhibited the highest activity against LNCaP cells, with an LC50 value of 10.89 μM. Furthermore, the compounds were evaluated for their potential as imaging agents in living prostate cells. The results demonstrated their favorable cell permeability and strong emission at 488 nm, positioning them as promising candidates for cancer cell imaging applications.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Photophysical Properties, Theoretical Studies, and Living Cancer Cell Imaging Applications of New 7-(Diethylamino)quinolone Chalcones

Insuasty,

Mutis,

Trilleras

et al. 2024

ACS Omega

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“…In addition, Slobodinyuk et al reported the electrochemical oxidation of series of asymmetric chalcones [34] . Kagatikar and co‐workers assessed pyrene‐based chalcones as functional materials applicable in organic electronics [35] . To further explore the electrochemical potentials of chalcones, Brovelli and others reported the electrochemical properties of heterocyclic chalcones [36] .…”

Section: Introductionmentioning

confidence: 99%

“…[34] Kagatikar and co-workers assessed pyrene-based chalcones as functional materials applicable in organic electronics. [35] To further explore the electrochemical potentials of chalcones, Brovelli and others reported the electrochemical properties of heterocyclic chalcones. [36] The applications of chalcones in galvanostatic electrosynthesis employing its reductive cyclodimerization and self-adaptability was recently reported by Garbini et al [37] β-diketones on the other hand are 1,3-substituted propan-1,3-diones.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical and Theoretical Modelled Reduction of β‐Diketone Inspired Chalcones

Izuchukwu Ugwu,

Conradie

2024

ChemistrySelect

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The growing interest in synthesizing electrochemically active organic ligands stems from extensive reports highlighting the applications of redox‐active organic molecules. These molecules play a crucial role in capturing and converting CO2 into valuable organic compounds, including carbonates used as solvents in lithium batteries. In this study, we present an electrochemical investigation of two chalcone derivatives, referred to as (1) and (2). We explored the influence of different solvent systems, specifically acetonitrile and dimethyl sulfoxide, on the reduction potential of these chalcones. The reported chalcone derivatives were characterized using various analytical techniques, including UV/Visible spectroscopy, Fourier Transform Infrared spectroscopy, Proton and Carbon‐13 nuclear magnetic resonance, as well as mass spectrometry. The characterization of the reported chalcones, exhibiting properties of both β‐diketones and 2‐hydroxyphenones, is underscored by a density functional theory (DFT) study of chalcones (1) and (2). This research establishes a correlation between the energies calculated through DFT and the experimental reduction potentials of chalcones (1) and (2), in comparing them with a series of β‐diketones and 2‐hydroxyphenones.

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“…Pyrene‐based chalcones are used for different applications, as reported recently, e.g., in ref. [26].…”

Section: Introductionmentioning

confidence: 99%

Photoinitiating Ability of Pyrene–Chalcone‐Based Oxime Esters with Different Substituents

Zhang,

Liu,

Zhu

et al. 2023

Macro Chemistry & Physics

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With the rapid development of new irradiation setups as well as the ongoing interest in 3D printing, photopolymerization is extensively studied during the last decades. In photopolymerization, a photoinitiator and/or photosensitizer play(s) a crucial role in the photoinitiation step as this component absorbs light, thus creating the initiating species. In this study, a series of 17 chalcone‐based oxime esters (OXEs) featuring the pyrene chromophore are designed, synthesized, and studied for their photoinitiation properties upon irradiation with visible light. Precisely, their photoinitiation abilities are examined during the free radical photopolymerization of acrylates under the irradiation of light‐emitting diode (LED) at 405 nm. In the series of oxime esters, five of them demonstrate excellent photoinitiation abilities. Their thermal initiation abilities are also examined. To improve their photoinitiation abilities, these type I photoinitiators are also tested as type II photoinitiators in two‐component photoinitiating systems using bis‐(4‐tert‐butylphenyl)iodonium or ethyl 4‐(dimethylamino)benzoate as additives. In this process, the OXE‐B/iodonium system shows the best photopolymerization. To develop the use of these chalcone‐based oxime esters, the best OXE is used as a monocomponent photoinitiating system in 2D laser writing at 405 nm. The design of composites using glass fibers or carbon fiber as fillers is also examined.

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Pyrene-based chalcones as functional materials for organic electronics application

Cited by 17 publications

References 47 publications

Synthesis, Photophysical Properties, Theoretical Studies, and Living Cancer Cell Imaging Applications of New 7-(Diethylamino)quinolone Chalcones

Synthesis, Photophysical Properties, Theoretical Studies, and Living Cancer Cell Imaging Applications of New 7-(Diethylamino)quinolone Chalcones

Electrochemical and Theoretical Modelled Reduction of β‐Diketone Inspired Chalcones

Photoinitiating Ability of Pyrene–Chalcone‐Based Oxime Esters with Different Substituents

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