Efficient one-pot three-component method for the synthesis of highly fluorescent coumarin-containing 3,5-disubstituted-2,6-dicyanoaniline derivatives under microwave irradiation

Aydıner, Burcu; Yalçın, Ergin; Korkmaz, Vildan; Seferoğlu, Zeynel

doi:10.1080/00397911.2017.1362438

Cited by 13 publications

(4 citation statements)

References 40 publications

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“…7-Diethylamino substituted coumarin 1b showed better photophysical properties (Φ F ) in solution than compounds 1-5, previously reported and shown in Figure 4 [6,7,10,16,52]. Then, compound 1b in solution and 2c in the solid-state could be evaluated in similar applications, since they have even better optical properties, and their synthesis is simpler and with higher chemical yields than the reported compounds 1-7.…”

Section: Uv-vis Absorption and Photoluminescence Spectramentioning

confidence: 70%

“…Photoluminescent compounds and materials with fluorescent and phosphorescent properties play a fundamental role in many areas, such as biology, pharmacology, chemistry, biomedicine, and optoelectronics [7][8][9][10][11][12]. For example, coumarin compounds coupled to phenylhydrazine have been reported as fluorescent probes for visualizing living tissues [13].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Optical Characterization in Solution and Solid-State, and DFT Calculations of 3-Acetyl and 3-(1′-(2′-Phenylhydrazono)ethyl)-coumarin-(7)-substituted Derivatives

Villa-Martínez

Magaña-Vergara²,

Rodríguez³

et al. 2022

Molecules

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Intramolecular charge transfer (ICT) effects are responsible for the photoluminescent properties of coumarins. Hence, optical properties with different applications can be obtained by ICT modulation. Herein, four 3-acetyl-2H-chromen-2-ones (1a–d) and their corresponding fluorescent hybrids 3- (phenylhydrazone)-chromen-2-ones (2a–d) were synthesized in 74–65% yields. The UV-Vis data were in the 295–428 nm range. The emission depends on the substituent in position C-7 bearing electron-donating groups. Compounds 1b–d showed good optical properties due to the D-π-A structural arrangement. In compounds 2a–d, there is a quenching effect of fluorescence in solution. However, in the solid, an increase is shown due to an aggregation-induced emission (AIE) effect given by the rotational restraints and stacking in the crystal. Computational calculations of the HOMO-LUMO orbitals indicate high absorbance and emission values of the molecules, and gap values represent the bathochromic effect and the electronic efficiency of the compounds. Compounds 1a–d and 2a–d are good candidates for optical applications, such as OLEDs, organic solar cells, or fluorescence markers.

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Section: Uv-vis Absorption and Photoluminescence Spectramentioning

confidence: 70%

Section: Introductionmentioning

confidence: 99%

Synthesis, Optical Characterization in Solution and Solid-State, and DFT Calculations of 3-Acetyl and 3-(1′-(2′-Phenylhydrazono)ethyl)-coumarin-(7)-substituted Derivatives

Villa-Martínez

Magaña-Vergara²,

Rodríguez³

et al. 2022

Molecules

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“…2-(1-(4-aminophenyl)ethylidene)malononitrile and 2-(1-(7-(diethylamino)-2oxo-2H-chromen-3-yl)ethylidene)malononitrile were obtained as described in the literature. 14 Thin-layer chromatography (TLC) was used for monitoring the domino reactions using precoated silica gel 60 F254 plates. 1 H/ 13 C NMR spectra were recorded on NMR spectrometer Bruker-Spectrospin Avance DPX 300 and Ultra-Shield in DMSO-d 6 .…”

Section: Methodsmentioning

confidence: 99%

Triphenylamine-based allylidenemalononitrile chromophores: synthesis, and photophysical and second-order nonlinear optical properties

et al. 2018

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“…Therefore, only a simple and direct approach to the synthesis of coumarin-containing highly fluorescent asymmetric/symmetric 3,5diaryl/heteroaryl-2,6-dicyanoaniline derivatives has been described in the past decade. The molecules have been synthesized in good yields via base-catalyzed three-component one-pot reaction of [2-(1-(7-(diethylamino)-3-coumarinyl)ethylidene]malononitrile with aliphatic, aromatic/heteroaromatic aldehydes and malononitrile, in solvent-free medium, catalyzed by piperidine, under a microwave irradiation method (Figure 9) [67].…”

Section: Construction Of the Benzene Ring At Position 3 Of The Coumarinmentioning

confidence: 99%

3-Phenylcoumarins as a Privileged Scaffold in Medicinal Chemistry: The Landmarks of the Past Decade

2021

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3-Phenylcoumarins are a family of heterocyclic molecules that are widely used in both organic and medicinal chemistry. In this overview, research on this scaffold, since 2010, is included and discussed, focusing on aspects related to its natural origin, synthetic procedures and pharmacological applications. This review paper is based on the most relevant literature related to the role of 3-phenylcoumarins in the design of new drug candidates. The references presented in this review have been collected from multiple electronic databases, including SciFinder, Pubmed and Mendeley.

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Efficient one-pot three-component method for the synthesis of highly fluorescent coumarin-containing 3,5-disubstituted-2,6-dicyanoaniline derivatives under microwave irradiation

Cited by 13 publications

References 40 publications

Synthesis, Optical Characterization in Solution and Solid-State, and DFT Calculations of 3-Acetyl and 3-(1′-(2′-Phenylhydrazono)ethyl)-coumarin-(7)-substituted Derivatives

Synthesis, Optical Characterization in Solution and Solid-State, and DFT Calculations of 3-Acetyl and 3-(1′-(2′-Phenylhydrazono)ethyl)-coumarin-(7)-substituted Derivatives

Triphenylamine-based allylidenemalononitrile chromophores: synthesis, and photophysical and second-order nonlinear optical properties

3-Phenylcoumarins as a Privileged Scaffold in Medicinal Chemistry: The Landmarks of the Past Decade

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