Browse
Submit Data
Databases
API
Help

Dataset Information

25 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis, structure and solvatochromic properties of some novel 5-arylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridone dyes.

ABSTRACT: UNLABELLED: BACKGROUND: A series of some novel arylazo pyridone dyes was synthesized from the corresponding diazonium salt and 6-hydroxy-4-phenyl-3-cyano-2-pyridone using a classical reaction for the synthesis of the azo compounds. RESULTS: The structure of the dyes was confirmed by UV-vis, FT-IR, 1H NMR and 13C NMR spectroscopic techniques and elemental analysis. The solvatochromic behavior of the dyes was evaluated with respect to their visible absorption properties in various solvents. CONCLUSIONS: The azo-hydrazone tautomeric equilibration was found to depend on the substituents as well as on the solvent. The geometry data of the investigated dyes were obtained using DFT quantum-chemical calculations. The obtained calculational results are in very good agreement with the experimental data.

SUBMITTER: Alimmari A

PROVIDER: S-EPMC3537587 | biostudies-literature | 2012

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Synthesis, structure and solvatochromic properties of some novel 5-arylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridone dyes.

Alimmari Adel A Mijin Dušan D Vukićević Radovan R Božić Bojan B Valentić Nataša N Vitnik Vesna V Vitnik Zeljko Z Ušćumlić Gordana G

Chemistry Central journal 20120723 1

<h4>Unlabelled</h4><h4>Background</h4>A series of some novel arylazo pyridone dyes was synthesized from the corresponding diazonium salt and 6-hydroxy-4-phenyl-3-cyano-2-pyridone using a classical reaction for the synthesis of the azo compounds.<h4>Results</h4>The structure of the dyes was confirmed by UV-vis, FT-IR, 1H NMR and 13C NMR spectroscopic techniques and elemental analysis. The solvatochromic behavior of the dyes was evaluated with respect to their visible absorption properties in vari ...[more]

PMID: 22824496

Similar Datasets

Synthesis of 5-Alkyl- and 5-Phenylamino-Substituted Azothiazole Dyes with Solvatochromic and DNA-Binding Properties.

Project description:A series of new 5-mono- and 5,5'-bisamino-substituted azothiazole derivatives was synthesized from the readily available diethyl azothiazole-4,4'-dicarboxylate. This reaction most likely comprises an initial Michael-type addition by the respective primary alkyl and aromatic amines at the carbon atom C5 of the substrate. Subsequently, the resulting intermediates are readily oxidized by molecular oxygen to afford the amino-substituted azothiazole derivatives. The latter exhibit remarkably red-shifted absorption bands (?abs =507-661?nm) with high molar extinction coefficients and show a strong positive solvatochromism. As revealed by spectrometric titrations and circular and linear dichroism studies, the water-soluble, bis-(dimethylaminopropylamino)-substituted azo dye associates with duplex DNA by formation of aggregates along the phosphate backbone at high ligand-DNA ratios (LDR) and by intercalation at low LDR, which also leads to a significant increase of the otherwise low emission intensity at 671?nm.

| S-EPMC6973281 | biostudies-literature

Synthesis, Characterization, Tautomeric Structure and Solvatochromic Behavior of Novel 4-(5-Arylazo-2-Hydroxystyryl)-1-Methylpyridinium Iodide as Potential Molecular Photoprobe.

Project description:A novel series of the title compound 4-(5-arylazo-2-hydroxystyryl)-1-methylpyridinium iodide 6 has been synthesized via condensation reactions of the arylazosalicylaldehyde derivatives 4a-i with 1-methyl-picolinium iodide 5. The structures of the new arylazo compounds were characterized by ¹H NMR, IR, mass spectroscopy, as well as spectral and elemental analyses. The electronic absorption spectra of arylazomerocyanine compounds 6 were measured in different buffer solutions and solvents. The pK's and pK*'s in both the ground and excited states, respectively, were determined for the series and their correlations with the Hammett equation were examined. The results indicated that the title arylazomerocyanine dyes 6 exist in the azo form 6A in both ground and excited states. The substituent and solvent effects (solvatochromism) of the title compound arylazomerocyanine dyes were determined using the Kamlet-Taft equation and subsequently discussed.

| S-EPMC5456979 | biostudies-other

Synthesis and Optical Properties of Near-Infrared meso-Phenyl-Substituted Symmetric Heptamethine Cyanine Dyes.

Project description:Heptamethine cyanine dyes are a class of near infrared fluorescence (NIRF) probes of great interest in bioanalytical and imaging applications due to their modifiability, allowing them to be tailored for particular applications. Generally, modifications at the meso-position of these dyes are achieved through Suzuki-Miyaura C-C coupling and SRN1 nucleophilic substitution of the chlorine atom at the meso-position of the dye. Herein, a series of 15 meso phenyl-substituted heptamethine cyanines was synthesized utilizing a modified dianil linker. Their optical properties, including molar absorptivity, fluorescence, Stokes shift, and quantum yield were measured. The HSA binding affinities of two representative compounds were measured and compared to that of a series of trimethine cyanines previously synthesized by our lab. The results indicate that the binding of these compounds to HSA is not only dependent on hydrophobicity, but may also be dependent on steric interferences in the binding site and structural dynamics of the NIRF compounds.

| S-EPMC6017188 | biostudies-literature

Solvatochromic and Single Crystal Studies of Two Neutral Triarylmethane Dyes with a Quinone Methide Structure.

Project description:The crystal structure of two neutral triarylmethane dyes with a p-quinone methide core was determined by X-ray diffraction analysis. The spectroscopic characteristics of both compounds in 23 solvents with different polarities or hydrogen-bonding donor (HBD) abilities has been studied as a function of three solvatochromic parameters (ET(30), π* and α). Both compounds 1 and 2 showed a pronounced bathochromic shift of the main absorption band on increasing solvent polarity and HBD ability. The correlation is better for compound 2 than for compound 1. The stronger effect and better correlation was observed for compound 2 with the increment of the solvent HBD ability (α parameter).

| S-EPMC6332080 | biostudies-literature

Optical Study of Solvatochromic Isocyanoaminoanthracene Dyes and 1,5-Diaminoanthracene.

Project description:Isocyanoaminoarenes (ICAAr-s) are a novel and versatile group of solvatochromic fluorophores. Despite their versatile applicability, such as antifungals, cancer drugs and analytical probes, they still represent a mostly unchartered territory among intramolecular charge-transfer (ICT) dyes. The current paper describes the preparation and detailed optical study of novel 1-isocyano-5-aminoanthrace (ICAA) and its N-methylated derivatives along with the starting 1,5-diaminoanthracene. The conversion of one of the amino groups of the diamine into an isocyano group significantly increased the polar character of the dyes, which resulted in a significant 50-70 nm (2077-2609 cm-1) redshift of the emission maximum and a broadened solvatochromic range. The fluorescence quantum yield of ICAAs is strongly influenced by the polarity of the solvent. The starting anthracene-diamine is highly fluorescent in every solvent (√f = 12-53%), while the isocyano derivatives are practically nonfluorescent in solvents more polar than dioxane. This phenomenon implies the potential application of ICAAs to probe the polarity of the medium and is favorable in practical applications, such as cell-staining, resulting in a reduced background fluorescence. The ICT character of the emission states of ICAAs are in good agreement with the computational findings presented in TD-DFT calculations and molecular electrostatic potential (MESP) isosurfaces.

| S-EPMC8835764 | biostudies-literature

Microwave-assisted chemoselective synthesis and photophysical properties of 2-arylazo-biphenyl-4-carboxamides from hydrazonals.

Project description:The reaction of 3-oxo-2-arylhydrazonopropanals with acetoacetanilide in an equimolar ratio, under DBU/1,4-dioxane/microwave irradiation reaction conditions, resulted in chemoselective formation of 4-arylazo-5-hydroxy-benzamide derivatives. The structures of the obtained biphenyl-4-carboxamides were characterized by several spectroscopic techniques including IR, 1H- and 13C-NMR, MS and HRMS, and X-ray single crystals of three examples. The photophysical properties of the new products were also evaluated, with a particular focus on their absorption and emission spectra, which provided valuable information regarding their optical properties. The new compounds emitted 513-549 nm green fluorescence in acetone solution under UV irradiation.

| S-EPMC10442861 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of 3-cyano-phenyl-boronic acid.

Project description:In the title compound, C7H6BNO2, the mean plane of the -B(OH)2 group is twisted by 21.28 (6)° relative to the cyano-phenyl ring mean plane. In the crystal, mol-ecules are linked by O-H⋯O and O-H⋯N hydrogen bonds, forming chains propagating along the [101] direction. Offset π-π and B⋯π stacking inter-actions link the chains, forming a three-dimensional network. Hirshfeld surface analysis shows that van der Waals inter-actions constitute a further major contribution to the inter-molecular inter-actions, with H⋯H contacts accounting for 25.8% of the surface.

| S-EPMC5946963 | biostudies-literature

7-Hydroxy-4-phenyl-1, 2-dihydroquinoline derivatives: synthesis via one-pot, three-component reaction and structure elucidation.

Project description:We have developed a new and facile one pot three component protocol catalyzed by ammonium acetate for construction of new functionalized 7-hydroxy-4-phenyl-1,2-dihydroquinoline derivatives. A variety of quinoline derivatives were obtained in good to excellent yield from inexpensive reagents and catalyst in mild reaction conditions that provide atom economy and cost efficacy. Various spectroscopic techniques like FTIR, 1HNMR and 13CNMR were employed to study their structure while mass of the synthesized compounds were confirmed through MALDI-TOF-MS and EI mass spectrometry.

| S-EPMC7527354 | biostudies-literature

5'-Hydroxy-5'-homoaristeromycin: Synthesis and antiviral properties.

Project description:Synthetically combining the C-4' side-chain structural features of the antiviral candidates 5'-methylaristeromycin and 5'-homoaristeromycin into a diastereomeric pair of C-4' side-chain dihydroxylated aristeromycins (6 and 7) is reported. Broad antiviral analyses of the both targets found promising effects towards HBV (6, 6.7??M and 7, 7.74??M) and HCMV (only 7, 0.72??M). No other activity was found. Neither of the diastereomers was cytotoxic in the assays performed.

| S-EPMC7126772 | biostudies-literature

tert-Butyl 4-cyano-phenyl carbonate.

Project description:The title compound, C(12)H(13)NO(3), was prepared by reacting one equivalent of di-tert-butyl dicarbonate with 4-cyano-phenol. Herringbone crystal packing is observed and there are no significant inter-molecular inter-actions.

| S-EPMC2983158 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data