Structural Diversity of Hydrogen-Bonded 4-Aryl-3,5-Dimethylpyrazoles for Supramolecular Materials

The 1H-pyrazoles have high versatility and ability to form hydrogen-bonded supramolecular materials. In this study, the thermal stability, fluorescence, and H-bonding ability of the studied 3,5-dimethyl-4-(4-X-phenyl)-1H-pyrazoles showed large differences depending on the terminal substituent. Supra...

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Published inMaterials Vol. 14; no. 16; p. 4550
Main Authors Moyano, Sandra, Diosdado, Beatriz, San Felices, Leire, Elduque, Anabel, Giménez, Raquel
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 13.08.2021
MDPI
Subjects
Aqueous solutions
Chromatography
Dimers
Ethanol
Fluorescence
Hydrogen bonding
Hydrogen bonds
Nitrogen
Nitrogen dioxide
NMR
Nuclear magnetic resonance
Radiation
Single crystals
Solvents
Substitutes
Supramolecular polymers
Thermal stability
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ISSN1996-1944
1996-1944
DOI10.3390/ma14164550

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Summary:The 1H-pyrazoles have high versatility and ability to form hydrogen-bonded supramolecular materials. In this study, the thermal stability, fluorescence, and H-bonding ability of the studied 3,5-dimethyl-4-(4-X-phenyl)-1H-pyrazoles showed large differences depending on the terminal substituent. Supramolecular structures were analyzed using X-ray diffraction and Hirshfeld surface calculations. Compounds were found to arrange in different hydrogen-bonded structures, depending on the substitution at the para position of the phenyl ring (X = OCH3, NO2, NH2). The methoxy-substituted compounds arranged in dimers through methanol bridges, the nitro-substituted compound formed supramolecular polymers or catemers, and the amino-substituted compound gave rise to a new structure based on a 2D hydrogen-bonded network.
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ISSN:1996-1944
1996-1944
DOI:10.3390/ma14164550