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 in | Materials Vol. 14; no. 16; p. 4550 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
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| ISSN | 1996-1944 1996-1944 |
| DOI | 10.3390/ma14164550 |
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| Abstract | 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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| AbstractList | The 1
H
-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)-1
H
-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 = OCH
3
, NO
2
, NH
2
). 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. 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. 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.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. |
| Author | Giménez, Raquel San Felices, Leire Elduque, Anabel Moyano, Sandra Diosdado, Beatriz |
| AuthorAffiliation | 2 Departamento de Química Inorgánica, Facultad de Ciencias, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC-Universidad de Zaragoza, 50009 Zaragoza, Spain; beadiosdado@hotmail.com 1 Instituto de Nanociencia y Materiales de Aragón (INMA), Departamento de Química Orgánica, Facultad de Ciencias, CSIC-Universidad de Zaragoza, 50009 Zaragoza, Spain; sandra.moyano.perez@gmail.com 3 Servicios Generales de Investigación SGIker, Universidad del País Vasco UPV/EHU, P.O. Box 644, 48080 Bilbao, Spain; leire.sanfelices@ehu.eus |
| AuthorAffiliation_xml | – name: 3 Servicios Generales de Investigación SGIker, Universidad del País Vasco UPV/EHU, P.O. Box 644, 48080 Bilbao, Spain; leire.sanfelices@ehu.eus – name: 1 Instituto de Nanociencia y Materiales de Aragón (INMA), Departamento de Química Orgánica, Facultad de Ciencias, CSIC-Universidad de Zaragoza, 50009 Zaragoza, Spain; sandra.moyano.perez@gmail.com – name: 2 Departamento de Química Inorgánica, Facultad de Ciencias, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC-Universidad de Zaragoza, 50009 Zaragoza, Spain; beadiosdado@hotmail.com |
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| Cites_doi | 10.1039/C8CS00155C 10.1021/ja403264c 10.1107/S0108768100008752 10.1039/C5DT00011D 10.1007/BF01668419 10.1038/pj.2017.55 10.1039/c2sm25726b 10.1002/adma.201401356 10.1515/znb-2019-0170 10.1002/zaac.201300094 10.1002/anie.199523111 10.1039/C4DT01880J 10.1039/c3sm27969c 10.1039/B307306H 10.1098/rsos.180564 10.1002/chem.201504779 10.1107/S1600576721002910 10.1021/ja5126275 10.1039/C8CC06235H 10.1002/ejic.200900694 10.1039/b815577a 10.1007/BF01669729 10.1021/cm101817h 10.1039/c3tc30174e 10.1021/jp907441p |
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| Snippet | The 1H-pyrazoles have high versatility and ability to form hydrogen-bonded supramolecular materials. In this study, the thermal stability, fluorescence, and... The 1 H -pyrazoles have high versatility and ability to form hydrogen-bonded supramolecular materials. In this study, the thermal stability, fluorescence, and... |
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| SubjectTerms | 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 |
| Title | Structural Diversity of Hydrogen-Bonded 4-Aryl-3,5-Dimethylpyrazoles for Supramolecular Materials |
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