Structural Diversity of Hydrogen-Bonded 4-Aryl-3,5-Dimethylpyrazoles for Supramolecular Materials
Sandra Moyano,
Beatriz Diosdado,
Leire San Felices,
Anabel Elduque,
Raquel Giménez
Affiliations
Sandra Moyano
Instituto de Nanociencia y Materiales de Aragón (INMA), Departamento de Química Orgánica, Facultad de Ciencias, CSIC-Universidad de Zaragoza, 50009 Zaragoza, Spain
Beatriz Diosdado
Departamento de Química Inorgánica, Facultad de Ciencias, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC-Universidad de Zaragoza, 50009 Zaragoza, Spain
Leire San Felices
Servicios Generales de Investigación SGIker, Universidad del País Vasco UPV/EHU, P.O. Box 644, 48080 Bilbao, Spain
Anabel Elduque
Departamento de Química Inorgánica, Facultad de Ciencias, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC-Universidad de Zaragoza, 50009 Zaragoza, Spain
Raquel Giménez
Instituto de Nanociencia y Materiales de Aragón (INMA), Departamento de Química Orgánica, Facultad de Ciencias, CSIC-Universidad de Zaragoza, 50009 Zaragoza, Spain
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.
