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Supramolecular networks in molecular complexes of pyridine boronic acids and polycarboxylic acids: Synthesis, structural characterization and fluorescent properties

Abstract

3- and 4-pyridineboronic acid have been combined with trimesic and pyromellitic acid to give three molecular complexes of compositions [(3-PBAH+)(H2TMA-)] (1), [(3-PBAH+)2(H2PMA2-)] (2), and [(4-PBAH+)2·(H2PMA2-)]·2H2O (3) (3-PBA = 3-pyridineboronic acid, 4-PBA = 4-pyridineboronic acid, H3TMA = trimesic acid, H4PMA = pyromellitic acid). The products have been characterized by elemental analysis, infrared spectroscopy, single-crystal X-ray diffraction analysis and luminescence spectroscopy. The structural analysis revealed that the hydrogen bonding interactions of the resulting 2D and 3D assemblies contain at least one of the following charge-assisted synthons: –B(OH)2···-OOCR, RCOOH···-OOCR or PyN+–H···-OOCR. The dimensions are enhanced by additional hydrogen bonds as well as π-π stacking interactions, which include B∙∙∙π interactions in two crystal structures. Intermolecular close contacts have been examined also by Hirshfeld surface analysis, which by means of the associated 2D fingerprint plots enabled to reveal similarities and differences in the crystal structures. Photoluminescence spectroscopy of compounds 1-3 revealed that the changes of the molecule aggregates in the solid state induced changes in the emission behavior.

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Publication details

The article was received on 22 Apr 2017, accepted on 05 Jun 2017 and first published on 05 Jun 2017


Article type: Paper
DOI: 10.1039/C7CE00762K
Citation: CrystEngComm, 2017, Accepted Manuscript
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    Supramolecular networks in molecular complexes of pyridine boronic acids and polycarboxylic acids: Synthesis, structural characterization and fluorescent properties

    J. J. Campos, B. A. García Grajeda, I. F. Hernández, J. A. Guerrero , H. Höpfl and A. Cruz, CrystEngComm, 2017, Accepted Manuscript , DOI: 10.1039/C7CE00762K

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