Effect of Co-Crystal Formers on the Supramolecular Patterns and Luminescence Properties of Co-Crystals Comprising Fenbufen and Diverse N-Heterocycles

Fa-Yuan Ge; Li-Hua Huo; Shu-Nan Zhao; Zhao-Peng Deng; Zhu-Yan Zhang; Shan Gao

doi:10.1071/CH15630

RESEARCH ARTICLE

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Effect of Co-Crystal Formers on the Supramolecular Patterns and Luminescence Properties of Co-Crystals Comprising Fenbufen and Diverse N-Heterocycles

Fa-Yuan Ge ^A , Li-Hua Huo ^A , Shu-Nan Zhao ^A , Zhao-Peng Deng ^A ^C , Zhu-Yan Zhang ^B and Shan Gao ^A ^C

+ Author Affiliations

- Author Affiliations

^A Key Laboratory of Functional Inorganic Material Chemistry, Ministry of Education, School of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, China.

^B Laboratory Centre of Pharmacy, College of Pharmacy Harbin Medical University, Harbin 150081, China.

^C Corresponding authors. Email: dengzhaopeng@hlju.edu.cn; shangao67@yahoo.com

Australian Journal of Chemistry 69(8) 836-845 https://doi.org/10.1071/CH15630
Submitted: 8 October 2015 Accepted: 4 February 2016 Published: 11 March 2016

Abstract

Four co-crystals [(2-apy)·(Fbf)] (1), [(2-apz)·(Fbf)] (2), [(4,4′-bipy)·2(Fbf)] (3), and [(4,4′-bpe)·2(Fbf)] (4) (Fbf = fenbufen, 4-(4-biphenylyl)-4-oxobutyric acid, 2-apy = 2-aminopyridine, 2-apz = 2-aminopyrazine, 4,4′-bipy = 4,4′-bipyridine, 4,4′-bpe = trans-1,2-bis(4-pyridyl)ethene) have been obtained from the reaction of Fbf and different N-heterocycles by either liquid-assisted grinding method or solution evaporation, and characterized by elemental analysis, infrared spectroscopy, differential scanning calorimetry, photoluminescence spectroscopy, and powder- and single-crystal X-ray diffraction. Structural analyses indicate that conformations of Fbf molecules are highly related to the lone pair···π, C–H···π, or C–H···O interactions, which lead to the formation of different dihedral angles in the four planes in Fbf. With these non-covalent interactions, Fbf presents trans conformation in compounds 1, 3, 4, and cis conformation in compound 2. Interestingly, the packing diagrams of compounds 1 and 2 are very similar to the different trigonometric functions. Compounds 3 and 4 exhibit discontiguous packing diagrams with short snake-shaped chains owing to the higher symmetry of 4,4′-bipy and 4,4′-bpe molecules. Moreover, the differential scanning calorimetry analyses indicate the lower melting point of all compounds when compared with that of free Fbf. Luminescence investigation shows that only compound 1 exhibits strong blue emission in the solid state at room temperature.

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Effect of Co-Crystal Formers on the Supramolecular Patterns and Luminescence Properties of Co-Crystals Comprising Fenbufen and Diverse N-Heterocycles

Abstract

References

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