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Anion-controlled supramolecular crystal structures and ionic liquids from fatty acid-substituted ethyl-nicotinate ionic compounds

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Abstract

A series of bio-inspired fatty acid-substituted ethyl-nicotinate ionic compounds, 1-(5-carboxypentyl)-3-(ethoxycarbonyl)pyridin-1-ium ionic compounds ([Nia-OEt-C5COOH] X, X = Br (1), B(Ph)4 (2), NO3 (3), BF4 (4), PF6 (5), and OTf (6)) were synthesized. The supramolecular crystal structures of 1 and 2 were characterized by single crystal X-ray diffraction. The Nia-OEt-C5COOH cations in the two crystal structures formed dimerized secondary rectangular motifs with weak C–H…O[double bond, length as m-dash]C hydrogen bonding which extended into a lipid-like bilayer and a β-sheet-like tape stacking, respectively. Four acidic ionic liquids (AILs) were formed by the other anions (3–6) because these anions and the two carbonyl O atoms of the Nia-OEt-C5COOH cation have small hydrogen bonding acceptor ability differences. In addition, the flexible ester group of Nia-OEt-C5COOH has a low barrier to the rotation of the C–O–C bonds, making it less rigid and it has a lower melting point. The four AILs were characterized by DSC thermal analysis, infrared spectroscopy and ionic conductivity.

Graphical abstract: Anion-controlled supramolecular crystal structures and ionic liquids from fatty acid-substituted ethyl-nicotinate ionic compounds

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Publication details

The article was received on 14 May 2018, accepted on 19 Sep 2018 and first published on 27 Sep 2018


Article type: Paper
DOI: 10.1039/C8CE00785C
Citation: CrystEngComm, 2018, Advance Article
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    Anion-controlled supramolecular crystal structures and ionic liquids from fatty acid-substituted ethyl-nicotinate ionic compounds

    W. Chang, P. Y. Su and K. Lee, CrystEngComm, 2018, Advance Article , DOI: 10.1039/C8CE00785C

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