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Crystals 2018, 8(1), 41; https://doi.org/10.3390/cryst8010041

Salts and Co-Crystalline Assemblies of Tetra(4-Pyridyl)Ethylene with Di-Carboxylic Acids

Department of Chemistry, University of Iowa, Iowa City, IA 52242, USA
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Received: 22 December 2017 / Revised: 9 January 2018 / Accepted: 15 January 2018 / Published: 17 January 2018
(This article belongs to the Special Issue Crystal Structure Analysis of Supramolecular and Porous Solids)
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Abstract

Tetraarylethylene derivatives are emerging as an increasingly important family of supramolecular building blocks in both solution phase and the solid state. The utility of tetraarylethylenes stems from appealing structural features (rigidity and symmetry) and their propensity to exhibit aggregation induced emission (AIE). In an effort to investigate the luminescent sensing ability of heteroaromatic tetraarylethylenes, we previously prepared tetra(4-pyridyl)ethylene and characterized its solution phase AIE properties. We here report the successful incorporation of tetra(4-pyridyl)ethylene into three distinct salts and co-crystalline assemblies with three organic di-carboxylic acids (oxalic acid, malonic acid, and fumaric acid). Interactions between the tetra(pyridyl)ethylene and di-acid components were found to vary from conventional to charge-assisted hydrogen bonding according to the extent of proton transfer between the acid and pyridine groups. Notably, the formation of pyridinium-carboxylate adducts in the salts does not appear to be strongly correlated with acid pKa. Three distinct network topologies were observed, and all featured the bridging of two or three tetra(pyridyl)ethylene groups through di-acid linkers. Crystalline assemblies also retained the AIE activity of tetra(pyridyl)ethylene and were luminescent under UV light. As tetra(4-pyridyl)ethylene features four Lewis basic and potentially metal ligating pyridine rings in a relatively well-defined geometry, this compound represents an attractive building block for the design of additional crystalline organic and metal–organic functional materials. View Full-Text
Keywords: supramolecular chemistry; crystal engineering; co-crystals; hydrogen bonded organic frameworks; aggregation induced emission supramolecular chemistry; crystal engineering; co-crystals; hydrogen bonded organic frameworks; aggregation induced emission
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Gabr, M.T.; Pigge, F.C. Salts and Co-Crystalline Assemblies of Tetra(4-Pyridyl)Ethylene with Di-Carboxylic Acids. Crystals 2018, 8, 41.

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