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Alkane-Shape-Selective Vapochromic Behavior Based on Crystal-State Host–Guest Complexation of Pillar[5]arene Containing One Benzoquinone Unit

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Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan
JST, PRESTO, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan
Cite this: J. Am. Chem. Soc. 2017, 139, 16, 5664–5667
Publication Date (Web):April 17, 2017
https://doi.org/10.1021/jacs.7b00631
Copyright © 2017 American Chemical Society
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Abstract

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Colored crystals of pillar[5]arene containing one benzoquinone unit were found to exhibit alkane-shape-selective vapochromic behavior. Activated pillar[5]arene crystals, prepared by removing solvated methanol from pillar[5]arene crystals, changed color from dark-brown to light-red after exposure to linear alkane vapors; however, no color changes were observed on exposure to branched or cyclic alkanes. Uptake of methanol vapor by the activated crystals induced a different color change, from dark-brown to black. This multi-vapochromism results from the different intermolecular π-stacking interactions between the benzoquinone and 1,4-diethoxybenzene units in the alkane- and methanol-containing crystals. Unlike most known vapochromic materials, these pillar[5]arene-based materials were highly stable; after uptake of n-alkanes or methanol the color of the crystals did not change after storage in air for 3 weeks. This is because the included guests were stabilized in the cavity by multiple CH/π interactions.

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The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/jacs.7b00631.

  • Experimental section, 1H NMR, monitoring of vapochromic behavior by diffuse reflectance spectroscopy, PXRD patterns after uptake of n-alkanes, sorption isotherms of activated crystals toward linear, cyclic and branched alkanes, complexation efficiency, and stability of color induced by uptake of n-hexane and methanol (PDF)

  • X-ray crystallographic data for (CIF)

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