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Issue 2, 2016
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Syntheses and characterization of aryl-substituted pyrogallol[4]arenes and resorcin[4]arenes

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Abstract

Seven aryl-substituted pyrogallol[4]arenes and six aryl-substituted resorcin[4]arenes were synthesized through the acid catalyzed reaction of either pyrogallol or resorcinol with a specific alkoxybenzaldehyde. Single crystal X-ray data was obtained for all thirteen compounds. In order to determine the effect of the different pendent –R groups, four properties were investigated: π–π distance, inward tilt, twist angle, and the angle between the planes containing the pendent –R groups. Positioning of the –R groups, the carbon atom chain length of the –R groups, the number of upper-rim hydroxyl groups (resorcin[4]arene vs. pyrogallol[4]arene), and the number of substituted phenyl groups all influenced these four properties. The trends that develop are investigated and discussed.

Graphical abstract: Syntheses and characterization of aryl-substituted pyrogallol[4]arenes and resorcin[4]arenes

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Publication details

The article was received on 08 Sep 2015, accepted on 20 Oct 2015 and first published on 11 Nov 2015


Article type: Paper
DOI: 10.1039/C5CE01792K
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CrystEngComm, 2016,18, 222-229
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    Syntheses and characterization of aryl-substituted pyrogallol[4]arenes and resorcin[4]arenes

    C. R. Pfeiffer, K. A. Feaster, S. J. Dalgarno and J. L. Atwood, CrystEngComm, 2016, 18, 222
    DOI: 10.1039/C5CE01792K

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