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

Constance R. Pfeiffer, Kyle A. Feaster, Scott J. Dalgarno, Jerry L Atwood

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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: p-p 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.

Original languageEnglish
Pages (from-to)222-229
Number of pages8
JournalCrystEngComm
Volume18
Issue number2
DOIs
Publication statusPublished - 14 Jan 2016

Keywords

  • CRYSTAL-STRUCTURE
  • CAPSULES

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