Rim-Differentiated C5-Symmetric Tiara-Pillar[5]arenes

Minjie Guo, Xuemei Wang, Caihong Zhan, Paul Demay-Drouhard, Wenjiao Li, Ke Du, Mark A. Olson, Han Zuilhof*, Andrew C.H. Sue

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

32 Scopus citations

Abstract

The synthesis of "rim-differentiated" C5-symmetric pillar[5]arenes, whose two rims are decorated with different chemical functionalities, has remained a challenging task. This is due to the inherent statistical nature of the cyclization of 1,4-disubstituted alkoxybenzenes with different substituents, which leads to four constitutional isomers with only 1/16th being rim-differentiated. Herein, we report a "preoriented" synthetic protocol based on FeCl3-catalyzed cyclization of asymmetrically substituted 2,5-dialkoxybenzyl alcohols. This yields an unprecedented 55% selectivity of the C5-symmetric tiara-like pillar[5]arene isomer among four constitutional isomers. Based on this new method, a series of functionalizable tiara-pillar[5]arene derivatives with C5-symmetry was successfully synthesized, isolated, and fully characterized in the solid state.

Original languageEnglish (US)
Pages (from-to)74-77
Number of pages4
JournalJournal of the American Chemical Society
Volume140
Issue number1
DOIs
StatePublished - Jan 10 2018
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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