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J Org Chem. 2016 May 6;81(9):3877-81. doi: 10.1021/acs.joc.6b00617. Epub 2016 Apr 27.

A1/A2-Diamino-Substituted Pillar[5]arene-Based Acid-Base-Responsive Host-Guest System.

Author information

1
Shanghai Advanced Research Institute, Chinese Academy of Science , Shanghai 201210, China.
2
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, and Department of Chemistry, East China Normal University , Shanghai 200062, China.
3
Medicinal Chemistry, ChemBridge Research Laboratories , San Diego, California 92127, United States.

Abstract

An acid-base-responsive supramolecular host-guest system based on a planarly chiral A1/A2-diamino-substituted pillar[5]arene (1)/imidazolium ion recognition motif was created. The pillar[4]arene[1]diaminobenzene 1 can bring an electron-deficient imidazolium cation into its cylindrically shaped cavity under neutral or basic conditions and release it under acidic conditions.

PMID:
27088317
DOI:
10.1021/acs.joc.6b00617

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