Hexaphenolic Rigid Cages Prepared by Self-Organization of C3 v Tridentates

J Org Chem. 2018 Mar 16;83(6):3132-3141. doi: 10.1021/acs.joc.7b03111. Epub 2018 Mar 7.

Abstract

Coordination cages were composed by self-organization of rigid C3 v-symmetric heptaarene tridentates and Pd(II) precursors. The heptaarene framework involves one mesitylene, three phenol, and three pyridine moieties, which were connected by Suzuki coupling reactions. The treatment of the tridentates with Pd(dppp)(OTf)2 or Pd(en)(NO3)2 in a 2:3 molar ratio furnished coordination cages, which was ascertained by crystallography, 1H NMR and DOSY measurements, and ESI-TOFMS and UV-vis spectra. The cages have six phenolic hydroxy groups inside and were expected to incorporate hydrogen-bonding guest molecules such as saccharides. CD and DOSY measurements showed that octyl hexoside guests could be incorporated into the cage.

Publication types

  • Research Support, Non-U.S. Gov't