Preparation and enantiomer recognition behaviour of azophenolic crown ethers containing cis-1-phenylcyclohexane-l,2-diol as the chiral subunit and 2,4-dinitrophenylazophenol as the chromophore

Abstract

Optically active azophenolic crown ethers 1 and 2 incorporating two cis-1-phenylcyclohexane-1,2-diol chiral subunits and a p-(2,4-dinitrophenylazo)phenol moiety as a chromophore have been prepared and the enantiomer recognitive coloration in complexation with chiral ethylamine and 2-aminoethanol derivatives has been examined. The observed enantiomer selectivities of crown ethers 1 and 2 have been interpreted on the basis of CPK molecular model examination of the diastereoisomeric complexes.