DETERMINATION OF THE ENANTIOMERIC COMPOSITION OF CHIRAL AMINES BASED ON THE QUENCHING OF THE FLUORESCENCE OF A CHIRAL CALIXARENE

The synthesis of three chiral calixarene derivatives is described. One of these, an (S)-di-2-naphthylprolinol tetramer, is shown to exhibit significant ability to discriminate between enantiomers of l-phenyleth ylamine (PEA) and norephedrine on the basis of the quenching of the (S )-di-2-naphthylprolinol fluorescence emission in chloroform. The chira l discrimination appears to arise from preorganization of the four (S) -di-2-naphthylprolinol substituents on the calixarene, which define a three-dimensional chiral space. The ability to measure the enantiomeri c composition of PEA and norephedrine to within an error of 4.1% and 2 .6%, respectively, on the basis of a single fluorescence measurement i s demonstrated.