Synthesis and characterization of novel optically active, poly(ester-imide)s bearing calix[4]arene and amino acid moieties: ionophoric properties and extraction abilities towards alkali-metal cations

Abstract

AbstractOptically active poly(ester-imide)s (PEIs) containing upper rim calix[4]arene were prepared in good yield by polycondensation reactions of distal calix[4]arene diol with some optically active diacid chlorides. Pyromellitic dianhydride (3) was reacted with chiral amino acids (4a-4e) to obtain the resulting imide-acids (6a-6e). The compounds (6a-6e) were converted into the corresponding diacid chlorides (7a-7e). The polycondensation reactions of calixarene diol with optically active compounds 7a-7e were carried out by two methods: bulk polycondensation under microwave irradiation and solution polycondensation in a system of triethyl amine (TEA)/dichloromethane (CH2Cl2). The optically active PEIs had good yield and moderate inherent viscosity ranging between 0.18-0.38 dL/g. The extraction ability measurements of PEIs towards alkali metal cations (Na+, K+, Cs+) and Ag+ showed a remarkable efficiency and selectivity toward Ag+.