A new method for the synthesis of Chromogenic ionophores; 4,4’–nitrophenyl-azo-O,O’-phenyl- 3, 6, 9-trioxaundecane-1, 10-dioate (R1), bis-[4,4’-nitrophenyl-azo-naphthyl-(2,2-dioxydiethyl ether)] (R2) and non-cyclic ionophores; 1,8- bis -(2-naphthyloxy)-3,6-dioxaoctane (R3), 1,11-bis-(2-naphthyloxy)-3,6,9-trioxaundecane (R4), 1,5-bis- (2-naphthyloxy)-3-oxapentane (R5) has been constructed and their interaction with lithium, sodium, potassium and calcium picrates has been studied. The Complexes were isolated in methanol and mixture of methanol and ethyl acetate. The stoichiometry of complexes was 1:1. Characterization of complexes was carried out by m.p., elemental analysis, IR, 1H NMR, FAB mass analysis. The ionophore R1 complexes with Na+ and Ca++, R2 and R5 with Li+ and Mg++ respectively while R3 and R4 complexes with all metal ions. The same trend is observed in liquid –liquid extraction studies. As the supramolecular interaction between host and guest is temporary, non-covalent and required less energy to break interaction the selectivity / specificity of these ionophores will be utilized in construction of ion selective electrodes and as metal ion indicators.