Electrochemical behaviour of different binaphthalene crown ethers. New electroformed polymer films as potential macromolecular hosts

The oxidation of bis-binaphtho-22-crown-6 (1) and binaphtho-20-crown-6 (2) in CH2Cl2 containing Bu4NBF4 leads to the one-step deposition of an electroactive polymer film onto the electrode surface. In other electrolytic media, the oxidation of these compounds causes the passivation of the electrode or leads reversibly to stable species. The potentiodynamic analysis of poly(1) and poly (2) shows that these polymers are sensitive to the used potential scan range, in particular a degradation of their electroactivity is evidenced for too positive potential values. The UV-Vis and IR spectroscopic properties of electroformed poly (1) and poly (2) films are also investigated. In order to determine the linkage of the naphthalene groups within the polymer structure, the voltammetric study of two non-electropolymerizable derivatives is undertaken. From the obtained results, a structure of poly (1) is then proposed.