Catalytic Oxidation of 2,7-Dihydroxynaphthalene

Abstract

Two polymer–metal complexes were used for catalytic oxidative polymerization of 2,7-dihydroxynaphthalene (DHN) with the aim of exploiting new and potent catalysts. The structure of the resulting poly(2,7-dihydroxynaphthalene) (PDHN) was confirmed by various spectral techniques: UV–vis, FT-IR, 1H NMR, 13C NMR, 1H–1H COSY, and 1H–13C HSQC. The 3 and 6 positions of the DHN ring were suggested as main coupling sites. The effect of the reaction conditions on the monomer conversions and the polymer molecular weight was determined: yields in the range 74–99% and number-average molecular weights in the range 1700–83 000 g mol–1 were obtained. Thermal, optical, and electrochemical behaviors of the polymer were also studied. From fluorescence analyses, a case of negative solvatochromism for PDHN was established.