Synthesis, characterization and electrochemical properties of poly(phenoxy-imine)s containing peril and tert-butyl units

Abstract

Schiff bases were obtained by condensation reactions of 2-aminophenol and 4-aminophenol with 4-isopropenylcyclohex-1-ene-1-carbaldehyde (peril aldehyde) and 3,5-di-tert-butyl-2-hydroxy benzaldehyde. Then, polymers of these compounds were prepared via oxidative polymerization method in THF in the presence of NaOCl as an oxidant. The structures of compounds were confirmed by some techniques such as FT-IR, 1H NMR, 13C NMR and UV–vis. Moreover, cyclic voltammetry (CV) was used to calculate the HOMO−LUMO energy levels and electrochemical band gaps (Eg′) of compounds. Electrochemical band gaps (Eg′) values of P1, P2, P3 and P4 polymers were found as 2.61, 2.65, 2.89 and 2.28 eV, respectively. Furthermore, TGA and DSC were employed to determine thermal properties of the Schiff bases and polymers. The photoluminescence (PL) properties of polymers were also determined in DMSO. Then, we found that their number-average molecular weight (Mn), weight average molecular weight (Mw) as well as polydispersity index (PDI) values by the size exclusion chromatography (SEC). Finally, we carried out their solubility tests in acetone, THF, chloroform, acetonitrile, methanol, ethyl acetate, n-hexane and DMSO. Keywords: Poly(phenoxy-imine)s, Poly(azomethine), Oxidative polycondensation, Conjugated polymers