Synthesis and characterization of fluorescent polyphenols anchored Schiff bases via oxidative polycondensation

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Abstract

A series of polyimines, bearing phenolic groups were successfully synthesized in aqueous alkaline solution via chemical oxidative polycondensation. Polymeric Schiff bases were synthesized by condensation of 2,4-dihydroxybenzaldehyde and 3-hydroxy-4-metoxybenzaldehyde with 2-aminophenol and 3-aminophenol. The molecular structures of the synthesized Schiff bases and their corresponding polymers were studied by FT-IR, UV-Vis, 1H-NMR and 13C-NMR spectroscopic methods. Thermal stability of the imine polymers was evidenced by their initial degradation temperatures found in the range of 170 °C to 271 °C without any sign of melting. The results of UV-Vis and cyclic voltammetry (CV) measurements were coherent with the optical Eg and the electrochemical E′g band gaps of the polyimines which were lower than those of their corresponding Schiff bases. Fluorescence spectral analysis of P4 (Schiff base polymer P4 derived from 3-aminophenol and 3-hydroxy-4-methoxybenzaldehyde) revealed a bicolor emission with blue and green light. Electrical conductivity of the synthesized imine polymers was measured by four-point probe technique. P4 showed the highest electrical conductivity as a result of iodine vapor contact time. Morphology characterization of the synthesized polyimines was carried out using a scanning electron microscope SEM at different magnifications. The study revealed that P4 is a promising candidate for both blue and green light emitters which could be used in the production of photovoltaic materials and solar cells.

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