Facile synthesis of self-stabilized polyphenol nanoparticles

We describe here the facile synthesis (in two-steps) of green light emitting phenol polymer with an azomethine side group. For this purpose, hydroxy functionalized-Schiff base monomer, HPMBT, was obtained by condensation of 2,3,4-trihydroxybenzaldehyde with 2-aminophenol. Subsequent oxidation of the monomer in alkaline medium by NaOCl yielded to corresponding phenol polymer (PHPMBT) with molecular weight ca. 34,500 Da. The characterizations were performed by NMR, FT-IR, UV-vis, gel permeation chromatography (GPC), thermogravimetry (TG), differential scanning calorimetry (DSC), dynamic mechanical analysis (DMA), cyclic voltammetry (CV), photoluminescence (PL), dynamic light scattering (DLS) and scanning electron microscope (SEM) analysis. PL analysis indicated that HPMBT was non-fluorescent whereas PHPMBT was a green light emitter. In addition, the redox behaviors of the polymer were explored by cyclic voltammetry (CV), assigned it's electroactive nature. The formation of nano-sized polyphenol particles was revealed by the SEM and DLS analyses. A possible mechanism for the formation and self-stabilization of the polyphenol nanoparticles was also suggested. (C) 2013 Elsevier B.V. All rights reserved.