Synthesis route to regioselectively functionalized bifunctional polyarene

We report the regioselective oxidative synthesis of polyaminonaphthol sulfonic acid (PANSA) particles and firstly obtained nanoparticles with molecular weight of ca 23200gmol(-1) using a template-free polymerization process in which NaOCl was used as an oxidant in aqueous basic medium. Nanoparticles were characterized using NMR, Fourier transform infrared and UV-visible spectroscopies, gel permeation chromatography, thermogravimetry (TG), differential scanning calorimetry (DSC), cyclic voltammetry, photoluminescence (PL), dynamic light scattering, X-ray diffraction, scanning electron microscopy (SEM), transmission electron microscopy (TEM) and conductivity techniques. SEM and TEM analyses showed that the nanoparticles had a self-stabilizing structure interconnecting with micro-channels. PANSA also exhibited reversible redox behaviour due to its electroactive nature. Nanoparticles display a slight hypsochromic shift and hyperchromic effect with higher intensity in PL spectra and also emitted an intense white light in dimethylsulfoxide. In addition, the thermal stability of PANSA was investigated using TG and DSC techniques. Finally, the kinetic parameters related to the solid-state thermal decomposition of PANSA were calculated from non-isothermal methods based on multiple heating rates. (c) 2015 Society of Chemical Industry