Microwave-assisted of new derivatives of polyimine conjugated polymer based on Schiff base: synthesis, characterization, and photo-physical properties as a photoluminescent materials

Abstract

The condensation of pyrrole-2,5-dicarbaldehyde (1) with 5-(2-amino-4-phenylthiazol-5-yl)-4-phenylthiazol-2-amine (2) and/or 5-(4-Amino-phenyl)-4-phenylthiazol-2-amine (3) gave new poly(Z)-N-((5-(iminomethyl)-1H-pyrrol-2-yl)methylene)-5-(2-((E)-(5-(iminomethyl)-I-pyrrol-2-yl)methyleneamino)-4-phenylthiazol-5-yl)-4-phenylthiaol-2-amine (P1) and/or poly(E)-N-((5-(iminomethyl)-1H-pyrrol-2-yl)methylene)-5-(4-((E)-(5-(iminomethyl)-1H-pyrrol-2-yl)methyleneamino)phenyl)-4-phenylthiaol-2-amine (P2) as a novel conjugated polymer by microwave irradiation and traditional heating. It is evident that the microwave irradiation technique quickly raised the molecular weight of polyimines. In addition to quantifying the molecular weight of the resultant polyimines. All the polyimines were characterized using FTIR, XRD, H1NMR, TGA, and DSC. The optical characteristics of polyimine derivatives were investigated using a UV–Vis spectrophotometer. The absorption spectra showed a main absorption band around 372 nm for polyimine (P1) and 381 nm for polyimine (P2). The optical energy was calculated and found to be 2.49 and 2.68 eV. The photoluminescence of the polyimine derivatives was measured and analyzed by spectrofluorometer and Laser photoluminescence experiment and the emission color was studied using CIE graphs. The fluorescence spectra showed an emission peak at 548 nm for polyimine (P1) with yellow green color in CIE graph, while for polyimine (P2) the emission band was located at 440.5 nm with blue color in CIE graph. Photoluminescence quantum yield PLQY was measured for the polyimine P1 and P2 in both liquid and Solid states and indicated the AIE behavior of the polyimines. TD-DFT simulations were applied to the polyimine derivatives where the structures were geometrically optimized and the spectroscopic characterizations were evaluated.