Kenawy El-Refaie, Ghazy Ahmed R, Rizk Hala F, Shendy S
Polymer Research Group, Chemistry Department, Faculty of Science, Tanta University, Tanta, 31527, Egypt.
Laser Laboratory, Physics Department, Faculty of Science, Tanta University, Tanta, 31527, Egypt.
Sci Rep. 2023 Oct 31;13(1):18686. doi: 10.1038/s41598-023-46051-w.
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.
吡咯 - 2,5 - 二甲醛(1)与5 - (2 - 氨基 - 4 - 苯基噻唑 - 5 - 基) - 4 - 苯基噻唑 - 2 - 胺(2)和/或5 - (4 - 氨基 - 苯基) - 4 - 苯基噻唑 - 2 - 胺(3)缩合,通过微波辐射和传统加热得到新型共轭聚合物聚(Z) - N - ((5 - (亚氨基甲基) - 1H - 吡咯 - 2 - 基)亚甲基) - 5 - (2 - ((E) - (5 - (亚氨基甲基) - 1 - 吡咯 - 2 - 基)亚甲基氨基) - 4 - 苯基噻唑 - 5 - 基) - 4 - 苯基噻唑 - 2 - 胺(P1)和/或聚(E) - N - ((5 - (亚氨基甲基) - 1H - 吡咯 - 2 - 基)亚甲基) - 5 - (4 - ((E) - (5 - (亚氨基甲基) - 1H - 吡咯 - 2 - 基)亚甲基氨基)苯基) - 4 - 苯基噻唑 - 2 - 胺(P2)。显然,微波辐射技术迅速提高了聚亚胺的分子量。除了对所得聚亚胺的分子量进行定量外,所有聚亚胺均使用傅里叶变换红外光谱(FTIR)、X射线衍射(XRD)、氢核磁共振(H1NMR)、热重分析(TGA)和差示扫描量热法(DSC)进行表征。使用紫外 - 可见分光光度计研究了聚亚胺衍生物的光学特性。吸收光谱显示聚亚胺(P1)在372 nm左右有一个主要吸收带,聚亚胺(P2)在381 nm左右有一个主要吸收带。计算得出光学能分别为2.49和2.68电子伏特。通过荧光分光光度计和激光光致发光实验测量并分析了聚亚胺衍生物的光致发光,并使用CIE图研究了发射颜色。荧光光谱显示聚亚胺(P1)在548 nm处有一个发射峰,在CIE图中为黄绿色,而聚亚胺(P2)的发射带位于440.5 nm处,在CIE图中为蓝色。测量了聚亚胺P1和P2在液态和固态下的光致发光量子产率PLQY,表明聚亚胺具有聚集诱导发光(AIE)行为。对聚亚胺衍生物进行了TD - DFT模拟,对其结构进行了几何优化并评估了光谱表征。