Faculty of Chemistry and Food Chemistry, Center for Advancing Electronics Dresden, Technische Universitat Dresden, 01062, Dresden, Germany.
Chair of Bioanalytical Chemistry, Technische Universität Dresden, 01062, Dresden, Germany.
Chemistry. 2018 Jul 25;24(42):10868-10875. doi: 10.1002/chem.201802631. Epub 2018 Jun 28.
Porous organic polymers (POPs) have attracted significant attention towards molecular adsorption in recent years due to their high porosity, diverse functionality and excellent chemical stability. In this work, we present a systematic case study on the formation of thiazolo[5,4-d]thiazole (TzTz) linkages through model compounds and its integration to synthesize a set of three novel, thermo-chemically stable TzTz-linked POPs, namely TzTz-POP-3, TzTz-POP-4, and TzTz-POP-5 with triphenylbenzene, tetraphenylpyrene and tetra(hydroxyphenyl)methane cores, respectively. Interestingly, the integrated TzTz moiety of the represented TzTz-POP-3 renders chemoselective removal of organic dye fluorescein (FL) from a mixture with parafuchsine (FU) in aqueous solution. The TzTz-POP-3 offered excellent chemoselectivity of ≈1:7 (FL:FU), compared to alike porous materials demonstrated for similar applications due to the presence of multiple active anchoring sites coupled with permanent porosity and appropriate pore window.
多孔有机聚合物（POPs）由于其高孔隙率、多样的功能和优异的化学稳定性，近年来在分子吸附方面引起了极大的关注。在这项工作中，我们通过模型化合物对噻唑并[5,4-d]噻唑（TzTz）键的形成进行了系统的案例研究，并将其集成到合成一组三种新型热稳定的 TzTz 键联的 POPs，分别为 TzTz-POP-3、TzTz-POP-4 和 TzTz-POP-5，它们的核分别为三苯基苯、四苯基芘和四（羟苯基）甲烷。有趣的是，所代表的 TzTz-POP-3 中的集成 TzTz 部分可在水溶液中从混合物中选择性地去除有机染料荧光素（FL）。与类似的用于类似应用的多孔材料相比，TzTz-POP-3 提供了 ≈1:7（FL:FU）的出色化学选择性，这是由于存在多个活性锚定点与永久孔隙率和适当的孔窗相结合。
