Synthesis of Functional Quinoxaline Derivatives for the Application in Biology and Materials Sciences

Download or read book Synthesis of Functional Quinoxaline Derivatives for the Application in Biology and Materials Sciences written by Laura Holzhauer and published by Logos Verlag Berlin GmbH. This book was released on 2024-02-19 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: Nitrogen-containing heterocycles belong to the most versatile and important compounds for medicinal chemistry and sustainable and advanced materials. Around 60 % of FDA-approved unique small molecule drugs incorporate a nitrogen heterocycle. N-heterocyclic compounds are essential components of organic light-emitting diodes and organic solar cells. Quinoxalines are a class of heterocyclic compounds accessible by straightforward syntheses, present in commercially available drugs and optoelectronic architectures. In this work, quinoxaline-containing compounds were synthesized and analyzed regarding their potential uses in biology and materials science, focusing on nitrogen-rich and dimeric quinoxalines. Various tetrazolo[1,5-a]quinoxalines were synthesized and converted to 1,2,3-triazoloquinoxalines and novel triazoloimidazoquinoxalines via a modified CuAAC procedure. A previously unknown copper-catalyzed denitrogenative annulation process was described in this context. As tankyrase inhibitors, substituted tetrazolo[1,5-a]quinoxaline derivatives were assembled and tested in biological studies. Moreover, the synthesis of quinoxaline dimers and metal complexation of selected 1,2,3-triazoloquinoxalines was investigated. Donor-acceptor emitter structures were assembled employing suitable tetrazolo [1,5-a]quinoxalines and 1,2,3-triazoloquinoxalines and their emissive properties were explored, highlighting the influence of the direction of the triazole linker on delayed fluorescence.