The Aza-Diels—Alder Reaction: Novel Chemistry for the Synthesis of Quinoline-based Materials
Abstract
Polyquinolines have been studied since the early 1970s for their favorable chemical, optical, electrical, and mechanical properties. These properties have allowed polyquinolines to demonstrate their value in optoelectronics and biomedical applications. To date, polyquinolines are prepared primarily through a limited number of synthetic strategies, including Suzuki couplings, the Sonogashira reaction, and the Friedlander synthesis. This work demonstrates the application of the aza-Diels–Alder (Povarov) reaction for the synthesis of AB-type, AABB-type, sequence-specific, and bioconjugate quinoline model compounds and polymers. Our approach furnishes molecules with a unique architecture and connectivity, and therefore, may represent a welcome addition to the polymer chemist’s toolkit, by providing facile access to a diverse library of quinoline-type materials.