A One-Step Synthesis of a Poly(iptycene) through an Unusual Diels−Alder Cyclization/Dechlorination of Tetrachloropentacene

Publisher Website
Google Scholar
Abstract
We have discovered the first reaction of a substituted pentacene molecule as a dienophile. A surprisingly clean Diels−Alder self-coupling of Cl4Pn leads to a novel ladder polymer, poly(iptycene), which can be converted to a conducting carbon at relatively low temperature (600−900 °C). Theoretical calculations of the former reaction suggest a biradical asymmetric mechanism, despite highly symmetric reactants.