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.
ASJC Scopus subject areas
- Colloid and Surface Chemistry