A Strategy Based on “Ambident Anthracene” for the Synthesis of Higher‐Order Iptycenes

Abstract

An efficient method for the synthesis of higher‐order iptycenes using an “ambident anthracene” building block is presented. For that purpose, an iterative elongation strategy involving the ring‐opening of an endoxide to give a highly reactive anthranoxide, followed by a Diels‐Alder reaction with an aryne was used. The method systematically provides higher‐order iptycenes, including trideciptycene, which is currently the iptycene with the longest chain to have been synthesized. X‐ray crystallography revealed interesting structures in which solvent molecules fill the cavities of these iptycenes, thus creating a “honeycomb” structure with the solvent molecules arranged in tubular spaces.