A Strategy Based on Ambident Anthracene for the Synthesis of Higher-Order Iptycenes

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. 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 the longest-chain iptycene synthesized so far.image

Automated summary

A highly efficient method for synthesizing higher-order iptycenes using an ambident anthracene building block is presented. The method provides systematic synthesis of higher-order iptycenes, including the longest-chain iptycene synthesized so far. X-ray crystallography reveals interesting structures of these iptycenes, with solvent molecules filling the cavities and forming a honeycomb structure.