Abstract: Approaches to the synthesise of rigid molecular rods containing syn-facially positioned 7-oxa functionality the building BLOCK 12 was identified by molecular modelling as a suitable starting substrate. However, once synthesised, 12 was found to be unstable under the reaction conditions used in an attempt to create rigid rods. This included such coupling protocols as the epoxide based ACE reaction as well as the s-tetrazine system. The foundations have now been laid for future incorporation of 12 into rigid rods.