Highly Strained Phenylene Bicyclophanes

Bending the rules: Strained bicyclophanes (see structure) with highly bent biphenylene units and a central aromatic moiety (yellow) forced into a perpendicular position were accessible in high yields by cyclization of the appropriate bromides by Yamamoto condensation. They were able to bind to graphite cutouts in solution and were adsorbed at the liquid/highly oriented pyrolytic graphite (HOPG) interface to form extended 2D structures.