Template-Controlled Face-to-Face Stacking of Olefinic and Aromatic Carboxylic Acids in the Solid State

A rigid 1,8-dipyridylnaphthalene template for supramolecular organization of unsaturated dicarboxylic acids in the solid state has been developed. Self-assembly of the template and aromatic dicarboxylic acids generates nondistorted paracyclophane and pyridinophane architectures with perfectly superimposed π-systems. The dipyridyl template can be used to promote stereoselective solid-state dimerization of olefinic dicarboxylic acids.