Macrodiscotic materials are liquid crystalline systems composed of an extended planar structure. It is anticipated that the self-ordering of such materials will result in interesting mechanical and electronic properties. Two synthetic strategies for the realisation of macrodiscotic materials are reviewed: firstly, the preparation of molecules which possess a single extended discotic core and secondly, the assembly of rigid, planar macromolecules composed of a random array of fused discotic units. Oxanthrene-based phthalonitrile precursors, prepared by high yielding reactions between catechols and 4,5-dichlorophthalonitrile, are used to explore both strategies for the synthesis of macrodiscotic materials that incorporate phthalocyanine (Pc) as the discotic unit.{Basis of a presentation given at Materials Discussion No. 4,[11][12][13][14]