An efficient and versatile synthetic approach has been developed for the synthesis of large carboxy-substituted polycyclic arenes. This strategy relies on Perkin reactions between arylacetic and arylglyoxylic acids for the formation of flexible precursors. A subsequent rigidification step, by catalyst-or light-induced intramolecular cyclization reactions, then yealds fully condensed polycyclic aromatic compounds. Protection and deprotection techniques have been developed to allow the controlled assembly of a large number of building blocks. This method can now be applied to the formation of planar or non-planar, linear or macrocyclic species of various sizes.