In this focus article, the recent syntheses of various (hetero)aromatic/macrocyclic molecules/scaffolds such as (thia)calixarenes, iptycenes, [poly](aza)arenes, 2,2′bipyridines, 1,2,4triazines, (ox)azoles and aziri(di)nes are reviewed. The employed rational synthetic schemes and green chemistry principles such as solventfree reactions, reactions in ionic liquids, arynemediated reactions, domino and multicomponent reactions, sono, photoand mechanoactivated processes, and direct C–H functionalization are described. The obtained compounds exhibited promising photophysical and coordination properties, intriguing supramolecular properties as well as biological activities. The possible application of these compounds as fluorophores, luminophores, organic phosphors, chemosensors, ligands and drug candidates is discussed.