A 6π Azaelectrocyclization Strategy towards the 1,5,9‐Triazacoronenes

Abstract

Abstract We present the instance of two aromatic double bonds and an imine double bond involved thermal 6π‐azaelectrocyclization and, on this basis, a one‐step synthesis of triazacoronenes (TACs) from triphenylene‐1,5,9‐triamines and aldehydes under nonacidic conditions. This method has several advantages such as simplicity, high yields, and extensive substrate scope. A plausible reaction mechanism has been proposed with several experimental supports. A typical derivative shows a unique dimer holding together via a π‐π interaction and six H‐bonds and a zigzag superstructure stabilized by three centered H‐bonds and Br ⋅⋅⋅ π interaction between the adjacent dimers. magnified image