Nonplanar aromatic compounds. 8. Synthesis, crystal structures, and aromaticity investigations of the 1,n-dioxa[n](2,7)pyrenophanes. How does bending affect the cyclic pi-electron delocalization of the pyrene system?


A series of 1,n-dioxa[n](2,7)pyrenophanes (n = 7-12) with increasingly nonplanar pyrene moieties was synthesized by a 9-10 step sequence starting from 5-hydroxyisophthalic acid. The crystal structure of each member of this series was determined crystallographically. Several spectroscopic properties were found to vary with the extent of the nonplanarity of… (More)