Synthesis of a Cyclophane Bearing Two Benz[a]anthracene Units Connected at the 5 and 7 Positions with Two Naphth-1,4-diyl Groups.

A synthetic pathway to a cyclophane bearing two benz[a]anthracene units connected at the 5 and 7 positions through two naphth-1,4-diyl groups was developed, and its structure was confirmed by X-ray structure analysis. Because of structural constraints, the two naphthyl groups are distorted from planarity and the bonds connecting them to the benz[a]anthracene units are bent significantly. The UV-vis and fluorescence spectra of the cyclophane are red-shifted from those of 7-(1-naphthalenyl)benz[a]anthracene, which is the corresponding monomeric polycyclic aromatic hydrocarbon.