Synthesis of N-annulated meta-phenylenediamines

ORGN 528

Lester T. Gray III, gray057@bama.ua.edu and Silas C. Blackstock, blackstock@ua.edu. Department of Chemistry, The University of Alabama, P.O. Box 870336, Tuscaloosa, AL 35487
The goal of this work is to synthesize an N-annulated meta-phenylenediamine structure. The addition of annulated rings will serve to minimize twisting or rotation about the N-phenyl bond, thereby reinforcing the molecule's planar geometry. A fixed, planar configuration will align the nitrogen n-orbitals with the pi-system of the central ring, affecting a greater degree of conjugation and favoring a putative triplet ground state for the corresponding diradical dication of such structures. Progress towards the development of N-annulated meta-phenylenediamine structures and the generation of said diradical dications will be herein described.