Cyclopentannulation and cyclodehydrogenation of isomerically pure 5,11-dibromo-anthradithiophenes leading to contorted aromatics

Abstract

Isomerically pure 5,11-dibromo-2,8-dihexylanthra[2,3-b:76-b′]dithiophene, a brominated analog of anthracenedithiophene (ADT), was prepared and utilized for a palladium catalyzed cyclopentannulation reaction with 3,3′-dimethoxy-phenylacetylene to give cyclopentannulated ADT (CP-ADTs). A further Scholl cyclodehydrogenation reaction gave contorted aromatics with large splay angles, low optical gaps, and low LUMOs.