Synthesis of chiral conjugated propeller-like polymers using optically active 1,1′-binaphthyl-2,2′-diamine derivatives

Abstract

Synthetic methods are developed to prepare the optically active derivatives of 1,1′-binaphthyl-2,2′-diamine by specific substitution at the 6,6′-positions and by tetraalkylation of the diamine groups. These optically active binaphthyldiamine compounds are used to build the propeller-like polymers by using the transition metal-catalyzed cross-coupling of aryl halides with terminal alkenes or alkynes. The resulting chiral conjugated aryleneethynylene and arylenevinylene polymers show significantly different UV and CD features from their 1,1′-bi-2-naphthol-based polymer analogs.