Effects of Substituent on Binaphthyl Hinge-Containing Conductive Polymers

Conductive polymers containing hinged 1,1′-binaphthyl were synthesized. Their conformational flexibility around the 1,1′ C–C bonds was found to vary with the substituents at the 2,2′-positionshydroxy, linear alkyloxy, and macrocyclic alkyloxy groups were compared. Macrocyclic alkyloxy groups appeared to immobilize the binaphthyl. The connection patterns of electroactive oligothiophenes to the binaphthyl groups were also investigated with 6,6′- and 7,7′-attachments. The substituents binaphthyl polymers were examined using cyclic voltammetry, <i>in situ</i> conductivity measurements, and spectroelectrochemistry. Their electronic properties were found to vary greatly with the substituents and their connectivity. Binaphthyl polymer with hydroxyls and 3,4-ethylenedioxythiophenes exhibited interesting charge-trapping properties. 7,7′-Substitution led to intrachain interactions, which were promoted by the presence of linear alkyl chains. The observed properties give binaphthyl hinge-containing conductive polymers potential applicability in chiral electroactive sensors, polymer actuators, and electrochromic and optoelectronic devices