Perylene Bisimides with Rigid 2,2′-Biphenol Bridges at Bay Area as Conjugated Chiral Platforms

Facile nucleophilic substitution of two chlorine atoms by 2,2'-biphenol at one of the two bay areas (1,12- and 6,7-positions) of core-tetrachlorinated perylene bisimide afforded a novel, completely desymmetrized perylene bisimide building block, which could be further functionalized by substitution of the remaining two chlorine atoms. The atropisomers (P- and M-enantiomers) of the core twisted perylene bisimides were resolved by HPLC on a chiral column at room temperature, and the activation parameters for racemization were elucidated.