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.
Xie
Zengqi
Z
Universität Würzburg, Institut für Organische Chemie and Röntgen Research Center for Complex Material Systems, Am Hubland, 97074 Würzburg, Germany.
Würthner
Frank
F
D007094:Imides / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D010569:Perylene / Q000031:analogs & derivatives* / Q000737:chemistry; D010636:Phenols / Q000737:chemistry*; D013237:Stereoisomerism
D007094:Imides; D010636:Phenols; C510697:perylene bisimide; D010569:Perylene; C038764:2,2'-biphenol