Chiral Perylene Bisimide Dyes by Interlocked Arene Substituents in the Bay Area.

ABSTRACT: A series of perylene bisimide (PBI) dyes bearing various aryl substituents in 1,6,7,12 bay positions has been synthesized by Suzuki cross-coupling reaction. These molecules exhibit an exceptionally large and conformationally fixed twist angle of the PBI π-core due to the high steric congestion imparted by the aryl substituents in bay positions. Single crystal X-ray analyses of phenyl-, naphthyl- and pyrenyl-functionalized PBIs reveal interlocked π-π-stacking motifs, leading to conformational chirality and the possibility for the isolation of enantiopure atropoisomers by semipreparative HPLC. The interlocked arrangement endows these molecules with substantial racemization barriers of about 120 kJ mol^-1 for the tetraphenyl- and tetra-2-naphthyl-substituted derivatives, which is am

SUBMITTER: Renner R 

PROVIDER: S-EPMC8456824 | biostudies-literature | 2021 Aug

REPOSITORIES: biostudies-literature