Chiral benzo-fused Aza-BODIPYs with optical activity extending into the NIR range

Chiral benzo-fused aza-BODIPYs, namely N,N-difluoroboryl-[(dinaphtho[1,2-e:1',2'-g]-1,4-dioxocine)-1-[N-(3-phenyl-2H-isoindole-1-yl)methylene]-3-phenyl-1H-isoindol-1-ylidene)amine] (1) and N,N-difluoroboryl-[(dinaphtho[1,2-e:1',2'-g]-1,4-dioxocine)-1-[(dinaphtho[1,2-e: 1',2'-g]-1,4-dioxocine)-N-(3-phenyl-2H-isoindole-1-yl)methylene]-3-phenyl-1H-isoindol-1-ylidene)amine] (2), have been synthesized and spectroscopically characterized. Fusion of benzene moieties onto the BODIPY periphery in combination with the introduction of peripheral chiral binaphthyl substituents renders the extension of optical activity of resulting chiral benzo-fused aza-BODIPYs into the near-IR (NIR) range, representing the first chiral BODIPYs with NIR optically activity. For comparative study, N,N-difluoroboryl-[N-(3-phenyl-2H-isoindol-1-yl)-N-(3-phenyl-1H-isoindol-1-ylidene)amine] (0) was also prepared and characterized in a similar manner. (C) 2016 Elsevier Ltd. All rights reserved.