Circularly Polarized Fluorescent Helicene-Boranils: Synthesis, Photophysical and Chiroptical Properties

Chemistry. 2021 May 20;27(29):7959-7967. doi: 10.1002/chem.202100356. Epub 2021 Apr 22.

Abstract

Mono- and di-boranil-substituted helicenes were prepared by BF2 -borylation of the corresponding anils, readily synthesized by condensation of 2-amino- and 2,15-diamino-helicenes with 4-(diethylamino)salicylaldehyde. After enantiomeric resolution using HPLC, their chiroptical properties including circularly polarized fluorescence in solution and in PMMA films were investigated and rationalized with the help of NMR, X-ray and quantum-chemical calculations.

Keywords: boranil; chirality; circularly polarized luminescence; helicene; quantum chemistry.