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Modular Synthesis of Organoboron Helically Chiral Compounds: Cutouts from Extended Helices.

ABSTRACT: Two types of helically chiral compounds bearing one and two boron atoms were synthesized by a modular approach. Formation of the helical scaffolds was executed by the introduction of boron to flexible biaryl and triaryl derived from small achiral building blocks. All-ortho-fused azabora[7]helicenes feature exceptional configurational stability, blue or green fluorescence with quantum yields (?_fl ) of 18-24?% in solution, green or yellow solid-state emission (?_fl up to 23?%), and strong chiroptical response with large dissymmetry factors of up to 1.12×10^-2 . Azabora[9]helicenes consisting of angularly and linearly fused rings are blue emitters exhibiting ?_fl of up to 47?% in CH₂ Cl₂ and 25?% in the solid state. As revealed by the DFT calculations, their P-M interconversion pathway is more complex than that of H1. Single-crystal X-ray analysis shows clear differences in the packing arrangement of methyl and phenyl derivatives. These molecules are proposed as primary structures of extended helices.

SUBMITTER: Full J

PROVIDER: S-EPMC7898935 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature

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