Fully-fused boron-doped olympicenes: modular synthesis, tunable optoelectronic properties, and one-electron reduction.

ABSTRACT: We report here a novel family of boraolympicenes, structurally featuring boron-doping at the concave 11a-position of their π-skeletons and synthetically prepared via a facile one-pot triply borylation-based double-fold borocyclization reaction. Despite having no bulky protecting groups, these boraolympicenes exhibit excellent chemical stability against air and moisture, ascribed to the significant π-electron delocalization over the vacant p _z orbitals of boron atoms as evidenced by both single-crystallographic and theoretical analyses. More importantly, the modular synthesis of these boraolympicenes allows the fine-tuning of their physicochemical properties, endowing them with intriguing electronic features, such as intense visible-to-NIR absorption and low-lying L

SUBMITTER: Guo J 

PROVIDER: S-EPMC10094210 | biostudies-literature | 2023 Apr

REPOSITORIES: biostudies-literature