A Highly Warped Heptagon-Containing sp(2) Carbon Scaffold via Vinylnaphthyl pi-Extension
Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Journal Volume
58
Journal Issue
46
Pages
16504-16507
Date Issued
2019
Author(s)
Abstract
A new strategy is demonstrated for the synthesis of warped, negatively curved, all-sp2-carbon π-scaffolds. Multifold C?C coupling reactions are used to transform a polyaromatic borinic acid into a saddle-shaped polyaromatic hydrocarbon (2) bearing two heptagonal rings. Notably, this Schwarzite substructure is synthesized in only two steps from an unfunctionalized alkene. A highly warped structure of 2 was revealed by X-ray crystallographic studies and pronounced flexibility of this π-scaffold was ascertained by experimental and computational studies. Compound 2 exhibits excellent solubility, visible range absorption and fluorescence, and readily undergoes two reversible one-electron oxidations at mild potentials. ? 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
Subjects
arenes; carbon; curvature; C?C coupling; polycyclic aromatic hydrocarbons
SDGs
Other Subjects
Carbon; Polycyclic aromatic hydrocarbons; X ray crystallography; arenes; C-coupling reactions; Computational studies; Crystallographic studies; curvature; One-electron oxidation; Polyaromatic hydrocarbons; Unfunctionalized alkenes; Scaffolds
Type
journal article