Crystallographic evidence for global aromaticity in the di-anion and tetra-anion of a cyclophane hydrocarbon.

ABSTRACT: [2₄]Paracyclophanetetraene is a classic example of a macrocyclic hydrocarbon that becomes globally aromatic on reduction to the di-anion, and switches to globally anti-aromatic in the tetra-anion. This redox activity makes it promising as an electrode material for batteries. Here, we report the solid-state structures of the di- and tetra-anions of this cyclophane, in several coordination environments. The changes in bond length on reduction yield insights into the global aromaticity of the di-anion (26π electrons), and anti-aromaticity of the tetra-anion (28π electrons), that were previously deduced from NMR spectra of species generated in situ. The experimental geometries of the aromatic di-anion and anti-aromatic tetra-anion from X-ray crystallographic data match well w

SUBMITTER: Stawski W 

PROVIDER: S-EPMC10718070 | biostudies-literature | 2023 Dec

REPOSITORIES: biostudies-literature