Synthesis, Structures, and Properties of Dehydrobiphenyleno[12]Annulenes: Carbon-Rich Compounds Comprising Two Different Antiaromatic Units.

ABSTRACT: In this work we report the synthesis, structure, and electronic properties of carbon-rich compounds dehydrobiphenyleno[12]annulenes (DBP[12]As) comprising antiaromatic four-membered rings (4MR) and 12-membered ring (12MR). Ultraviolet-visible absorption spectra and electrochemical behaviors of DBP[12]As confirmed their relatively narrow highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital (LUMO) gap values and high HOMO energy levels, which were supported by density functional theory simulations. Parent DBP[12]A adopts a slipped herringbone structure in a crystalline state, with the molecules forming 1D stacks via π-π interactions. The experimentally derived bond lengths, bonding analyses using the Wiberg bond indices, and localized orbital locator calculation supp

SUBMITTER: Suzuki K 

PROVIDER: S-EPMC12450042 | biostudies-literature | 2025 Sep

REPOSITORIES: biostudies-literature