AI Article Synopsis
- - The study focuses on stabilizing antiaromatic compounds by using bulky groups and fusing aromatic rings, which can reduce their antiaromatic characteristics.
- - Researchers synthesized and analyzed four isomers of naphthothiophene-fused -indacene, with one isomer showing greater antiaromaticity than the original -indacene.
- - Various computational and experimental techniques, including NMR spectroscopy and UV-Vis spectrophotometry, were employed to investigate the unique properties of this compound, highlighting its exceptionally low energy gap between its highest occupied and lowest unoccupied molecular orbitals.
Article Abstract
Addressing the instability of antiaromatic compounds often involves protection with bulky groups and/or fusion of aromatic rings, thus decreasing paratropicity. We report four naphthothiophene-fused -indacene isomers, one of which is more antiaromatic than parent -indacene. This surprising result is examined computationally through nucleus-independent chemical shift XY calculations and experimentally via nuclear magnetic resonance spectroscopy, X-ray crystallography, ultraviolet-visible spectrophotometry, and cyclic voltammetry, with the latter two indicating that this molecule possesses the lowest highest occupied molecular orbital-lowest unoccupied molecular orbital energy gap observed for heterocycle-fused -indacene.
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| http://dx.doi.org/10.1021/acs.orglett.1c01514 | DOI Listing |
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