Ngoc TT,
Grabicki N,
Irran E,
Dumele O,
*,
Teichert JF.
*
Technische Universität Chemnitz, Humboldt-Universität zu Berlin and IRIS Adlershof,
Germany
Photoswitching Neutral Homoaromatic Hydrocarbons.
Nat. Chem. 2023;
15: 377-385
DOI:
10.1038/s41557-022-01121-w
Key words
neutral homoaromatics - intramolecular Buchner reaction - dearomatization - photoswitch
Significance
Neutral homoaromatic molecules are considered as a class of veiled species mainly
owing to the difficulty inherent to their syntheses, isolation and characterizations.
Inspired by the previously studied unstable elassovalene, the authors herein achieve
a series of novel neutral homoaromatic hydrocarbons with enhanced stability by reducing
the ring strain.
Comment
Facilitated by Cu(hFacac)2, an intramolecular Buchner dearomatization is performed to afford triasterane, which
upon oxidation produces a stable homoaromatic molecule. Interestingly, this homoannulene
ester is found to undergo a reversible photochemical rearrangement via [1,11]-sigmatropic
shift, thereby switching between the 6π and 10π homoaromatic structures.
