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- Title
An Unusually Small Singlet-Triplet Gap in a Quinoidal 1,6- Methano[10]annulene Resulting from Baird's 4n π-Electron Triplet Stabilization.
- Authors
Streifel, Benjamin C.; Zafra, José L.; Espejo, Guzmán L.; Gómez-García, Carlos J.; Casado, Juan; Tovar, John D.
- Abstract
Within the continuum of p-extended quinoidal electronic structures exist molecules that by design can support open-shell diradical structures. The prevailing molecular design criteria for such structures involve proaromatic nature that evolves aromaticity in open-shell diradical resonance structures. A new diradical species built upon a quinoidal methano[10]annulene unit is synthesized and spectroscopically evaluated. The requisite intersystem crossing in the open-shell structure is accompanied by structural reorganization from a contorted Möbius aromatic-like shape in S0 to a more planar shape in the Hückel aromatic-like T1. This stability was attributed to Baird's Rule which dictates the aromaticity of 4n p-electron triplet excited states.
- Subjects
ANNULENES; ELECTRONIC structure; COMPUTER-assisted molecular design; RESONANCE; AROMATIC compounds
- Publication
Angewandte Chemie International Edition, 2015, Vol 54, Issue 20, p5888
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201500879