Is Excited State Aromaticity a Driving Force for Planarization of Dibenzannelated 8π-Electron Heterocycles?
dc.contributor.author
dc.date.accessioned
2019-06-12T10:09:20Z
dc.date.available
2021-04-07T08:03:01Z
dc.date.issued
2019-06-01
dc.identifier.issn
2192-6506
dc.identifier.uri
dc.description.abstract
Compounds with dibenzannelated heterocycles with eight π‐electrons are found in a range of applications. These molecules often adopt a bent structure in the ground state (S0) but can become planar in the first excited states (S1 and T1) because of the cyclically conjugated 4nπ central ring, which fulfils the requirements for excited state aromaticity. We report on a quantum chemical investigation of the aromatic character in the S1 and T1 states of dibenzannelated seven‐ and six‐membered heterocycles with one, two, or three heteroatoms in the 8π‐electron ring. These states could have ππ* or nπ* character. We find that compounds with one or two heteroatoms in the central ring have ππ* states as their S1 and T1 states. They are to a significant degree influenced by excited state aromaticity, and their optimal structures are planar or nearly planar. Among the heteroatoms, nitrogen provides for the strongest excited state aromaticity whereas oxygen provides for the weakest, following the established trend of the S0 state. Yet, dibenzannelated seven‐membered‐ring compounds with N=N bonds have non‐aromatic nπ* states with strongly puckered structures as their S1 and T1 states
dc.format.extent
10 p.
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application/pdf
dc.language.iso
eng
dc.publisher
Wiley
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Versió postprint del document publicat a: https://doi.org/10.1002/cplu.201900066
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© ChemPlusChem, 2019, vol. 84, núm. 6, p. 712-721
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Articles publicats (D-Q)
dc.rights
Tots els drets reservats
dc.source
Toldo, Josene El Bakouri, Ouissam Solà i Puig, Miquel Norrby, Per‐Ola Ottosson, Henrik 2019 Is Excited State Aromaticity a Driving Force for Planarization of Dibenzannelated 8π-Electron Heterocycles? ChemPlusChem 84 6 712 721
dc.title
Is Excited State Aromaticity a Driving Force for Planarization of Dibenzannelated 8π-Electron Heterocycles?
dc.type
info:eu-repo/semantics/article
dc.rights.accessRights
info:eu-repo/semantics/openAccess
dc.embargo.terms
2020-06-01T00:00:00Z
dc.date.embargoEndDate
info:eu-repo/date/embargoEnd/2020-06-01
dc.type.version
info:eu-repo/semantics/acceptedVersion
dc.identifier.doi
dc.identifier.idgrec
029948
dc.type.peerreviewed
peer-reviewed