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Can Baird's and Clar's Rules Combined Explain Triplet State Energies of Polycyclic Conjugated Hydrocarbons with Fused 4nπ- and (4n + 2)π-Rings?

Ayub, Rabia (author)
Uppsala universitet,Molekylär biomimetik,Uppsala University, Sweden
Bakouri, O. E. (author)
Univ Girona, IQCC, C Maria Aurelia Capmany 6, Girona 17003, Catalonia, Spain.
Jorner, Kjell (author)
Uppsala universitet,Molekylär biomimetik
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Solà, M. (author)
Univ Girona, IQCC, C Maria Aurelia Capmany 6, Girona 17003, Catalonia, Spain.
Ottosson, Henrik (author)
Uppsala universitet,Molekylär biomimetik
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 (creator_code:org_t)
2017-06-07
2017
English.
In: Journal of Organic Chemistry. - : American Chemical Society. - 0022-3263 .- 1520-6904. ; 82:12, s. 6327-6340
  • Journal article (peer-reviewed)
Abstract Subject headings
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  • Compounds that can be labeled as "aromatic chameleons" are π-conjugated compounds that are able to adjust their π-electron distributions so as to comply with the different rules of aromaticity in different electronic states. We used quantum chemical calculations to explore how the fusion of benzene rings onto aromatic chameleonic units represented by biphenylene, dibenzocyclooctatetraene, and dibenzo[a,e]pentalene modifies the first triplet excited states (T1) of the compounds. Decreases in T1 energies are observed when going from isomers with linear connectivity of the fused benzene rings to those with cis- or trans-bent connectivities. The T1 energies decreased down to those of the parent (isolated) 4nπ-electron units. Simultaneously, we observe an increased influence of triplet state aromaticity of the central 4n ring as given by Baird's rule and evidenced by geometric, magnetic, and electron density based aromaticity indices (HOMA, NICS-XY, ACID, and FLU). Because of an influence of triplet state aromaticity in the central 4nπ-electron units, the most stabilized compounds retain the triplet excitation in Baird π-quartets or octets, enabling the outer benzene rings to adapt closed-shell singlet Clar π-sextet character. Interestingly, the T1 energies go down as the total number of aromatic cycles within a molecule in the T1 state increases. 

Subject headings

NATURVETENSKAP  -- Kemi -- Organisk kemi (hsv//swe)
NATURAL SCIENCES  -- Chemical Sciences -- Organic Chemistry (hsv//eng)

Keyword

Aromatization
Benzene
Electronic states
Electrons
Excited states
Isomers
Quantum chemistry
Aromaticities
Aromaticity indices
Closed shells
Electron distributions
Quantum chemical calculations
Triplet excitation
Triplet state
Triplet state energies
Quantum theory
hydrocarbon
polycyclic aromatic hydrocarbon derivative
Article
conjugation
electron
excitation
geometry
magnet

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ref (subject category)
art (subject category)

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Ayub, Rabia
Bakouri, O. E.
Jorner, Kjell
Solà, M.
Ottosson, Henrik
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NATURAL SCIENCES
NATURAL SCIENCES
and Chemical Science ...
and Organic Chemistr ...
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Journal of Organ ...
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Uppsala University

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