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  • 1.
    Messersmith, Reid E.
    et al.
    Johns Hopkins Univ, Dept Chem, 3400 North Charles St, Baltimore, MD 21218 USA..
    Yadav, Sangeeta
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
    Siegler, Maxime A.
    Johns Hopkins Univ, Dept Chem, 3400 North Charles St, Baltimore, MD 21218 USA..
    Ottosson, Henrik
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Molecular Biomimetics.
    Tovar, John D.
    Johns Hopkins Univ, Dept Chem, 3400 North Charles St, Baltimore, MD 21218 USA.;Johns Hopkins Univ, Dept Mat Sci & Engn, 3400 North Charles St, Baltimore, MD 21218 USA..
    Benzo[b]thiophene Fusion Enhances Local Borepin Aromaticity in Polycyclic Heteroaromatic Compounds2017In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 82, no 24, p. 13440-13448Article in journal (Refereed)
    Abstract [en]

    This report documents the synthesis, characterization, and computational evaluation of two isomeric borepin-containing polycyclic aromatics. The syntheses of these two isomers involved symmetrical disubstituted alkynes that were reduced to Z-olefins followed by borepin formation either through an isolable stannocycle intermediate or directly from the alkene via the trapping of a transient dilithio intermediate. Comparisons of their magnetic, crystallographic, and computational characterization to literature compounds gave valuable insights about the aromaticity of these symmetrically fused [b,f]borepins. The fusion of benzo[b]thiophene units to the central borepin cores forced a high degree of local aromaticity within the borepin moieties relative to other known borepin-based polycyclic aromatics. Each isomer had unique electronic responses in the presence of fluoride anions. The experimental data demonstrate that the local borepin rings in these two compounds have a relatively high amount of aromatic character. Results from quantum chemical calculations provide a more comprehensive understanding of local and global aromatic characters of various rings in fused ring systems built upon boron heterocycles.

  • 2.
    Yadav, Sangeeta
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström.
    El Bakouri, Ouissam
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström.
    Jorner, Kjell
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström.
    Tong, Hui
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Dahlstrand, Christian
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Sola, Miquel
    Univ Girona, IQCC, C Maria Aurelia Capmany 69, Girona 17003, Catalonia, Spain;Univ Girona, Dept Quim, C Maria Aurelia Capmany 69, Girona 17003, Catalonia, Spain.
    Ottosson, Henrik
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström.
    Exploiting the Aromatic Chameleon Character of Fulvenes for Computational Design of Baird-Aromatic Triplet Ground State Compounds2019In: Chemistry - An Asian Journal, ISSN 1861-4728, E-ISSN 1861-471X, Vol. 14, no 10, p. 1870-1878Article in journal (Refereed)
    Abstract [en]

    Due to the reversal in electron counts for aromaticity and antiaromaticity in the closed-shell singlet state (normally ground state, S-0) and lowest * triplet state (T-1 or T-0), as given by Huckel's and Baird's rules, respectively, fulvenes are influenced by their substituents in the opposite manner in the T-1 and S-0 states. This effect is caused by a reversal in the dipole moment when going from S-0 to T-1 as fulvenes adapt to the difference in electron counts for aromaticity in various states; they are aromatic chameleons. Thus, a substituent pattern that enhances (reduces) fulvene aromaticity in S-0 reduces (enhances) aromaticity in T-1, allowing for rationalizations of the triplet state energies (E-T) of substituted fulvenes. Through quantum chemical calculations, we now assess which substituents and which positions on the pentafulvene core are the most powerful for designing compounds with low or inverted E-T. As a means to increase the -electron withdrawing capacity of cyano groups, we found that protonation at the cyano N atoms of 6,6-dicyanopentafulvenes can be a route to on-demand formation of a fulvenium dication with a triplet ground state (T-0). The five-membered ring of this species is markedly Baird-aromatic, although less than the cyclopentadienyl cation known to have a Baird-aromatic T-0 state.

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