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- W2938289585 abstract "Abstract With the view to altering the lipophilicity and electron accepting ability of the tetraphenyl‐ carbo ‐benzene scaffold, peripheral fluorination of the C 18 ring through aromatic linkers was envisaged from the C 18 Ph 6 and o ‐ t Bu 2 C 18 Ph 4 references, by replacement of two Ph substituents with two p ‐CF 3 ‐C 6 H 4 counterparts ( F Tol). The synthesis relied on a [8+10] macrocyclization involving a common bis(trifluorotolyl)‐tetraynedione, followed by reductive aromatization of the resulting [6]pericyclynediols. While p ‐ F Tol 2 C 18 Ph 4 proved to be hardly tractable due to an extremely low solubility, p ‐ F Tol 2 ‐ o ‐ t Bu 2 C 18 Ph 2 could be extensively studied by X‐ray crystallography, NMR and UV/Vis spectroscopy, voltammetry, STM imaging of monolayers, and AFM imaging of binary films with P3HT or PC 71 BM fabricated by spin‐coating for organic photovoltaic cells and J − V curve measurement thereof. The electronic and polarity properties are correlated with moderate but consistent electron‐withdrawing effects of the CF 3 groups, in agreement with the DFT‐calculated frontier orbitals and multipole moments. The results provide guidelines for optimization of fluorinated carbo ‐benzene targets." @default.
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- W2938289585 date "2019-04-17" @default.
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- W2938289585 title "Expanding the <i>carbo</i> ‐Benzene Chemical Space for Electron‐Accepting Ability: Trifluorotolyl/Tertiobutyl Substitution Balance" @default.
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- W2938289585 doi "https://doi.org/10.1002/hlca.201900049" @default.
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