Department of Chemistry and Biochemistry

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Browsing Department of Chemistry and Biochemistry by Subject "Chemical synthesis"

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    Quinoidal diindenothienoacenes: synthesis and properties of new functional organic materials
    (Royal Society of Chemistry, 2014-06-16) Rudebusch, Gabriel; Fix, Aaron; Henthorn, Hilary; Vonnegut, Chris; Zakharov, Lev; Haley, Michael
    We report the preparation and characterization of a new class of quinoidal thienoacenes. The synthetic route is efficient, high-yielding and scalable with the potential for further functionalization. Single crystal X-ray diffraction reveals that, as size increases, the molecules pack in progressively closer 1D arrangements. The title compounds are shown to have amphoteric redox behaviour by cyclic voltammetry. The anion radicals are studied by EPR spectrometry and by computations. The electron-accepting nature, NIR absorption and the low-lying LUMO energies (ca. −4.0 eV) allude to potential use in materials applications.
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    Synthesis and properties of fully-conjugated indacenedithiophenes
    (Chemical Science, 2013-12-10) Young, Brian; Chase, Daniel Tyler, 1983-; Marshall, Jonathan; Vonnegut, Chris; Zakharov, Lev; Haley, Michael
    The synthesis and characterization of four fully-conjugated indacenedithiophenes (IDTs) are disclosed. In contrast to anthradithiophenes, regioselective synthesis of both syn and anti isomers is readily achieved. Thiophene fusion imparts increased paratropic character on the central indacene core as predicted by DFT calculations and confirmed by 1H NMR spectroscopy. IDTs exhibit red-shifted absorbance maxima with respect to their all-carbon analogues and undergo two-electron reduction and one-electron oxidation.