Quinoidal diindenothienoacenes: synthesis and properties of new functional organic materials
Loading...
Date
2014-06-16
Authors
Rudebusch, Gabriel
Fix, Aaron
Henthorn, Hilary
Vonnegut, Chris
Zakharov, Lev
Haley, Michael
Journal Title
Journal ISSN
Volume Title
Publisher
Royal Society of Chemistry
Abstract
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.
Description
Keywords
Quinoidal thienoacenes, Chemical synthesis, Organic electronics
Citation
1. Rudebusch GE, Fix AG, Henthorn HA, Vonnegut CL, Zakharov LN, Haley MM. Quinoidal diindenothienoacenes: synthesis and properties of new functional organic materials. Chem Sci. 2014;5(9):3627. doi:10.1039/C4SC01432D.