Issue 9, 2014

Quinoidal diindenothienoacenes: synthesis and properties of new functional organic materials

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.

Graphical abstract: Quinoidal diindenothienoacenes: synthesis and properties of new functional organic materials

Supplementary files

Article information

Article type
Edge Article
Submitted
15 May 2014
Accepted
16 Jun 2014
First published
16 Jun 2014
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2014,5, 3627-3633

Author version available

Quinoidal diindenothienoacenes: synthesis and properties of new functional organic materials

G. E. Rudebusch, A. G. Fix, H. A. Henthorn, C. L. Vonnegut, L. N. Zakharov and M. M. Haley, Chem. Sci., 2014, 5, 3627 DOI: 10.1039/C4SC01432D

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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