Synthesis and electronic properties of dibenzothieno-isoindole dione building blocks for organic electronic devices
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Date
2017
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University of New Brunswick
Abstract
The ability to control the physical and electronic properties of conjugated polymers and
small molecules has led to considerable focus on developing new electron-accepting
(EA) and electron-donating (ED) building blocks, which are essential for obtaining new
and efficient organic electronic materials. This work involves the design, synthesis and
characterization of fused thieno-isoindole scaffolds as versatile electronic building
blocks. The advantages of the dibenzothieno-isoindole dione scaffold include the
potential for a concise, 3-step synthetic route from easily available starting materials and
the capacity to fine-tune physical, optical, and electronic properties via numerous
synthetic handles. A short efficient synthesis to dibenzothieno-isoindole dione
derivatives was therefore developed from commercially available starting materials.
Two steps are required; a Suzuki-Miyaura coupling followed by an oxidative
cyclization. The synthesis of several dibenzothieno-isoindole dione derivatives will be
discussed as well as structure activity relationships, solid-state structure, and physicochemical
properties.
The investigation of noncovalent interactions involving halogens has led to the
discovery of numerous reliable motifs for supramolecular design. Four isomers of
diiodo-xylene were synthesized and their single crystal X-ray structures determined. I⋯I
interactions were found to play a strong role in defining the crystal packing patterns of
these simple aromatic structures.