Hydrogen bond-rigidified planar squaraine dye and its electronic and organic semiconductor properties
Takeshi Maeda, Andreas Liess, Astrid Kudzus, Ana‐Maria Krause, Matthias Stolte, Hitoshi Amitani, Shigeyuki Yagi, Hideki Fujiwara, Frank Würthner
Abstract
The one-step reaction of a dicyanovinyl-functionalized squaric acid with Fischer bases afforded C2v symmetric squaraine dyes with rigid planar structures due to intramolecular N-HO hydrogen bonds. Dense molecular packing, decrease of HOMO level, and sufficient thermal stability for sublimation enabled vacuum-processed OTFTs with hole mobility up to 0.32 cm2 V-1 s-1 and current on/off ratio of 106.
Topics & Concepts
PlanarSemiconductorHydrogen bondOrganic semiconductorMaterials sciencePhotochemistryHydrogenChemistryOptoelectronicsMoleculeOrganic chemistryComputer scienceComputer graphics (images)Organic Electronics and PhotovoltaicsPhotochromic and Fluorescence ChemistryConducting polymers and applications