Symmetric Mixed Sulfur–Selenium Fused Ring Systems as Potential Materials for Organic Field‐Effect Transistors. Issue 13 (9th January 2020)

• Record Type: Journal Article
• Authors: Holzer, Brigitte; Dellago, Barbara; Thamm, Ann‐Katrin; Mathis, Thomas; Stöger, Berthold; Horkel, Ernst; Hametner, Christian; Batlogg, Bertram; Fröhlich, Johannes; Lumpi, Daniel
• Is Part Of: Chemistry. Volume 26:Issue 13(2020)
• Page Start: 2869
• Page End: 2882
• Publication Date: 2020-01-09
• Subjects: heterocycles -- intermolecular interactions -- organic field effect transistor -- organic semiconductor -- selenium chemistry; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201903958
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A reliable synthetic protocol toward a series of fused chalcogenopheno[1]benzochalcogenophene (CBC) building blocks was developed based on a Fiesselmann reaction. The obtained CBC units were applied in McMurry and Stille coupling reactions toward symmetric regioisomeric ene‐linked dimers. These π‐conjugated compounds were characterized regarding their photophysical and electrochemical properties and proved to be materials with reduced HOMO–LUMO gaps compared to their sulfur‐based analogues. Single‐crystal X‐ray diffraction experiments revealed strong intermolecular selenium–selenium and selenium–carbon interactions depending on the position and number of incorporated selenium atoms. Good field‐effect transistor performance with charge carrier mobilities up to 4×10 −3 cm 2 V −1 s −1 and high on/off ratios could be observed. Abstract : This study introduces a series of regioisomeric symmetric sulfur–selenium fused materials for organic field‐effect transistors (OFETs). These π‐conjugated materials show strong intermolecular interactions beneficial for charge carrier transport.