Supramolecular Chalcogen‐Bonded Semiconducting Nanoribbons at Work in Lighting Devices

• Published in: Angewandte Chemie International Edition 2022-09, Vol.61 (38), p.e202202137-n/a
• Main Authors: Romito, Deborah, Fresta, Elisa, Cavinato, Luca M., Kählig, Hanspeter, Amenitsch, Heinz, Caputo, Laura, Chen, Yusheng, Samorì, Paolo, Charlier, Jean‐Christophe, Costa, Rubén D., Bonifazi, Davide
• Format: Article
• Language: English
• Subjects: Chalcogen Bond; Chalcogen bonds; Charge density; Charge transport; Chemical Sciences; Congeners; Crystal Engineering; Crystals; Electrochemical cells; Electrochemistry; Electron states; Material chemistry; Nanoribbons; Organic Semiconductor; Single crystals; Supramolecular Architectures; Thin films; Transport properties
• ISSN: 1433-7851; 1521-3773; 1521-3773
• DOI: 10.1002/anie.202202137

This work describes the design and synthesis of a π‐conjugated telluro[3,2‐β][1]‐tellurophene‐based synthon that, embodying pyridyl and haloaryl chalcogen‐bonding acceptors, self‐assembles into nanoribbons through chalcogen bonds. The ribbons π‐stack in a multi‐layered architecture both in single crystals and thin films. Theoretical studies of the electronic states of chalcogen‐bonded material showed the presence of a local charge density between Te and N atoms. OTFT‐based charge transport measurements showed hole‐transport properties for this material. Its integration as a p‐type semiconductor in multi‐layered CuI‐based light‐emitting electrochemical cells (LECs) led to a 10‐fold increase in stability (38 h vs. 3 h) compared to single‐layered devices. Finally, using the reference tellurotellurophene congener bearing a C−H group instead of the pyridyl N atom, a herringbone solid‐state assembly is formed without charge transport features, resulting in LECs with poor stabilities (