Supramolecular Chalcogen-Bonded Semiconducting Nanoribbons at Work in Lighting Devices

Deborah Romito, Dr. Elisa Fresta, Luca M. Cavinato, Prof. Dr. Hanspeter Kählig, Dr. Heinz Amenitsch, Laura Caputo, Yusheng Chen, Prof. Dr. Paolo Samorì, Prof. Dr. Jean-Christophe Charlier, Prof. Dr. Rubén D. Costa, Prof. Dr. Davide Bonifazi

Angew. Chem. Int. Ed. 2022, e202202137

DOI: 10.1002/anie.202202137

Abstract

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 (<1 h).

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