D. Romito, E. Fresta, L. M. Cavinato, H. Kählig, H. Amenitsch, L. Caputo, Y. Chen, P. Samorì, J.- C. Charlier, R. D. Costa, D. Bonifazi.
Angew. Chem. Int. Ed. 2022, e202202137.
This work describes the design and synthesis of a π-conjugated telluro[3,2-β]-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).