Supramolecular Chalcogen‐Bonded Semiconducting Nanoribbons at Work in Lighting Devices

Romito, Deborah;Fresta, Elisa;Cavinato, Luca M.;Kählig, Hanspeter;Bonifazi, Davide;et.al.
(2022) Angewandte Chemie (International Edition) — p. e202202137 (2022)

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Authors
  • Romito, Deborahorcid-logoDepartment of Organic Chemistry, Faculty of Chemistry, University of Vienna, Währinger Straße 38, 1090 Vienna (Austria)
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  • Fresta, ElisaTechnical University of Munich, Chair of Biogenic Functional Materials, Schulgasse 22, 94315 Straubing (Germany)
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  • Cavinato, Luca M.Technical University of Munich, Chair of Biogenic Functional Materials, Schulgasse 22, 94315 Straubing (Germany)
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  • Kählig, HanspeterDepartment of Organic Chemistry, Faculty of Chemistry, University of Vienna, Währinger Straße 38, 1090 Vienna (Austria)
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  • Caputo, Lauraorcid-logoUCLouvain
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  • Charlier, Jean-Christopheorcid-logoUCLouvain
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  • Bonifazi, Davideorcid-logoDepartment of Organic Chemistry, Faculty of Chemistry, University of Vienna, Währinger Straße 38, 1090 Vienna (Austria)
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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. OTFTbased charge transport measurements showed holetransport properties for this material. Its integration as a p-type semiconductor in multi-layered CuI-based lightemitting electrochemical cells (LECs) led to a 10-fold increase in stability (38 h vs. 3 h) compared to singlelayered 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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Romito, D., Fresta, E., Cavinato, L. M., Kählig, H., Amenitsch, H., Caputo, L., Chen, Y., Samorì, P., Charlier, J.-C., Costa, R. D., & Bonifazi, D. (2022). Supramolecular Chalcogen‐Bonded Semiconducting Nanoribbons at Work in Lighting Devices. Angewandte Chemie (International Edition), e202202137. https://doi.org/10.1002/anie.202202137 (Original work published 2022)