Supramolecular Chalcogen‐Bonded Semiconducting Nanoribbons at Work in Lighting Devices. Issue 38 (28th April 2022)

• Record Type: Journal Article
• 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
• Is Part Of: Angewandte Chemie international edition. Volume 61:Issue 38(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-04-28
• Subjects: Chalcogen Bond -- Crystal Engineering -- Organic Semiconductor -- Supramolecular Architectures; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.202202137
• Languages: English
• ISSNs: 1433-7851

Abstract

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 Cu I ‐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). Abstract : Chalcogen‐bonded p‐type semiconducting ribbons have been engineered through the self‐assembly of tailored π‐conjugated modules. Theoretical studies of the electronic states showed the presence of a local charge density between Te and N atoms. Implementation of the ribbons as hole‐transport layers in light‐emitting electrochemical cells gave rise to devices with performances similar to those obtained with state‐of‐art semiconductors.