Wavy Graphene Nanoribbons Containing Periodic Eight-Membered Rings for Light-Emitting Electrochemical Cells.

Autor: Obermann S; Center for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, Mommsenstrasse 4, 01069, Dresden, Germany., Zhou X; Max-Planck-Institute for Polymer Research, Ackermannweg 10, 55128, Mainz, Germany., Guerrero-León LA; Center for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, Mommsenstrasse 4, 01069, Dresden, Germany., Serra G; Department of Chemistry, Materials, Chemical Engineering, Politecnico di Milano, Piazza Leonardo da Vinci 32, 20133, Milano, Italy., Böckmann S; Institute of Physical Chemistry, University of Münster, 48149, Münster, Germany., Fu Y; Center for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, Mommsenstrasse 4, 01069, Dresden, Germany., Dmitrieva E; Leibniz Institute for Solid State and Materials Research, Helmholtzstr. 20, 01069, Dresden, Germany., Zhang JJ; Max-Planck-Institute of Microstructure Physics, Weinberg 2, 06120, Halle, Germany., Liu F; Leibniz Institute for Solid State and Materials Research, Helmholtzstr. 20, 01069, Dresden, Germany., Popov AA; Leibniz Institute for Solid State and Materials Research, Helmholtzstr. 20, 01069, Dresden, Germany., Lucotti A; Department of Chemistry, Materials, Chemical Engineering, Politecnico di Milano, Piazza Leonardo da Vinci 32, 20133, Milano, Italy., Hansen MR; Institute of Physical Chemistry, University of Münster, 48149, Münster, Germany., Tommasini M; Department of Chemistry, Materials, Chemical Engineering, Politecnico di Milano, Piazza Leonardo da Vinci 32, 20133, Milano, Italy., Li Y; Max-Planck-Institute for Polymer Research, Ackermannweg 10, 55128, Mainz, Germany., Blom PWM; Max-Planck-Institute for Polymer Research, Ackermannweg 10, 55128, Mainz, Germany., Ma J; Center for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, Mommsenstrasse 4, 01069, Dresden, Germany.; College of Materials Science and Opto-Electronic Technology & Center of Materials Science and Optoelectronics Engineering, University of Chinese Academy of Science, 100049, Beijing, P. R. China., Feng X; Center for Advancing Electronics Dresden (cfaed) & Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, Mommsenstrasse 4, 01069, Dresden, Germany.; Max-Planck-Institute of Microstructure Physics, Weinberg 2, 06120, Halle, Germany.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2024 Sep 13, pp. e202415670. Date of Electronic Publication: 2024 Sep 13.
DOI: 10.1002/anie.202415670
Abstrakt: Precision graphene nanoribbons (GNRs) offer distinctive physicochemical properties that are highly dependent on their geometric topologies, thereby holding great potential for applications in carbon-based optoelectronics and spintronics. While the edge structure and width control has been a popular strategy for engineering the optoelectronic properties of GNRs, non-hexagonal-ring-containing GNRs remain underexplored due to synthetic challenges, despite offering an equally high potential for tailored properties. Herein, we report the synthesis of a wavy GNR (wGNR) by embedding periodic eight-membered rings into its carbon skeleton, which is achieved by the A 2 B 2 -type Diels-Alder polymerization between dibenzocyclooctadiyne (6) and dicyclopenta[e,l]pyrene-5,11-dione derivative (8), followed by a selective Scholl reaction of the obtained ladder-type polymer (LTP) precursor. The obtained wGNR, with a length of up to 30 nm, has been thoroughly characterized by solid-state NMR, FT-IR, Raman, and UV/Vis spectroscopy with the support of DFT calculations. The non-planar geometry of wGNR efficiently prevents the inter-ribbon π-π aggregation, leading to photoluminescence in solution. Consequently, the wGNR can function as an emissive layer for organic light-emitting electrochemical cells (OLECs), offering a proof-of-concept exploration in implementing luminescent GNRs into optoelectronic devices. The fast-responding OLECs employing wGNR will pave the way for advancements in OLEC technology and other optoelectronic devices.
(© 2024 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)
Databáze: MEDLINE
Externí odkaz: