Wavy Graphene Nanoribbons Containing Periodic Eight‐Membered Rings for Light‐Emitting Electrochemical Cells
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<sub>2</sub>B<sub>2</sub>-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.
Authors
- Yubin Fu (ORCID: https://orcid.org/0000-0002-2613-394X)
- Andrea Lucotti (ORCID: https://orcid.org/0000-0003-2148-1408)
- Ji Ma (ORCID: https://orcid.org/0000-0002-1308-3226)
- Sebastian Obermann (ORCID: https://orcid.org/0000-0002-3035-5772)
- Matteo Tommasini (ORCID: https://orcid.org/0000-0002-7917-426X)
- Paul W. M. Blom (ORCID: https://orcid.org/0000-0002-6474-9497)
- Gianluca Serra (ORCID: https://orcid.org/0000-0003-2095-9852)
- Evgenia Dmitrieva (ORCID: https://orcid.org/0000-0001-7490-617X)
- Xin Zhou (ORCID: https://orcid.org/0000-0002-7200-9819)
- Alexey A. Popov (ORCID: https://orcid.org/0000-0002-7596-0378)
- Fupin Liu (ORCID: https://orcid.org/0000-0002-8454-726X)
- Michael Ryan Hansen (ORCID: https://orcid.org/0000-0001-7114-8051)
- Steffen Böckmann (ORCID: https://orcid.org/0000-0003-4383-7719)
- Xinliang Feng (ORCID: https://orcid.org/0000-0003-3885-2703)
- Yungui Li (ORCID: https://orcid.org/0000-0001-7813-279X)
Institutions
- University of Münster (DE)
- Leibniz Institute for Solid State and Materials Research (DE)
- Max Planck Institute of Microstructure Physics (DE)
- Max Planck Institute for Polymer Research (DE)
- University of Chinese Academy of Sciences (CN)
- Technische Universität Dresden (DE)
- Politecnico di Milano (IT)
Publication Details
- Journal
- Angewandte Chemie International Edition
- Published
- 2024-09-13
- DOI
- https://doi.org/10.1002/anie.202415670
- Citations
- 7
- Primary Topic
- Molecular Junctions and Nanostructures
- Type
- article
- Field-Weighted Citation Impact
- 1.46
Funders
- Graphene Flagship
- Deutsche Forschungsgemeinschaft
- Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung
- Technische Universität Dresden
- China Scholarship Council
- Horizon 2020 Framework Programme
- Helmholtz-Zentrum Berlin für Materialien und Energie