Obermann, S.; Zhou, X.; Guerrero-León, L.A.; Serra, G.; Böckmann, S.; Fu, Y.; Dmitrieva, E.; Zhang, J.J.; Liu, F.; Popov, A.A.; Lucotti, A.; Hansen, M.R.; Tommasini, M.; Li, Y.; Blom, P.W.M.; Ma, J.; Feng, X.: Wavy Graphene Nanoribbons Containing Periodic Eight-Membered Rings for Light-Emitting Electrochemical Cells. Angewandte Chemie - International Edition 63 (2024), p. e202415670/1-9
10.1002/anie.202415670
Open Access Version (externer Anbieter)
Abstract:
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 A2B2-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.