Sebastian Obermann, Xin Zhou, L. Andrés Guerrero-León, Gianluca Serra, Steffen Böckmann, Dr. Yubin Fu, Dr. Evgenia Dmitrieva, Dr. Jin-Jiang Zhang, Dr. Fupin Liu, Dr. Alexey A. Popov, Dr. Andrea Lucotti, Prof. Dr. Michael Ryan Hansen, Prof. Dr. Matteo Tommasini, Dr. Yungui Li, Prof. Dr. Paul W. M. Blom, Dr. Ji Ma, Prof. Dr. Xinliang Feng
{"title":"用于发光电化学电池的含周期性八元环的波浪状石墨烯纳米带","authors":"Sebastian Obermann, Xin Zhou, L. Andrés Guerrero-León, Gianluca Serra, Steffen Böckmann, Dr. Yubin Fu, Dr. Evgenia Dmitrieva, Dr. Jin-Jiang Zhang, Dr. Fupin Liu, Dr. Alexey A. Popov, Dr. Andrea Lucotti, Prof. Dr. Michael Ryan Hansen, Prof. Dr. Matteo Tommasini, Dr. Yungui Li, Prof. Dr. Paul W. M. Blom, Dr. Ji Ma, Prof. Dr. Xinliang Feng","doi":"10.1002/anie.202415670","DOIUrl":null,"url":null,"abstract":"<p>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 (<b>wGNR</b>) 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 (<b>6</b>) and dicyclopenta[<i>e</i>,<i>l</i>]pyrene-5,11-dione derivative (<b>8</b>), followed by a selective Scholl reaction of the obtained ladder-type polymer (<b>LTP</b>) precursor. The obtained <b>wGNR</b>, 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 <b>wGNR</b> efficiently prevents the inter-ribbon π–π aggregation, leading to photoluminescence in solution. Consequently, the <b>wGNR</b> 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 <b>wGNR</b> will pave the way for advancements in OLEC technology and other optoelectronic devices.</p>","PeriodicalId":125,"journal":{"name":"Angewandte Chemie International Edition","volume":"63 50","pages":""},"PeriodicalIF":16.1000,"publicationDate":"2024-09-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/anie.202415670","citationCount":"0","resultStr":"{\"title\":\"Wavy Graphene Nanoribbons Containing Periodic Eight-Membered Rings for Light-Emitting Electrochemical Cells\",\"authors\":\"Sebastian Obermann, Xin Zhou, L. Andrés Guerrero-León, Gianluca Serra, Steffen Böckmann, Dr. Yubin Fu, Dr. Evgenia Dmitrieva, Dr. Jin-Jiang Zhang, Dr. Fupin Liu, Dr. Alexey A. Popov, Dr. Andrea Lucotti, Prof. Dr. Michael Ryan Hansen, Prof. Dr. Matteo Tommasini, Dr. Yungui Li, Prof. Dr. Paul W. M. Blom, Dr. Ji Ma, Prof. Dr. Xinliang Feng\",\"doi\":\"10.1002/anie.202415670\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>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 (<b>wGNR</b>) 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 (<b>6</b>) and dicyclopenta[<i>e</i>,<i>l</i>]pyrene-5,11-dione derivative (<b>8</b>), followed by a selective Scholl reaction of the obtained ladder-type polymer (<b>LTP</b>) precursor. The obtained <b>wGNR</b>, 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 <b>wGNR</b> efficiently prevents the inter-ribbon π–π aggregation, leading to photoluminescence in solution. Consequently, the <b>wGNR</b> 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. 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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.
期刊介绍:
Angewandte Chemie, a journal of the German Chemical Society (GDCh), maintains a leading position among scholarly journals in general chemistry with an impressive Impact Factor of 16.6 (2022 Journal Citation Reports, Clarivate, 2023). Published weekly in a reader-friendly format, it features new articles almost every day. Established in 1887, Angewandte Chemie is a prominent chemistry journal, offering a dynamic blend of Review-type articles, Highlights, Communications, and Research Articles on a weekly basis, making it unique in the field.