Solution Synthesis and Characterization of a Long and Curved Graphene Nanoribbon with Hybrid Cove–Armchair–Gulf Edge Structures
Abstract Curved graphene nanoribbons (GNRs) with hybrid edge structures have recently attracted increasing attention due to their unique band structures and electronic properties as a result of their nonplanar conformation. This work reports the solution synthesis of a long and curved multi‐edged GN...
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| Format: | Article |
| Language: | English |
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Wiley
2022-07-01
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| Series: | Advanced Science |
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| Online Access: | https://doi.org/10.1002/advs.202200708 |
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| author | Lin Yang Ji Ma Wenhao Zheng Silvio Osella Jörn Droste Hartmut Komber Kun Liu Steffen Böckmann David Beljonne Michael Ryan Hansen Mischa Bonn Hai I. Wang Junzhi Liu Xinliang Feng |
| author_facet | Lin Yang Ji Ma Wenhao Zheng Silvio Osella Jörn Droste Hartmut Komber Kun Liu Steffen Böckmann David Beljonne Michael Ryan Hansen Mischa Bonn Hai I. Wang Junzhi Liu Xinliang Feng |
| author_sort | Lin Yang |
| collection | DOAJ |
| description | Abstract Curved graphene nanoribbons (GNRs) with hybrid edge structures have recently attracted increasing attention due to their unique band structures and electronic properties as a result of their nonplanar conformation. This work reports the solution synthesis of a long and curved multi‐edged GNR (cMGNR) with unprecedented cove–armchair–gulf edge structures. The synthesis involves an efficient A2B2‐type Diels–Alder polymerization between a diethynyl‐substituted prefused bichrysene monomer (3b) and a dicyclopenta[e,l]pyrene‐5,11‐dione derivative (6) followed by FeCl3‐mediated Scholl oxidative cyclodehydrogenation of the obtained polyarylenes (P1). Model compounds 1a and 1b are first synthesized to examine the suitability and efficiency of the corresponding polymers for the Scholl reaction. The successful formation of cMGNR from polymer P1 bearing prefused bichrysene units is confirmed by FTIR, Raman, and solid‐state NMR analyses. The cove‐edge structure of the cMGNR imparts the ribbon with a unique nonplanar conformation as revealed by density functional theory (DFT) simulation, which effectively enhances its dispersibility in solution. The cMGNR has a narrow optical bandgap of 1.61 eV, as estimated from the UV–vis absorption spectrum, which is among the family of low‐bandgap solution‐synthesized GNRs. Moreover, the cMGNR exhibits a carrier mobility of ≈2 cm2 V−1 s−1 inferred from contact‐free terahertz spectroscopy. |
| first_indexed | 2024-12-11T03:33:10Z |
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| id | doaj.art-cb92d8f711dd4e45a63281ce507d9b3d |
| institution | Directory Open Access Journal |
| issn | 2198-3844 |
| language | English |
| last_indexed | 2024-12-11T03:33:10Z |
| publishDate | 2022-07-01 |
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| series | Advanced Science |
| spelling | doaj.art-cb92d8f711dd4e45a63281ce507d9b3d2022-12-22T01:22:20ZengWileyAdvanced Science2198-38442022-07-01919n/an/a10.1002/advs.202200708Solution Synthesis and Characterization of a Long and Curved Graphene Nanoribbon with Hybrid Cove–Armchair–Gulf Edge StructuresLin Yang0Ji Ma1Wenhao Zheng2Silvio Osella3Jörn Droste4Hartmut Komber5Kun Liu6Steffen Böckmann7David Beljonne8Michael Ryan Hansen9Mischa Bonn10Hai I. Wang11Junzhi Liu12Xinliang Feng13Centre for Advancing Electronics Dresden (cfaed) Department of Chemistry and Food Chemistry Technische Universität Dresden Dresden 01062 GermanyCentre for Advancing Electronics Dresden (cfaed) Department of Chemistry and Food Chemistry Technische Universität Dresden Dresden 01062 GermanyMax Planck Institute for Polymer Research Ackermannweg 10 Mainz 55128 GermanyChemical and Biological Systems Simulation Lab Centre of New Technologies University of Warsaw Banacha 2C Warsaw 02–097 PolandInstitute of Physical Chemistry Westfal̈ische Wilhelms‐Universitaẗ (WWU) Münster Corrensstraße 28/30 Münster D‐48149 GermanyLeibniz‐Institut für Polymerforschung Dresden e.V. Hohe Straße 6 Dresden 01069 GermanyCentre for Advancing Electronics Dresden (cfaed) Department of Chemistry and Food Chemistry Technische Universität Dresden Dresden 01062 GermanyInstitute of Physical Chemistry Westfal̈ische Wilhelms‐Universitaẗ (WWU) Münster Corrensstraße 28/30 Münster D‐48149 GermanyLaboratory for Chemistry of Novel Materials Université de Mons Mons B‐7000 BelgiumInstitute of Physical Chemistry Westfal̈ische Wilhelms‐Universitaẗ (WWU) Münster Corrensstraße 28/30 Münster D‐48149 GermanyMax Planck Institute for Polymer Research Ackermannweg 10 Mainz 55128 GermanyMax Planck Institute for Polymer Research Ackermannweg 10 Mainz 55128 GermanyDepartment of Chemistry and State Key Laboratory of Synthetic Chemistry The University of Hong Kong Pokfulam Road Hong Kong 999077 ChinaCentre for Advancing Electronics Dresden (cfaed) Department of Chemistry and Food Chemistry Technische Universität Dresden Dresden 01062 GermanyAbstract Curved graphene nanoribbons (GNRs) with hybrid edge structures have recently attracted increasing attention due to their unique band structures and electronic properties as a result of their nonplanar conformation. This work reports the solution synthesis of a long and curved multi‐edged GNR (cMGNR) with unprecedented cove–armchair–gulf edge structures. The synthesis involves an efficient A2B2‐type Diels–Alder polymerization between a diethynyl‐substituted prefused bichrysene monomer (3b) and a dicyclopenta[e,l]pyrene‐5,11‐dione derivative (6) followed by FeCl3‐mediated Scholl oxidative cyclodehydrogenation of the obtained polyarylenes (P1). Model compounds 1a and 1b are first synthesized to examine the suitability and efficiency of the corresponding polymers for the Scholl reaction. The successful formation of cMGNR from polymer P1 bearing prefused bichrysene units is confirmed by FTIR, Raman, and solid‐state NMR analyses. The cove‐edge structure of the cMGNR imparts the ribbon with a unique nonplanar conformation as revealed by density functional theory (DFT) simulation, which effectively enhances its dispersibility in solution. The cMGNR has a narrow optical bandgap of 1.61 eV, as estimated from the UV–vis absorption spectrum, which is among the family of low‐bandgap solution‐synthesized GNRs. Moreover, the cMGNR exhibits a carrier mobility of ≈2 cm2 V−1 s−1 inferred from contact‐free terahertz spectroscopy.https://doi.org/10.1002/advs.202200708curvedDiels–Alder polymerizationgraphene nanoribbonlow bandgapmulti‐edge structure |
| spellingShingle | Lin Yang Ji Ma Wenhao Zheng Silvio Osella Jörn Droste Hartmut Komber Kun Liu Steffen Böckmann David Beljonne Michael Ryan Hansen Mischa Bonn Hai I. Wang Junzhi Liu Xinliang Feng Solution Synthesis and Characterization of a Long and Curved Graphene Nanoribbon with Hybrid Cove–Armchair–Gulf Edge Structures Advanced Science curved Diels–Alder polymerization graphene nanoribbon low bandgap multi‐edge structure |
| title | Solution Synthesis and Characterization of a Long and Curved Graphene Nanoribbon with Hybrid Cove–Armchair–Gulf Edge Structures |
| title_full | Solution Synthesis and Characterization of a Long and Curved Graphene Nanoribbon with Hybrid Cove–Armchair–Gulf Edge Structures |
| title_fullStr | Solution Synthesis and Characterization of a Long and Curved Graphene Nanoribbon with Hybrid Cove–Armchair–Gulf Edge Structures |
| title_full_unstemmed | Solution Synthesis and Characterization of a Long and Curved Graphene Nanoribbon with Hybrid Cove–Armchair–Gulf Edge Structures |
| title_short | Solution Synthesis and Characterization of a Long and Curved Graphene Nanoribbon with Hybrid Cove–Armchair–Gulf Edge Structures |
| title_sort | solution synthesis and characterization of a long and curved graphene nanoribbon with hybrid cove armchair gulf edge structures |
| topic | curved Diels–Alder polymerization graphene nanoribbon low bandgap multi‐edge structure |
| url | https://doi.org/10.1002/advs.202200708 |
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