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Unveiling the formation mechanism of the biphenylene network
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- Niu, Kaifeng, 1994- (author)
- Linköpings universitet,Materialdesign,Tekniska fakulteten,Institute of Functional Nano & Soft Materials (FUNSOM) and Jiangsu Key Laboratory for Carbon-Based Functional Materials & Devices, Soochow University, Suzhou China
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- Fan, Qitang (author)
- Department of Chemistry, Philipps-Universität Marburg, Germany
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- Chi, Lifeng (author)
- Institute of Functional Nano & Soft Materials (FUNSOM) and Jiangsu Key Laboratory for Carbon-Based Functional Materials & Devices, Soochow University, Suzhou, China; Department of Materials Science and Engineering, Macau University of Science and Technology, Macau, China
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- (creator_code:org_t)
- 2023
- 2023
- English.
- In: Nanoscale Horizons. - : ROYAL SOC CHEMISTRY. - 2055-6764 .- 2055-6756. ; 8:3, s. 368-376
- Journal article (peer-reviewed)
Abstract
Subject headings
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- We have computationally studied the formation mechanism of the biphenylene network via the intermolecular HF zipping, as well as identified key intermediates experimentally, on the Au(111) surface. We elucidate that the zipping process consists of a series of defluorinations, dehydrogenations, and C–C coupling reactions. The Au substrate not only serves as the active site for defluorination and dehydrogenation, but also forms C–Au bonds that stabilize the defluorinated and dehydrogenated phenylene radicals, leading to "standing" benzyne groups. Despite that the C–C coupling between the "standing" benzyne groups is identified as the rate-limiting step, the limiting barrier can be reduced by the adjacent chemisorbed benzyne groups. The theoretically proposed mechanism is further supported by scanning tunneling microscopy experiments, in which the key intermediate state containing chemisorbed benzyne groups can be observed. This study provides a comprehensive understanding towards the on-surface intermolecular HF zipping, anticipated to be instructive for its future applications.
Subject headings
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
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- art (subject category)
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