An endergonic synthesis of single Sondheimer–Wong diyne by local probe chemistry

Recent advances in scanning probe microscopy on surface enable not only direct observation of molecular structures but also local probe reactions, in which unstable short-lived products have been synthesized and analyzed. Now, an endergonic reaction to synthesize a single Sondheimer–Wong diyne from...

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Main Authors: Kawai, Shigeki, Sang, Hongqian, Kantorovich, Lev, Takahashi, Keisuke, Nozaki, Kyoko, Ito, Shingo
Other Authors: School of Chemistry, Chemical Engineering and Biotechnology
Format: Article
Language:English
Published: 2023
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Online Access:https://hdl.handle.net/10356/170445
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1704452023-09-12T05:42:49Z An endergonic synthesis of single Sondheimer–Wong diyne by local probe chemistry Kawai, Shigeki Sang, Hongqian Kantorovich, Lev Takahashi, Keisuke Nozaki, Kyoko Ito, Shingo School of Chemistry, Chemical Engineering and Biotechnology Science::Chemistry CO Functionalized Tip Density Functional Calculations Recent advances in scanning probe microscopy on surface enable not only direct observation of molecular structures but also local probe reactions, in which unstable short-lived products have been synthesized and analyzed. Now, an endergonic reaction to synthesize a single Sondheimer–Wong diyne from 6,13-dibromopentaleno[1,2-b:4,5-b’]dinaphthalene by local probe chemistry on a ultra-thin film of NaCl formed on a Cu(111) surface at 4.3 K is presented. The structures of the precursor, two intermediates, and the final product were directly identified by the differential conductance imaging with a CO functionalized tip. DFT calculations revealed that the multiple-step reaction, being endergonic overall, is facilitated by temporal charging and discharging of the molecule placed in the nanometric junction between the Cu tip and the Cu substrate underneath the ultra-thin NaCl film. This local probe reaction expands possibilities to synthesize nanocarbon materials in a bottom-up manner. Ministry of Education (MOE) Nanyang Technological University This work was supported in part by Japan Society for the Promotion of Science (JSPS) KAKENHI Grant Number19H00856, by Nanyang Technological University, by the Singapore Ministry of Education via Academic Research Fund Tier 1: 2018-T1-002-021, by the National Natural Science Foundation of China (Grant No. 21603086), and by China Scholarship Council (Grant No. 201608420186). 2023-09-12T05:42:49Z 2023-09-12T05:42:49Z 2020 Journal Article Kawai, S., Sang, H., Kantorovich, L., Takahashi, K., Nozaki, K. & Ito, S. (2020). An endergonic synthesis of single Sondheimer–Wong diyne by local probe chemistry. Angewandte Chemie, 132(27), 10934-10939. https://dx.doi.org/10.1002/ange.202001268 0044-8249 https://hdl.handle.net/10356/170445 10.1002/ange.202001268 27 132 10934 10939 en 2018-T1-002-021 Angewandte Chemie © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. All rights reserved.
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Science::Chemistry
CO Functionalized Tip
Density Functional Calculations
spellingShingle Science::Chemistry
CO Functionalized Tip
Density Functional Calculations
Kawai, Shigeki
Sang, Hongqian
Kantorovich, Lev
Takahashi, Keisuke
Nozaki, Kyoko
Ito, Shingo
An endergonic synthesis of single Sondheimer–Wong diyne by local probe chemistry
description Recent advances in scanning probe microscopy on surface enable not only direct observation of molecular structures but also local probe reactions, in which unstable short-lived products have been synthesized and analyzed. Now, an endergonic reaction to synthesize a single Sondheimer–Wong diyne from 6,13-dibromopentaleno[1,2-b:4,5-b’]dinaphthalene by local probe chemistry on a ultra-thin film of NaCl formed on a Cu(111) surface at 4.3 K is presented. The structures of the precursor, two intermediates, and the final product were directly identified by the differential conductance imaging with a CO functionalized tip. DFT calculations revealed that the multiple-step reaction, being endergonic overall, is facilitated by temporal charging and discharging of the molecule placed in the nanometric junction between the Cu tip and the Cu substrate underneath the ultra-thin NaCl film. This local probe reaction expands possibilities to synthesize nanocarbon materials in a bottom-up manner.
author2 School of Chemistry, Chemical Engineering and Biotechnology
author_facet School of Chemistry, Chemical Engineering and Biotechnology
Kawai, Shigeki
Sang, Hongqian
Kantorovich, Lev
Takahashi, Keisuke
Nozaki, Kyoko
Ito, Shingo
format Article
author Kawai, Shigeki
Sang, Hongqian
Kantorovich, Lev
Takahashi, Keisuke
Nozaki, Kyoko
Ito, Shingo
author_sort Kawai, Shigeki
title An endergonic synthesis of single Sondheimer–Wong diyne by local probe chemistry
title_short An endergonic synthesis of single Sondheimer–Wong diyne by local probe chemistry
title_full An endergonic synthesis of single Sondheimer–Wong diyne by local probe chemistry
title_fullStr An endergonic synthesis of single Sondheimer–Wong diyne by local probe chemistry
title_full_unstemmed An endergonic synthesis of single Sondheimer–Wong diyne by local probe chemistry
title_sort endergonic synthesis of single sondheimer–wong diyne by local probe chemistry
publishDate 2023
url https://hdl.handle.net/10356/170445
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