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on-surface synthesis of Electron-Deficient Bisanthene Tetraimide

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CCS Chemistry 2024年第3期6卷 672-681页

作者： Ye Liu Liangliang Chen Hailong Li Xi-Sha Zhang Qigang Zhong Zhengming Hao Minghui Wu Yan-Ying Huang Lina Wang Minchong Sheng Miao Xie Haiming Zhang Deqing Zhang Lifeng Chi Jiangsu Key Laboratory for Carbon-Based Functional Materials and Devices Institute of Functional Nano&Soft Materials(FUNSOM)Soochow UniversitySuzhouJiangsu 215123 CAS Key Laboratory for Organic Solids Institute of ChemistryChinese Academy of SciencesBeijing 100190 Institute of Applied Physics Justus Liebig University GiessenGiessen 35392

Imide-based conjugated molecules have emerged as a highly promising class of building blocks for constructing n-type semiconducting materials with lowlying lowest unoccupied molecular orbitals and exceptional *** imides,such as naphthalene diimides,perylene diimides and their lateral fused analogs,have been synthesized extensively,the design and synthesis of largerπ-extended molecules incorporating more than two imide groups are desirable but still very ***,we report the synthesis of an unprecedented electron-deficient bisanthene tetraimide(ATI)containing a bisantheneconjugated core and four five-membered imide groups,which was successfully achieved via a combined approach of solution and on-surface *** chemical structures,electronic states,formation mechanism and aromaticity of ATI were systematically investigated by scanning tunneling microscopy,noncontact atomic force microscopy,scanning tunneling spectroscopy,and density functional theory calculations.

关键词： on-surface synthesis electron-deficient bisanthene tetraimide dehydrocyclization low lowest unoccupied molecular orbital level

on-surface synthesis of Anthracene-Fused Zigzag Graphene Nanoribbons from 2,7-Dibromo-9,9′-bianthryl Reveals Unexpected Ring Rearrangements

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Precision Chemistry 2024年第2期2卷 81-87页

作者： Xiushang Xu Amogh Kinikar Marco Di Giovannantonio Carlo A.Pignedoli Pascal Ruffieux Klaus Müllen Roman Fasel Akimitsu Narita Max Planck Institute for Polymer Research 55128 MainzGermany Organic and Carbon Nanomaterials Unit Okinawa Institute of Science and Technology Graduate UniversityKunigami-gunOkinawa 904-0495Japan Empa Swiss Federal Laboratories for Materials Science and Technologynanotech@surfaces Laboratory8600 DübendorfSwitzerland Institute of Structure of Matter-CNR(ISM-CNR) 00133 RomaItaly Institute of Physical Chemistry Johannes Gutenberg University Mainz55128 MainzGermany Department of Chemistry Biochemistry and Pharmaceutical SciencesUniversity of Bern3012 BernSwitzerland

on-surface synthesis has emerged as a powerful strategy to fabricate unprecedented forms of atomically precise graphene nanoribbons(GNRs).However,the on-surface synthesis of zigzag GNRs(ZGNR)has met with only limited ***,we report the synthesis and on-surface reactions of 2,7-dibromo-9,9′-bianthryl as the precursor towardπ-extended *** by scanning tunneling microscopy and high-resolution noncontact atomic force microscopy clearly demonstrated the formation of anthracene-fused *** skeletal rearrangements were also observed,which could be explained by intramolecular Diels-Alder *** calculations of the electronic properties of the anthracene-fused ZGNRs revealed spin-polarized edge-states and a narrow bandgap of 0.20 eV.

关键词： on-surface synthesis Graphene nanoribbon On-surface reaction Rearrangement Edge state

on-surface synthesis of covalent coordination polymers on micrometer scale

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Nano Research 2017年第3期10卷 933-940页

作者： Mathieu Koudia Elena Nardi Olivier Siri Mathieu Abel Aix Marseille UniversitY CNRS IM2NP UMR 7334 13397 Marseille France Aix Marseille UniversitY CNRS CINaM UMR 7325 13288 Marseille France

on-surface synthesis under ultrahigh vacuum provides a promising strategy to control matter at the atomic level, with important implications for the design of new two-dimensional materials having remarkable electronic, magnetic, or catalytic properties. This strategy must address the problem of limited extension of the domains due to the irreversible nature of covalent bonds, which prevents the ripening of defects. We show here that extended materials can be produced by a controlled co-deposition process. In particular, co-deposition of quinoid zwitterion molecules with iron atoms on a Ag（111） surface held at 570 K allows the formation of micrometer-sized domains based on covalent coordination bonds. This work opens up the construction of micrometer-scale single-layer covalent coordination materials under vacuum conditions.

关键词： on-surface synthesis scanning tunnelingmicroscopy (STM) two-dimensional polymer covalent organic frameworks

on-surface synthesis of one-dimensional carbyne-like nanostructures with sp-carbon

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Chinese Physics B 2022年第12期31卷 551-557页

作者： Wenze Gao Chi Zhang Zheng Zhou Wei Xu Interdisciplinary Materials Research Center College of Materials Science and EngineeringTongji UniversityShanghai 201804China

Carbyne is an infinite one-dimensional carbon chain comprising of sp-hybridized *** to its high chemical reactivity and extreme instability,the synthesis and structural diversity of carbyne have been much less investigated in the past decades compared to carbon allotropes built with sp^(2)hybridized carbons,such as fullerenes,carbon nanotubes,and *** emerging on-surface synthesis strategy provides an extremely promising approach for the fabrication of novel carbyne-like nanostructures with atomic ***,we summarize recent exciting progress in the synthesis of carbyne-like nanostructures with one-dimensional sp-carbon on surfaces,including polyynes,cumulenes,and organometallic *** also point out the scientific challenges and prospects,encouraging scientists to explore the fabrication and characterization of single strands of carbyne in this young and promising research field.

关键词： on-surface synthesis carbyne scanning tunneling microscopy atomic force microscopy

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On-surface activation of benzylic C-H bonds for the synthesis of pentagon-fused graphene nanoribbons

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Nano Research 2021年第12期14卷 4754-4759页

作者： Xiushang Xu Marco Di Giovannantonio José I.Urgel Carlo A.Pignedoli Pascal Ruffieux Klaus Müllen Roman Fasel Akimitsu Narita Present address:Istituto di Struttura della Materia-CNR(ISM-CNR) via Fosso del Cavaliere 10000133RomaItaly Present address:IMDEA Nanoscience C/Faraday 9Campus de Cantoblanco28049MadridSpain Max Planck Institute for Polymer Research 55128MainzGermany Empa Swiss Federal Laboratories for Materials Science and Technologynanotech@surfaces Laboratory8600DübendorfSwitzerland Organic and Carbon Nanomaterials Unit Okinawa Institute of Science and Technology Graduate University1919-1 TanchaOnna-sonKunigami-gunOkinawa904-0495Japan Institute of Physical Chemistry Johannes Gutenberg University MainzDuesbergweg 10-1455128MainzGermany

Graphene nanoribbons (GNRs) have potential for applications in electronic devices. A key issue, thereby, is the fine-tuning of their electronic characteristics, which can be achieved through subtle structural modifications. These are not limited to the conventional armchair, zigzag, and cove edges, but also possible through incorporation of non-hexagonal rings. on-surface synthesis enables the fabrication and visualization of GNRs with atomically precise chemical structures, but strategies for the incorporation of non-hexagonal rings have been underexplored. Herein, we describe the on-surface synthesis of armchair-edged GNRs with incorporated five-membered rings through the C-H activation and cyclization of benzylic methyl groups. Ortho-Tolyl-substituted dibromobianthryl was employed as the precursor monomer, and visualization of the resulting structures after annealing at 300 °C on a gold surface by high-resolution noncontact atomic force microscopy clearly revealed the formation of methylene-bridged pentagons at the GNR edges. These persisted after annealing at 340 °C, along with a few fully conjugated pentagons having singly-hydrogenated apexes. The benzylic methyl groups could also migrate or cleave-off, resulting in defects lacking the five-membered rings. Moreover, unexpected and unique structural rearrangements, including the formation of embedded heptagons, were observed. Despite the coexistence of different reaction pathways that hamper selective synthesis of a uniform structure, our results provide novel insights into on-surface reactions en route to functional, non-benzenoid carbon nanomaterials.

关键词： graphene nanoribbons on-surface synthesis scanning-tunneling microscope noncontact atomic force microscope C-H activation

On-surface photo-induced dechlorination

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Chinese Chemical Letters 2024年第9期35卷 198-201页

作者： Yu He Hao Jiang Shaoxuan Yuan Jiayi Lu Qiang Sun Materials Genome Institute Shanghai UniversityShanghai 200444China

On-surface Ullmann-type reaction,or the dehalogenated coupling,is arguably the most pivotal reaction in on-surface synthesis for the fabrications of carbon ***,the vast majority of works rely on activating the C-Br bond of aryl bromide which has a moderate bond dissociation *** C-Cl bond of aryl chloride has a higher dissociation energy and requires much higher thermal energy to break the *** this study,we have explored the on-surface photo-induced dechlorination and achieved the activation of three distinct aryl chlorines on the Au(111)surface with mild *** work enriches our understanding of on-surface photo-induced reactions and highlights the potential of photochemistry in realizing unconventional reactions.

关键词： on-surface synthesis Scanning probe microscopy On-surface photochemistry Dechlorination reaction

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Direct transformation of n-alkane into all-trans conjugated polyene via cascade dehydrogenation

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National Science Review 2021年第10期8卷 42-49页

作者： Xuechao Li Kaifeng Niu Junjie Zhang Xiaojuan Yu Haiming Zhang Yuemin Wang Qing Guo Pengdong Wang Fangsen Li Zhengming Hao Chaojie Xu Yanning Tang Zhichao Xu Shuai Lu Peng Liu Guigu Xue Yen Wei Lifeng Chi Jiangsu Key Laboratory for Carbon Based Functional Materials & Devices Institute of Functional Nano & Soft Materials Soochow University Department of Physics Chemistry and Biology IFMLink?ping University Institute of Functional Interfaces Karlsruhe Institute of Technology Department of Chemistry Southern University of Science and Technology Vacuum Interconnected Nanotech Workstation (Nano-X) Suzhou Institute of Nano-Tech and Nano-BionicsChinese Academy of Sciences Key Laboratory of Organic Optoelectronics and Molecular Engineering Department of Chemistry Tsinghua University

Selective C(sp~3)-H activation is of fundamental importance in processing alkane feedstocks to produce high-value-added chemical products. By virtue of an on-surface synthesis strategy, we report selective cascade dehydrogenation of n-alkane molecules under surface constraints, which yields monodispersed all-trans conjugated polyenes with unprecedented length controllability. We are also able to demonstrate the generality of this concept for alkyl-substituted molecules with programmable lengths and diverse functionalities, and more importantly its promising potential in molecular wiring.

关键词： C(sp3)-H activation alkane transformation on-surface synthesis dehydrogenation molecular wiring

Substrate orientation effect in covalent organic frameworks/2D materials heterostructure by high-resolution atomic force microscopy

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Nano Research 2023年第7期16卷 10047-10052页

作者： Lu Wang Cheng Lu Huijuan Yan Dong Wang CAS Key Laboratory of Molecular Nanostructure and Nanotechnology CAS Research/Education Center for Excellence in Molecular SciencesBeijing National Laboratory for Molecular Science(BNLMS)Institute of ChemistryChinese Academy of SciencesBeijing 100190China University of Chinese Academy of Sciences Beijing 100049China

Heterostructures based on covalent organic frameworks(COFs)and other two-dimensional(2D)materials attract considerable attention due to their extraordinary properties and tremendous application *** effects play a crucial role in the integration of ultrathin COF films onto 2D materials through direct *** this study,highly ordered monolayer COFs were successfully constructed on the surfaces of highly oriented pyrolytic graphite(HOPG),hexagonal boron nitride(hBN),and molybdenum disulfide(MoS_(2)).High-resolution atomic force microscopy(HR-AFM)imaging clearly reveals the substrate orientation effect in COFs/2D materials *** networks formed via Schiff-base reaction and boronic acid condensation reaction can epitaxially grow in specific orientations relative to the underlying substrate *** work provides direct evidence for substrate effects in the on-surface synthesis of COFs and paves the way for further investigation into the intrinsic electronic properties of monolayer COFs and the development of multifunctional hybrid devices.

关键词： substrate orientation effect covalent organic frameworks(COFs) on-surface synthesis high-resolution atomic force microscopy(HR-AFM)

Oxygen-promoted synthesis of armchair graphene nanoribbons on Cu(111)

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Science China Chemistry 2021年第4期64卷 636-641页

作者： Penghui Ji Oliver MacLean Gianluca Galeotti Dominik Dettmann Giulia Berti Kewei Sun Haiming Zhang Federico Rosei Lifeng Chi Jiangsu Key Laboratory for Carbon-Based Functional Materials&Devices Institute of Functional Nano&Soft MaterialsSoochow UniversitySuzhou 215123China Centre Energie Matériaux et TélécommunicationsInstitut National de la Recherche Scientifique1650 Boulevard Lionel-BouletVarennesQCCanada Institute of Fundamental and Frontier Sciences University of Electronic Science and Technology of ChinaChengdu 610054China Deutsches Museum Museumsinsel 180538 MunichGermany Research Center for Advanced Measurement and Characterization National Institute for Materials ScienceTsukubaIbaraki 305-0047Japan

We report the systematic investigation of the effects of oxygen on the synthesis of 3 p sub-family armchair graphene nanoribbons(3 p-AGNRs),which revealed a strong catalytic effect with a reduction in the reaction temperature by approximately 180 K without degradation of the ***(para-phenylene)(3-AGNR)was generated through Ullmann-type coupling of4,4’’-dibromo-p-terphenyl on Cu(111),which was then converted into wider 3 p-AGNRs via lateral *** tunneling microscopy(STM)and X-ray photoelectron spectroscopy demonstrated the formation of different ribbons up to 12-AGNR,which contained regions exhibiting increased STM contrast that we attribute to the intercalation of Br atoms during lateral fusion.

关键词： on-surface synthesis graphene nanoribbons C–H activation scanning tunneling microscopy X-ray photoelectron spectroscopy

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