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Host-guest supramolecular chemistry at solid-liquid interface:An important strategy for preparing two-dimensional functional nanostructures

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Science China Chemistry 2014年第1期57卷 13-25页

作者： ZHANG XueMei zeng qingdao WANG Chen National Center for Nanoscience and Technology (NCNST)

Supramolecular self-assembly,an important strategy in nanotechnology,has been widely studied in the past two decades.In this review,we have introduced the recent progress on construction of two-dimensional(2D)nanostructures by host-guest supramolecular chemistry at solid-liquid interface,and the interactions between the host assembly and the guest molecules are the major concerns.At first,the hydrogen bonds connected hybrid structures are discussed.And then we have paid a close attention on the surface-confined condensation reactions that has flourished recently in direct preparing novel nanostructures with increasing structural complexity.In the end,the cavity confinement of the 2D supramolecular host-guest architectures has been studied.On the basis of the above-mentioned interactions,a group of functional hybrid structures have been prepared.Notably,scanning tunneling microscopy(STM),a unique technique to probe the surface morphology and information at the single molecule level,has been used to probe the formed structures on highly oriented pyrolytic graphite(HOPG)surface.

关键词： self-assembly,STM,hydrogen bond,host-guest chemistry,supramocular coordination,Schiff-base reaction

Structure of self-assembled monolayer of NPAN on Au(111) electrode

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Chinese Science Bulletin 2003年第18期48卷 1952-1955页

作者： YANG Guangzheng zeng qingdao WAN Lijun BAI Chunli Institute of Chemistry Chinese Academy of Sciences(CAS)Beijing 100080China Graduate School of CAS Beijing 100080China

Adsorption of 4-(4-nitrophenylazo)-1-naphthol (NPAN), an azobenzene derivative, on Au(111) has been in-vestigated in aqueous HClO4 solution by using the cyclic voltammetry and scanning tunneling microscopy (STM). The molecule is found to form a stable monolayer on the elec-trode with a (6×4) structure relative to the underlying Au(111) lattice. Cyclic voltammograms show that the redox reactions occurring on the electrode are retarded by the formation of the monolayer. A structural model is proposed for the two-dimensional adlayer.

关键词： Au(111) azobenzene self-assembled monolayer STM.

Constructing supramolecular nanostructure by hydrogen-bonding

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Chinese Science Bulletin 2008年第10期53卷 1613-1616页

作者： LI YiBao zeng qingdao WANG ZhiHui QI GuiCun GUAN Li FAN XiaoLin WANG Chen College of Chemistry and Life Science Gannan Normal University Ganzhou 341000 China National Center of Nanoscience and Technology Beijing 100080 China

The diquinoxalino (2.3-2′.3′-a.c) phenazine (DQP), containing 6 nitrogen atoms, was synthesized, and its adsorption and self-assembling behavior on highly oriented pyrolytic graphite (HOPG) was studied by scanning tunneling microscopy (STM) under ambient conditions. With 1,14-tetradecanedioic acid as a bridge, uniform two-dimensional arrays of 1,14-tetradecanedioic acid/DQP nanostructure were successfully fabricated. The result illustrates that it is possible to construct and control supramolecular nanostructure by intermolecular hydrogen-bonding.

关键词： STM 氢键自我组核装置超分子纳米结构纳米重建结构

Insight into the structural transformation of tetraphenylethylene acids at liquid–solid interface induced by linear aminofunctionalized triazine derivatives and annealing treatment

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Nano Research 2023年第12期16卷 13335-13342页

作者： Ting Meng Xuan Peng Xunwen Xiao Ke Deng Yu-Wu Zhong qingdao zeng CAS Key Laboratory of Standardization and Measurement for Nanotechnology CAS Center for Excellence in NanoscienceNational Center for Nanoscience and Technology(NCNST)Beijing 100190China Center of Materials Science and Optoelectronics Engineering University of Chinese Academy of SciencesBeijing 100049China School of Science Nanchang Institute of TechnologyNanchang 330099China Beijing National Laboratory for Molecular Sciences CAS Key Laboratory of PhotochemistryInstitute of ChemistryChinese Academy of SciencesBeijing 100190China College of Materials and Chemical Engineering Ningbo University of TechnologyNingbo 315211China

The interaction between organic photoelectric molecules leads to the formation of a certain aggregation structure,which plays a pivotal role in the charge transport at the intermolecular interface.In view of this,we investigated the mechanism and law of intermolecular interaction by detecting the self-assembled behaviors between organic photoelectric molecules at the interface by scanning tunneling microscopy(STM).In this work,the structural transformations of tetraphenylethylene acids(H_(4)ETTCs)on graphite surface induced by temperature and triazine derivatives(zcy-19,zcy-27,and zcy-38 molecules)were studied by STM technology and density functional theory(DFT)calculations.At room temperature,zcy-19 and H_(4)ETTC molecules formed a small range of ordered co-assembled nanostructure,while for zcy-27 or zcy-38 molecules,no co-assembled nanostructures were observed and only their own self-assembled structures existed on graphite surface,individually.In the thermal annealing trials,the original co-assembled H_(4)ETTC/zcy-19 structure disappeared,and only zcy-19 and H_(4)ETTC self-assembled in separate domains.Nevertheless,new well-ordered H_(4)ETTC/zcy-27 or H_(4)ETTC/zcy-38 co-assembled structures appeared at different annealing temperatures,respectively.Combined with DFT calculations,we further analyzed the mechanism of such structural transformations by triazine derivatives and temperature.Results reveal that triazine derivatives could interact with H_(4)ETTC by N–H···O and O–H···N hydrogen bondings,and whether temperature or zcy series compounds could achieve successful regulation of H_(4)ETTC assembly behavior is closely associated with the conjugated skeleton length of zcy series compounds.

关键词： tetraphenylethylene acids triazine derivatives annealing treatment scanning tunneling microscopy(STM)

Coronene and Bipyridine Derivatives Inducing Diversified Structural Transitions of Carboxylic Acids at the Liquid/Solid Interface

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Chinese Journal of Chemistry 2022年第23期40卷 2727-2733页

作者： Ting Meng Peng Lei Yufei Zhang Ke Deng Xunwen Xiao qingdao zeng CAS Key Laboratory of Standardization and Measurement for Nanotechnology CAS Centerfor Excellence in NanoscienceNational Center forNanoscienceandTechnology(NCNST)Beijing 100190China Center of Materials Scienceand Optoelectronics Engineering University of Chinese Academy of SciencesBeijing 100049China School of Materials and Chemical Engineering Ningbo University of TechnologyNingboZhejiang 315211China

In recent years, the construction of stable multicomponent assembled structures on surfaces and the exploration of the assembled mechanism have become research hotspots. In this paper, the azobenzene-carboxylic acid called (E)-4’,4”’-(diazene-1,2-diyl) bis(([1,1’-biphenyl]-3,5-dicarboxylic acid)) (H4DBBD) could self-assemble into regular network structure at heptanoic acid/graphite via hydrogen bonding, and could be regulated into analogous kagomé network by coronene (COR) molecules. In addition, a series of bipyridine derivatives were further introduced to construct bi-component systems with H4DBBD molecules, and successfully induced diversified structural transitions of H4DBBD on the graphite surface. Combined with scanning tunneling microscope (STM) and density functional theory (DFT) calculations, we have investigated the diversified structural transitions and analyzed the formation mechanism of the assembled systems.

关键词： Self-assembly Supramolecular chemistry Scanning tunneling microscope DFT calculations Hydrogen bonds

The effect of multiple pairs of meta-dicarboxyl groups on molecular self-assembly and the selective adsorption of coronene by hydrogen bonding and van der Waals forces

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Nano Research 2022年第2期15卷 1691-1697页

作者： Jianqiao Li Wendi Luo Siqi Zhang Chunyu Ma Xunwen Xiao Wubiao Duan qingdao zeng CAS Key Laboratory of Standardization and Measurement for Nanotechnology CAS Center for Excellence in NanoscienceNational Center for Nanoscience and Technology(NCNST)Beijing 100190China Department of Chemistry School of ScienceBeijing Jiaotong UniversityBeijing 100044China School of Materials and Chemical Engineering Ningbo University of TechnologyNingbo 315211China

The prediction of two-dimensional molecular self-assembly structures has always been a problem to be solved.The molecules with meta-dicarboxyl groups can self-assemble into a specific hexagonal cavity,which has an important influence on the prediction of molecular self-assembly structures and the application of functional molecules with meta-dicarboxyl groups.Two kinds of molecules with four pairs of meta-dicarboxyl groups,1,3,6,8-tet「akis(3,5-isophthalic acid)pyrene(H_(8)TIAPy)and 4′,4′",4′"",4""-(ethene-1,1,2,2-tetrayl)tetrakis(([1,1′-biphenyl]-3,5-dicarboxylic acid))(H8ETTB)molecules were chosen to observe the self-assembly behavior at the heptanoic acid/highly oriented pyrolytic graphite(HA/HOPG)interface.H8TIAPy molecules self-assembled into well-ordered quadrilateral structures and could be regulated into kagome networks with hexagonal pores by coronene(COR)molecules.H8ETTB molecules self-assembled into lamellar structures and transformed into acid-COR-acid-COR co-assembled structures at low concentration of COR solution and acid-COR dimer-acid-COR dimer co-assembled structures at high concentration of COR solution.The reason that H8ETTB molecules could not be regulated into hexagonal porous architecture was attributed to the steric hindrance by the similar length and width of H8ETTB molecules.The H8ETTB templates had stronger adsorption for COR than that of hexaphenylbenzene(HPB),regardless of the order of molecular introduction.

关键词： meta-dicarboxyl groups hexagonal cavity selective adsorption self-assembly steric hindrance

Electric field controlled superlubricity of fullerene-based host–guest assembly

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Nano Research 2023年第1期16卷 583-588页

作者： Shanchao Tan Hongyu Shi Xin Du Kunpeng Wang Haijun Xu Junhua Wan Ke Deng qingdao zeng Yuhong Liu State Key Laboratory of Tribology Tsinghua UniversityBeijing 100084China CAS Key Laboratory of Standardization and Measurement for Nanotechnology CAS Center for Excellence in NanoscienceNational Center for Nanoscience and Technology(NCNST)Beijing 100190China College of Chemical Engineering Jiangsu Key Lab of Biomass-based Green Fuels and ChemicalsNanjing Forestry UniversityNanjing 210037China Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education Hangzhou Normal UniversityHangzhou 310012China Center of Materials Science and Optoelectonics Engineering University of Chinese Academy of SciencesBeijing 100049China

Controlling friction by the electric field is a promising way to improve the tribological performance of a variety of movable mechanical systems.In this work,the assembly structure and microscale superlubricity of a host–guest assembly are effectively controlled by the electric field.With the help of the scanning tunneling microscopy(STM)technique,the host–guest assembly structures constructed by the co-assembly of fullerene derivative(Fluorene-C60)with macrocycles(4B2A and 3B2A)are explicitly characterized.Combined with density functional theory(DFT),the distinct different assembly behaviors of fullerene derivatives are revealed at different probe biases,which is attributed to the molecular polarity of the fullerene derivative.Through the control on the adsorption behavior,the friction coefficient of host–guest assembly is demonstrated to be controllable in the electric field by using atomic force microscopy(AFM).At positive probe bias,the friction coefficient of the host–guest assembly is significantly reduced and achieves superlubricity(μmin=0.0049).The efforts not only help us gain insight into the host–guest assembly mechanism controlled by the electric field,but also promote the further application of fullerene in micro-electro-mechanical systems(MEMS).

关键词： superlubricity electric field friction control fullerene derivative host-guest assembly

Self-assemblies of TTF derivatives with fluorinated phenyls and pyridine group

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Chinese Chemical Letters 2022年第2期33卷 1100-1104页

作者： Jianghua Fang Xiaoyang Zhu Wendi Luo Jianxun Shi Lejia Wang Bin Tu qingdao zeng Xunwen Xiao College of Material Science and Chemical Engineering Ningbo University of TechnologyNingbo 315211China CAS Key Laboratory of Standardization and Measurement for Nanotechnology CAS Center for Excellence in NanoscienceNational Center for Nanoscience and Technology(NCNST)Beijing 100190China Zhejiang Pharmaceutical College Ningbo 315100China

The self-assembly characteristics of tetrathiafulvalene(TTF) derivatives molecules 1-3 at the 1-phenyloctane/HOPG(HOPG = highly oriented pyrolytic graphite) interface had been carefully studied by scanning tunneling microscopy(STM) method. The number of F atoms on the phenyl group had significantly affected the self-assembly structures. High-resolution STM images make clear the different assembly structures between the molecules 1-3, which attribute to the different F atom numbers and pyridine group in the molecule. Density functional theory(DFT) calculations have been performed to reveal the formation mechanism.

关键词： TTF Self-assembly STM DFT calculation Hydrogen bonds

Self-assembled nanostructures of a series of linear oligothiophene derivatives adsorbed on surfaces

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Chinese Chemical Letters 2023年第2期34卷 630-635页

作者： Xuan Peng Ting Meng Lilei Wang Linxiu Cheng Wenchao Zhai Ke Deng Chang-Qi Ma qingdao zeng CAS Key Laboratory of Standardization and Measurement for Nanotechnology CAS Center for Excellence in NanoscienceNational Center for Nanoscience and Technology(NCNST)Beijing 100190China Center of Materials Science and Optoelectronics Engineering University of Chinese Academy of SciencesBeijing 100049China Printable Electronics Research Center Suzhou Institute of Nano-Tech and Nano-BionicsChinese Academy of SciencesSuzhou 215123China

Many previous studies have shown that the molecular structures of oligothiophene derivatives including molecular skeleton and alkyl chains have a significant effect on their self-assemblies on the surface.In this work, a series of linear oligothiophene derivatives(DCV-n T-Hex, n = 3~11) modified with terminal dicyanovinyls and alkyl chains were adopted to further investigate the different assembly behaviors at liquid-solid interface by scanning tunneling microscopy(STM). Interestingly, via the hydrogen bonding and van der Waals interactions, DCV-3T-Hex formed zigzag and flower structures while DCV-n T-Hex(n = 4~11) formed lamellar structures. Density functional theory(DFT) calculations show that for the most energetically favorable configurations of DCV-n T-Hex, the different distribution of alkyl chains affected intermolecular interactions, and ultimately led to the different assembled structures. The zigzag and flower structures of DCV-3T-Hex had preferential thermodynamic stability compared to other structures of DCV-n T-Hex(n = 4~11). In addition, self-assembled nanostructures of DCV-n T-Hex molecules with even numbers(n = 4, 6, 8, 10) were overall more stable than those with odd numbers(n = 5, 7, 9,11), and the stability of the self-assembled structure was weakened with the extension of the molecular backbone, individually. The orientation of molecular alkyl chains was found to greatly affect the intermolecular interactions and thus leading to various self-assembly structures of DCV-n T-Hex(n = 3~11).

关键词： Oligothiophene derivatives Scanning tunneling microscopy Supramolecular self-assembly Van der Waals force DFT calculations