Structural transition control between dipole–dipole and hydrogen bonds induced chirality and achirality

Hu, Yi; Miao, Kai; Peng, Shan; Zha, Bao; Xu, Li; Miao, Xinrui; Deng, Wenli

doi:10.1039/c5ce02321a

Cited by 27 publications

(25 citation statements)

References 64 publications

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“…S1 †). As we previously reported, [24][25][26][27][28] monosubstituted anthraquinone derivatives 1-A and 2-A can selfassemble into linear structures, denoted as linear I ( Fig. 1a) and linear II ( Fig.…”

Section: Resultssupporting

confidence: 59%

“…Anthraquinone derivatives 1-A, 2-A, 1,8-A, 1,5-A, 1,4-A, 2,6-A, 1,2,4-A, and 1,2,3-A were synthesized using previously reported methods. [24][25][26][27] The solvent, 1-octanoic acid, was purchased from Tokyo Chemical Industry (TCI) and used without purication. Samples were prepared by depositing a droplet (about 1 mL) of solution onto a freshly cleaved atomically at surface of HOPG (quality ZYB, Bruker, USA).…”

Section: Methodsmentioning

confidence: 99%

“…Herein, we investigate the effects of alkyl chain number and position on self-assembling behavior, comprising a comprehensive study based on our previous research. We have previously reported self-assemblies of anthraquinone derivatives with one, 24,25 two, 26 and three side chains. 27,28 These studies emphasized the diverse assembled structures induced by changing the alkyl chain lengths.…”

Section: Introductionmentioning

confidence: 99%

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Effects of alkyl chain number and position on 2D self-assemblies

Miao

et al. 2017

RSC Adv.

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Section: Resultssupporting

confidence: 59%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Effects of alkyl chain number and position on 2D self-assemblies

Miao

et al. 2017

RSC Adv.

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“…In consideration of energy, polar molecules tend to pack in antiparallel way in order to minimize the overall polarity. [8b,12a,17] Therefore, the opposite configurations are necessary to offset the potential dipole repulsion and then extinguish the dipole moment in the assembled area to zero . The dipole moments from the paired DPF molecules in these three configurations are denoted with arrows in Figure in the same color.…”

Section: Discussionmentioning

confidence: 99%

Exploration of Chirality and Achirality of Self‐Assembled Monolayer Formed by Unsymmetrically Substituted Fluorenone Derivative at the Liquid/Solid Interface

Miao

Dong

et al. 2017

Adv Materials Inter

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noncovalent forces, such as dipole-dipole interaction, [3] electrostatic interaction, [4] van der Waals interaction, [5] hydrogen bonds, [6] and π-π stacking. [7] Through physical adsorption, achiral molecules can self-assemble into chiral configurations on the achiral substrate due to the reduced freedom and constraint of the substrate lattice. [2d,8] Because of the rotation characteristics, porous networks show great potential in the process of chiral recognition and have received wide attentions. [9] However, nonporous networks also possess possibility of forming chiral polymorphs as long as the molecules are properly designed. Thus obtaining chirality via tiny structure modification will be a new attempt on fabricating chiral structures and will provide a new method on designing advanced functional materials in the field of surface science.Fluorenone derivatives have been reported to be used as liquid crystals. [10] Moreover, they were also good candidates for studying the self-assemblies at the liquid/highly oriented pyrolytic graphite (HOPG) interface, which have been widely explored in our group. We have previously reported that structural diversity was common to be observed and could be induced via changing the length of the alkyl chain, the concentration, and the solvent. For the bis-substituted fluorenone derivatives, molecules were arranged into a variety of nanopatterns which were regularly ordered but not chiral. [3,11] For the monosubstituted fluorenone derivatives, molecules adopted both chiral and achiral configurations and structural transition could be regulated between them. [12] Therefore, fabrication of chiral nanostructures using unsymmetrically substituted fluorenone derivatives seems to be a challenging but meaningful target. Fortunately, we realized this goal by efficient modification of the side chains.When the π-conjugated fluorenone core was substituted at the equal positions but substituted by unequal alkyl chains, chiral nanostructures were observed in its self-assembled monolayer on HOPG. The molecule we use in this study is 2-decyloxy-7-pentadecyloxy-9-fluorenone (DPF), as shown in Figure 1a. The first typical feature induced by the two different alkyl chains (C 10 H 21 and C 15 H 31 ) is that the long chains and the short chains are orderly interdigitated. As a result of this interdigitation, DPF molecules are usually notThe self-assemblies of 2-decyloxy-7-pentadecyloxy-9-fluorenone (DPF) are characterized by scanning tunneling microscopy at the liquid/solid interface. Achiral Dimer and chiral S-like structures are observed in 1-octanoic acid. The solvent molecule takes part in the self-assembly via forming COOH⋯OC and COOH⋯COOH hydrogen bonds. When 1-phenyloctane and n-tetradecane are used as the solvents, DPF self-assembles into chiral Z-like structure, which are classified into Types I-IV according to the packing styles. For the purpose of exploring the effect of solvent and the competition between these three structures, the self-assemblies of DPF in mixed solvents and ...

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“…Characterizing two-dimensional nanostructures and nanoarchitectures [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19] at the atomic scale is a challenge of nanosciences for the development of new functionalized nanomaterials for nanotechnology. 20,21 Scanning probe microscopy (SPM) is a powerful technique to assess locally the topographic and electronic properties of nanostructured surfaces.…”

Section: Introductionmentioning

confidence: 99%

Enhancing intramolecular features and identifying defects in organic and hybrid nanoarchitectures on a metal surface at room temperature using a NaCl-functionalized scanning tunneling microscopy tip

Peyrot

Silly

2017

RSC Adv.

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International audienceScanning tunneling microscopy (STM) is a powerful method to characterize two-dimensional organic structures and their local electronic properties. Intermolecular features are usually routinely revealed using STM at very low temperature. The resolution of STM images recorded at room temperature is in comparison quite limited. We investigate here the morphology and local electronic properties of organic and hybrid nanoarchitectures laying on metal surface at room temperature using STM with a classical PtIr tip and a novel NaCl-functionalised tip. STM images show that the NaCl-functionalized tip allows revealing at room temperature intermolecular features and variation of molecular local electronic properties, that are not visible using a PtIr tip. This new method opens new opportunities for characterizing and assessing at the atomic scale the morphology and electronic properties of organic nanoarchitectures on highly conductive surfaces not only at room temperature but also at low temperature

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Structural transition control between dipole–dipole and hydrogen bonds induced chirality and achirality

Abstract: This study presents efficient strategies on manipulation of hydrogen bonds and dipole–dipole induced chiral and achiral self-assembly nanostructures.

Cited by 27 publications

References 64 publications

Effects of alkyl chain number and position on 2D self-assemblies

Effects of alkyl chain number and position on 2D self-assemblies

Exploration of Chirality and Achirality of Self‐Assembled Monolayer Formed by Unsymmetrically Substituted Fluorenone Derivative at the Liquid/Solid Interface

Enhancing intramolecular features and identifying defects in organic and hybrid nanoarchitectures on a metal surface at room temperature using a NaCl-functionalized scanning tunneling microscopy tip

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