Hydrogen‐Bonding‐Induced Polymorphous Phase Transitions in 2D Organic Nanostructures

Xu, Li; Miao, Xinrui; Zha, Bao; Deng, Wenli

doi:10.1002/asia.201201229

Cited by 37 publications

(40 citation statements)

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“…A model for the zigzag configuration was proposed on the basis of a previous report (Figure 5d). 28 Whereafter, the sample was placed under ambient conditions for more than 24 h. The self-assembly of HPF displayed that only the zigzag pattern existed on the HOPG surface ( Figure S9), which indicates that the zigzag pattern was the most stable configuration.…”

Section: ■ Resultsmentioning

confidence: 99%

Chiral Transition of the Supramolecular Assembly by Concentration Modulation at the Liquid/Solid Interface

Miao

Cui

et al. 2015

J. Phys. Chem. C

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Global hetero-and homochiral polymorphous assemblies from an achiral fluorenone derivative were successfully constructed with multiple intermolecular hydrogen bonds by concentration modulation. Scanning tunneling microscopy investigations reveal that a heterochiral supramolecular double rosette-like structure was fabricated for the first time via hydrogen bond interactions with achiral 1-octanoic acid under low concentrations. When the solution concentration was increased, the structural transition from a heterochiral double rosette-like structure to a homochiral windmill-like pattern was observed. Interestingly, these two metastable structures ultimately could transform into a stable zigzag pattern at a bias voltage prompted by the STM tip. At high concentrations, only an achiral octamer arrangement could be obtained, owing to the changes of intermolecular hydrogen bonding, van der Waals force, and dipole−dipole interactions. The present results provided an important impetus for the induction and control of polymorphous chiral structural transformation through modulated solution concentration of achiral 1-octanoic acid.

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Section: ■ Resultsmentioning

confidence: 99%

Chiral Transition of the Supramolecular Assembly by Concentration Modulation at the Liquid/Solid Interface

Miao

Cui

et al. 2015

J. Phys. Chem. C

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“…[27][28][29][30] In the structural model (Fig. 2c), six HPF molecules in one hexamer unit present combined cycle dipoles, which can maximize dipolar interactions and result in the lowest energy.…”

Section: Resultsmentioning

confidence: 98%

“…Similar to the assembled structure of the HPF molecule in 1-phenloctane, 27 all the different structures of the HPF adlayers would ultimately convert into the most stable zigzag conformation after being scanned for a period of time. The high-resolution image (Fig.…”

Section: Resultsmentioning

confidence: 99%

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Concentration-dependent structure and structural transition from chirality to nonchirality at the liquid–solid interface by coassembly

Miao

Cui

et al. 2015

Nanoscale

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Understanding the formation and structural transition of the two-dimensional chirality of self-assembly is a subject which still gains significant interest in surface or interface chirality studies. Here, we present the solvent-induced chiral structural transition of a 2-hydroxy-7-pentadecyloxy-9-fluorenone (HPF) molecules' self-assembled adlayer through coassembly with achiral aliphatic solvents under different concentrations. Polymorphic chiral patterns are obtained at low concentrations of aliphatic solvents with different chain lengths. The HPF molecules form coassembled structures with these solvents through van der Waals interactions. At the same time, at high concentrations, HPF molecules uniformly form a nonchiral multimer structure without coadsorbed aliphatic solvent molecules. What is interesting is that these structures under different concentrations will finally change into a zigzag structure, which is the thermodynamically most stable configuration. Especially when using n-hexadecane as the solvent, the adlayer shows perfect steric matching due to the close chain length of HPF and n-hexadecane, which can maximize the molecule-solvent interactions. Thus, HPF molecules in n-hexadecane exhibit the most diversiform configuration. The distinct concentration-dependence has proven that the solvent molecules can act as a coadsorbed component through van der Waals interactions rather than simply a dispersant and further result in the probability and stability of chiral self-assembled monolayers by subtle tuning of the solvent-molecule and solvent-substrate interactions. This result provides a simple and alternative strategy to construct the 2D chiral assembled monolayer.

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“…[20] Such structural modulations due to the odd-even effect of alkyl chains have also been reported in an anthracene derivative, dicarbamate compounds, and so on. [1,[21][22][23][24][25] For the study of physisorbed monolayers, the typical substrate is highly oriented pyrolytic graphite (HOPG). Scanning tunneling microscopy (STM) enables the 2D structural analysis at the molecular level.…”

Section: Introductionmentioning

confidence: 99%

2D Structural Modulation by Odd-Even Effect of Alkyl Chains Revealed by Scanning Tunneling Microscopy at Solid/Liquid Interface

Kikkawa

2014

Trans. Mat. Res. Soc. Japan

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This review paper presents our recent progress on the formation of self-assembled two-dimensional (2D) structures, and their modulation by the odd-even effect of alkyl chains on porphyrin derivatives, isobutenyl compounds and bipyridine derivatives. The 2D structures were directly visualized by scanning tunneling microscopy (STM) at the highly oriented pyrolytic graphite (HOPG)/solvent interface. The alkyl tails in the compounds work as moleculemolecule and molecule-substrate interaction sites, and the nature of the 2D structures depended on the alkyl chain length. These STM observations revealed that, for each compound, an odd-even effect exists for a specific range of alkyl chain lengths.

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Hydrogen‐Bonding‐Induced Polymorphous Phase Transitions in 2D Organic Nanostructures

Cited by 37 publications

References 61 publications

Chiral Transition of the Supramolecular Assembly by Concentration Modulation at the Liquid/Solid Interface

Chiral Transition of the Supramolecular Assembly by Concentration Modulation at the Liquid/Solid Interface

Concentration-dependent structure and structural transition from chirality to nonchirality at the liquid–solid interface by coassembly

2D Structural Modulation by Odd-Even Effect of Alkyl Chains Revealed by Scanning Tunneling Microscopy at Solid/Liquid Interface

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