Coexisting Chiral Two-Dimensional Self-Assembled Structures of 1,2,3,4-Tetrahydronaphthalene Molecules: Porous Pinwheel Nanoarchitecture and Close-Packed Herringbone Arrangement

Silly, Fabien; Ausset, Sandrine; Sun, Xiaoduan

doi:10.1021/acs.jpcc.7b04926

Cited by 12 publications

(12 citation statements)

References 72 publications

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“…2D molecular self-assembly at the solid–liquid interface has been widely investigated over the past few decades by scanning tunneling microscopy (STM) under ambient conditions. − The adlayers are stabilized by supramolecular interactions including van der Waals force, − hydrogen bond, − halogen bond, − and interfacial molecule–substrate interactions. The halogen bond is an important new weak noncovalent interaction in the engineering of 2D self-assembly.…”

Section: Introductionmentioning

confidence: 99%

Solvent Effect on Halogen-Bonded Self-Assembled Nanostructures of a 2,9-Dibromo-Phenanthridine Derivative at the Liquid–Solid Interface

Peng

Zeng

et al. 2021

J. Phys. Chem. C

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Probing the halogen-bonded nanostructures of two-dimensional (2D) supramolecular self-assembly is essential to understand and engineer the nature of halogen bonding. However, exploring the formation mechanism of the halogen bond still remains a challenge because it is a new weak noncovalent interaction. Herein, we introduce nitrogen atoms and Br groups in the conjugated core to synthesize 2,9-dibromo-6-(hexadecyloxy)phenanthridine (2,9-DHP) in order to fabricate multiple action sites of halogen bonds. We investigate the solvent effect on the 2D molecular self-assembly at the liquid–solid interface by using scanning tunneling microscopy. 1-Octanoic acid, n-tridecane, n-tetradecane, and n-hexadecane are chosen as the solvents. The coadsorption of 1-octanoic acid molecules at low concentrations by the molecule–solvent Br···O halogen bonds could change the molecular arrangement. n-Tridecane, n-tetradecane, and n-hexadecane also coadsorb in the adlayers; however, the molecular packing and intermolecular interactions of 2,9-DHP remain the same at different solution concentrations. The results demonstrate that the molecule–molecule N···Br···H halogen bonds are strong enough to overcome the transformation of intermolecular interactions.

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Section: Introductionmentioning

confidence: 99%

Solvent Effect on Halogen-Bonded Self-Assembled Nanostructures of a 2,9-Dibromo-Phenanthridine Derivative at the Liquid–Solid Interface

Peng

Zeng

et al. 2021

J. Phys. Chem. C

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“…The details of the DFT calculation are given in the method section. The orientation of the pyridine rings is the result of a balance between the established N•••H-N hydrogen bond [53,[66][67][68] and a small van der Waals attraction [55,68,[71][72][73][74] in the ortho pyridine. As a consequence, the interaction between the two bipyridine rings (each from a neighboring molecule) is very strong (stronger than between two pyridine rings).…”

Section: Resultsmentioning

confidence: 99%

Visualization and Comprehension of Electronic and Topographic Contrasts on Cooperatively Switched Diarylethene-Bridged Ditopic Ligand

Hnid¹,

Guan²,

Chatir³

et al. 2022

Preprint

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Diarylethene is a prototypical molecular switch that can be reversibly photoisomerized between its open and closed forms. Ligands bpy-DAE-bpy, consisting of a phenyl-diarylethene-phenyl (DAE) central core and bipyridine (bpy) terminal substituents, are able to self-organize. They are investigated by scanning tunneling microscopy at the solid-liquid interface. Upon light irradiation, cooperative photochromic switching of the ligands is recognized down to the sub-molecular level. The closed isomers show different electron density of states (DOS) contrasts, attributed to the HOMO or LUMO molecular orbitals observed. More importantly, the LUMO images show remarkable differences between the open and closed isomers, attributed to combined topographic and electronic contrasts mainly on the DAE moieties. The electronic contrasts from multiple HOMO or LUMO distributions, combined with topographic distortion of the open or closed DAE, are interpreted by density functional theory (DFT) calculations.

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“…This appearance may be explained as a higher degree of mobility of solvent molecules, which has also been observed for other systems. 40,41 A corresponding molecular model of the box-like structure is presented in Figure 4c, the measured unit cell parameters are a = 4.09 ± 0.01 nm, b = 6.58 ± 0.02 nm, α = 69 ± 1°. Each unit cell contains two FHP-C14 molecules, and the calculated area density is one molecule per 0.080 nm 2 .…”

Section: Resultsmentioning

confidence: 99%

Solvent-Dependent Molecular Isomerization and 2D Self-Assembled Phase Transitions of Benzothiadiazole-Based π-Conjugated Fluorophore

Tan

Wang

et al. 2021

J. Phys. Chem. C

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Two-dimensional molecular assemblies of benzothiadiazolebased fluorophores with liquid crystalline properties (FHP-C14) have been investigated on a graphite surface in different solvents (n-tetradecane, ntridecane, and n-heptanoic acid) by scanning tunneling microscopy. The FHP-C14 molecule shows cis−trans isomerization due to different orientations of two flanked thiophene groups relative to acetylene units. The solvent and solution concentration effects on the adlayers are observed in the systems. With the concentration gradually decreasing, FHP-C14 molecules successively self-assemble into the linear structure, the box-like structure, and the double-C structure at the n-tetradecane/graphite interface. The molecular cis−trans−cis isomerization is observed, due to different arrangement fashions of the side chains. When using n-tridecane and n-heptanoic acid as the solvents, the double-C structure could not be observed resulting from the mismatch of side chains in FHP-C14 molecules and solvent molecules. The coadsorption of solvent molecules influences the assembly of FHP-C14 molecules and promotes the conformer transformation. Our work provides guidance for the design of benzothiadiazole-based fluorophore from the molecular packing point of view.

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Coexisting Chiral Two-Dimensional Self-Assembled Structures of 1,2,3,4-Tetrahydronaphthalene Molecules: Porous Pinwheel Nanoarchitecture and Close-Packed Herringbone Arrangement

Cited by 12 publications

References 72 publications

Solvent Effect on Halogen-Bonded Self-Assembled Nanostructures of a 2,9-Dibromo-Phenanthridine Derivative at the Liquid–Solid Interface

Solvent Effect on Halogen-Bonded Self-Assembled Nanostructures of a 2,9-Dibromo-Phenanthridine Derivative at the Liquid–Solid Interface

Visualization and Comprehension of Electronic and Topographic Contrasts on Cooperatively Switched Diarylethene-Bridged Ditopic Ligand

Solvent-Dependent Molecular Isomerization and 2D Self-Assembled Phase Transitions of Benzothiadiazole-Based π-Conjugated Fluorophore

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