Solvent‐Dependent Self‐Assembly of 4,7‐Dibromo‐5,6‐bis(octyloxy)benzo[c][1,2,5] Thiadiazole on Graphite Surface by Scanning Tunneling Microscopy

Zha, Bao; Miao, Xinrui; Li, Yijing; Liu, Pei; Miao, Kai; Deng, Wenli

doi:10.1155/2013/624927

Cited by 2 publications

(3 citation statements)

References 30 publications

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“…Self-assembled nanoarchitectures of the DBT molecule (Scheme 1d) were investigated by STM at the liquid/HOPG interface in three kinds of solvents (1-phenyloctane, 1-octanoic acid, and 1-octanol) [79]. Dramatic differences in 2D self-assembly patterns are observed.…”

Section: Self-assembled Patterns Of Thiadiazole Derivatives At the Liquid/hopg Interfacementioning

confidence: 99%

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Halogen Bonds Fabricate 2D Molecular Self-Assembled Nanostructures by Scanning Tunneling Microscopy

2020

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Halogen bonds are currently new noncovalent interactions due to their moderate strength and high directionality, which are widely investigated in crystal engineering. The study about supramolecular two-dimensional architectures on solid surfaces fabricated by halogen bonding has been performed recently. Scanning tunneling microscopy (STM) has the advantages of realizing in situ, real-time, and atomic-level characterization. Our group has carried out molecular self-assembly induced by halogen bonds at the liquid–solid interface for about ten years. In this review, we mainly describe the concept and history of halogen bonding and the progress in the self-assembly of halogen-based organic molecules at the liquid/graphite interface in our laboratory. Our focus is mainly on (1) the effect of position, number, and type of halogen substituent on the formation of nanostructures; (2) the competition and cooperation of the halogen bond and the hydrogen bond; (3) solution concentration and solvent effects on the molecular assembly; and (4) a deep understanding of the self-assembled mechanism by density functional theory (DFT) calculations.

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Section: Self-assembled Patterns Of Thiadiazole Derivatives At the Liquid/hopg Interfacementioning

confidence: 99%

“…Possible interactions are shown in the enlarged insets by yellow and blue dashed lines. Reproduced from [79] with permission from the Hindawi.…”

Section: Self-assembled Patterns Of Thiadiazole Derivatives At the Liquid/hopg Interfacementioning

confidence: 99%

Halogen Bonds Fabricate 2D Molecular Self-Assembled Nanostructures by Scanning Tunneling Microscopy

2020

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“…Two-dimensional (2D) molecular self-assembly is of great significance for building preprogrammed structures and patterns on such a scale using the bottom–top approach . The formation of 2D self-assembled nanostructures is a result of thermodynamic equilibrium, affected by temperature, − molecular chemical structure, − solvent, − solution concentration, − substrate, , and so on. These factors essentially change the intermolecular interaction and/or molecule–substrate interaction of self-assembly adlayers.…”

Section: Introductionmentioning

confidence: 99%

Solvent Co-adsorption Changing the Type of Halogen-Based Bonds Associated with the Position of Bromine Substituents Revealed by Scanning Tunneling Microscopy

et al. 2021

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A systematic investigation of the solvent co-adsorption effect on the self-assembly of 3,8-dibromo-6-(hexadecyloxy)phenanthridine (3,8-BHP) was performed at the liquid/graphite interface by scanning tunneling microscopy. 1-Octanoic acid, n-tetradecane, n-pentadecane, n-hexadecane, and n-heptadecane were chosen as the solvents. 3,8-BHP molecules formed the same twist-shaped nanopattern by forming intermolecular Br···N and Br···H bonds in all the solvents at high solution concentrations. The co-adsorption of 1-octanoic acid solvents at low concentrations changed the molecular arrangement by forming the stronger molecule–solvent COOH···N and C–H···O–H(COOH) hydrogen bonds. n-Pentadecane, n-hexadecane, and n-heptadecane also co-adsorbed in the adlayers at low concentrations, which resulted in the change in intermolecular interactions. In n-pentadecane and n-hexadecane solvents, the molecular packing and intermolecular interactions in the two-row lamella of 3,8-BHP were the same, in which the intermolecular C–H···Br hydrogen bonds and Br···Br interactions were the main driving forces. The difference among the nanostructures in n-pentadecane and n-hexadecane solvents depended on the number and length of the alkyl chain of the co-adsorbed solvents, which determined the probability of single-row lamellae. The results demonstrate that the molecule–solvent van der Waals forces are strong enough to transform the intermolecular forces involving bromine groups. Our work will help to understand the importance of the solvent co-adsorption effect on the change of halogen-based bonds associated with the position of the bromine substituent for the construction of polymorphic self-assembled structures.

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Solvent‐Dependent Self‐Assembly of 4,7‐Dibromo‐5,6‐bis(octyloxy)benzo[c][1,2,5] Thiadiazole on Graphite Surface by Scanning Tunneling Microscopy

Cited by 2 publications

References 30 publications

Halogen Bonds Fabricate 2D Molecular Self-Assembled Nanostructures by Scanning Tunneling Microscopy

Halogen Bonds Fabricate 2D Molecular Self-Assembled Nanostructures by Scanning Tunneling Microscopy

Solvent Co-adsorption Changing the Type of Halogen-Based Bonds Associated with the Position of Bromine Substituents Revealed by Scanning Tunneling Microscopy

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