Halogen-Bond-Controlled Self-Assembly of Regioisomeric Phenanthridine Derivatives into Nanowires and Nanosheets

Peng, Ping; Miao, Xinrui; Ying, Lei; Kong, Gang; Che, Chunshan; Deng, Wenli

doi:10.1021/acs.jpcc.9b10935

Cited by 16 publications

(22 citation statements)

References 42 publications

(65 reference statements)

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“…Experimentally, halogen-bond mediated intermolecular interactions have been reported to influence the spectroscopic and photophysical properties of organic film materials. 118 In regioisometric phenanthridine derivatives, it was shown that the different intermolecular Br•••N halogen bonds, H•••Br hydrogen bonds, and Br•••Br type-II halogen bonds were the dominant factors in determining the different nanostructures and film morphologies. SEM images provided further insights of the self-assembly process, as shown in Figure 15.…”

Section: Controllable Functionalized Surfacesmentioning

confidence: 99%

Halogen bonding regulated functional nanomaterials

et al. 2021

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Section: Controllable Functionalized Surfacesmentioning

confidence: 99%

Halogen bonding regulated functional nanomaterials

et al. 2021

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“…2.8. Self-Assembled Patterns of Phenanthridine Derivatives at the Liquid/HOPG Interface Four regioisomeric phenanthridine derivatives with different positions of halogen substituents and alkoxy chains (2,9-BHP, 2,9-BHPO, 3,8-BHP, and 3,8-BHPO) (Scheme 1j and Figure 13a-d) were synthesized in order to investigate the XBs in 2D self-assembled nanostructures by STM at the 1-phenyloctane/HOPG interfaces [85]. For 2,9-BHP and 3,8-BHP molecules, these two molecules form linear structures with the π-conjugated cores parallel to each other in each lamella (Figure 13i,k).…”

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

confidence: 99%

“…The stronger intermolecular XBs and HBs are the dominated forces to govern the arrangement of 2,9-BHP and 3,8-BHP molecules in 2D self-assembled adlayers. [85] with permission from the American Chemical Society.…”

Section: Self-assembled Patterns Of Phenanthrene 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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“…The phenanthridine derivatives with different positions of bromine and side chain substituents formed entirely different self-assembly patterns, resulting in the directionality of halogen bonds. 45 The solvent effect on halogen-bonded self-assembly nanostructures of 2,9-dibromo-6-(hexadecyloxy)phenanthridine was also explored. Although solvents take part in the self-assembly process, the intermolecular interaction and molecular arrangement remain the same at different solution concentrations, resulting in the strong intermolecular N•••Br•••H halogen bonds and H•••Br hydrogen bonds, so the vdW interactions are not competitive with them.…”

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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Halogen-Bond-Controlled Self-Assembly of Regioisomeric Phenanthridine Derivatives into Nanowires and Nanosheets

Cited by 16 publications

References 42 publications

Halogen bonding regulated functional nanomaterials

Halogen bonding regulated functional nanomaterials

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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