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

Peng, Ping; Li, Bang; Zeng, Xiaofang; Miao, Xinrui; Wang, Yi; Deng, Wenli

doi:10.1021/acs.jpcc.0c10024

Cited by 9 publications

(8 citation statements)

References 42 publications

(47 reference statements)

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“…Compared with our previous work, , the bonding energy of dimer-I in 3,8-BHP adlayers (−5.59 kcal/mol) is higher than that of dimer-I in 2,9-BHP adlayers (−7.12 kcal/mol), indicating that the Br···N···H bonds in 3,8-BHP adlayer are weaker. Moreover, the bonding energy of dimer-I (−8.77 kcal/mol) involved in H···Br hydrogen bonds is the lowest in all the dimers, which is the main reason for the structural transformation once the solvents participate in the formation of nanostructures.…”

Section: Resultscontrasting

confidence: 88%

“…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 . In common, once the position of bromine substituent changes, it may directly affect the formation of the intermolecular interactions and nanostructure resulting from the directionality of halogen and hydrogen bonds. − Thus, it is necessary to investigate the solvent and solution concentration effects on the molecular self-assembly for phenanthridine derivatives with the position of the bromine substituent.…”

Section: Introductionmentioning

confidence: 99%

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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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Section: Resultscontrasting

confidence: 88%

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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“…The strength of “σ-hole” decreases with the electronegativity and increases with the polarizability of the halogen atom, which affects the directionality and tunability of the halogen bond. Generally, the strength of “σ-hole” follows the order I > Br > Cl > F = 0. , In homo-halogen bonds, halogen atoms act concurrently as both the donor and acceptor, and the electron-deficient “σ-hole” is toward the central “belt” of an electron-rich contiguous halogen atom. , Alternatively, other atoms (N, O, S...) act as acceptor sites in hetero-halogen bonds. − …”

Section: Introductionmentioning

confidence: 99%

Solvent Coadsorption Effect on I···O Halogen-Bonded 2D Self-Assembled Nanostructures

et al. 2022

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A halogen bond, as an important driving force, has tremendous application and potential in drug design, crystal engineering, organic photoelectric material, and catalysis. However, reports on the I···O heterogeneous halogen bond-induced 2D self-assembly are rare. Herein, we explore the effect of solvent coadsorption on the I···O heterogeneous halogen-bonded 2D self-assembled nanostructures of 4-(5-iodothiophen-2-yl)phenyl 3,4,5-tris(octadecyloxy)benzoate (I-TPB) at the aliphatic solvent/graphite interfaces by scanning tunneling microscopy and density functional theory calculation. n-Tridecane, n-tetradecane, and n-pentadecane are chosen as the solvents. I-TPB molecules form the same linear pattern in all the solvents at high solution concentrations. The dot-like nanostructure in n-tetradecane and n-pentadecane at low concentrations is observed. The solvent coadsorption in the dot-like nanostructure of the I-TPB adlayer does not change the intermolecular I···O halogen bonds, I···H hydrogen bonds, and S···H interactions in each dimer. The results illustrate that the intermolecular I···O halogen bonds, I···H bonds, and S···H interactions in those dimers are the main driving forces to stabilize the self-assembled nanostructures, whereas the dipole–dipole interactions are the complementary forces. This work presents significant insights into the formation mechanism of self-assembled nanostructures associated with the I···O heterohalogen bond in order to construct ideal self-assembled structures.

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“…Researchers have explored the self-assembly polymorphs of π-conjugated molecules via changing the solvent, , concentration, , temperature, , scanning tunneling microscopy (STM) bias, − molecular functional group, , the length of the alkyl chains, , and the substrate. , The used substrate contains highly oriented pyrolytic graphite (HOPG), Au (111), Ag (111), Si (111), Cu (110), and so on. − In particular, STM is the widely used visualization tool due to its atomic-level resolution. The driving forces that stabilize the self-assembled nanostructures include the weak hydrogen bonds, van der Waals interaction, dipolar interaction, halogen bonds, and π–π attractions. − …”

Section: Introductionmentioning

confidence: 99%

Odd-Even Effect on Supramolecular Co-Assemblies: Control over the Two-Dimensional Self-Assemblies of a Fluorenone Derivative with Asymmetrically Substituted Alkyl Chains

Lee

Deng

2022

Langmuir

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The precise control of two-dimensional supramolecular co-assemblies presents a research topic related to advance nanotechnology. Here, we report a scanning tunneling microscopy (STM) study of the mixture behavior of three fluorenone derivatives at the liquid–solid interface. The target molecule is F–C12C13 whose structure bears asymmetrical alkyls, whereas the regulating molecules, either F–C12C12 or F–C13C13, are structurally symmetric. By STM imaging of systematic mixtures with various volumes among the sample solutions, we found that the mixing ratio mainly determined the binary outcomes. Compared with F–C12C12, F–C13C13 shows a stronger ability to dominate the patterning, explained by the larger binding and adsorption energies calculated by the force field simulations. Moreover, the odd-even effect exists in the system. Overall, we acquired knowledge about the regulating ability of bi-component supramolecular assembling, especially for structurally asymmetric molecular systems.

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

Cited by 9 publications

References 42 publications

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

Solvent Coadsorption Effect on I···O Halogen-Bonded 2D Self-Assembled Nanostructures

Odd-Even Effect on Supramolecular Co-Assemblies: Control over the Two-Dimensional Self-Assemblies of a Fluorenone Derivative with Asymmetrically Substituted Alkyl Chains

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