Rod and Helical Organic Fiber Structures Revealing Lamellar and Rosette Ordering Pathways in Self-Assembly of Barbiturate Oligothiophene Derivatives

Silly, Fabien; Kawaura, Maika; Aizawa, Takumi; Ouchi, Hayato; Yagai, Shiki

doi:10.1021/acs.jpcc.1c09077

Cited by 3 publications

References 51 publications

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Identifying Target Molecule and Trace Amount of the Byproduct by Two-Dimensional Self-Assembly with Different Solution Concentrations

Zhang,

Zhao,

Miao

et al. 2024

Langmuir

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Scanning tunneling microscopy (STM) is a powerful way to realize the recognition of self-assembled nanostructures on the atomic scale. In this article, dihexadecyl 6,9-bis((4-(hexadecyloxy)phenyl)ethynyl) phenanthro[9,10-c]thiophene-1,3-dicarboxylate (D-PT) and dihexadecyl 6-bromo-9-((4-(hexadecyloxy) phenyl)ethynyl)phenanthrol[9,10-c]thiophene-1,3-dicarboxylate (S-BrPT) with different substituents were chosen as the target system. D-PT with four side chains as the target molecule and S-BrPT with three side chains and a bromine substituent as the byproduct were mixed in a molar concentration ratio of 20:1. The effect of solution concentration on the molecular self-assembly of the mixture was investigated by STM at the hexadecane/HOPG interface. At high concentrations, only D-PT molecules formed a dimer pattern resulting from the intermolecular van der Waals force and self-adaption. Further diluting the solution, D-PT formed the coexisting dimer and linear structures, in which the linear pattern was formed via solvent coadsorption. At low concentrations, S-BrPT molecules forming N-shaped dimers appeared and filled the linear structure fabricated by D-PT molecules. With further decrease in the concentration, S-BrPT molecules formed N-shaped dimers covering almost half of the surface area, resulting from the C−Br•••π and Br•••H−C bonds. At very low concentrations, S-BrPT molecules formed N-shaped dimers to arrange the matrix architecture due to the coadsorption of more hexadecane molecules. Density functional theory (DFT) calculations demonstrated that the stronger intermolecular C−Br•••π and Br•••H−C bonds were significant factors in determining the formation of N-shaped dimers and the stability of this nanostructure. This work enriches the diversity of self-assembled motifs and provides a strategy to characterize different symmetric molecules with trace amounts in a mixed system by STM.

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Identifying Target Molecule and Trace Amount of the Byproduct by Two-Dimensional Self-Assembly with Different Solution Concentrations

Zhang,

Zhao,

Miao

et al. 2024

Langmuir

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Tuning the Photophysical Properties of BODIPY Dyes and Studying Their Self-Assembly via Hydrogen Bonding

Akyol,

Çokluk,

Ayhan

et al. 2024

ACS Omega

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Here, BODIPY derivatives were functionalized with barbituric acid, which has multiple hydrogen bonding abilities that are directional, to have highly ordered hydrogen bond−mediated self-assembled structures to tune BODIPY's photophysical properties. The synthesis of barbituric acid-functionalized BODIPY derivatives via Vilsmeier and Knoevenagel reactions was achieved, and the resulting compounds were characterized with FT-IR, 1 H NMR, 13 C NMR spectroscopy, and mass spectrometry. Hydrogen bond-mediated self-assembled structures were investigated through UV−vis and fluorescence spectrophotometry, 1 H NMR spectroscopy, and a dynamic light scattering method in solution. Moreover, SEM, HR-TEM, and PXRD were used to study the self-assembly of compounds in bulk.

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Selective Two-Dimensional Adsorption of Binary Solutes System by Varying Solution Concentration

Zhao,

Miao,

Wang

et al. 2023

Preprint

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Rod and Helical Organic Fiber Structures Revealing Lamellar and Rosette Ordering Pathways in Self-Assembly of Barbiturate Oligothiophene Derivatives

Cited by 3 publications

References 51 publications

Identifying Target Molecule and Trace Amount of the Byproduct by Two-Dimensional Self-Assembly with Different Solution Concentrations

Identifying Target Molecule and Trace Amount of the Byproduct by Two-Dimensional Self-Assembly with Different Solution Concentrations

Tuning the Photophysical Properties of BODIPY Dyes and Studying Their Self-Assembly via Hydrogen Bonding

Selective Two-Dimensional Adsorption of Binary Solutes System by Varying Solution Concentration

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