Silver(I) Ion Induced Monolayer Formation of 2-Substituted Benzimidazoles at the Air/Water Interface

Liu, Minghua; Kira, A.; Nakahara, Hiroyuki

doi:10.1021/la9703252

Cited by 39 publications

(41 citation statements)

References 21 publications

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“…The concept of the formation and/or stabilization of membranes or monolayers by metal‐ion coordination has also been applied to aromatic nitrogen ligands. Monolayer formation at the water/air interface was observed for benzimidazole35 and naphthimidazole36 systems such as 7 (Chart ). Remarkably, the latter forms a helical assembly from achiral building blocks as circular dichroism spectra suggested.…”

Section: Overview Of Supramolecular Coordination Polymersmentioning

confidence: 99%

Metallosupramolecular approach toward functional coordination polymers

Dobrawa

Würthner

2005

J. Polym. Sci. A Polym. Chem.

293

221

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An appropriate definition of metallosupramolecular coordination polymer is offered, and the relationship between the polymer length, binding constant, and concentration is clarified. The possibility of influencing the binding constant with chelating ligands is discussed on the basis of examples of different Zn 2þ complexes and their respective binding constants. In the main part, coordination polymers constructed by a supramolecular approach from different metal ions and pyridine-ligand systems are highlighted, and their applications as functional materials for artificial membrane and enzyme models, responsive gels, light-harvesting systems, and organic light-emitting diodes are discussed on the basis of individual examples.

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Section: Overview Of Supramolecular Coordination Polymersmentioning

confidence: 99%

Metallosupramolecular approach toward functional coordination polymers

Dobrawa

Würthner

2005

J. Polym. Sci. A Polym. Chem.

293

221

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“…In addition, as versatile units, the covalently bound benzimidazole/benzothiazole groups, of which one type of rings is benzene rings and the other type is a fivemember ring with N or S elements, have been widely chosen for designing new amphiphiles because of their unique directional self-association through -stacking and van der Waals interactions in the process of supramolecular 2 Journal of Nanomaterials assembly [16][17][18]. For example, some benzimidazole and benzothiazole derivatives formed chiral assembly films through a cooperative stereoregular -stacking of the functional groups together with the long alkyl chains in a helical sense [18].…”

Section: Introductionmentioning

confidence: 99%

Nanostructures and Self‐Assembly of Organogels via Benzimidazole/Benzothiazole Imide Derivatives with Different Alkyl Substituent Chains

Shen

Jiao

Zhang

et al. 2013

Journal of Nanomaterials

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New benzimidazole/benzothiazole imide derivatives with different alkyl substituent chains were designed and synthesized. Their gelation behaviors in 22 solvents were tested as novel low-molecular-mass organic gelators. The test showed that the alkyl substituent chains and headgroups of benzimidazole/benzothiazole residues in gelators played a crucial role in the gelation behavior of all compounds in various organic solvents. More alkyl chains in molecular skeletons in present gelators are favorable for the gelation of organic solvents. SEM and AFM observations revealed that the gelator molecules self-assemble into different aggregates from wrinkle, lamella and belt to dot with change of solvents. Spectral studies indicated that there existed different H-bond formation between imide groups and hydrophobic force of alkyl substituent chains in molecular skeletons. The present work may give some insights into design and character of new organogelators and soft materials with special molecular structures.

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“…9−11 The reason behind this is due to its multiple ways to form π–π stacking and hydrogen bonding interaction. 12−14…”

Section: Introductionmentioning

confidence: 99%

Water-Assisted Self-Aggregation of Benzimidazole and Triazole Adducts

Sahay

Ghalsasi

2019

ACS Omega

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The manuscript revolves around an interesting observation of solidification of a solution of N -((1-((1-ethyl-1 H -benzo[ d ]imidazol-2-yl)methyl)-1 H -1,2,3-triazole-4-yl)methyl)aniline ( A6) in the NMR tube after around 12 h. Real-time images showed fibrillar and spherulitic growth with tip branching and side branching, which is thermoreversible. The compound under investigation is unique because it is synthesized to understand the anticancer activity with two pharmacophores, benzimidazole and triazole. Click chemistry is employed for in situ generation of triazole moiety on benzimidazole. Previously, benzimidazole-based compounds have shown self-aggregation-induced gel-like behavior because of hydrogen bonding and/or π–π stacking interactions. In the present case, NMR titrations with D 2 O addition showed two distinct changes in the chemical shift for methylene bridges (connecting benzimidazole and triazole ring) and ortho protons of the phenyl ring (attached to triazole ring). Interestingly, a single-crystal X-ray structure shows the absence of hydrogen bonds and π–π stacking while in the presence of only two distinct close contacts, completely correlating NMR data discussed in detail. A similar “molecular origin” for self-aggregation is observed in seven other flexible but regioisomeric compounds, which were designed and synthesized for inducing hydrogen bonding through the removal of N -ethyl group and insertion of aniline and/or fluoro group.

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Silver(I) Ion Induced Monolayer Formation of 2-Substituted Benzimidazoles at the Air/Water Interface

Cited by 39 publications

References 21 publications

Metallosupramolecular approach toward functional coordination polymers

Metallosupramolecular approach toward functional coordination polymers

Nanostructures and Self‐Assembly of Organogels via Benzimidazole/Benzothiazole Imide Derivatives with Different Alkyl Substituent Chains

Water-Assisted Self-Aggregation of Benzimidazole and Triazole Adducts

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