Systematic elucidation of crystal structure of fluorinated gemini-type diamide derivatives having different lengths with thixotropic induced-ability to solvents

Maruyama, Haruka; Fukushi, Keito; Okano, Rei; Satou, Eiichi; Yajima, Tomoko; Fujimori, Atsuhiro

doi:10.1016/j.jfluchem.2020.109505

Cited by 5 publications

(5 citation statements)

References 50 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Previous studies have shown that 2C 18 (OH)‐dA has an absorption band in the Ultraviolet‐visible absorption (UV‐vis) spectra [33,35–36] . Based on the difference in the conformation of molecules with similar chemical structures, [34] the absorption was predicted to be based on the formation of a pseudo‐conjugated system between two molecules owing to the tail‐to‐tail conformation of the amide site. Therefore, this molecule can be evaluated using its CD spectrum [33,35–36] .…”

Section: Resultsmentioning

confidence: 99%

“…[33] The helical fiber film of the derivative has circular dichroism (CD) spectral activity, and its chirality can be evaluated; however, fluorocarbon-based derivatives with similar structures are CD inactive. [34] In this study, we investigated the loss-of-function behavior of thixotropic additive molecules with a 12-hydroxystearyl chain and the characteristics of chirality/ helical fibrosis when exposed to high temperatures (…”

Section: Chemistryselectmentioning

confidence: 99%

“…A double‐chain diamide derivative, in which two 12‐hydroxystearyl chains are bonded via a hexamethylene linker, forms a head‐to‐tail double‐layer structure, resulting in a pseudo‐conjugated chromophore [33] . The helical fiber film of the derivative has circular dichroism (CD) spectral activity, and its chirality can be evaluated; however, fluorocarbon‐based derivatives with similar structures are CD inactive [34] . In this study, we investigated the loss‐of‐function behavior of thixotropic additive molecules with a 12‐hydroxystearyl chain and the characteristics of chirality/helical fibrosis when exposed to high temperatures (Figure 1(b)).…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Correlation between Chirality and Spherical Particle Formation Related to the Loss of Function of Thixotropic Additive Molecules

2022

Self Cite

View full text Add to dashboard Cite

The relationship between chirality and loss of function of thixotropic additive molecules with asymmetric carbon and helical fiber growth under high‐temperature exposure was investigated. Among the thixotropic additive molecules that impart gelation/fluidization ability during pressurization of the solvent, derivatives with high‐performance, helical fiber growth ability became mesoscopic spherical particles upon high‐temperature exposure. Conversely, derivatives that lost their fiber growth ability could not achieve solvent gelation. The growth pattern was such that the helical fibers were transformed into straight fibers. The right‐handed helical signal of the circular dichroism spectrum, which is indicative of chirality by structure formation, was inactivated upon high‐temperature exposure. Therefore, a low‐temperature process or heat treatment in an inert state under a N2 atmosphere is essential for maintaining chirality and helical fibrosis.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Chemistryselectmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Correlation between Chirality and Spherical Particle Formation Related to the Loss of Function of Thixotropic Additive Molecules

2022

Self Cite

View full text Add to dashboard Cite

show abstract

“…The entanglement of nanofibers seems to be involved in efficient gelation. In the system, the presence of asymmetric carbons and/or helical units in the additive molecule can induce the formation of helical fibers; it is possible that the fibers are well entangled to form an organized structure that is easy to gel [40,41] . An example is R ‐12‐hydroxystearic acid ( abbrev.…”

Section: Introductionmentioning

confidence: 99%

“…In the system, the presence of asymmetric carbons and/or helical units in the additive molecule can induce the formation of helical fibers; it is possible that the fibers are well entangled to form an organized structure that is easy to gel. [40,41] An example is R-12-hydroxystearic acid (abbrev. R-12-HSA), [42] and waste oil treatment agents containing it have been commercialized by taking advantage of the function of wrapping solvent molecules by forming helical nanofibers.…”

Section: Introductionmentioning

confidence: 99%

Characterization of Molecular Arrangement of Long‐chain Ferrocenyl Derivatives Having Asymmetric Carbon by Method of Organized Molecular Films and Formation of Its Helical Nanofibers

et al. 2021

Self Cite

View full text Add to dashboard Cite

Formation of organized molecular film and helical nanofibers of ferrocene derivatives having R‐12‐hydroxystearyl chains with asymmetric carbon was investigated. The 12‐hydroxystearyl chain, which induces “thixotropy” due to the formation and breakage of intermolecular hydrogen bonds, was introduced into the ferrocenyl unit. The structure of this derivative as a monolayer on the water surface and its Langmuir‐Blodgett (LB) film properties were analyzed. The monolayer showed a two‐dimensional phase transition, corresponding to the formation of fibrous morphology. In the LB multilayers, intermolecular hydrogen bonding between hydroxyl groups at the 12‐position of the chain and crystalline packing was observed. Raman mapping revealed the difference in surface morphology of each derivative depending on the number of 12‐hydroxystearyl chains. The derivative having the single chain showed a right‐handed helical morphology in the film and this behavior is similar to those having two and three chains. In circular dichroism spectra, the film showed a positive Cotton effect. Since the helical chains easily entangle with each other to form a sponge‐like organization, it was expected that the solvent uptake was the origin of gelation induction to its contact solvent.

show abstract

Verification of interfacial monolayer conformation of weakly hydrophilic diamide derivatives possessing a fluorocarbon-sandwiched hydrocarbon

Maruyama

Mashiyama

Kimura

et al. 2020

Colloids and Surfaces A: Physicochemical and Engineering Aspect

View full text Add to dashboard Cite

Systematic elucidation of crystal structure of fluorinated gemini-type diamide derivatives having different lengths with thixotropic induced-ability to solvents

Cited by 5 publications

References 50 publications

Correlation between Chirality and Spherical Particle Formation Related to the Loss of Function of Thixotropic Additive Molecules

Correlation between Chirality and Spherical Particle Formation Related to the Loss of Function of Thixotropic Additive Molecules

Characterization of Molecular Arrangement of Long‐chain Ferrocenyl Derivatives Having Asymmetric Carbon by Method of Organized Molecular Films and Formation of Its Helical Nanofibers

Verification of interfacial monolayer conformation of weakly hydrophilic diamide derivatives possessing a fluorocarbon-sandwiched hydrocarbon

Contact Info

Product

Resources

About