Molecular origin for helical winding of fibrils formed by perfluorinated gelators

Sato, Hisako; Yajima, Tomoko; Yamagishi, Akihiko

doi:10.1039/c0cc05802e

Cited by 37 publications

(55 citation statements)

References 29 publications

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“…Recently, extensive work has been performed to develop gelators with perfluoroalkyl chains. A basic concept was formed on the interplay of their dual characters, hydrophobicity and fluorophilicity . From the practical point of view, gelators with perfluoroalkyl chains are a promising application to gelate fluorous solvents .…”

Section: Chartmentioning

confidence: 99%

Helical Inversion of Gel Fibrils by Elongation of Perfluoroalkyl Chains as Studied by Vibrational Circular Dichroism

2016

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Vibrational circular dichroism (VCD) spectroscopy was applied to gelation by a chiral low-molecular mass weight gelator, N,N'-diperfluoroalkanoyl-1,2-trans-diaminocyclohexane. Attention was focused on the winding effects of (-CF2 )n chains on the gelating ability. For this purpose, a series of gelators were synthesized with perfluoroalkyl chains of different length (n = 6-8). When gelation was studied using acetonitrile as a solvent, the fibrils took different morphologies, depending on the chain length: twisted saddle-like ribbon or helical ribbon from fibril (n = 6) and a helical ribbon from platelet (n = 8). The signs of VCD peaks assigned to the couplet of C=O stretching and to the C-F stretching were also dependent on n, indicating that a gelator molecule changed conformation on elongating perfluoroalkyl chains. A model is proposed for the aggregation modes in fibrils. Chirality 28:361-364, 2016. © 2016 Wiley Periodicals, Inc.

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Section: Chartmentioning

confidence: 99%

Helical Inversion of Gel Fibrils by Elongation of Perfluoroalkyl Chains as Studied by Vibrational Circular Dichroism

2016

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“…Quite substantial values are obtained, which are likely due to the strong cationanion attraction in the ionic liquids. 24 …”

Section: Thermostabilitymentioning

confidence: 99%

Self-recovering stimuli-responsive macrocycle-equipped supramolecular ionogels with unusual mechanical properties

Traulsen

Molina

et al. 2014

Org. Biomol. Chem.

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A chiral, crown-ether-functionalized bisurea gelator forms supramolecular gels in ionic liquids. The resulting ionogels show a remarkably high thermal stability with gel-sol transition temperatures (T gs ) reaching more than 100°C. The mechanical strength of these ionogels is surprisingly high and even comparable to that of cross-linked protein fibres. Furthermore, the ionogels exhibit rapid self-recovery properties after structural damage caused by deformation. Pseudorotaxanes form from the gelators' benzo[21]-crown-7 ethers as the wheels and secondary ammonium ions as the axles despite the competition between that cation and the imidazolium ions of the ionic liquid for crown ether binding. Pseudorotaxane formation as an external chemical stimulus triggers the gel-sol transition of the ionogels.

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“…of little populated conformers. [11][12][13] Furthermore, VCD spectroscopy has been shown to be a very powerful technique to study intermolecular interactions such as solutesolvent [14][15][16][17] or solute-solute [18][19][20][21][22] interactions as well as chirality transfer phenomena. Slight warming of the solid matrix also enables the diffusion controlled generation of larger molecular clusters.…”

Section: Introductionmentioning

confidence: 99%

Conformational distortion of α-phenylethyl amine in cryogenic matrices – a matrix isolation VCD study

Pollok

Merten

2016

Phys. Chem. Chem. Phys.

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The chiral amine α-phenylethyl amine (PEA) was isolated in cryogenic matrices and investigated using vibrational circular dichroism (VCD) and infrared spectroscopy. The potential energy surface (PES) of PEA features five different conformers connected by relatively low conformational transition states. Based on the IR spectra, it could be confirmed that all conformational energy barriers are passed at a deposition temperature of 20 K, and that only the global minimum conformation of PEA is populated in both argon and nitrogen matrices. However, differences in the calculated and experimental VCD spectra indicate deviations from the minimum structure by perturbation of the phenyl ring as well as of the amine orientation. The degree of the perturbation is found to also depend on the choice of the host gas, which shows the subtle influence of the environment on the conformational distortion of PEA.

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Molecular origin for helical winding of fibrils formed by perfluorinated gelators

Cited by 37 publications

References 29 publications

Helical Inversion of Gel Fibrils by Elongation of Perfluoroalkyl Chains as Studied by Vibrational Circular Dichroism

Helical Inversion of Gel Fibrils by Elongation of Perfluoroalkyl Chains as Studied by Vibrational Circular Dichroism

Self-recovering stimuli-responsive macrocycle-equipped supramolecular ionogels with unusual mechanical properties

Conformational distortion of α-phenylethyl amine in cryogenic matrices – a matrix isolation VCD study

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