Perfluorinated gelators for solidifying fluorous solvents: effects of chain length and molecular chirality

Yajima, Tomoko; Tabuchi, Erika; Nogami, Emiko; Yamagishi, Akihiko; Sato, Hisako

doi:10.1039/c5ra12656h

Cited by 17 publications

(30 citation statements)

References 33 publications

(42 reference statements)

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“…SEM observation of fibril structures. A series of chiral low‐molecular weight gelators were synthesized (Chart ) . The compounds were identified by 1 H NMR, mass spectra, 19 F NMR, and differential scanning calorimetry .…”

Section: Methodsmentioning

confidence: 99%

“…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%

“…CF7 , CF8 , and CF9 correspond to a compound with n = 6, 7, and 8. The synthesis and characterization were reported in the previous article …”

Section: Chartmentioning

confidence: 99%

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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: Methodsmentioning

confidence: 99%

Section: Chartmentioning

confidence: 99%

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

2016

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“…Although this method has proven useful for the structural analysis of small naturally occurring molecules, 17-20 this topic is not the scope of this review. Similarly, because the aim of this 'Focus Review' is to describe the authors' own research, the details of recent advances in theoretical studies on the VCD couplet phenomenon 21,22 as well as applications to the structural analysis of films 23 and gels 24,25 are not discussed here.…”

Section: Introductionmentioning

confidence: 98%

Studying the stereostructures of biomolecules and their analogs by vibrational circular dichroism

Taniguchi

Hongen

Monde

2016

Polym J

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The functions of biomacromolecules are largely governed by their stereostructure (i.e., configuration and conformation). Therefore, detailed understanding of their structural properties should help in regulating the functions of artificial macromolecules. However, studying the stereostructure of a molecule in the solution state is typically difficult due to the lack of suitable analytical techniques. Vibrational circular dichroism (VCD) spectroscopy, which measures circular dichroism in the infrared region, exhibits high sensitivity toward molecular stereostructures. In this paper, we first discuss a method for the elucidation of the stereostructures of small to large molecules based on theoretical calculations of VCD. The rest of the paper is dedicated to the applications of a VCD exciton chirality method, a novel approach recently developed by the authors to interpret VCD data by observing a VCD couplet in the C = O stretching region, to various biomolecules such as peptides, carbohydrates, polyesters and lipids.

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“…The nearest distance between the two F atoms of each perfluoroalkyl chain is 2.734 Å, which is slightly shorter than the sum of the van der Waals radii of two F atoms (2.94 Å). Moreover, the packing diagram of trans-PtCl 2 (Ph 2 P n C 10 F 21 ) 2 shows that the long perfluoroalkyl chains are assembled into a fluorous layer (Figure 2) [23][24][25]. In the case of the reported light fluorous phosphine-metal complexes, such a parallel direction of the fluorous group was not observed [18,19].…”

Section: (3)mentioning

confidence: 99%

P-Fluorous Phosphines as Electron-Poor/Fluorous Hybrid Functional Ligands for Precious Metal Catalysts: Synthesis of Rh(I), Ir(I), Pt(II), and Au(I) Complexes Bearing P-Fluorous Phosphine Ligands

et al. 2017

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P-Fluorous phosphine (R 2 PR f ), in which the perfluoroalkyl group is directly bonded to the phosphorus atom, is a promising ligand because it has a hybrid functionality, i.e., electron-poor and fluorous ligands. However, examples of P-fluorous phosphine-metal complexes are still rare, most probably because the P-fluorous group is believed to decrease the coordination ability of the phosphines dramatically. In contrast, however, we have succeeded in synthesizing a series of P-fluorous phosphine-coordinated metal complexes such as rhodium, iridium, platinum, and gold. Furthermore, the electronic properties of R 2 P n C 10 F 21 are investigated by X-ray analysis of PtCl 2 (Ph 2 P n C 10 F 21 ) 2 and the infrared CO stretching frequency of RhCl(CO)(R 2 P n C 10 F 21 ) 2 . IrCl(CO)(Ph 2 P n C 10 F 21 ) 2 -and AuCl(R 2 P n C 10 F 21 )-catalyzed reactions are also demonstrated.

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Perfluorinated gelators for solidifying fluorous solvents: effects of chain length and molecular chirality

Abstract: With a purpose of solidifying fluorous solvents, a novel series of perfluorinated gelators based on 1,2-diaminocyclohexane (denoted as CFn: n = the number of carbon chain in perfluoroalkanoyl moiety) were developed.

Cited by 17 publications

References 33 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

Studying the stereostructures of biomolecules and their analogs by vibrational circular dichroism

P-Fluorous Phosphines as Electron-Poor/Fluorous Hybrid Functional Ligands for Precious Metal Catalysts: Synthesis of Rh(I), Ir(I), Pt(II), and Au(I) Complexes Bearing P-Fluorous Phosphine Ligands

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