Prominent Gelation and Chiral Aggregation of Alkylamides Derived from <i>trans</i>‐1,2‐Diaminocyclohexane

Hanabusa, Kenji; Yamada, Manabu; Kimura, Mutsumi; Shirai, Hirofusa

doi:10.1002/anie.199619491

Cited by 452 publications

(312 citation statements)

References 22 publications

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“…10-30 nm in diameter and several micrometers in length, which eventually form developed nanofiber networks. From the scanning electron and atomic force microscopic analyses, we found that no remarkable, helically twisted fiber morphologies 170,171 are observable (Figure 26). In order to get further insight into the molecular packing and orientation within the nanofibers, we measured X-Ray diffraction of a freeze-dried hydrogel of 25 (20).…”

Section: Nanofiber Formation From Nucleotide-appended Bolaamphiphilicmentioning

confidence: 99%

Bottom-Up Synthesis and Morphological Control of High-Axial-Ratio Nanostructures through Molecular Self-Assembly

Shimizu

2003

Polym J

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ABSTRACT:Based on our recent results, the present paper overviews noncovalent formation of high-axial-ratio nanostructures (HARNs), such as fibers, rods, tubes and ropes, through molecular self-assembly of bola-form amphiphilic (bolaamphiphilic) monomers. A variety of bolaamphiphiles, in which sugars, peptides, or nucleobases as headgroups are connected to both ends of a hydrocarbon spacer, were newly designed and synthesized. Their self-assembling behavior was examined in aqueous solutions in terms of bottom-up fabrication of organic nanostructures. The morphologies proved to strongly depend on the headgroup structure, spacer chain lengths and even-odd carbon numbers of used oligo(methylene) spacers. Typical examples of self-assembled morphologies include nanofibers from 1-glucosamide-or thymidine-appended bolaamphiphiles, vesicle-encapsulated microtubes from glycylglycine-appended bolaamphiphiles, double-helical ropes from thymine-appended bolaamphiphiles. These self-assembled HARNs are constructed hierarchically in a manner similar to biological structures. On the basis of several solid-state analyses, molecular packing and orientation within the HARNs are discussed and compared with the single crystal structures in terms of hydrogen-bond networks. Furthermore, pH-dependent reversible polymer formation was achieved using the combination of glucuronamideand aromatic boronic acid-appended bola-form derivatives. Polymerization of bola-form 1-glucosamide derivatives with a 1,4-butadiyne group was performed in self-assembled nanometer-sized fibers, giving a single polydiacetylene chain of 64-mer that can be seen in TEM.KEY WORDS High-Axial-Ratio Nanostructure (HARN) / Bolaamphiphile / Self-Assembly / Noncovalent Synthesis / Hydrogen Bond / Nanofiber / Microtube / Nano-Rod / Rope / Hydrogel / Crystal Structure / Biomaterials possess highly organized non-covalent structures formed spontaneously in bottom-up fashion, 1 shaping natural body and functioning as energyconverting and information-converting materials. In contrast, conventional polymers are so-called linear macromolecules in which tens of thousands to millions of low-molecular-weight monomer units are connected to each other through covalent bonds. Very recently, a new family of polymers, including topologically complex polymers 2-13, 18-25 and self-assembled nanostructures, [14][15][16][17]26 has attracted much attention. 27,28 In particular, Kunitake and his co-worker built up the fundamental concept behind the polymolecular materials based on bilayer-containing molecular assemblies. 29,30 Stupp et al., 31, 32 Percec et al., 33 and Whitesides et al. 34,35 also succeeded in a molecule-up fabrication using polymer building blocks to realize nanometersized assemblies with well-defined shapes. The advantage of non-covalent self-assembly technique, unlike chemical reaction or polymerization, is in that it can directly produce ordered two-and three-dimensional structures like sheets, rods, fibers, tubes, disks, and spheres. It is more important that nanostruct...

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Section: Nanofiber Formation From Nucleotide-appended Bolaamphiphilicmentioning

confidence: 99%

Bottom-Up Synthesis and Morphological Control of High-Axial-Ratio Nanostructures through Molecular Self-Assembly

Shimizu

2003

Polym J

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“…The sol-gel transcription method [7] using gelators and lipids is a simple and powerful method to control the morphological shapes of 1D nanostructures. Especially, chiral gelators and lipids can form helical morphological shapes [8]. Up to now, the helical structures in organogel fibers [9] and self-assemblies of lipids [10] have been successfully transcribed into inorganic silica and titania.…”

Section: Introductionmentioning

confidence: 99%

Fabrication of Helical Mesoporous Silica Nanostructures Using Gelators and the Mixtures with CTAC

et al. 2009

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“…The diamide derivative 3 24 and diurea derivative 4 25 are both synthesized in one step reaction from trans-(1R,2R)-diaminocyclohexane ( Figure 3). Compounds 3 and 4 are excellent gelators comparable to L-isoleucine derivative 1.…”

Section: Cyclohexane-based Gelatorsmentioning

confidence: 99%

Physical Gelation by Low-Molecular-Weight Compounds and Development of Gelators

Hanabusa¹,

Suzuki²

2015

Bulletin of the Chemical Society of Japan

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We discuss low-molecular-weight compounds, which undergo physical gelation, as gelators. There is a close relationship between crystallization and gelation with respect to the driving forces. Both crystallization and gelation are driven by noncovalent interactions such as hydrogen bonding, van der Waals forces, electrostatic interactions, and ππ interactions. Typical gelators, which include amino acid derivatives, trans-1,2-diaminocyclohexane derivatives, and cyclic(dipeptide)s, are discussed. A concept of "gelation-driving segment" has been proposed. Hydrogelators, functional gelators, and polymer-type gelators are developed by using gelation-driving segments.

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Prominent Gelation and Chiral Aggregation of Alkylamides Derived from trans‐1,2‐Diaminocyclohexane

Cited by 452 publications

References 22 publications

Bottom-Up Synthesis and Morphological Control of High-Axial-Ratio Nanostructures through Molecular Self-Assembly

Bottom-Up Synthesis and Morphological Control of High-Axial-Ratio Nanostructures through Molecular Self-Assembly

Fabrication of Helical Mesoporous Silica Nanostructures Using Gelators and the Mixtures with CTAC

Physical Gelation by Low-Molecular-Weight Compounds and Development of Gelators

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