Functional organic gels Chirality induction through formation of highly-oriented structure

Takafuji, Makoto; Ihara, Hirotaka; Hirayama, Chuichi; Hachisako, Hiroshi; Yamada, Kimiho

doi:10.1080/02678299508036596

Cited by 54 publications

(35 citation statements)

References 19 publications

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“…In addition, ® gure 2(d ) shows the SEM image of the ment of optical activity [1,2] . It is known that the formation of highly oriented structures is accompanied powders obtained by recrystallization from a methanol by chirality enhancement in the case of chiral lipids in moiety can act as hydrogen bonding interaction sources for formation of the aggregate network (® gure 4).…”

Section: Resultsmentioning

confidence: 98%

“…derived lipids, the chirality was remarkably enhanced through the molecular orienting e ect, and the enhanced Hydrogels have been investigated for biomedical uses and related applications such as drug delivery, chirality induced distinct enantioselectivity for the elution of amino acids through them [2,4] . In addition, controlled-release and enzyme immobilization.…”

Section: Introductionmentioning

confidence: 99%

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Detection of highly oriented aggregation of L-glutamic acid-derived lipids in dilute organic solution

Ihara¹,

Yoshitake²,

Takafuji³

et al. 1999

Liquid Crystals

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Aggregation structures in organic gels and xerogels formed from l-glutamic acid-derived lipids were investigated by scanning and transmission electron microscopies, X-ray analyses, and 1 H NMR and IR spectroscopic methods. These analyses showed that the gels were produced through the formation of highly oriented aggregates based on a single layer and a remarkable development of their ® brous morphology. We also describe how the critical aggregation concentration can be observed at a concentration below the critical gel concentration by using a dye-complexation method with a cyanine dye, NK-77.

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Section: Resultsmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

Detection of highly oriented aggregation of L-glutamic acid-derived lipids in dilute organic solution

Ihara¹,

Yoshitake²,

Takafuji³

et al. 1999

Liquid Crystals

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“…22,[30][31][32][33][34][35][36][37][38][39][40][41][42][43] When the functional group is hydrophilic, such as an amino (G-C 2 -NH 2 ) or pyridinium (G-C 2 -Py + ) group (Figure 3), the glutamide will form tubular and helical bilayer membranes in polar solvents such as water 31,44-46 and acetonitrile. 46 However, the glutamide forms fibrous aggregates in nonpolar solvents such as benzene, and the solution gels at concentrations above the critical gelation concentration.…”

Section: Supramolecular Gelsmentioning

confidence: 99%

Polymer functionalization by luminescent supramolecular gels

Ihara

Takafuji

Kuwahara

2016

Polym J

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In this review, we describe luminescent supramolecular gels that are formed by the self-assembly of low-molecular-weight compounds, focusing specifically on glutamide-based derivatives. We have developed various glutamides as supramolecular gel-forming compounds, and their unique features are characterized by the fact that most of the derivatives can form nanofibrils based on highly ordered aggregation in aqueous and organic solutions. The aggregated states are often accompanied by supramolecular functions. For example, when the glutamide has an optically functional group, such as a fluorophore, the produced aggregates show unique optical functions such as enhanced chirality (circular dichroism), fluorescence with a large Stokes shift and circularly polarized luminescence. Interestingly, these functions can be achieved in polymer-mixed systems. Because the glutamides form nanofibrillar networks even in polymers, the obtained polymer composites remain transparent because of low light scattering. Supramolecular functions are introduced in the presence of glutamide aggregates. This paper also describes polymer functionalization with glutamide-based supramolecular gels and their applications in light management technologies.

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“…On the other hand, a carboxylic acid-containing L-glutamate derivative (14) produced organogel with developed fibrous aggregates in several organic solvents. [80] This specific chiral properties stimulated us to implement optical resolution with chiral organogels. We reported the first example in 1995.…”

Section: Chemical Stabilization Of Organogelsmentioning

confidence: 99%

Self‐Assembled Nanofibrillar Aggregates with Amphiphilic and Lipophilic Molecules

Sagawa

Chowdhury

Takafuji

et al. 2006

Macromolecular Symposia

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Summary: This article gives a review on self-assembled nanofibrillar aggregates such as helical, twisted ribbon-like and tubular forms, those are produced in aqueous bilayer membrane and organogel systems. Two common features necessary for the chemical structure that yields special morphology are a chiral carbon atom and moieties feasible for intermolecular interactions although there are some exceptions. In aqueous systems, a hydrophobic effect is also an essential driving force for molecular aggregates in aqueous solution systems but almost disappear in organic media. More positive intermolecular interactions play an important role in molecular aggregation in organic media. Hydrogen bonding interaction is especially effective and many organogelators are classified into this category. Some lipophilic peptides have been investigated not only as organogelators but also with respect to their selfassembling behaviors. This latter property gives them distinct advantages compared with conventional gel systems because the gels include highly-ordered structures supramolecular functions like aqueous lipid membranes through molecular orientation. This article also introduces applicability of the organogel system.

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Functional organic gels Chirality induction through formation of highly-oriented structure

Abstract: An L-glutamate derivative having one carboxylic and two dodecylamide groups form highly-oriented aggregates in benzene, which interact with a cationic achiral dye to produce extremely strong exciton coupling around the absorption band of the dye.

Cited by 54 publications

References 19 publications

Detection of highly oriented aggregation of L-glutamic acid-derived lipids in dilute organic solution

Detection of highly oriented aggregation of L-glutamic acid-derived lipids in dilute organic solution

Polymer functionalization by luminescent supramolecular gels

Self‐Assembled Nanofibrillar Aggregates with Amphiphilic and Lipophilic Molecules

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