Sugar-integrated gelators of organic solvents - Their remarkable diversity in gelation ability and aggregate structure

Kenji Yoza, Natsuki Amanokura, Yoshiyuki Ono, Tetsuyuki Akao, Hideyuki Shinmori, Masayuki Takeuchi, Seiji Shinkai, David N. Reinhoudt

Research output: Contribution to journalArticle

218 Citations (Scopus)

Abstract

Five 1-O-methyl-4,6-O-benzylidene derivatives of the monosaccharides D-glucose, D-galactose, and D-mannose were synthesized. The β-isomer of the D-glucose derivative was sparingly soluble in most organic solvents, whereas the α-isomer of the D-mannose derivative was soluble in many organic solvents. The α-isomer of the D-glucose derivative and the α- and β-isomers of the D-galactose derivative acted as versatile gelators of various organic solvents; this indicates that saccharides are useful as potential templates for the molecular design of chiral gelators. In particular, the two D-galactose-based gelators behaved as "excellent gelators". It is very surprising that a change in the configuration of only one carbon atom results in such a drastic change in the solubility and the gelation properties. The possible relationship between the saccharide structure and the gelation properties is discussed on the basis of FT-IR and 1H NMR spectroscopic data, differential scanning calorimetric (DSC) measurements, scanning electron microscopy (SEM) observations, and computational studies. FT-IR spectroscopy showed that the gelation properties are related to the formation of "moderate" intermolecular hydrogen bonds. The SEM observations showed that the gelators can form various fibrous structures (straight, puckered, and helical). The present study shows that this saccharide family is a potential combinatorial library of organic gelators and more generally, of molecular assembly systems.

Original languageEnglish
Pages (from-to)2722-2729
Number of pages8
JournalChemistry - A European Journal
Volume5
Issue number9
DOIs
Publication statusPublished - Jan 1 1999
Externally publishedYes

Fingerprint

Gelation
Sugars
Organic solvents
Isomers
Derivatives
Galactose
Glucose
Mannose
Scanning electron microscopy
Monosaccharides
Infrared spectroscopy
Hydrogen bonds
Carbon
Solubility
Nuclear magnetic resonance
Scanning
Atoms

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Sugar-integrated gelators of organic solvents - Their remarkable diversity in gelation ability and aggregate structure. / Yoza, Kenji; Amanokura, Natsuki; Ono, Yoshiyuki; Akao, Tetsuyuki; Shinmori, Hideyuki; Takeuchi, Masayuki; Shinkai, Seiji; Reinhoudt, David N.

In: Chemistry - A European Journal, Vol. 5, No. 9, 01.01.1999, p. 2722-2729.

Research output: Contribution to journalArticle

Yoza, Kenji ; Amanokura, Natsuki ; Ono, Yoshiyuki ; Akao, Tetsuyuki ; Shinmori, Hideyuki ; Takeuchi, Masayuki ; Shinkai, Seiji ; Reinhoudt, David N. / Sugar-integrated gelators of organic solvents - Their remarkable diversity in gelation ability and aggregate structure. In: Chemistry - A European Journal. 1999 ; Vol. 5, No. 9. pp. 2722-2729.
@article{f4838e9134e94de19eed5bea087b14d0,
title = "Sugar-integrated gelators of organic solvents - Their remarkable diversity in gelation ability and aggregate structure",
abstract = "Five 1-O-methyl-4,6-O-benzylidene derivatives of the monosaccharides D-glucose, D-galactose, and D-mannose were synthesized. The β-isomer of the D-glucose derivative was sparingly soluble in most organic solvents, whereas the α-isomer of the D-mannose derivative was soluble in many organic solvents. The α-isomer of the D-glucose derivative and the α- and β-isomers of the D-galactose derivative acted as versatile gelators of various organic solvents; this indicates that saccharides are useful as potential templates for the molecular design of chiral gelators. In particular, the two D-galactose-based gelators behaved as {"}excellent gelators{"}. It is very surprising that a change in the configuration of only one carbon atom results in such a drastic change in the solubility and the gelation properties. The possible relationship between the saccharide structure and the gelation properties is discussed on the basis of FT-IR and 1H NMR spectroscopic data, differential scanning calorimetric (DSC) measurements, scanning electron microscopy (SEM) observations, and computational studies. FT-IR spectroscopy showed that the gelation properties are related to the formation of {"}moderate{"} intermolecular hydrogen bonds. The SEM observations showed that the gelators can form various fibrous structures (straight, puckered, and helical). The present study shows that this saccharide family is a potential combinatorial library of organic gelators and more generally, of molecular assembly systems.",
author = "Kenji Yoza and Natsuki Amanokura and Yoshiyuki Ono and Tetsuyuki Akao and Hideyuki Shinmori and Masayuki Takeuchi and Seiji Shinkai and Reinhoudt, {David N.}",
year = "1999",
month = "1",
day = "1",
doi = "10.1002/(SICI)1521-3765(19990903)5:9<2722::AID-CHEM2722>3.0.CO;2-N",
language = "English",
volume = "5",
pages = "2722--2729",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "9",

}

TY - JOUR

T1 - Sugar-integrated gelators of organic solvents - Their remarkable diversity in gelation ability and aggregate structure

AU - Yoza, Kenji

AU - Amanokura, Natsuki

AU - Ono, Yoshiyuki

AU - Akao, Tetsuyuki

AU - Shinmori, Hideyuki

AU - Takeuchi, Masayuki

AU - Shinkai, Seiji

AU - Reinhoudt, David N.

PY - 1999/1/1

Y1 - 1999/1/1

N2 - Five 1-O-methyl-4,6-O-benzylidene derivatives of the monosaccharides D-glucose, D-galactose, and D-mannose were synthesized. The β-isomer of the D-glucose derivative was sparingly soluble in most organic solvents, whereas the α-isomer of the D-mannose derivative was soluble in many organic solvents. The α-isomer of the D-glucose derivative and the α- and β-isomers of the D-galactose derivative acted as versatile gelators of various organic solvents; this indicates that saccharides are useful as potential templates for the molecular design of chiral gelators. In particular, the two D-galactose-based gelators behaved as "excellent gelators". It is very surprising that a change in the configuration of only one carbon atom results in such a drastic change in the solubility and the gelation properties. The possible relationship between the saccharide structure and the gelation properties is discussed on the basis of FT-IR and 1H NMR spectroscopic data, differential scanning calorimetric (DSC) measurements, scanning electron microscopy (SEM) observations, and computational studies. FT-IR spectroscopy showed that the gelation properties are related to the formation of "moderate" intermolecular hydrogen bonds. The SEM observations showed that the gelators can form various fibrous structures (straight, puckered, and helical). The present study shows that this saccharide family is a potential combinatorial library of organic gelators and more generally, of molecular assembly systems.

AB - Five 1-O-methyl-4,6-O-benzylidene derivatives of the monosaccharides D-glucose, D-galactose, and D-mannose were synthesized. The β-isomer of the D-glucose derivative was sparingly soluble in most organic solvents, whereas the α-isomer of the D-mannose derivative was soluble in many organic solvents. The α-isomer of the D-glucose derivative and the α- and β-isomers of the D-galactose derivative acted as versatile gelators of various organic solvents; this indicates that saccharides are useful as potential templates for the molecular design of chiral gelators. In particular, the two D-galactose-based gelators behaved as "excellent gelators". It is very surprising that a change in the configuration of only one carbon atom results in such a drastic change in the solubility and the gelation properties. The possible relationship between the saccharide structure and the gelation properties is discussed on the basis of FT-IR and 1H NMR spectroscopic data, differential scanning calorimetric (DSC) measurements, scanning electron microscopy (SEM) observations, and computational studies. FT-IR spectroscopy showed that the gelation properties are related to the formation of "moderate" intermolecular hydrogen bonds. The SEM observations showed that the gelators can form various fibrous structures (straight, puckered, and helical). The present study shows that this saccharide family is a potential combinatorial library of organic gelators and more generally, of molecular assembly systems.

UR - http://www.scopus.com/inward/record.url?scp=0032844074&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0032844074&partnerID=8YFLogxK

U2 - 10.1002/(SICI)1521-3765(19990903)5:9<2722::AID-CHEM2722>3.0.CO;2-N

DO - 10.1002/(SICI)1521-3765(19990903)5:9<2722::AID-CHEM2722>3.0.CO;2-N

M3 - Article

VL - 5

SP - 2722

EP - 2729

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 9

ER -