New sugar-based gelators bearing a p-nitrophenyl chromophore

Remarkably large influence of a sugar structure on the gelation ability

Natsuki Amanokura, Kenji Yoza, Hideyuki Shinmori, Seiji Shinkai, David N. Reinhoudt

Research output: Contribution to journalArticle

81 Citations (Scopus)

Abstract

Three sugar-integrated gelators bearing a p-nitrophenyl group as a chromophore were synthesised. D-Mannose-based compound 3 was too soluble in most organic solvents to act as a gelator whereas D-galactose-based compound 2 was sparingly soluble in most organic solvents. D-Glucose-based compound 1 was moderately soluble and acted as an excellent gelator, gelating 10 solvents tested. The possible correlation between the gelation ability and the gelator structure is discussed on the basis of the intermolecular hydrogen-bonding interactions detectable by FT-IR spectroscopy. CD spectral measurements showed that the p-nitrophenyl groups in the gel fibrils of 1 are stacked in the clockwise direction [i.e., with (R)-helicity]. SEM observation of the xerogels showed that in most cases the gelator forms a three-dimensional network with 30-100 nm frizzled fibrils. Only when they were prepared from the methylcyclohexane solution, was the helical structure (although in part) observed.

Original languageEnglish
Pages (from-to)2585-2591
Number of pages7
JournalJournal of the Chemical Society. Perkin Transactions 2
Issue number12
Publication statusPublished - Dec 1 1998

Fingerprint

Bearings (structural)
Gelation
Chromophores
Sugars
Organic solvents
Xerogels
Mannose
Galactose
Infrared spectroscopy
Hydrogen bonds
Gels
Glucose
Scanning electron microscopy

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

New sugar-based gelators bearing a p-nitrophenyl chromophore : Remarkably large influence of a sugar structure on the gelation ability. / Amanokura, Natsuki; Yoza, Kenji; Shinmori, Hideyuki; Shinkai, Seiji; Reinhoudt, David N.

In: Journal of the Chemical Society. Perkin Transactions 2, No. 12, 01.12.1998, p. 2585-2591.

Research output: Contribution to journalArticle

Amanokura, Natsuki ; Yoza, Kenji ; Shinmori, Hideyuki ; Shinkai, Seiji ; Reinhoudt, David N. / New sugar-based gelators bearing a p-nitrophenyl chromophore : Remarkably large influence of a sugar structure on the gelation ability. In: Journal of the Chemical Society. Perkin Transactions 2. 1998 ; No. 12. pp. 2585-2591.
@article{16398cb5128d46e3a2b04997c0a93b7e,
title = "New sugar-based gelators bearing a p-nitrophenyl chromophore: Remarkably large influence of a sugar structure on the gelation ability",
abstract = "Three sugar-integrated gelators bearing a p-nitrophenyl group as a chromophore were synthesised. D-Mannose-based compound 3 was too soluble in most organic solvents to act as a gelator whereas D-galactose-based compound 2 was sparingly soluble in most organic solvents. D-Glucose-based compound 1 was moderately soluble and acted as an excellent gelator, gelating 10 solvents tested. The possible correlation between the gelation ability and the gelator structure is discussed on the basis of the intermolecular hydrogen-bonding interactions detectable by FT-IR spectroscopy. CD spectral measurements showed that the p-nitrophenyl groups in the gel fibrils of 1 are stacked in the clockwise direction [i.e., with (R)-helicity]. SEM observation of the xerogels showed that in most cases the gelator forms a three-dimensional network with 30-100 nm frizzled fibrils. Only when they were prepared from the methylcyclohexane solution, was the helical structure (although in part) observed.",
author = "Natsuki Amanokura and Kenji Yoza and Hideyuki Shinmori and Seiji Shinkai and Reinhoudt, {David N.}",
year = "1998",
month = "12",
day = "1",
language = "English",
pages = "2585--2591",
journal = "Journal of the Chemical Society, Perkin Transactions 2",
issn = "1470-1820",
publisher = "Royal Society of Chemistry",
number = "12",

}

TY - JOUR

T1 - New sugar-based gelators bearing a p-nitrophenyl chromophore

T2 - Remarkably large influence of a sugar structure on the gelation ability

AU - Amanokura, Natsuki

AU - Yoza, Kenji

AU - Shinmori, Hideyuki

AU - Shinkai, Seiji

AU - Reinhoudt, David N.

PY - 1998/12/1

Y1 - 1998/12/1

N2 - Three sugar-integrated gelators bearing a p-nitrophenyl group as a chromophore were synthesised. D-Mannose-based compound 3 was too soluble in most organic solvents to act as a gelator whereas D-galactose-based compound 2 was sparingly soluble in most organic solvents. D-Glucose-based compound 1 was moderately soluble and acted as an excellent gelator, gelating 10 solvents tested. The possible correlation between the gelation ability and the gelator structure is discussed on the basis of the intermolecular hydrogen-bonding interactions detectable by FT-IR spectroscopy. CD spectral measurements showed that the p-nitrophenyl groups in the gel fibrils of 1 are stacked in the clockwise direction [i.e., with (R)-helicity]. SEM observation of the xerogels showed that in most cases the gelator forms a three-dimensional network with 30-100 nm frizzled fibrils. Only when they were prepared from the methylcyclohexane solution, was the helical structure (although in part) observed.

AB - Three sugar-integrated gelators bearing a p-nitrophenyl group as a chromophore were synthesised. D-Mannose-based compound 3 was too soluble in most organic solvents to act as a gelator whereas D-galactose-based compound 2 was sparingly soluble in most organic solvents. D-Glucose-based compound 1 was moderately soluble and acted as an excellent gelator, gelating 10 solvents tested. The possible correlation between the gelation ability and the gelator structure is discussed on the basis of the intermolecular hydrogen-bonding interactions detectable by FT-IR spectroscopy. CD spectral measurements showed that the p-nitrophenyl groups in the gel fibrils of 1 are stacked in the clockwise direction [i.e., with (R)-helicity]. SEM observation of the xerogels showed that in most cases the gelator forms a three-dimensional network with 30-100 nm frizzled fibrils. Only when they were prepared from the methylcyclohexane solution, was the helical structure (although in part) observed.

UR - http://www.scopus.com/inward/record.url?scp=0347651203&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0347651203&partnerID=8YFLogxK

M3 - Article

SP - 2585

EP - 2591

JO - Journal of the Chemical Society, Perkin Transactions 2

JF - Journal of the Chemical Society, Perkin Transactions 2

SN - 1470-1820

IS - 12

ER -