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Systematic Design of Amide- and Urea-Type Gelators with Tailored Properties

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Low Molecular Mass Gelator

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 256))

Abstract

The formation of gels by structurally highly diverse low molecular weight organic molecules is paradigmatically a supramolecular phenomenon. It is based on the self-assembly of certain organic molecules and involves highly specific noncovalent intermolecular interactions, in particular those inducing predominantly unidirectional aggregation. In this chapter, the design of low molecular weight gelators that incorporate single or multiple amide units as intermolecular hydrogen-bonding functionalities and methods of their preparation are given. Many efficient gelators of organic solvents and water could be prepared by the structural combination of amidic, carbamate, urea, or oxalamide groups and long aliphatic chains or aromatic groups with a large surface. The numerous potential applications in slow drug-delivery systems, the fabrication of templated materials, and in sensing devices are also discussed.

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Abbreviations

AFM:

Atomic force microscopy

BuOH:

Butanol

Boc:

Butoxycarbonyl

CD:

Circular dichroism

DCC:

N,N-Dicyclohexylcarbodiimide

DMAP:

4-(Dimethylamino)pyridine

DMF:

Dimethylformamide

DMSO:

Dimethyl sulfoxide

EtOH:

Ethanol

FTIR:

Fourier-transform infrared spectroscopy

MeOH:

Methanol

mgc:

Minimal gelation concentration

NMR:

Nuclear magnetic resonance

SEM:

Scanning electron microscopy

T gel :

Gel melting temperature

TEM:

Transmission electron microscopy

TFA:

Trifluoroacetic acid

THF:

Tetrahydrofuran

UV:

Ultraviolet

vol:

Volume

wt:

Weight

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Authors and Affiliations

  1. Faculté des Sciences de Luminy, Université de la Méditerranée, Case 901, 13288, Marseille Cedex 9, France

    Frédéric Fages

  2. Kekulé-Institute für Organische Chemie und Biochemie, Universität Bonn, Gehard-Domagk-Str. 1, 53121, Bonn, Germany

    Fritz Vögtle

  3. Rudjer Boskovic Institute, P.O.B. 180, 10002, Zagreb, Croatia

    Mladen Žinic

Authors
  1. Frédéric Fages
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  2. Fritz Vögtle
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  3. Mladen Žinic
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Correspondence to Mladen Žinic .

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Fages, F., Vögtle, F., Žinic, M. (2005). Systematic Design of Amide- and Urea-Type Gelators with Tailored Properties. In: Low Molecular Mass Gelator. Topics in Current Chemistry, vol 256. Springer, Berlin, Heidelberg. https://doi.org/10.1007/b107172

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