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Binary organogelators which show light and temperature responsiveness.

Masatsugu Ayabe1, Takanori Kishida, Norifumi Fujita

  • 1Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, 6-10-1 Hakozaki, Higashi-ku, Fukuoka, 812-8581, Japan.

Organic & Biomolecular Chemistry
|September 2, 2003
PubMed
Summary

Alkylammonium anthracene-9-carboxylates can form gels in cyclohexane, with specific chain lengths showing optimal gelation. Photoirradiation disrupts the gel structure, preventing regeneration at lower temperatures but allowing it upon cooling from boiling point.

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Organic Chemistry

Background:

  • Alkylammonium anthracene-9-carboxylates are a class of compounds with potential self-assembly properties.
  • Understanding the factors influencing gelation is crucial for developing novel soft materials.

Purpose of the Study:

  • To evaluate the gelation ability of a series of alkylammonium anthracene-9-carboxylates in cyclohexane.
  • To investigate the effect of alkyl chain length on gel formation and morphology.
  • To explore the stimuli-responsive behavior of the formed gels.

Main Methods:

  • Synthesis and characterization of alkylammonium anthracene-9-carboxylates.
  • Gelation studies in cyclohexane at varying concentrations.
  • Scanning Electron Microscopy (SEM) for morphological analysis.

Related Experiment Videos

  • UV-VIS spectroscopy and dark-field optical microscopy to monitor photoirradiation effects.

    • Main Results:

    • Compounds with alkyl chain lengths n=8, 9, and 10 exhibited significant gelation in cyclohexane, with 1(10) showing a low critical gelation concentration.
    • SEM revealed a transition in fibril morphology from straight to frizzy with increasing alkyl chain length in the gel phase.
    • Photoirradiation (λ > 300 nm) of the 1(10) gel led to its transformation into a sol, evidenced by decreased anthracene absorption and disappearance of fibrillar structures.
    • The gel was not regenerated upon warming the sol to 30°C but could be reformed by heating to the boiling point of cyclohexane and cooling.

    Conclusions:

    • The gelation ability of alkylammonium anthracene-9-carboxylates is strongly dependent on the alkyl chain length.
    • Photoirradiation triggers a reversible solation process by disrupting the self-assembled fibrillar network.
    • The thermal reversibility of gel formation is dependent on the cooling process from a sufficiently high temperature, indicating a specific pathway for fibril reconstruction.