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Issue 15, 2003
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Binary organogelators which show light and temperature responsiveness

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The gelation ability of 10 alkylammonium (CnH2n + 1NH3+ where n = 4–11, 12 and 16) anthracene-9-carboxylates (1n) has been evaluated. In cyclohexane, 14, 15, 16 and 17 only provided precipitates whereas 111, 112 and 116 provided very viscous solutions. In contrast, 18, 19 and 110 resulted in gels. The critical gelation concentration of 110 was very low (5.0 × 10−4 mol dm−3). SEM observations showed that in the gel phase the morphology changes from straight fibrils to frizzy fibrils with the increase in n, whereas in the sol phase the formation of the sheet-like, two-dimensional aggregate is recognized. When the cyclohexane 110 gel was photoirradiated (λ > 300 nm), the UV-VIS absorption bands assignable to monomeric anthracene were decreased and the gel was changed into the sol. It was confirmed by dark-field optical microscopy that the fibrillar bundles supporting the gel formation gradually disappear with photoirradiation time. When this sol was warmed at 30 °C in the dark, the gel was not regenerated but the precipitation of 110 resulted. When this sol was heated once at the bp of cyclohexane and cooled to 15 °C, the solution was changed into the gel again. This finding indicates that the fibrillar structure required for the gel formation is not reconstructed at 30 °C but obtained only when the hot cyclohexane solution is cooled.

Graphical abstract: Binary organogelators which show light and temperature responsiveness

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Publication details

The article was received on 22 Apr 2003, accepted on 16 Jun 2003 and first published on 30 Jun 2003

Article type: Paper
DOI: 10.1039/B304224C
Org. Biomol. Chem., 2003,1, 2744-2747

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    Binary organogelators which show light and temperature responsiveness

    M. Ayabe, T. Kishida, N. Fujita, K. Sada and S. Shinkai, Org. Biomol. Chem., 2003, 1, 2744
    DOI: 10.1039/B304224C

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