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Issue 9, 2008
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Photoresponsive dithienylethene-urea-based organogels with “reversed” behavior

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Abstract

Dithienylperhydrocyclopentene-bisurea-based low molecular weight gelators are described that function as photoresponsive organogels that show a remarkable gel-to-liquid transition upon irradiation. The two series of derivatives, with and without alkyl spacers between the urea hydrogen bonding groups and the photochromic unit, show different gelation behavior. Upon UV irradiation of the gels, a gel liquified at only 1.4% conversion of the photochromic unit. Transmission electron microscopy (TEM) shows that the gel fibres consist of thin ribbons. Semi-empirical (PM3) calculations indicate that the hydrogen bonding between the open-ring isomer (o) molecules is weak, and that formation of the closed-ring isomer (c) destabilises the hydrogen bonding further. The results indicate that a small amount of the closed-ring isomer will disrupt the intermolecular hydrogen-bonding, leading to disintegration of the gel fibre ribbons and hence reversible liquification.

Graphical abstract: Photoresponsive dithienylethene-urea-based organogels with “reversed” behavior

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Supplementary files

Article information


Submitted
14 Feb 2008
Accepted
19 Mar 2008
First published
01 Apr 2008

Org. Biomol. Chem., 2008,6, 1544-1547
Article type
Communication

Photoresponsive dithienylethene-urea-based organogels with “reversed” behavior

M. Akazawa, K. Uchida, J. J. D. de Jong, J. Areephong, M. Stuart, G. Caroli, W. R. Browne and B. L. Feringa, Org. Biomol. Chem., 2008, 6, 1544
DOI: 10.1039/B802580K

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