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Issue 9, 2013
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Spiropyran–cholesterol conjugate as a photoresponsive organogelator

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Abstract

We synthesized a spiropyran–cholesterol conjugate (1) and studied its gelation and photochromic properties. The compound 1, when dissolved in carbon disulfide (CS2), forms a homogeneous gel at −40 °C due to the van der Waals interaction between the cholesterol moieties. UV or visible light irradiation of the CS2 sol or gel promotes a reversible change in color between yellow and purple without phase transition. This is promoted by reversible photoisomerization of the spiropyran moiety between the spirocyclic (SP) and the spirocycle-opened merocyanine (MC) form. In contrast, 1 forms a gel in benzyl alcohol (BA) at room temperature. The BA gel also exhibits a reversible color change upon UV/visible light irradiation, but the BA sol always shows a purple color due to the stabilization of the MC form by strong H-bonding interaction with solvents. The BA gel is successfully applied as a material for information storage, easily writable and erasable by light irradiation.

Graphical abstract: Spiropyran–cholesterol conjugate as a photoresponsive organogelator

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Publication details

The article was received on 27 Mar 2013, accepted on 04 Jun 2013 and first published on 04 Jun 2013


Article type: Paper
DOI: 10.1039/C3NJ00322A
Citation: New J. Chem., 2013,37, 2642-2647

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    Spiropyran–cholesterol conjugate as a photoresponsive organogelator

    S. Sumiya, Y. Shiraishi and T. Hirai, New J. Chem., 2013, 37, 2642
    DOI: 10.1039/C3NJ00322A

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