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Issue 5, 2003
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Proton-sensitive fluorescent organogels

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Abstract

A 1,10-phenanthroline-appended cholesterol-based gelator (1) and its nongelling reference compound (2) were synthesized. Among 19 solvents tested herein, gelator 1 could gelate 11 solvents including alcohols, dipolar aprotic solvents, organic acids and a base (triethylamine), indicating that 1 acts as a versatile gelator. The TEM observation gave a visual image showing that fibrillar aggregates are entangled in the three-dimensional network structure. In the fluorescence measurements, most gels afforded an emission maximum at 394 nm (purple emission), whereas only the acetic acid gel afforded an emission maximum at 522 nm (yellow emission). Thus, the influence of protonation of the 1,10-phenanthroline nitrogens (by trifluoroacetic acid) on the fluorescence properties in the gel phase was investigated in detail. The results have established that the fluorescence intensity of 1·H+ becomes particularly strong in the gel phase, presumably because of the energy transfer from neutral 1* to protonated 1·H+ and the restriction of the 1·H+ molecular motion. The finding suggests the possibility that the gel system would be useful not only as a new proton-sensitive fluorescence system but also as a new medium for designing efficient energy transfer systems.

Graphical abstract: Proton-sensitive fluorescent organogels

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Publication details

The article was received on 08 Nov 2002, accepted on 15 Jan 2003 and first published on 11 Feb 2003


Article type: Paper
DOI: 10.1039/B210968A
Org. Biomol. Chem., 2003,1, 895-899

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    Proton-sensitive fluorescent organogels

    K. Sugiyasu, N. Fujita, M. Takeuchi, S. Yamada and S. Shinkai, Org. Biomol. Chem., 2003, 1, 895
    DOI: 10.1039/B210968A

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