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Molecules 2007, 12(7), 1316-1324; doi:10.3390/12071316

Design and Synthesis of a Coumarin-based Acidichromic Colorant

,  and *
Department of Chemistry and Center for Nanoscience and Technology, Tunghai University, 181, Taichung-Kang Rd. Sec.3, Taichung, Taiwan 407
* Author to whom correspondence should be addressed.
Received: 6 June 2007 / Revised: 1 July 2007 / Accepted: 1 July 2007 / Published: 6 July 2007
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This paper describes the fine-tuning of the acidichromic properties of a coumarin-containing colorant 1 by incorporation of electron-donating and electron-withdrawing substituents on the coumarin moiety. Colorant 1 can undergo two distinct and reversible color changes under both strongly acidic and basic conditions, but not in the presence of gaseous ammonia. The results indicated that the bromo-substituted compound 5b changes from red to yellow when exposed to gaseous ammonia, both in solution and on polycarbonate film, suggesting that an electron-withdrawing group at the 7-position of the coumarin moiety made the enolic hydrogen on 5b more susceptible to deprotonation by a base than in the unsubstituted compound 1.
Keywords: Coumarin; triketone; acidichromism; gas sensor; acid-base sensor Coumarin; triketone; acidichromism; gas sensor; acid-base sensor
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Lin, S.-L.; Kuo, P.-Y.; Yang, D.-Y. Design and Synthesis of a Coumarin-based Acidichromic Colorant. Molecules 2007, 12, 1316-1324.

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