Abstract
The receptor, 1,8-oxybis(ethyleneethoxyethyleneethoxy)-9-(phenylazo)-10-anthraquinone, (1) shows a visible colorimetric and emission response to tetrabutylammonium hydroxide (TBA-OH) in acetonitrile. The selectivity of 1 toward various monovalent anions is investigated by UV-Vis and luminescence experiments using micromolar (μM) solutions of 1. The experimental results revealed that the receptor (1) underwent an irreversible chemical change (a chemodosimeter) with hydroxide ion (OH−), and this phenomenon is signaled by the development of a vivid color change and an intense fluorescent green emission. Compound 1 showed a roughly 200-fold enhancement in emission with high sensitivity and selectivity with long-lived luminescence and impressive stability. A reaction of the receptor 1 with an excess of TBA-OH on the milligram scale was performed for a better understanding of the reaction mechanism, which led to the isolation of compounds 1,8-oxybis(ethyleneethoxyethyleneethoxy)-9-(2-methylene-nitrile)-10-anthraquinone (2) and 1,8-oxybis(ethyleneethoxyethyleneethoxy)-9-(N-sodiumphenylazo)-10-anthraquinone (3). Emission of 3 in solution is attributed to anthracenol-diazo fluorophore moiety. NMR and X-ray diffraction studies support the formation of compounds 2 and 3.
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