The recognition of both mono- and dicarboxylic acids by a large number of receptors of different architectures is known. In relation to this, imidazole as a binding motif is less explored in carboxylic acid recognition. To explore the imidazole receptor further, we have synthesized a series of anthracene-based imidazole receptors for aromatic carboxylic acids sensing. Anthracene appended imidazole sensors (1, 2  ) have been synthesized for the sensing of salicylic acid (SA) derivatives. The preorganizition of sensors allowed three-point binding with SA through multiple hydrogen-bonding interaction with amino N-H group as well as F-F interaction with anthracene The sensing ability of 1  toward various SA derivatives has been examined by UV-vis and fluorescence spectroscopy. The sensing of SA derivatives resulted in significant monomer emission. Sensor 1  showed the highest binding constant with 3,5-dinitrosalicylic acid among all the tested SA derivatives.

Selective fluorescence sensing of salicylic acid by a cooperative F-F and hydrogen bond interactions

248th National Meeting (2014)

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