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Preparation and absorption spectral property of a multifunctional water-soluble azo compound with D-π-A structure, 4-(4-hydroxy-1-naphthylazo)benzoic acid

Journal of Applied Spectroscopy, ISSN: 0021-9037, Vol: 82, Issue: 3, Page: 445-449
2015
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A multifunctional water-soluble azo dye with the D-n-A conjugated structure, 4-(4-hydroxy-1-naphthylazo)benzoic acid (HNBA), was designed and synthesized using 1-naphanol as the electron donator, benzoic acid as the electron acceptor, and —N=N— as the bridging group. After its structure was characterized by FTIR, 1H NMR, and element analysis, the UV-Vis absorption spectral performance of the target dye was studied in detail. The results showed that the dye, combining hydroxyl group, azo group, and carboxyl group, possessed excellent absorption spectral properties (e = 1.2-104 lmol 1 cm 1) changing with pH and solvents. In particular, in polar andprotonic water, it had excellent optical response to some metal ions, i.e., Fe and Pb, which might make it a latent colorimetric sensor for detecting heavy metal ions.

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