Abstract
A naphthopyran derivative 3, 3-diphenyl-3H-benzo[f]chromen-5-ol having a suitably positioned hydroxyl group has been synthesized via condensation of naphthalene-2,3-diol with 1,1-diphenylprop-2-yn-1-ol. The naphthopyran derivative has been characterized by various techniques such as NMR, IR, HRMS, and single-crystal X-ray crystallography. The intermolecular short contacts have been quantitatively investigated. The suitably positioned OH group allowed complexation of metal ions with an optical signal. The screening of metal ions with naphthopyran derivative led to selective and sensitive binding of Cu2+ ions with a perceptible color change (colorless to light yellow). The metal binding by naphthopyran derivative was analyzed by using UV-vis spectrophotometry. The detection was also accomplished using digital colorimetry based on a paper-based device and solution method. Furthermore, calculations based on density functional theory were performed to inspect the formation of a complex and find a suitable complex geometry. The time-dependent theory was also used to compare the observed changes in the absorption spectra for a solution containing naphthopyran derivative and copper ions with the calculated excitation parameter, which provided further evidence of complex formation.
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