Abstract
Nonclassical protomeric tautomerism in Schiff bases have the advantage of controlling and differentiating specific interactions in the −C═N– linkage since its interactions are not governed by keto–enol tautomerism. Here, we report about the optical properties of a Schiff base probe (P1). X-ray structure analysis evidenced the existence of an intramolecular hydrogen bond which is responsible of a photochromic-fluorescent behavior. The properties of P1 were investigated by UV–vis and fluorescence spectroscopy in solution and solid state. A positive solvatochromism resulting from specific interactions taking place in P1 was studied by three different solvent scales, namely Lippert–Mataga, Kamlet–Taft, and Catalan, finding consistent results. Moreover, a strong acidochromic behavior was detected and the pKa and pKa* values were determined, finding a photobasic character. Further, an ionochromic behavior was stablished. P1 exhibits a λ-ratiometric fluorescence response toward Sn(IV) giving a luminescence color...
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