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Pure Appl. Chem., 2004, Vol. 76, No. 10, pp. 1903-1919

Pyridinium N-phenolate betaine dyes as empirical indicators of solvent polarity: Some new findings

C. Reichardt

Department of Chemistry, Philipps University, Hans-Meerwein-Strasse, D-35032 Marburg, Germany

Abstract: Solutions of the zwitterionic betaine dye 4-(2,4,6-triphenylpyridinium-1-yl)-2,6-di- phenylphenolate are solvatochromic, thermochromic, piezochromic, and halochromic. That means the position of its longest-wavelength intramolecular charge-transfer absorption band depends on solvent polarity, solution temperature, external pressure, and the nature and concentration of added salts. The extraordinarily large negative solvatochromism of this standard betaine dye has been used to establish UV/vis spectroscopically an empirical scale of solvent polarity, called ET(30), respectively ETN scale, meanwhile known for many organic solvents and solvent mixtures. In this review, the solvatochromic properties of some new hydrophilic and lipophilic betaine dyes with better solubility in water (respectively, nonpolar solvents), as well as some recent applications of these betaine dyes in various fields of interest [e.g., microheterogeneous (micellar) and polymer solutions, chemical sensors, as well as surface polarity of silicas, aluminas, and cellulose derivatives] are described.