Pyridinium N-phenoxide betaines and their application to the determination of solvent polarities, XXIV. Syntheses and UV-vis spectroscopic properties of new lipophilic tert-butyl- and 1-adamantyl substituted, negatively solvatochromic pyridinium N-phenolate betaine dyes

Abstract

Syntheses and negative solvatochromism of two new lipophilic pentaphenyl pyridinium N-phenolate betaine dyes, substituted with seven tert-butyl groups (9) or with three tert-butyl and two 1-adamantyl groups (13) in the peripheral phenyl rings, are described in order to get zwitterionic dyes that are more soluble in nonpolar solvents such as the standard betaine dye, 1, which has been used for the construction of an empirical scale of solvent polarity, called the ET(30) scale.Key words: betaine dyes, ET(30) values, lipophilic dyes, pyridinium N-phenolate betaine dyes, solvatochromism, solvent polarity.