Synthesis, acidity and 19F NMR characteristics of imidazoles bearing 1-fluorinated substituents with potential application as probes for intracellular pH determination.

Article abstract of DOI:10.1016/S0040-4020(97)00487-0

A series of 1-substituted imidazoles containing fluorine have been prepared. These compounds were identified as potentially useful probes for intracellular pH determination based on ¹⁹F NMR. Key parameters including pK(a), ¹⁹F NMR chemical shift sensitivity, water solubility and low toxicity were identified and included in the target molecule selection process. The pK(a) and ¹⁹F NMR parameters of the molecules are reported and trends analysed.