Coumarinyl(pyrrolyl)ethenes for the detection of Pd2+, CN− and F− ions, test strips based on them and logic gates

Abstract

New coumarinyl(pyrrolyl)ethenes with a 1,3-thiazole bridge were synthesized. When irradiated at 365 nm, a hexatriene-cyclohexadiene rearrangement of the ring-opened form into a colored non-fluorescent ring-closed isomer occurs. The back reaction takes place when exposed to visible light at 540 nm. Furthermore, the compound with terminal 2,4-di-tert-butyl-6-hydroxybenzylidene receptor group represents a multifunctional sensor exhibiting selective chromogenic activity towards palladium(II) ions and CN− and F− anions. This probe interacts with Pd2+ cations with a noticeable naked eye effect - a change in the solution color from yellow to orange. The complexation stoichiometry is 1:1 and the detection limit was found to be 4.5 × 10−7 mol L−1. Similarly, CN− and F− anions cause a contrast naked eye effect with a change in the color of the solution from yellow to rose-red. For convenient detection of the above ions, test strips containing 4-(2-(2-(2,4-di-tert-butyl-6-hydroxybenzylidene)hydrazinyl)-5-(2-oxo-2H-chromen-3-yl)thiazol-4-yl)-1,5-dimethyl-1H-pyrrole-2-carbonitrile have been developed. In addition, a combinatorial molecular logic gate was designed based on multi-controllable photoswitching properties of the obtained probe.