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Novel N-acylaminovinyl ketones of the benzo[b]thiophene series (AAB) capable of molecular switching of fluorescence or complexation with metal ions have been synthesized and their photochromic behavior studied using UV-Vis absorption/emission and 1 H- / 7 Li- NMR spectroscopy. Under UV irradiation the AAB compounds 2a–c containing fluorescent labels as their N-aryl substituents undergo Z/E- photo-isomerization and N→O acyl rearrangement resulting in the formation of O-acyl isomers 3a–c. The photo-switching of fluorescence has been found in the 4-fluorenonyl derivative 2a. The benzo-15-crown-5- containing AAB 2d,e are also susceptible to the same type of photo-initiated rearrangement. The corresponding O-acyl isomers 3d–e represent a group of chemosensors which readily form stable complexes with alkali- and alkali-earth- metal cations. The AAB 2d exhibits specific selectivity for Li + ion in the presence of Na + , K + and Cs + .

Photochromic 2-(N-acyl-N-arylaminomethylene)benzo[b]thiophene-3(2H)-ones with fluorescent labels and/or crown-ether receptors