The reaction of sodium cyanate with benzo­[b]­quinolizinium substrates at room temperature gave 3-hydroxy-4-pyridyl-isoquinoline derivatives in good yields. Presumably, the overall reaction proceeds through an ANRORC-type sequence, that is, addition of the nucleophile, ring opening, and ring closure. Preliminary photophysical investigation of the parent compound revealed a pronounced sensitivity of its emission properties toward solvent effects and the pH of the medium.

The suitability of 3-hydroxy-4-pyridylisoquinoline to operate as fluorescent chemosensor for the detection of metal ions was investigated. For that purpose, the interactions of the title compound with selected metal ions were investigated by absorption and emission spectroscopy. The complexation of Zn2+, Fe2+, Mg2+ with 1:1 and 2:1 stoichiometry leads to characteristic optical responses that depend significantly on the employed solvents, thus allowing for the fluorimetric identification and detection of particular metal cations in a matrix-based pattern analysis or by fluorimetric titrations. Graphical abstract