A new calix[4]azacrown ether based boradiazaindacene (Bodipy): Selective fluorescence changes towards trivalent lanthanide ions

•Calix[4]azacrown ether based boradiazaindacene (Bodipy) were synthesized.•The spectroscopic data indicated that the new compound was in the cone conformation.•Spectrofluorometric studies of both ligand and lanthanide ions were carried out.•Lanthanides recognition ability of calix[4]azacrown were investigated.

We report on the synthesis and photophysical properties of a new calix[4]azacrown derivative, capped with two amide bridges, in the cone conformation bearing two boradiazaindacene (Bodipy) groups at the narrow rim. Its binding properties towards trivalent lanthanide ions such as La3+, Gd3+, Tb3+, Dy3+, Er3+ and Yb3+ were investigated by using spectroscopic techniques. With respect to fluorescence intensity changes upon trivalent lanthanide ion complexation, calix[4]azacrown ether based Bodipy showed higher selectivity towards Yb3+ ion over other ions. Presence of proximal two amide groups in calix[4]azacrown ether based Bodipy were observed to play an important role in exhibiting its lanthanide ion binding.

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