Click synthesis of a quinoline-functionalized hexahomotrioxacalix[3]arene: A turn-on fluorescence chemosensor for Fe3+

•A quinoline-functionalized hexahomotrioxacalix[3]arene L was synthesized via Click chemistry.•Chemosensor L exhibited a favourable selectivity for Fe3+ ions with a 'turn on' fluorescence emission.•The binding behaviour between sensor L and Fe3+ has been confirmed by 1H NMR spectroscopic titration experiments.•The role of the calixarene platform has been addressed by making a non-calixarene-based analogue.

A novel quinoline-functionalized hexahomotrioxacalix[3]arene L was synthesized via Click chemistry and its chemosensing properties with various metal ions were investigated. The chemosensor L exhibited a high selectivity for Fe3+ with little interference from other environmentally and biologically relevant metal ions, leading to a prominent 'off-on' type fluorescent signalling behaviour. Our studies demonstrated that the detection limit on fluorescence response of the sensor to Fe3+ is in the 10−7 M range. The mechanism of the interaction between the L and Fe3+ has been investigated in detail by 1H NMR spectroscopic titration experiments.

Graphical abstractA novel quinoline-functionalized hexahomotrioxacalix[3]arene L was synthesized via Click chemistry, which was found to be a selective fluorescence turn on chemosensor for Fe3+ with little interference from the other metal ions studied.Download high-res image (170KB)Download full-size image