9-N-Alkylaminomethylanthracenes (1 and 2) were synthesised for halophenol sensing, and their selectivity and sensitivity towards pentafluorophenol (PFP) in ethanol were investigated. Probe 1 exhibited a good selectivity and sensitivity for PFP with a high association constant (4.35 × 105 M−1) without any interference from other halophenols. The relatively high selectivity and sensitivity of probe 1 are caused by strong intermolecular hydrogen bonding interactions. The interaction of PFP with probes 1 and 2 was analysed through UV-Vis, fluorescence, and 1H NMR spectroscopy, and was further supported by DFT calculations. The limit of detection for PFP was 2 μM in ethanol using probe 1.
