A simple and colorimetric fluoride receptor and its fluoride-responsive organogel

In this paper, a new p-nitrophenylhydrozine-based anion receptor 1 containing cholesterol group had been designed and synthesized. It could selectively recognize fluoride among different anions tested with color changes from pale yellow to red for visual detection. Simultaneously, it could gel in cyclohexane, and the gel was also fluoride-responsive. When treated with TBAF (tetra-n-butylammonium fluoride), the gel could undergo gel-sol transition accompanied by color, morphology and surface changes. The binding mechanism had been investigated by UV-vis and (1)HNMR (proton nuclear magnetic resonance spectra) titrations. From SEM (scanning electron microscope), SAXS (small-angle X-ray scattering), IR (Infrared Spectroscopy) and CA (contact angle) experiments, it was indicated that the addition of F(-) could destroy the molecule assembly of host 1 in the gel state, thus resulting in the gel-to-sol transition due to the binding site competition effect. To the best of our knowledge, this was the simplest fluoride-responsive organogel with high selectivity.