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  • Title: Synthesis, recognition and sensing properties of dipyrrolylmethane-based anion receptors.
    Author: Zhou Y, Bao X.
    Journal: Spectrochim Acta A Mol Biomol Spectrosc; 2019 Mar 05; 210():1-8. PubMed ID: 30415108.
    Abstract:
    Two tweezer-like anion receptors 2,2'‑bis(2‑cyano‑2‑phenylvinyl)‑5,5'‑dimethyl dipyrromethane (1) and 2,2'‑bis[2‑cyano‑2‑(4‑nitrophenyl)vinyl]‑5,5'‑dimethyl dipyrromethane (2) were synthesized in good yields, via a facile condensation of diformyldipyrromethane and the appropriate phenylacetonitrile. Anion recognition properties of these receptors were studied in detail in DMSO solution, by means of UV-vis and 1H NMR titration techniques. The obtained results indicated that receptor 2 containing a terminal nitro group exhibited the strong and selective binding to biologically important fluoride and dihydrogenphosphate ions over other anions. In addition, the binding strength of receptor 2 with fluoride was enhanced by a factor of 18, relative to receptor 1 lacking the nitro group. Remarkably, the presence or absence of nitro group within receptor compounds also had a great influence on the anion-binding selectivity. In particular, a distinct color change of DMSO solution of receptor 2 was observed only upon addition of fluoride, showing the potential of 2 acting as an effective colorimetric sensor for the detection of fluoride anion.
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