Synthesis, Fluorescence and NMR Spectroscopic Studies of a Novel Phosphinoxido-18-crown-6 Ether Containing an Anthracene Fluorophore Unit

Authors

  • Hajnalka Szabó-Szentjóbi
    Affiliation

    Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, H-1521 Budapest, P.O.B. 91, Hungary

  • Anna Márton
    Affiliation

    Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, H-1521 Budapest, P.O.B. 91, Hungary

  • Dávid Pál
    Affiliation

    Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, H-1521 Budapest, P.O.B. 91, Hungary

  • Gergő Dargó
    Affiliation

    Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, H-1521 Budapest, P.O.B. 91, Hungary; Chemistry Department, Gedeon Richter Plc., H-1103 Budapest, Gyömrői út 19-21, Hungary

  • Áron Szigetvári
    Affiliation

    Spectroscopic Research Department, Gedeon Richter Plc., H-1475 Budapest, P.O.B. 27, Hungary

  • Csaba Szántay
    Affiliation

    Spectroscopic Research Department, Gedeon Richter Plc., H-1475 Budapest, P.O.B. 27, Hungary

  • György Tibor Balogh
    Affiliation

    Chemistry Department, Gedeon Richter Plc., H-1103 Budapest, Gyömrői út 19-21, Hungary

  • Tünde Tóth
    Affiliation

    Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, H-1521 Budapest, P.O.B. 91, Hungary; Institute for Energy Security and Environmental Safety, Centre for Energy Research, Hungarian Academy of Sciences, H-1525 Budapest, P.O.B. 49, Hungary

  • Péter Huszthy
    Affiliation

    Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, H-1521 Budapest, P.O.B. 91, Hungary

https://doi.org/10.3311/PPch.14646

Abstract

The synthesis of the (R,R) and (S,S) enantiomers of a new enantiopure monophospha-18-crown-6 ether (1), which contains an anthracene fluorophore unit and methyl groups at its stereogenic centers, was accomplished. The structure of one enantiomer ((S,S)-1) was studied using one-dimensional (1H, 13C{1H}, and 31P{1H}) and two-dimensional NMR spectra. Because (R,R)-1 and (S,S)-1 can act as new fluorescent chemosensors, we examined their enantiomeric differentiation abilities toward the enantiomers of protonated chiral primary amines and amino acid esters (PEA, 1-NEA, PGME, PAME) using UV-Vis and fluorescence spectroscopies. These monophospha-crown ethers showed moderate enantiomeric discrimination abilities.

Keywords:

crown ethers, fluorescence spectroscopy, sensor molecules, enantiomeric recognition

Published Online

2019-10-17

How to Cite

Szabó-Szentjóbi, H., Márton, A., Pál, D., Dargó, G., Szigetvári, Áron, Szántay, C. “Synthesis, Fluorescence and NMR Spectroscopic Studies of a Novel Phosphinoxido-18-crown-6 Ether Containing an Anthracene Fluorophore Unit”, Periodica Polytechnica Chemical Engineering, 64(1), pp. 37–45, 2020. https://doi.org/10.3311/PPch.14646

Issue

Vol. 64 No. 1 (2020)

Section

Articles