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

  • Hajnalka Szabó-Szentjóbi 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 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 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 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 Spectroscopic Research Department, Gedeon Richter Plc., H-1475 Budapest, P.O.B. 27, Hungary
  • Csaba Szántay Spectroscopic Research Department, Gedeon Richter Plc., H-1475 Budapest, P.O.B. 27, Hungary
  • György Tibor Balogh Chemistry Department, Gedeon Richter Plc., H-1103 Budapest, Gyömrői út 19-21, Hungary
  • Tünde Tóth 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 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

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., Balogh, G., Tóth, T. and Huszthy, P. (2020) “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. doi: https://doi.org/10.3311/PPch.14646.
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Articles