Synthesis, fluorescence and nmr spectroscopic studies of a novel phosphinoxido-18-crown-6 ether containing an anthracene fluorophore unit

Hajnalka Szabó-Szentjóbi, Anna Márton, Dávid Pál, Gergő Dargó, Áron Szigetvári, Csaba Szántay, György Tibor Balogh, Tünde Tóth, Péter Huszthy

Research output: Contribution to journalArticle

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}, and31P{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.

Original languageEnglish
Pages (from-to)37-45
Number of pages9
JournalPeriodica Polytechnica Chemical Engineering
Volume64
Issue number1
DOIs
Publication statusPublished - Jan 1 2020

Keywords

  • Crown ethers
  • Enantiomeric recognition
  • Fluorescence spectroscopy
  • Sensor molecules

ASJC Scopus subject areas

  • Chemical Engineering(all)

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