Larger Groups, Smaller Enantioselectivity? Two Anthracene-Containing, Pyridino-Crown Ether-Based Fluorescent Sensor Molecules

Authors

  • Balázs Szemenyei
    Affiliation
    Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111 Budapest, Hungary
  • Marianna Firisz
    Affiliation
    Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111 Budapest, Hungary
  • Péter Baranyai
    Affiliation
    Wigner Research Centre for Physics, Eötvös Loránd Research Network, Konkoly-Thege Miklós út 29–33., H-1121 Budapest, Hungary
  • Péter Bagi
    Affiliation
    Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111 Budapest, Hungary
  • László Drahos
    Affiliation
    Institute of Organic Chemistry, Research Centre for Natural Sciences, Eötvös Loránd Research Network, Magyar tudósok körútja 2., H-1117 Budapest, Hungary
  • Ildikó Móczár
    Affiliation
    Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111 Budapest, Hungary
  • Péter Huszthy
    Affiliation
    Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111 Budapest, Hungary
https://doi.org/10.3311/PPch.20468

Abstract

(R,R)- and (S,S)-enantiomers of anthracene-containing pyridino-18-crown-6 ether having tert-butyl groups at the stereogenic centers were prepared with the aim of achieving higher enantioselectivity than for the reported (S,S)-analogue having isobutyl groups. The enantiomeric recognition abilities of the new sensor molecules toward chiral protonated primary amines and amino acid esters were studied in acetonitrile by UV–vis and fluorescence spectroscopies. The pKa values of these pyridino-crown ethers and their reported (S,S)-analogues having methyl or isobutyl groups have also been determined in acetonitrile.

Keywords:

anthracene, crown ether, enantiomeric discrimination, fluorescence spectroscopy, Suzuki–Miyaura coupling

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Published Online

2022-10-03

How to Cite

Szemenyei, B., Firisz, M., Baranyai, P., Bagi, P., Drahos, L., Móczár, I. “Larger Groups, Smaller Enantioselectivity? Two Anthracene-Containing, Pyridino-Crown Ether-Based Fluorescent Sensor Molecules”, Periodica Polytechnica Chemical Engineering, 66(4), pp. 541–549, 2022. https://doi.org/10.3311/PPch.20468

Issue

Vol. 66 No. 4 (2022)

Section

Articles