Synthesis and Complexation Studies of Optically Active Aza- and Diazacrown Ethers Containing a Pyrene Fluorophore Unit

  • Dávid Pál Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, P.O.B. 91, H-1521 Budapest, Hungary https://orcid.org/0000-0003-3573-0233
  • Martin Gede Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, P.O.B. 91, H-1521 Budapest, Hungary
  • Ildikó Móczár Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, P.O.B. 91, H-1521 Budapest, Hungary https://orcid.org/0000-0002-1968-6925
  • Péter Baranyai Department of Applied and Nonlinear Optics, Institute of Solid State Physics and Optics, Wigner Research Center for Physics, Hungarian Academy of Sciences, P.O.B. 49, H-1525 Budapest, Hungary https://orcid.org/0000-0003-1499-0925
  • Péter Bagi Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, P.O.B. 91, H-1521 Budapest, Hungary https://orcid.org/0000-0002-9043-6435
  • Péter Huszthy Department of Organic Chemistry and Technology, Faculty of Chemical Technology and Biotechnology, Budapest University of Technology and Economics, P.O.B. 91, H-1521 Budapest, Hungary https://orcid.org/0000-0001-7305-3312

Abstract

Novel enantiopure azacrown [(R,R)-1 and (S,S)-1] and diazacrown [(R,R)-2–(R,R)-4 and (S,S)-2–(S,S)-4] ethers containing a pyrene fluorophore unit and two phenyl groups at their chiral centers were obtained in multistep syntheses. The action of these chemosensors is based on the photoinduced electron transfer (PET) process, thus they show fluorescence enhancement in the presence of protonated primary amines and amino acid esters. Their recognition abilities toward the enantiomers of 1-phenylethylamine hydrogen perchlorate (PEA), 1-(1-naphthyl) ethylamine hydrogen perchlorate (NEA), phenylglycine methyl ester hydrogen perchlorate (PGME), and phenylalanine methyl ester hydrogen perchlorate (PAME) were examined in acetonitrile using fluorescence spectroscopy.

Keywords: molecular recognition, fluorescence, PET sensor, azacrown ether, chiral crown ether
Published online
2019-10-21
How to Cite
Pál, D., Gede, M., Móczár, I., Baranyai, P., Bagi, P. and Huszthy, P. (2020) “Synthesis and Complexation Studies of Optically Active Aza- and Diazacrown Ethers Containing a Pyrene Fluorophore Unit”, Periodica Polytechnica Chemical Engineering, 64(1), pp. 20-36. doi: https://doi.org/10.3311/PPch.14467.
Section
Articles