Synthesis and complexation studies of optically active aza-and diazacrown ethers containing a pyrene fluorophore unit

Dávid Pál; Martin Gede; Ildikó Móczár; Péter Baranyai; Péter Bagi; Péter Huszthy

doi:10.3311/PPch.14467

Synthesis and complexation studies of optically active aza-and diazacrown ethers containing a pyrene fluorophore unit

Dávid Pál, Martin Gede, Ildikó Móczár, Péter Baranyai, Péter Bagi, Péter Huszthy^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

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.

Original language	English (US)
Pages (from-to)	20-36
Number of pages	17
Journal	Periodica Polytechnica Chemical Engineering
Volume	64
Issue number	1
DOIs	https://doi.org/10.3311/PPch.14467
State	Published - 2020

Bibliographical note

Funding Information:
Financial supports of the National Research, Development and Innovation Office – NKFIH (earlier OTKA) (NKFIH No. K 112289, K 128473, and NVKP 16-1-2016-0043) and the New Széchenyi Development Plan (TÁMOP-4.2.1/B-09/1/KMR-2010-0002) are gratefully acknowledged. The authors thank Dr. György Tibor Balogh, Dr. Judit Müller, and Zsófia Petrik for chiral HPLC measurements.

Publisher Copyright:
© 2020, Budapest University of Technology and Economics. All rights reserved.

Keywords

Azacrown ether
Chiral crown ether
Fluorescence
Molecular recognition
PET sensor

ASJC Scopus subject areas

General Chemical Engineering

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10.3311/PPch.14467

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title = "Synthesis and complexation studies of optically active aza-and diazacrown ethers containing a pyrene fluorophore unit",

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 = "Azacrown ether, Chiral crown ether, Fluorescence, Molecular recognition, PET sensor",

author = "D{\'a}vid P{\'a}l and Martin Gede and Ildik{\'o} M{\'o}cz{\'a}r and P{\'e}ter Baranyai and P{\'e}ter Bagi and P{\'e}ter Huszthy",

note = "Funding Information: Financial supports of the National Research, Development and Innovation Office – NKFIH (earlier OTKA) (NKFIH No. K 112289, K 128473, and NVKP 16-1-2016-0043) and the New Sz{\'e}chenyi Development Plan (T{\'A}MOP-4.2.1/B-09/1/KMR-2010-0002) are gratefully acknowledged. The authors thank Dr. Gy{\"o}rgy Tibor Balogh, Dr. Judit M{\"u}ller, and Zs{\'o}fia Petrik for chiral HPLC measurements. Publisher Copyright: {\textcopyright} 2020, Budapest University of Technology and Economics. All rights reserved.",

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language = "English (US)",

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AU - Gede, Martin

AU - Móczár, Ildikó

AU - Baranyai, Péter

AU - Bagi, Péter

AU - Huszthy, Péter

N1 - Funding Information: Financial supports of the National Research, Development and Innovation Office – NKFIH (earlier OTKA) (NKFIH No. K 112289, K 128473, and NVKP 16-1-2016-0043) and the New Széchenyi Development Plan (TÁMOP-4.2.1/B-09/1/KMR-2010-0002) are gratefully acknowledged. The authors thank Dr. György Tibor Balogh, Dr. Judit Müller, and Zsófia Petrik for chiral HPLC measurements. Publisher Copyright: © 2020, Budapest University of Technology and Economics. All rights reserved.

PY - 2020

Y1 - 2020

N2 - 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.

AB - 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.

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Synthesis and complexation studies of optically active aza-and diazacrown ethers containing a pyrene fluorophore unit

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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