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

Fingerprint

Crown Ethers
Crown ethers
Stereochemistry
Spectroscopic analysis
Ethers
Enantiomers
Fluorophores
Anthracene
Fluorescence spectroscopy
Ether
Nuclear magnetic resonance spectroscopy
Amines
propylene glycol methyl ether
Fluorescence
Ligands
Ultraviolet spectroscopy
Amino acids
Esters
Nuclear magnetic resonance
Amino Acids

Keywords

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

ASJC Scopus subject areas

  • Chemical Engineering(all)

Cite this

Synthesis, fluorescence and nmr spectroscopic studies of a novel phosphinoxido-18-crown-6 ether containing an anthracene fluorophore unit. / Szabó-Szentjóbi, Hajnalka; Márton, Anna; Pál, Dávid; Dargó, Gergő; Szigetvári, Áron; Szántay, Csaba; Balogh, György Tibor; Tóth, Tünde; Huszthy, Péter.

In: Periodica Polytechnica Chemical Engineering, Vol. 64, No. 1, 01.01.2020, p. 37-45.

Research output: Contribution to journalArticle

Szabó-Szentjóbi, Hajnalka ; Márton, Anna ; Pál, Dávid ; Dargó, Gergő ; Szigetvári, Áron ; Szántay, Csaba ; Balogh, György Tibor ; Tóth, Tünde ; Huszthy, Péter. / Synthesis, fluorescence and nmr spectroscopic studies of a novel phosphinoxido-18-crown-6 ether containing an anthracene fluorophore unit. In: Periodica Polytechnica Chemical Engineering. 2020 ; Vol. 64, No. 1. pp. 37-45.
@article{f5b8852697404364bb1f9c610940c6e7,
title = "Synthesis, fluorescence and nmr spectroscopic studies of a novel phosphinoxido-18-crown-6 ether containing an anthracene fluorophore unit",
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.",
keywords = "Crown ethers, Enantiomeric recognition, Fluorescence spectroscopy, Sensor molecules",
author = "Hajnalka Szab{\'o}-Szentj{\'o}bi and Anna M{\'a}rton and D{\'a}vid P{\'a}l and Gergő Darg{\'o} and {\'A}ron Szigetv{\'a}ri and Csaba Sz{\'a}ntay and Balogh, {Gy{\"o}rgy Tibor} and T{\"u}nde T{\'o}th and P{\'e}ter Huszthy",
year = "2020",
month = "1",
day = "1",
doi = "10.3311/PPch.14646",
language = "English",
volume = "64",
pages = "37--45",
journal = "Periodica Polytechnica: Chemical Engineering",
issn = "0324-5853",
publisher = "Budapest University of Technology and Economics",
number = "1",

}

TY - JOUR

T1 - Synthesis, fluorescence and nmr spectroscopic studies of a novel phosphinoxido-18-crown-6 ether containing an anthracene fluorophore unit

AU - Szabó-Szentjóbi, Hajnalka

AU - Márton, Anna

AU - Pál, Dávid

AU - Dargó, Gergő

AU - Szigetvári, Áron

AU - Szántay, Csaba

AU - Balogh, György Tibor

AU - Tóth, Tünde

AU - Huszthy, Péter

PY - 2020/1/1

Y1 - 2020/1/1

N2 - 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.

AB - 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.

KW - Crown ethers

KW - Enantiomeric recognition

KW - Fluorescence spectroscopy

KW - Sensor molecules

UR - http://www.scopus.com/inward/record.url?scp=85074389142&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85074389142&partnerID=8YFLogxK

U2 - 10.3311/PPch.14646

DO - 10.3311/PPch.14646

M3 - Article

AN - SCOPUS:85074389142

VL - 64

SP - 37

EP - 45

JO - Periodica Polytechnica: Chemical Engineering

JF - Periodica Polytechnica: Chemical Engineering

SN - 0324-5853

IS - 1

ER -