A New pH-Dependent Macrocyclic Rhodamine B-Based Fluorescent Probe for Copper Detection in White Wine

For efficiently measuring copper (II) ions in the acidic media of white wine, a new chemosensor based on rhodamine B coupled to a tetraazamacrocyclic ring (13aneN<sub>4</sub>CH<sub>2</sub>NH<sub>2</sub>) was designed and synthesized by a one-pot reaction using eth...

Full description

Bibliographic Details
Main Authors: Nour Doumani, Elias Bou-Maroun, Jacqueline Maalouly, Maya Tueni, Adrien Dubois, Claire Bernhard, Franck Denat, Philippe Cayot, Nicolas Sok
Format: Article
Language:English
Published: MDPI AG 2019-10-01
Series:Sensors
Subjects:
Online Access:https://www.mdpi.com/1424-8220/19/20/4514
_version_ 1828390320775102464
author Nour Doumani
Elias Bou-Maroun
Jacqueline Maalouly
Maya Tueni
Adrien Dubois
Claire Bernhard
Franck Denat
Philippe Cayot
Nicolas Sok
author_facet Nour Doumani
Elias Bou-Maroun
Jacqueline Maalouly
Maya Tueni
Adrien Dubois
Claire Bernhard
Franck Denat
Philippe Cayot
Nicolas Sok
author_sort Nour Doumani
collection DOAJ
description For efficiently measuring copper (II) ions in the acidic media of white wine, a new chemosensor based on rhodamine B coupled to a tetraazamacrocyclic ring (13aneN<sub>4</sub>CH<sub>2</sub>NH<sub>2</sub>) was designed and synthesized by a one-pot reaction using ethanol as a green solvent. The obtained chemosensor was characterized via NMR, UV and fluorescent spectra. It was marked with no color emission under neutral pH conditions, with a pink color emission under acidic conditions, and a magenta color emission under acidic conditions where copper (II) ions were present. The sensitivity towards copper (II) ions was tested and verified over Ca<sup>2+</sup>, Ag<sup>+</sup>, Zn<sup>2+</sup>, Mg<sup>2+</sup>, Co<sup>2+</sup>, Ni<sup>2+</sup>, Fe<sup>2+</sup>, Pb<sup>2+</sup>, Cd<sup>2+</sup>, Fe<sup>3+</sup>, and Mn<sup>2+</sup>, with a detection limit of 4.38 <inline-formula> <math display="inline"> <semantics> <mrow> <mo>&#215;</mo> </mrow> </semantics> </math> </inline-formula> 10<sup>&#8722;8</sup> M in the fluorescence spectrum.
first_indexed 2024-12-10T06:42:21Z
format Article
id doaj.art-40b800ac7ebd4cfc8a74a435da218219
institution Directory Open Access Journal
issn 1424-8220
language English
last_indexed 2024-12-10T06:42:21Z
publishDate 2019-10-01
publisher MDPI AG
record_format Article
series Sensors
spelling doaj.art-40b800ac7ebd4cfc8a74a435da2182192022-12-22T01:58:44ZengMDPI AGSensors1424-82202019-10-011920451410.3390/s19204514s19204514A New pH-Dependent Macrocyclic Rhodamine B-Based Fluorescent Probe for Copper Detection in White WineNour Doumani0Elias Bou-Maroun1Jacqueline Maalouly2Maya Tueni3Adrien Dubois4Claire Bernhard5Franck Denat6Philippe Cayot7Nicolas Sok8UMR PAM Procédés Alimentaires et Microbiologiques, Université de Bourgogne Franche-Comté/AgroSup Dijon, 1 esplanade Erasme, 21000 Dijon, FranceUMR PAM Procédés Alimentaires et Microbiologiques, Université de Bourgogne Franche-Comté/AgroSup Dijon, 1 esplanade Erasme, 21000 Dijon, FranceDépartement de Chimie et de Biochimie, Faculté des Sciences II, Université Libanaise, Jdeideth El Matn, Fanar 90656, LebanonDépartement des Sciences de la Vie et de la Terre - Nutrition, Faculté des Sciences II, Université Libanaise, Jdeideth El Matn, Fanar 90656, LebanonInstitut de Chimie Moléculaire de l’Université de Bourgogne, UMR 5260, CNRS-12 Université de Bourgogne, 9 Avenue Alain Savary, 21078 Dijon, FranceInstitut de Chimie Moléculaire de l’Université de Bourgogne, UMR 5260, CNRS-12 Université de Bourgogne, 9 Avenue Alain Savary, 21078 Dijon, FranceInstitut de Chimie Moléculaire de l’Université de Bourgogne, UMR 5260, CNRS-12 Université de Bourgogne, 9 Avenue Alain Savary, 21078 Dijon, FranceUMR PAM Procédés Alimentaires et Microbiologiques, Université de Bourgogne Franche-Comté/AgroSup Dijon, 1 esplanade Erasme, 21000 Dijon, FranceUMR PAM Procédés Alimentaires et Microbiologiques, Université de Bourgogne Franche-Comté/AgroSup Dijon, 1 esplanade Erasme, 21000 Dijon, FranceFor efficiently measuring copper (II) ions in the acidic media of white wine, a new chemosensor based on rhodamine B coupled to a tetraazamacrocyclic ring (13aneN<sub>4</sub>CH<sub>2</sub>NH<sub>2</sub>) was designed and synthesized by a one-pot reaction using ethanol as a green solvent. The obtained chemosensor was characterized via NMR, UV and fluorescent spectra. It was marked with no color emission under neutral pH conditions, with a pink color emission under acidic conditions, and a magenta color emission under acidic conditions where copper (II) ions were present. The sensitivity towards copper (II) ions was tested and verified over Ca<sup>2+</sup>, Ag<sup>+</sup>, Zn<sup>2+</sup>, Mg<sup>2+</sup>, Co<sup>2+</sup>, Ni<sup>2+</sup>, Fe<sup>2+</sup>, Pb<sup>2+</sup>, Cd<sup>2+</sup>, Fe<sup>3+</sup>, and Mn<sup>2+</sup>, with a detection limit of 4.38 <inline-formula> <math display="inline"> <semantics> <mrow> <mo>&#215;</mo> </mrow> </semantics> </math> </inline-formula> 10<sup>&#8722;8</sup> M in the fluorescence spectrum.https://www.mdpi.com/1424-8220/19/20/4514copper (ii) sensorfluorescent chemosensortetraazamacrocycle rhodamine-basedwater-solubleacidic ph
spellingShingle Nour Doumani
Elias Bou-Maroun
Jacqueline Maalouly
Maya Tueni
Adrien Dubois
Claire Bernhard
Franck Denat
Philippe Cayot
Nicolas Sok
A New pH-Dependent Macrocyclic Rhodamine B-Based Fluorescent Probe for Copper Detection in White Wine
Sensors
copper (ii) sensor
fluorescent chemosensor
tetraazamacrocycle rhodamine-based
water-soluble
acidic ph
title A New pH-Dependent Macrocyclic Rhodamine B-Based Fluorescent Probe for Copper Detection in White Wine
title_full A New pH-Dependent Macrocyclic Rhodamine B-Based Fluorescent Probe for Copper Detection in White Wine
title_fullStr A New pH-Dependent Macrocyclic Rhodamine B-Based Fluorescent Probe for Copper Detection in White Wine
title_full_unstemmed A New pH-Dependent Macrocyclic Rhodamine B-Based Fluorescent Probe for Copper Detection in White Wine
title_short A New pH-Dependent Macrocyclic Rhodamine B-Based Fluorescent Probe for Copper Detection in White Wine
title_sort new ph dependent macrocyclic rhodamine b based fluorescent probe for copper detection in white wine
topic copper (ii) sensor
fluorescent chemosensor
tetraazamacrocycle rhodamine-based
water-soluble
acidic ph
url https://www.mdpi.com/1424-8220/19/20/4514
work_keys_str_mv AT nourdoumani anewphdependentmacrocyclicrhodaminebbasedfluorescentprobeforcopperdetectioninwhitewine
AT eliasboumaroun anewphdependentmacrocyclicrhodaminebbasedfluorescentprobeforcopperdetectioninwhitewine
AT jacquelinemaalouly anewphdependentmacrocyclicrhodaminebbasedfluorescentprobeforcopperdetectioninwhitewine
AT mayatueni anewphdependentmacrocyclicrhodaminebbasedfluorescentprobeforcopperdetectioninwhitewine
AT adriendubois anewphdependentmacrocyclicrhodaminebbasedfluorescentprobeforcopperdetectioninwhitewine
AT clairebernhard anewphdependentmacrocyclicrhodaminebbasedfluorescentprobeforcopperdetectioninwhitewine
AT franckdenat anewphdependentmacrocyclicrhodaminebbasedfluorescentprobeforcopperdetectioninwhitewine
AT philippecayot anewphdependentmacrocyclicrhodaminebbasedfluorescentprobeforcopperdetectioninwhitewine
AT nicolassok anewphdependentmacrocyclicrhodaminebbasedfluorescentprobeforcopperdetectioninwhitewine
AT nourdoumani newphdependentmacrocyclicrhodaminebbasedfluorescentprobeforcopperdetectioninwhitewine
AT eliasboumaroun newphdependentmacrocyclicrhodaminebbasedfluorescentprobeforcopperdetectioninwhitewine
AT jacquelinemaalouly newphdependentmacrocyclicrhodaminebbasedfluorescentprobeforcopperdetectioninwhitewine
AT mayatueni newphdependentmacrocyclicrhodaminebbasedfluorescentprobeforcopperdetectioninwhitewine
AT adriendubois newphdependentmacrocyclicrhodaminebbasedfluorescentprobeforcopperdetectioninwhitewine
AT clairebernhard newphdependentmacrocyclicrhodaminebbasedfluorescentprobeforcopperdetectioninwhitewine
AT franckdenat newphdependentmacrocyclicrhodaminebbasedfluorescentprobeforcopperdetectioninwhitewine
AT philippecayot newphdependentmacrocyclicrhodaminebbasedfluorescentprobeforcopperdetectioninwhitewine
AT nicolassok newphdependentmacrocyclicrhodaminebbasedfluorescentprobeforcopperdetectioninwhitewine