Imine ligands based on ferrocene: Synthesis, structural and Mössbauer characterization and evaluation as chromogenic and electrochemical sensors for Hg2+

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Abstract

The compounds 1-naphthyliminoferrocene, 1, and 2-methyl-1-naphthyliminoferrocene, 2, were prepared by the reaction of ferrocenecarboxaldehyde and the corresponding amine, 1-naphthylamine and 2-methyl-1-naphthylamine with one drop of pyrrolidine as the catalyst, in CH2Cl2, under an inert atmosphere. The compounds were fully characterized by elemental analyses, matrix-assisted laser desorption/ionization-time-of-flight mass spectrometry (MALDI-TOF), FT-IR, 1H and 13C NMR as well as two-dimensional, NOESY, COSY and HSQC, NMR spectroscopy. Mössbauer spectroscopic studies were performed to characterize iron species in both compounds. The solid-state molecular structures of compounds 1 and 2 were determined by single crystal X-ray diffraction. Analysis of the electrochemical behaviour of complexes 1 and 2 was performed by cyclic and square wave voltammetry. Compounds 1 and 2 were tested as chromogenic and electrochemical sensors for Hg2+.

Original languageEnglish
Pages (from-to)3334-3343
Number of pages10
JournalNew Journal of Chemistry
Volume42
Issue number5
DOIs
Publication statusPublished - 1 Jan 2018

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1-Naphthylamine
Chromogenics
Electrochemical sensors
Imines
Voltammetry
Molecular structure
Nuclear magnetic resonance spectroscopy
Ionization
Mass spectrometry
Amines
Desorption
Ligands
Nuclear magnetic resonance
Single crystals
Iron
X ray diffraction
Catalysts
Lasers
ferrocene

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@article{b1197c8437bc4634bd4ba574eaaccb50,
title = "Imine ligands based on ferrocene: Synthesis, structural and M{\"o}ssbauer characterization and evaluation as chromogenic and electrochemical sensors for Hg2+",
abstract = "The compounds 1-naphthyliminoferrocene, 1, and 2-methyl-1-naphthyliminoferrocene, 2, were prepared by the reaction of ferrocenecarboxaldehyde and the corresponding amine, 1-naphthylamine and 2-methyl-1-naphthylamine with one drop of pyrrolidine as the catalyst, in CH2Cl2, under an inert atmosphere. The compounds were fully characterized by elemental analyses, matrix-assisted laser desorption/ionization-time-of-flight mass spectrometry (MALDI-TOF), FT-IR, 1H and 13C NMR as well as two-dimensional, NOESY, COSY and HSQC, NMR spectroscopy. M{\"o}ssbauer spectroscopic studies were performed to characterize iron species in both compounds. The solid-state molecular structures of compounds 1 and 2 were determined by single crystal X-ray diffraction. Analysis of the electrochemical behaviour of complexes 1 and 2 was performed by cyclic and square wave voltammetry. Compounds 1 and 2 were tested as chromogenic and electrochemical sensors for Hg2+.",
author = "Vitor Rosa and Gaspari, {Ana P. S.} and Filipe Folgosa and Cordas, {Cristina M.} and Pedro Tavares and Teresa Santos-Silva and S{\'o}nia Barroso and Teresa Avil{\'e}s",
note = "info:eu-repo/grantAgreement/FCT/5876/147218/PT# info:eu-repo/grantAgreement/WT//019407# info:eu-repo/grantAgreement/FCT/5876/147258/PT# info:eu-repo/grantAgreement/FCT/SFRH/SFRH{\%}2FBPD{\%}2F48430{\%}2F2008/PT# info:eu-repo/grantAgreement/FCT/SFRH/SFRH{\%}2FBPD{\%}2F44262{\%}2F2008/PT# info:eu-repo/grantAgreement/FCT/3599-PPCDT/127013/PT# info:eu-repo/grantAgreement/FCT/3599-PPCDT/125363/PT# PT2020 Partnership Agreement (POCI-01-0145-FEDER-007728). Program Ciencia 2008, from Fundacao para a Ciencia e Tecnologia, (FCT) Portugal. Sem PDF conforme despacho.",
year = "2018",
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TY - JOUR

T1 - Imine ligands based on ferrocene: Synthesis, structural and Mössbauer characterization and evaluation as chromogenic and electrochemical sensors for Hg2+

AU - Rosa, Vitor

AU - Gaspari, Ana P. S.

AU - Folgosa, Filipe

AU - Cordas, Cristina M.

AU - Tavares, Pedro

AU - Santos-Silva, Teresa

AU - Barroso, Sónia

AU - Avilés, Teresa

N1 - info:eu-repo/grantAgreement/FCT/5876/147218/PT# info:eu-repo/grantAgreement/WT//019407# info:eu-repo/grantAgreement/FCT/5876/147258/PT# info:eu-repo/grantAgreement/FCT/SFRH/SFRH%2FBPD%2F48430%2F2008/PT# info:eu-repo/grantAgreement/FCT/SFRH/SFRH%2FBPD%2F44262%2F2008/PT# info:eu-repo/grantAgreement/FCT/3599-PPCDT/127013/PT# info:eu-repo/grantAgreement/FCT/3599-PPCDT/125363/PT# PT2020 Partnership Agreement (POCI-01-0145-FEDER-007728). Program Ciencia 2008, from Fundacao para a Ciencia e Tecnologia, (FCT) Portugal. Sem PDF conforme despacho.

PY - 2018/1/1

Y1 - 2018/1/1

N2 - The compounds 1-naphthyliminoferrocene, 1, and 2-methyl-1-naphthyliminoferrocene, 2, were prepared by the reaction of ferrocenecarboxaldehyde and the corresponding amine, 1-naphthylamine and 2-methyl-1-naphthylamine with one drop of pyrrolidine as the catalyst, in CH2Cl2, under an inert atmosphere. The compounds were fully characterized by elemental analyses, matrix-assisted laser desorption/ionization-time-of-flight mass spectrometry (MALDI-TOF), FT-IR, 1H and 13C NMR as well as two-dimensional, NOESY, COSY and HSQC, NMR spectroscopy. Mössbauer spectroscopic studies were performed to characterize iron species in both compounds. The solid-state molecular structures of compounds 1 and 2 were determined by single crystal X-ray diffraction. Analysis of the electrochemical behaviour of complexes 1 and 2 was performed by cyclic and square wave voltammetry. Compounds 1 and 2 were tested as chromogenic and electrochemical sensors for Hg2+.

AB - The compounds 1-naphthyliminoferrocene, 1, and 2-methyl-1-naphthyliminoferrocene, 2, were prepared by the reaction of ferrocenecarboxaldehyde and the corresponding amine, 1-naphthylamine and 2-methyl-1-naphthylamine with one drop of pyrrolidine as the catalyst, in CH2Cl2, under an inert atmosphere. The compounds were fully characterized by elemental analyses, matrix-assisted laser desorption/ionization-time-of-flight mass spectrometry (MALDI-TOF), FT-IR, 1H and 13C NMR as well as two-dimensional, NOESY, COSY and HSQC, NMR spectroscopy. Mössbauer spectroscopic studies were performed to characterize iron species in both compounds. The solid-state molecular structures of compounds 1 and 2 were determined by single crystal X-ray diffraction. Analysis of the electrochemical behaviour of complexes 1 and 2 was performed by cyclic and square wave voltammetry. Compounds 1 and 2 were tested as chromogenic and electrochemical sensors for Hg2+.

UR - http://www.scopus.com/inward/record.url?scp=85042660639&partnerID=8YFLogxK

U2 - 10.1039/c7nj04319h

DO - 10.1039/c7nj04319h

M3 - Article

VL - 42

SP - 3334

EP - 3343

JO - New Journal of Chemistry

JF - New Journal of Chemistry

SN - 1144-0546

IS - 5

ER -