A seleno-pyrene selective probe for Hg2+ detection in either aqueous or aprotic systems

Augusto C. Gonçalves, José Luis Capelo, Carlos Lodeiro, Alcindo A Dos Santos

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

A new fluorescent molecular probe (compound 7) assembled from the amide bond between the 1-pyrenecarboxylic acid (6) and 2-(butylselenyl)ethanamine (5) was designed, synthesized and its structure accurately characterized. The photophysical properties of 7 were evaluated among a wide range of metallic cations (Na+, K+, Ca2+, Co2+, Ni2+, Cu2+, Zn2+, Cd2+, Pb2+, Hg2+, Ag+, Al3+, Fe3+, Ga3+and Cr3+) in water and in acetonitrile, which showed selective interaction with Hg2+. However, the sensing mechanism was found to be different in each solvent. Dynamic light scattering (DLS) studies revealed that compound 7 organizes itself as monodisperse aggregates in aqueous solution, nonetheless, as Hg2+ was added to the aqueous solution, disruption of aggregates was observed, resulting in a coordination complex under strong CHEQ (Chelation-Enhanced Fluorescent Quenching). Conversely, in acetonitrile solution, 7 exhibited monomeric pyrene emissive pattern and, as the addition of Hg2+ proceeded, a coordination compound of excimer-type fluorescence emission was observed. UV–vis absorption, steady state, and time-resolved emission spectroscopy were employed. The stoichiometry of the 7-Hg2+ complexes was found to be 1:1 for both aqueous (log β = 6.19 ± 0.009) and acetonitrile (log β = 8.59 ± 0.04) solutions. The lowest value of a detectable amount of 0.15 μmol/L for Hg2+ was achieved for fluorescence measurements in aqueous solution. The aqueous system was applied for the detection of Hg2+ in real samples of spring water, where the added amounts of the analyte could be detected and quantified.

Original languageEnglish
Pages (from-to)311-318
Number of pages8
JournalSensors And Actuators B-Chemical
Volume239
DOIs
Publication statusPublished - Feb 2017

Fingerprint

Pyrene
pyrenes
acetonitrile
aqueous solutions
Acetonitrile
probes
springs (water)
fluorescence
chelation
excimers
amides
Fluorescence
stoichiometry
light scattering
Molecular Probes
quenching
Springs (water)
Coordination Complexes
Emission spectroscopy
cations

Keywords

  • Emission
  • Fluorescence
  • Mercury (II) recognition
  • Organic selenide

Cite this

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title = "A seleno-pyrene selective probe for Hg2+ detection in either aqueous or aprotic systems",
abstract = "A new fluorescent molecular probe (compound 7) assembled from the amide bond between the 1-pyrenecarboxylic acid (6) and 2-(butylselenyl)ethanamine (5) was designed, synthesized and its structure accurately characterized. The photophysical properties of 7 were evaluated among a wide range of metallic cations (Na+, K+, Ca2+, Co2+, Ni2+, Cu2+, Zn2+, Cd2+, Pb2+, Hg2+, Ag+, Al3+, Fe3+, Ga3+and Cr3+) in water and in acetonitrile, which showed selective interaction with Hg2+. However, the sensing mechanism was found to be different in each solvent. Dynamic light scattering (DLS) studies revealed that compound 7 organizes itself as monodisperse aggregates in aqueous solution, nonetheless, as Hg2+ was added to the aqueous solution, disruption of aggregates was observed, resulting in a coordination complex under strong CHEQ (Chelation-Enhanced Fluorescent Quenching). Conversely, in acetonitrile solution, 7 exhibited monomeric pyrene emissive pattern and, as the addition of Hg2+ proceeded, a coordination compound of excimer-type fluorescence emission was observed. UV–vis absorption, steady state, and time-resolved emission spectroscopy were employed. The stoichiometry of the 7-Hg2+ complexes was found to be 1:1 for both aqueous (log β = 6.19 ± 0.009) and acetonitrile (log β = 8.59 ± 0.04) solutions. The lowest value of a detectable amount of 0.15 μmol/L for Hg2+ was achieved for fluorescence measurements in aqueous solution. The aqueous system was applied for the detection of Hg2+ in real samples of spring water, where the added amounts of the analyte could be detected and quantified.",
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A seleno-pyrene selective probe for Hg2+ detection in either aqueous or aprotic systems. / Gonçalves, Augusto C.; Capelo, José Luis; Lodeiro, Carlos; Santos, Alcindo A Dos.

In: Sensors And Actuators B-Chemical, Vol. 239, 02.2017, p. 311-318.

Research output: Contribution to journalArticle

TY - JOUR

T1 - A seleno-pyrene selective probe for Hg2+ detection in either aqueous or aprotic systems

AU - Gonçalves, Augusto C.

AU - Capelo, José Luis

AU - Lodeiro, Carlos

AU - Santos, Alcindo A Dos

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N2 - A new fluorescent molecular probe (compound 7) assembled from the amide bond between the 1-pyrenecarboxylic acid (6) and 2-(butylselenyl)ethanamine (5) was designed, synthesized and its structure accurately characterized. The photophysical properties of 7 were evaluated among a wide range of metallic cations (Na+, K+, Ca2+, Co2+, Ni2+, Cu2+, Zn2+, Cd2+, Pb2+, Hg2+, Ag+, Al3+, Fe3+, Ga3+and Cr3+) in water and in acetonitrile, which showed selective interaction with Hg2+. However, the sensing mechanism was found to be different in each solvent. Dynamic light scattering (DLS) studies revealed that compound 7 organizes itself as monodisperse aggregates in aqueous solution, nonetheless, as Hg2+ was added to the aqueous solution, disruption of aggregates was observed, resulting in a coordination complex under strong CHEQ (Chelation-Enhanced Fluorescent Quenching). Conversely, in acetonitrile solution, 7 exhibited monomeric pyrene emissive pattern and, as the addition of Hg2+ proceeded, a coordination compound of excimer-type fluorescence emission was observed. UV–vis absorption, steady state, and time-resolved emission spectroscopy were employed. The stoichiometry of the 7-Hg2+ complexes was found to be 1:1 for both aqueous (log β = 6.19 ± 0.009) and acetonitrile (log β = 8.59 ± 0.04) solutions. The lowest value of a detectable amount of 0.15 μmol/L for Hg2+ was achieved for fluorescence measurements in aqueous solution. The aqueous system was applied for the detection of Hg2+ in real samples of spring water, where the added amounts of the analyte could be detected and quantified.

AB - A new fluorescent molecular probe (compound 7) assembled from the amide bond between the 1-pyrenecarboxylic acid (6) and 2-(butylselenyl)ethanamine (5) was designed, synthesized and its structure accurately characterized. The photophysical properties of 7 were evaluated among a wide range of metallic cations (Na+, K+, Ca2+, Co2+, Ni2+, Cu2+, Zn2+, Cd2+, Pb2+, Hg2+, Ag+, Al3+, Fe3+, Ga3+and Cr3+) in water and in acetonitrile, which showed selective interaction with Hg2+. However, the sensing mechanism was found to be different in each solvent. Dynamic light scattering (DLS) studies revealed that compound 7 organizes itself as monodisperse aggregates in aqueous solution, nonetheless, as Hg2+ was added to the aqueous solution, disruption of aggregates was observed, resulting in a coordination complex under strong CHEQ (Chelation-Enhanced Fluorescent Quenching). Conversely, in acetonitrile solution, 7 exhibited monomeric pyrene emissive pattern and, as the addition of Hg2+ proceeded, a coordination compound of excimer-type fluorescence emission was observed. UV–vis absorption, steady state, and time-resolved emission spectroscopy were employed. The stoichiometry of the 7-Hg2+ complexes was found to be 1:1 for both aqueous (log β = 6.19 ± 0.009) and acetonitrile (log β = 8.59 ± 0.04) solutions. The lowest value of a detectable amount of 0.15 μmol/L for Hg2+ was achieved for fluorescence measurements in aqueous solution. The aqueous system was applied for the detection of Hg2+ in real samples of spring water, where the added amounts of the analyte could be detected and quantified.

KW - Emission

KW - Fluorescence

KW - Mercury (II) recognition

KW - Organic selenide

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