(Oligo)thienyl-imidazo-benzocrown ether derivatives: Synthesis, photophysical studies and evaluation of their chemosensory properties

Rosa M. F. Batista; E. Oliveira; Susana P. G. Costa; C. Lodeiro; M. M. M. Raposo

doi:10.1016/j.talanta.2011.07.107

(Oligo)thienyl-imidazo-benzocrown ether derivatives: Synthesis, photophysical studies and evaluation of their chemosensory properties

Rosa M. F. Batista, E. Oliveira, Susana P. G. Costa, C. Lodeiro, M. M. M. Raposo

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

9 Citations (Scopus)

Abstract

A series of novel (oligo)thienyl-imidazo-benzocrown ethers were synthesised through a simple method and evaluated as fluorimetric chemosensors for transition metal cations. Interaction with Ni2+, Pd2+, and Hg2+ in ACN/DMSO solution (99:1) was studied by absorption and emission spectroscopy. Chemoselectivity studies in the presence of Na + were also carried out and a fluorescence enhancement upon chelation (CHEF) effect was observed following Hg2+ complexation. Considering that most systems using fluorescence spectroscopy for detecting Hg2+ are based on the complexation enhancement of the fluorescence quenching (CHEQ) effect, the present work represents one of the few examples for sensing of Hg2+ based on a CHEF effect. © 2011 Elsevier B.V. All rights reserved.

Original language	English
Pages (from-to)	2470-2478
Number of pages	9
Journal	Talanta
Volume	85
Issue number	5
DOIs	https://doi.org/10.1016/j.talanta.2011.07.107
Publication status	Published - 15 Oct 2011

Keywords

(Oligo)thiophene
Benzo-15-crown-5 ether
CHEF effect
Fluorescent chemosensors
Hg2+
Imidazole
Pd2+
Absorption and emission spectroscopy
Benzo-15-crown-5
Chemo-selectivity
Chemo-sensors
Ether derivatives
Fluorescence enhancement
Fluorescence quenching
Fluorimetric
Photophysical studies
SIMPLE method
Transition metal cations
Crown ethers
Emission spectroscopy
Ethers
Fluorescence
Fluorescence spectroscopy
Organic compounds
Palladium
Physiology
Thiophene
Transition metals
Mercury (metal)

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@article{e284f32a89594048a22340bc29fd2ed2,

title = "(Oligo)thienyl-imidazo-benzocrown ether derivatives: Synthesis, photophysical studies and evaluation of their chemosensory properties",

abstract = "A series of novel (oligo)thienyl-imidazo-benzocrown ethers were synthesised through a simple method and evaluated as fluorimetric chemosensors for transition metal cations. Interaction with Ni2+, Pd2+, and Hg2+ in ACN/DMSO solution (99:1) was studied by absorption and emission spectroscopy. Chemoselectivity studies in the presence of Na + were also carried out and a fluorescence enhancement upon chelation (CHEF) effect was observed following Hg2+ complexation. Considering that most systems using fluorescence spectroscopy for detecting Hg2+ are based on the complexation enhancement of the fluorescence quenching (CHEQ) effect, the present work represents one of the few examples for sensing of Hg2+ based on a CHEF effect. {\textcopyright} 2011 Elsevier B.V. All rights reserved.",

keywords = "(Oligo)thiophene, Benzo-15-crown-5 ether, CHEF effect, Fluorescent chemosensors, Hg2+, Imidazole, Pd2+, Absorption and emission spectroscopy, Benzo-15-crown-5, Chemo-selectivity, Chemo-sensors, Ether derivatives, Fluorescence enhancement, Fluorescence quenching, Fluorimetric, Photophysical studies, SIMPLE method, Transition metal cations, Crown ethers, Emission spectroscopy, Ethers, Fluorescence, Fluorescence spectroscopy, Organic compounds, Palladium, Physiology, Thiophene, Transition metals, Mercury (metal)",

author = "Batista, {Rosa M. F.} and E. Oliveira and Costa, {Susana P. G.} and C. Lodeiro and Raposo, {M. M. M.}",

note = "Thanks are due to Fundacao para a Ciencia e Tecnologia (Portugal) for financial support through project PTDC/QUI/66250/2006 (FCOMP-01-0124-FEDER-007428) and PhD grants to R.M.F. Batista (SFRH/BD/36396/2007) and Postdoctoral grant to E. Oliveira (SRFH/BPD/72557/2010). The NMR spectrometer Bruker Avance III 400 is part of the National NMR Network, and was purchased within the framework of the National Program for Scientific Reequipment, contract REDE/1517/RMN/2005 with funds from POCI 2010 (FEDER) and FCT. C.L. thanks Xunta de Galicia, Spain, for the Isidro Parga Pondal Research Program. We thank to Mr. Tiago Silva for some of the initial metal titrations reported.",

year = "2011",

month = oct,

day = "15",

doi = "10.1016/j.talanta.2011.07.107",

language = "English",

volume = "85",

pages = "2470--2478",

journal = "Talanta",

issn = "0039-9140",

publisher = "Elsevier",

number = "5",

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TY - JOUR

T1 - (Oligo)thienyl-imidazo-benzocrown ether derivatives: Synthesis, photophysical studies and evaluation of their chemosensory properties

AU - Batista, Rosa M. F.

AU - Oliveira, E.

AU - Costa, Susana P. G.

AU - Lodeiro, C.

AU - Raposo, M. M. M.

N1 - Thanks are due to Fundacao para a Ciencia e Tecnologia (Portugal) for financial support through project PTDC/QUI/66250/2006 (FCOMP-01-0124-FEDER-007428) and PhD grants to R.M.F. Batista (SFRH/BD/36396/2007) and Postdoctoral grant to E. Oliveira (SRFH/BPD/72557/2010). The NMR spectrometer Bruker Avance III 400 is part of the National NMR Network, and was purchased within the framework of the National Program for Scientific Reequipment, contract REDE/1517/RMN/2005 with funds from POCI 2010 (FEDER) and FCT. C.L. thanks Xunta de Galicia, Spain, for the Isidro Parga Pondal Research Program. We thank to Mr. Tiago Silva for some of the initial metal titrations reported.

PY - 2011/10/15

Y1 - 2011/10/15

N2 - A series of novel (oligo)thienyl-imidazo-benzocrown ethers were synthesised through a simple method and evaluated as fluorimetric chemosensors for transition metal cations. Interaction with Ni2+, Pd2+, and Hg2+ in ACN/DMSO solution (99:1) was studied by absorption and emission spectroscopy. Chemoselectivity studies in the presence of Na + were also carried out and a fluorescence enhancement upon chelation (CHEF) effect was observed following Hg2+ complexation. Considering that most systems using fluorescence spectroscopy for detecting Hg2+ are based on the complexation enhancement of the fluorescence quenching (CHEQ) effect, the present work represents one of the few examples for sensing of Hg2+ based on a CHEF effect. © 2011 Elsevier B.V. All rights reserved.

AB - A series of novel (oligo)thienyl-imidazo-benzocrown ethers were synthesised through a simple method and evaluated as fluorimetric chemosensors for transition metal cations. Interaction with Ni2+, Pd2+, and Hg2+ in ACN/DMSO solution (99:1) was studied by absorption and emission spectroscopy. Chemoselectivity studies in the presence of Na + were also carried out and a fluorescence enhancement upon chelation (CHEF) effect was observed following Hg2+ complexation. Considering that most systems using fluorescence spectroscopy for detecting Hg2+ are based on the complexation enhancement of the fluorescence quenching (CHEQ) effect, the present work represents one of the few examples for sensing of Hg2+ based on a CHEF effect. © 2011 Elsevier B.V. All rights reserved.

KW - (Oligo)thiophene

KW - Benzo-15-crown-5 ether

KW - CHEF effect

KW - Fluorescent chemosensors

KW - Hg2+

KW - Imidazole

KW - Pd2+

KW - Absorption and emission spectroscopy

KW - Benzo-15-crown-5

KW - Chemo-selectivity

KW - Chemo-sensors

KW - Ether derivatives

KW - Fluorescence enhancement

KW - Fluorescence quenching

KW - Fluorimetric

KW - Photophysical studies

KW - SIMPLE method

KW - Transition metal cations

KW - Crown ethers

KW - Emission spectroscopy

KW - Ethers

KW - Fluorescence

KW - Fluorescence spectroscopy

KW - Organic compounds

KW - Palladium

KW - Physiology

KW - Thiophene

KW - Transition metals

KW - Mercury (metal)

U2 - 10.1016/j.talanta.2011.07.107

DO - 10.1016/j.talanta.2011.07.107

M3 - Article

C2 - 21962670

SN - 0039-9140

VL - 85

SP - 2470

EP - 2478

JO - Talanta

JF - Talanta

IS - 5

ER -

(Oligo)thienyl-imidazo-benzocrown ether derivatives: Synthesis, photophysical studies and evaluation of their chemosensory properties

Abstract

Keywords

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