Imidazo-benzo-15-crown-5 ethers bearing arylthienyl and bithienyl moieties as novel fluorescent chemosensors for Pd2+ and Cu2+

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

doi:10.1016/j.tet.2011.06.106

Imidazo-benzo-15-crown-5 ethers bearing arylthienyl and bithienyl moieties as novel fluorescent chemosensors for Pd2+ and Cu2+

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

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

31 Citations (Scopus)

Abstract

Novel fluorescent ionophores bearing imidazo-arylthienyl or imidazo-bithienyl π-conjugated bridges functionalized with one or two fused benzo-15-crown-5 ethers as receptor units are reported. The sensing ability of the compounds in the presence of metallic cations (Li+, Na +, K+, Ca2+, Zn2+, Cu2+, Ni2+, Pd2+, and Hg2+) and fluoride ion was studied in MeCN/DMSO solutions by absorption and emission spectroscopy. The experimental results indicate that all compounds could act as selective fluorimetric sensors for Cu2+ and Pd2+ and also for the fluoride ion, in the case of the bis-substituted crown ether derivatives. © 2011 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	7106-7113
Number of pages	8
Journal	Tetrahedron
Volume	67
Issue number	37
DOIs	https://doi.org/10.1016/j.tet.2011.06.106
Publication status	Published - 16 Sept 2011

Keywords

Arylthiophene
Bithiophene
CHEQ effect
Crown ethers
Cu2+
F-
Fluorescent chemosensors
Imidazole
Pd2+
calcium ion
cation
copper ion
ether derivative
fluoride ion
imidazo benzo 15 crown 5 ether derivative
ionophore
lithium ion
mercury
nickel
palladium ion
potassium ion
proton
sodium ion
unclassified drug
zinc ion
absorption spectroscopy
article
chemical analysis
chemical interaction
flame photometry
fluorescence
priority journal
sensor
spectrofluorometry
spectrophotometry
synthesis

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@article{119d400e8d734651b3c09ebb60df2868,

title = "Imidazo-benzo-15-crown-5 ethers bearing arylthienyl and bithienyl moieties as novel fluorescent chemosensors for Pd2+ and Cu2+",

abstract = "Novel fluorescent ionophores bearing imidazo-arylthienyl or imidazo-bithienyl π-conjugated bridges functionalized with one or two fused benzo-15-crown-5 ethers as receptor units are reported. The sensing ability of the compounds in the presence of metallic cations (Li+, Na +, K+, Ca2+, Zn2+, Cu2+, Ni2+, Pd2+, and Hg2+) and fluoride ion was studied in MeCN/DMSO solutions by absorption and emission spectroscopy. The experimental results indicate that all compounds could act as selective fluorimetric sensors for Cu2+ and Pd2+ and also for the fluoride ion, in the case of the bis-substituted crown ether derivatives. {\textcopyright} 2011 Elsevier Ltd. All rights reserved.",

keywords = "Arylthiophene, Bithiophene, CHEQ effect, Crown ethers, Cu2+, F-, Fluorescent chemosensors, Imidazole, Pd2+, calcium ion, cation, copper ion, ether derivative, fluoride ion, imidazo benzo 15 crown 5 ether derivative, ionophore, lithium ion, mercury, nickel, palladium ion, potassium ion, proton, sodium ion, unclassified drug, zinc ion, absorption spectroscopy, article, chemical analysis, chemical interaction, flame photometry, fluorescence, priority journal, sensor, spectrofluorometry, spectrophotometry, synthesis",

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 the Fundacao para a Ciencia e Tecnologia (Portugal) and FEDER for financial support through the Centro de Quimica and Centro de Fisica-Universidade do Minho, and Project PTDC/QUI/66250/2006 (FCOMP-01-0124-FEDER-007428), Ph. D. grant to R.M.F.B. (SFRH/BD/36396/2007) and Postdoctoral grant to E.O. (SFRH/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 Re-equipment, 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.",

year = "2011",

month = sep,

day = "16",

doi = "10.1016/j.tet.2011.06.106",

language = "English",

volume = "67",

pages = "7106--7113",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

number = "37",

}

TY - JOUR

T1 - Imidazo-benzo-15-crown-5 ethers bearing arylthienyl and bithienyl moieties as novel fluorescent chemosensors for Pd2+ and Cu2+

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 the Fundacao para a Ciencia e Tecnologia (Portugal) and FEDER for financial support through the Centro de Quimica and Centro de Fisica-Universidade do Minho, and Project PTDC/QUI/66250/2006 (FCOMP-01-0124-FEDER-007428), Ph. D. grant to R.M.F.B. (SFRH/BD/36396/2007) and Postdoctoral grant to E.O. (SFRH/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 Re-equipment, 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.

PY - 2011/9/16

Y1 - 2011/9/16

N2 - Novel fluorescent ionophores bearing imidazo-arylthienyl or imidazo-bithienyl π-conjugated bridges functionalized with one or two fused benzo-15-crown-5 ethers as receptor units are reported. The sensing ability of the compounds in the presence of metallic cations (Li+, Na +, K+, Ca2+, Zn2+, Cu2+, Ni2+, Pd2+, and Hg2+) and fluoride ion was studied in MeCN/DMSO solutions by absorption and emission spectroscopy. The experimental results indicate that all compounds could act as selective fluorimetric sensors for Cu2+ and Pd2+ and also for the fluoride ion, in the case of the bis-substituted crown ether derivatives. © 2011 Elsevier Ltd. All rights reserved.

AB - Novel fluorescent ionophores bearing imidazo-arylthienyl or imidazo-bithienyl π-conjugated bridges functionalized with one or two fused benzo-15-crown-5 ethers as receptor units are reported. The sensing ability of the compounds in the presence of metallic cations (Li+, Na +, K+, Ca2+, Zn2+, Cu2+, Ni2+, Pd2+, and Hg2+) and fluoride ion was studied in MeCN/DMSO solutions by absorption and emission spectroscopy. The experimental results indicate that all compounds could act as selective fluorimetric sensors for Cu2+ and Pd2+ and also for the fluoride ion, in the case of the bis-substituted crown ether derivatives. © 2011 Elsevier Ltd. All rights reserved.

KW - Arylthiophene

KW - Bithiophene

KW - CHEQ effect

KW - Crown ethers

KW - Cu2+

KW - F-

KW - Fluorescent chemosensors

KW - Imidazole

KW - Pd2+

KW - calcium ion

KW - cation

KW - copper ion

KW - ether derivative

KW - fluoride ion

KW - imidazo benzo 15 crown 5 ether derivative

KW - ionophore

KW - lithium ion

KW - mercury

KW - nickel

KW - palladium ion

KW - potassium ion

KW - proton

KW - sodium ion

KW - unclassified drug

KW - zinc ion

KW - absorption spectroscopy

KW - article

KW - chemical analysis

KW - chemical interaction

KW - flame photometry

KW - fluorescence

KW - priority journal

KW - sensor

KW - spectrofluorometry

KW - spectrophotometry

KW - synthesis

U2 - 10.1016/j.tet.2011.06.106

DO - 10.1016/j.tet.2011.06.106

M3 - Article

SN - 0040-4020

VL - 67

SP - 7106

EP - 7113

JO - Tetrahedron

JF - Tetrahedron

IS - 37

ER -

Imidazo-benzo-15-crown-5 ethers bearing arylthienyl and bithienyl moieties as novel fluorescent chemosensors for Pd2+ and Cu2+

Abstract

Keywords

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