Dicarboxylated ethynylarenes as buffer-dependent chemosensors for Cd(II), Pb(II), and Zn(II)

James T. Fletcher; Brent S. Bruck; Douglas E. Deever

doi:10.1016/j.tetlet.2013.07.111

Dicarboxylated ethynylarenes as buffer-dependent chemosensors for Cd(II), Pb(II), and Zn(II)

James T. Fletcher, Brent S. Bruck, Douglas E. Deever

Department of Chemistry

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

7 Scopus citations

Abstract

Two dicarboxylated ethynylarenes were prepared efficiently from condensation of 1,3-bis(3-aminophenylethynyl)benzene with 2 equiv of either succinic anhydride or glutaric anhydride. These compounds behave as fluorescent chemosensors selective for Cd(II), Pb(II), and Zn(II) cations under buffered aqueous conditions, with analyte binding observed as bathochromically shifted, intensified fluorescence. It was noteworthy that the fluorescence responses varied significantly with buffer identity. A conformational restriction mechanism involving reversible interactions between the fluorophore, metal cation, and buffer itself is proposed.

Original language	English (US)
Pages (from-to)	5366-5369
Number of pages	4
Journal	Tetrahedron Letters
Volume	54
Issue number	39
DOIs	https://doi.org/10.1016/j.tetlet.2013.07.111
State	Published - Sep 25 2013

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2013.07.111

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title = "Dicarboxylated ethynylarenes as buffer-dependent chemosensors for Cd(II), Pb(II), and Zn(II)",

abstract = "Two dicarboxylated ethynylarenes were prepared efficiently from condensation of 1,3-bis(3-aminophenylethynyl)benzene with 2 equiv of either succinic anhydride or glutaric anhydride. These compounds behave as fluorescent chemosensors selective for Cd(II), Pb(II), and Zn(II) cations under buffered aqueous conditions, with analyte binding observed as bathochromically shifted, intensified fluorescence. It was noteworthy that the fluorescence responses varied significantly with buffer identity. A conformational restriction mechanism involving reversible interactions between the fluorophore, metal cation, and buffer itself is proposed.",

author = "Fletcher, {James T.} and Bruck, {Brent S.} and Deever, {Douglas E.}",

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N1 - Funding Information: This publication was made possible by grants from the National Center for Research Resources ( 5P20RR016469 ) and the National Institute for General Medical Science (NIGMS) ( 5P20GM103427 ), a component of the National Institutes of Health (NIH) and its contents are the sole responsibility of the authors and do not necessarily represent the official views of NIGMS or NIH.

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N2 - Two dicarboxylated ethynylarenes were prepared efficiently from condensation of 1,3-bis(3-aminophenylethynyl)benzene with 2 equiv of either succinic anhydride or glutaric anhydride. These compounds behave as fluorescent chemosensors selective for Cd(II), Pb(II), and Zn(II) cations under buffered aqueous conditions, with analyte binding observed as bathochromically shifted, intensified fluorescence. It was noteworthy that the fluorescence responses varied significantly with buffer identity. A conformational restriction mechanism involving reversible interactions between the fluorophore, metal cation, and buffer itself is proposed.

AB - Two dicarboxylated ethynylarenes were prepared efficiently from condensation of 1,3-bis(3-aminophenylethynyl)benzene with 2 equiv of either succinic anhydride or glutaric anhydride. These compounds behave as fluorescent chemosensors selective for Cd(II), Pb(II), and Zn(II) cations under buffered aqueous conditions, with analyte binding observed as bathochromically shifted, intensified fluorescence. It was noteworthy that the fluorescence responses varied significantly with buffer identity. A conformational restriction mechanism involving reversible interactions between the fluorophore, metal cation, and buffer itself is proposed.

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Dicarboxylated ethynylarenes as buffer-dependent chemosensors for Cd(II), Pb(II), and Zn(II)

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