Zn2+-Ion Sensing by Fluorescent Schiff Base Calix[4]arene Macrocycles

Steve Ullmann; René Schnorr; Marcel Handke; Christian Laube; Bernd Abel; Jörg Matysik; Matthias Findeisen; Robert Rüger; Thomas Heine; Berthold Kersting

doi:10.1002/chem.201700253

Zn²⁺-Ion Sensing by Fluorescent Schiff Base Calix[4]arene Macrocycles

Steve Ullmann, René Schnorr, Marcel Handke, Christian Laube, Bernd Abel, Jörg Matysik, Matthias Findeisen, Robert Rüger, Thomas Heine, Berthold Kersting

Department of Chemistry

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

28 Citations (Scopus)

Abstract

A macrocyclic ligand (H₂L) containing two o,o′-bis(iminomethyl)phenol and two calix[4]arene head units has been synthesized and its coordination chemistry towards divalent Ni and Zn investigated. The new macrocycle forms complexes of composition [ML] (M=Zn, M=Ni) and [ZnL(py)₂], which were characterized by elemental analysis; IR, UV/Vis, and NMR spectroscopy; electrospray ionization mass spectrometry (ESI-MS); and X-ray crystallography (for [ZnL(py)₂] and [NiL]). H₂L allows the sensitive optical detection of Zn²⁺ among a series of biologically relevant metal ions by a dual fluorescence enhancement/quenching effect in solution. The fluorescence intensity of the macrocycle increases by a factor of ten in the presence of Zn²⁺ with a detection limit in the lower nanomolar region.

Original language	English
Pages (from-to)	3824-3827
Number of pages	4
Journal	Chemistry - A European Journal
Volume	23
Issue number	16
DOIs	https://doi.org/10.1002/chem.201700253
Publication status	Published - 2017 Mar 17

Bibliographical note

Funding Information:
We are thankful to Prof. Dr. H. Krautscheid for providing facilities for X-ray crystallographic measurements. The financial support by the German Federal Ministry of Education and Research (BMBF, r4project SE-FLECX, 033R132A) is gratefully acknowledged.

Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

All Science Journal Classification (ASJC) codes

Catalysis
Organic Chemistry

Access to Document

10.1002/chem.201700253

Cite this

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title = "Zn2+-Ion Sensing by Fluorescent Schiff Base Calix[4]arene Macrocycles",

abstract = "A macrocyclic ligand (H2L) containing two o,o′-bis(iminomethyl)phenol and two calix[4]arene head units has been synthesized and its coordination chemistry towards divalent Ni and Zn investigated. The new macrocycle forms complexes of composition [ML] (M=Zn, M=Ni) and [ZnL(py)2], which were characterized by elemental analysis; IR, UV/Vis, and NMR spectroscopy; electrospray ionization mass spectrometry (ESI-MS); and X-ray crystallography (for [ZnL(py)2] and [NiL]). H2L allows the sensitive optical detection of Zn2+ among a series of biologically relevant metal ions by a dual fluorescence enhancement/quenching effect in solution. The fluorescence intensity of the macrocycle increases by a factor of ten in the presence of Zn2+ with a detection limit in the lower nanomolar region.",

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note = "Funding Information: We are thankful to Prof. Dr. H. Krautscheid for providing facilities for X-ray crystallographic measurements. The financial support by the German Federal Ministry of Education and Research (BMBF, r4project SE-FLECX, 033R132A) is gratefully acknowledged. Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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AU - Ullmann, Steve

AU - Schnorr, René

AU - Handke, Marcel

AU - Laube, Christian

AU - Abel, Bernd

AU - Matysik, Jörg

AU - Findeisen, Matthias

AU - Rüger, Robert

AU - Heine, Thomas

AU - Kersting, Berthold

N1 - Funding Information: We are thankful to Prof. Dr. H. Krautscheid for providing facilities for X-ray crystallographic measurements. The financial support by the German Federal Ministry of Education and Research (BMBF, r4project SE-FLECX, 033R132A) is gratefully acknowledged. Publisher Copyright: © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2017/3/17

Y1 - 2017/3/17

N2 - A macrocyclic ligand (H2L) containing two o,o′-bis(iminomethyl)phenol and two calix[4]arene head units has been synthesized and its coordination chemistry towards divalent Ni and Zn investigated. The new macrocycle forms complexes of composition [ML] (M=Zn, M=Ni) and [ZnL(py)2], which were characterized by elemental analysis; IR, UV/Vis, and NMR spectroscopy; electrospray ionization mass spectrometry (ESI-MS); and X-ray crystallography (for [ZnL(py)2] and [NiL]). H2L allows the sensitive optical detection of Zn2+ among a series of biologically relevant metal ions by a dual fluorescence enhancement/quenching effect in solution. The fluorescence intensity of the macrocycle increases by a factor of ten in the presence of Zn2+ with a detection limit in the lower nanomolar region.

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