Selective Anion Sensing by Chiral Macrocyclic Receptors with Multiple Hydrogen-Bonding Sites

Chiral macrocycles featuring sulfonamide and/or amide groups as anion-binding sites were synthesized. X-ray crystal structures and DFT calculations have shown that they adopt different conformations that may lead to unique binding behavior. Indeed, various anions could be sensed by their colorimetri...

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Bibliographic Details
Published in:Organic letters 2014-03, Vol.16 (5), p.1302-1305
Main Authors: Ema, Tadashi, Okuda, Keiichi, Watanabe, Sagiri, Yamasaki, Takayuki, Minami, Tsuyoshi, Esipenko, Nina A, Anzenbacher, Pavel
Format: Article
Language:English
Subjects:
Amides - chemistry
Anions - chemistry
Crystallography, X-Ray
Hydrogen Bonding
Macrocyclic Compounds - chemistry
Magnetic Resonance Spectroscopy
Molecular Conformation
Molecular Structure
Phosphates - chemistry
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Summary:Chiral macrocycles featuring sulfonamide and/or amide groups as anion-binding sites were synthesized. X-ray crystal structures and DFT calculations have shown that they adopt different conformations that may lead to unique binding behavior. Indeed, various anions could be sensed by their colorimetric and/or fluorescence signal output. The chiral macrocycles showed chiral recognition for chiral anions. Furthermore, a multisensor array with two or four chiral receptors discriminated seven phosphate anions (AMP, ADP, ATP, CMP, GMP, Pi, and PPi) with 100% classification accuracy.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol403643d