Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 42, Pages 10058-10067Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201700954
Keywords
fluorescence; iron; phosphoric acids; sensors; supramolecular chemistry
Categories
Funding
- Fonds der Chemischen Industrie
- PhD fellowship
- University of Duisburg-Essen
- Stiftung Mercator (Global Young Faculty)
- DFG [SFB-TRR 61]
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We describe the straightforward synthesis of a series of bis-phosphoric acids (R,R)-1a-d, featuring two chiral 1,1-binaphthyl-phosphoric acid units that are tethered by rigid, -conjugated linkers. The nature of the linker has a profound influence on the properties of the bis-phosphoric acids, such as their self-association behavior and their interaction with metal ions. This led to the identification of one preferred bis-phosphoric acid (R,R)-1d, which shows selective fluorescence quenching in the presence of ferric ions (Fe3+). Thus, (R,R)-1d could be applied for the detection of Fe3+, even in the presence of a variety of other metal ions. The chiral nature of the bis-phosphoric acid enables the interaction with Fe3+ to be followed by CD spectroscopy, providing a complementary detection mode with the same probe.
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