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Synthesis and Fluorescence Ion‐Sensory Properties of the First Dehydropyridoannulene‐Type Cyclophane with Enforced Exotopic Metal Ion Binding Sites
Author(s) -
Baxter Paul. N. W.
Publication year - 2003
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.2003044561
Subject(s) - fluorescence , metal ions in aqueous solution , chemistry , quenching (fluorescence) , metal , ion , conjugated system , crystallography , photochemistry , polymer , organic chemistry , quantum mechanics , physics
The new twistophane 4 has been synthesised, which comprises a conjugated dehydropyridoannulene‐type macrocyclic scaffold with outwardly projecting nitrogen‐donor sites for the purpose of metal ion coordination. The macrocyclíc structure of 4 was assigned by using spectroscopic methods, and shown to exist in a twisted and chiral ground state conformation by semi‐empirical theoretical calculations. A detailed spectroscopic investigation into the metal ion binding properties of 4 and precursor 11 revealed that they functioned as selective complexants, affording a fluorescence quenching output response characteristic of Pd II and Hg II ions. Furthermore, 4 also signalled the presence of Fe II , Co II , Ni II and Ag I ions by the precipitation of coordination polymers, and exhibited reversible proton‐triggered fluorescence quenching behaviour. Macrocycle 4 thus represents a unique type of molecular sensory platform, which may find a wealth of potential applications such as the detection of heavy‐metal pollutants, as well as for the fabrication of proton‐switchable materials and coordination polymers with novel electronic and magnetic properties.