Abstract
A new amido−amine cage receptor, which combines 1,8‐anthracene diacarboxamide subunit and a polyammonium azamacrocycle, is reported. Bearing both the hydrogen bond donor and the acceptor binding sites, the receptor is able to bind phosphate selectively under neutral (pH 7.2) aqueous conditions. The recognition events for phosphate and dicarboxylates are accomplished by a fluorescence enhancement in the anthracene emission. As revealed by experimental and theoretical studies, phosphate and oxalate show different recognition modes. Phosphate demonstrates hydrogen bond acceptor properties, while the coordination of oxalate favours the protonation of the receptor.
Highlights
Dedicated to Jean-Marie Lehn for his 80th birthday and great inspiration to develop the supramolecular chemistry
One of the most strongly binding receptors for anions in water are azacryptands pioneered by Simmons, Park and
This class of synthetic hosts has grown in a broad variety of rigid and flexible, high affinity binding receptors during the last two decades.[3b,c,5]
Summary
A new amido amine cage receptor, which combines 1,8anthracene diacarboxamide subunit and a polyammonium azamacrocycle, is reported. Bearing both the hydrogen bond donor and the acceptor binding sites, the receptor is able to bind phosphate selectively under neutral (pH 7.2) aqueous conditions. The recognition events for phosphate and dicarboxylates are accomplished by a fluorescence enhancement in the anthracene emission. As revealed by experimental and theoretical studies, phosphate and oxalate show different recognition modes. Phosphate demonstrates hydrogen bond acceptor properties, while the coordination of oxalate favours the protonation of the receptor. Recognition and sensing of anions in an aqueous solution is an important challenge in supramolecular chemistry.[1] The fact that anions play important roles in living systems and in the environment inspires researchers to design highly selective synthetic receptors and probes.
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