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Synthesis and binding properties of hybrid cyclophane - Azamacrocyclic receptors

Lookup NU author(s): Professor Andrew Benniston


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(Chemical Equation Presented). Three new azamacrocyclic-cyclophane hybrid receptors L1, L2, and L3 have been synthesized that incorporate either 1,4,7,10-tetraazacyclododecane (cyclen) or 1,4,7-triazacyclononane (tacn) unit-(s) tethered via a short amidic spacer to an electron donor and a H-bonding crown ether polycycle. The crown ether is designed to act as a host toward biologically relevant guests, whereas the macrocycle can coordinate a zinc(II) or a copper(II) ion. The pKa of this bound water in the zinc(II) complex of L1 and L2 is ∼7.5. Isothermal calorimetry experiments carried out on [ZnL 1(OH2)](CF3SO3)2 and [Zn2L2(OH2)2](CF3SO 3)4 in buffered water (pH 7.4) at 25°C show that the host strongly binds a series of phosphate derivatives. In comparison, the complex [CuL3(OH2)2](CF3SO 3)2 is a poor receptor toward phosphate substrates.

Publication metadata

Author(s): Benniston AC, Gunning P, Peacock RD

Publication type: Article

Publication status: Published

Journal: Journal of Organic Chemistry

Year: 2005

Volume: 70

Issue: 1

Pages: 115-123

ISSN (print): 0022-3263

ISSN (electronic): 1520-6904

Publisher: American Chemical Society


DOI: 10.1021/jo048621o

PubMed id: 15624913


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