Synthesis and binding properties of hybrid cyclophane-azamacrocyclic receptors |
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Authors: | Benniston Andrew C Gunning Patrick Peacock Robert D |
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Institution: | Molecular Photonics Laboratory, School of Natural Sciences (Chemistry), Bedson Building, University of Newcastle, Newcastle upon Tyne NE1 7RU, UK. A.C.Benniston@ncl.ac.uk |
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Abstract: | Three new azamacrocyclic-cyclophane hybrid receptors L(1), L(2), and L(3) 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 pK(a) of this bound water in the zinc(II) complex of L(1) and L(2) is approximately 7.5. Isothermal calorimetry experiments carried out on ZnL(1)(L2)(OH(2))](CF(3)SO(3))(2) and Zn(2)L(2)(OH(2))(2)](CF(3)SO(3))(4) in buffered water (pH 7.4) at 25 degrees C show that the host strongly binds a series of phosphate derivatives. In comparison, the complex CuL(3)(OH(2))(2)](CF(3)SO(3))(2) is a poor receptor toward phosphate substrates. |
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