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The synthesis of the new cofacial binuclear zinc complex [Zn(2)(L)] of a Schiff-base pyrrole macrocycle is reported. It was discovered that the binuclear microenvironment between the two metals of [Zn(2)(L)] is suited for the encapsulation of anions, leading to the formation of [K(THF)(6)][Zn(2)(μ-Cl)(L)]·2THF and [Bu(n)(4)N][Zn(2)(μ-OH)(L)] which were characterized by X-ray crystallography. Unusually obtuse Zn-X-Zn angles (X = Cl: 150.54(9)° and OH: 157.4(3)°) illustrate the weak character of these interactions and the importance of the cleft preorganization to stabilize the host. In the absence of added anion, aggregation of [Zn(2)(L)] was inferred and investigated by successive dilutions and by the addition of coordinating solvents to [Zn(2)(L)] solutions using NMR spectroscopy as well as isothermal microcalorimetry (ITC). On anion addition, evidence for deaggregation of [Zn(2)(L)], combined with the formation of the 1:1 host-guest complex, was observed by NMR spectroscopy and ITC titrations. Furthermore, [Zn(2)(L)] binds to Cl(-) selectively in THF as deduced from the ITC analyses, while other halides induce only deaggregation. These conclusions were reinforced by density functional theory (DFT) calculations, which indicated that the binding energies of OH(-) and Cl(-) were significantly greater than for the other halides.

Selective Anion Binding by a Cofacial Binuclear Zinc Complex of a Schiff-Base Pyrrole Macrocycle