An efficient metal-templated route to C-functionalised derivatives of [12]aneN₄

The cyclo cocondensation of triethylenetetramine with arylpyruvaldehydes is templated by iron(III) chloride, to give a [12]aneN₄ type diimine complex intermediate which may be reduced and demetallated in situ with sodium borohydride giving the saturated [12]aneN₄ metal-free macrocycle in up to 60% overall yields; photophysical studies are used to demonstrate the similarity between the aryl functionalised [12]aneN₄ derivatives formed by this route and analogues derived from [12]aneN₄ itself.