Synthesis and polycondensation of difunctional tetraazacyclododecanes

We have developed a method for getting the tetraazacyclododecane structure into the backbone of a macromolecular chain. Two different reaction processes were investigated: polycondensation from diacid macrocycles using activation of the acid functions by thionyl chloride and polycondensation from diester macrocycles by aminolysis with different aliphatic diamines. Cyclic and linear oligomers have been obtained by polycondensation of 1,7-di(ethylacetate)-4,10-ditosyl-1,4,7,10-tetraazacyclododecane with ethylenediamine and dodecanediamine. In both cases, we managed to get oligomers containing several macrocycle units into their backbone. Furthermore, these results highlighted the classical problem of the competition between cyclisation and macromolecular chain formation encountered during polycondensation reactions.