Ordered Layered Dendrimers: the Marriage between Phosphorhydrazone Dendrimers and Triazine–Piperazine Dendrimers

Within the dendrimer family1, phosphorus dendrimers are of paramount interest due to the remarkable versatility of phosphorus chemistry, which enables: a) a large scope for... [ view full abstract ]

Within the dendrimer family¹, phosphorus dendrimers are of paramount interest due to the remarkable versatility of phosphorus chemistry, which enables: a) a large scope for original methodologies for the synthesis of new dendrimers, b) access to several different types of phosphorus dendritic structures, each having their own chemical properties, and c) many applications, spanning from nanomedicine to materials science². In this dendrimer family, triazine dendrimers offer also many potentialities. These materials are derived from cyanuric chloride and diamines; their developpment takes advantage of the wide range of available diamines and the stepwise substitution of the triazine nucleus³.

           We have developed a new approach for the synthesis of dendrimers intrinsically composed in alternation of building blocks pertaining to two known families of dendrimers: phosphorhydrazone dendrimers and triazine–piperazine dendrimers⁴.  To this extend, 4-hydroxybenzaldehyde, classically used in the synthesis of phosphorhydrazone dendrimers, was substituted by a triazine-piperazine monomer bearing one phenol group and two aldehyde functions. These mixed dendrimers with layered controlled architecture exhibit properties coming not only from their dendrimer precursors but are also inherent from their unique combination. Remarkably, these dendrimers incorporating redox-active organic entities allow for the first time the monitoring of the growth of an organic dendrimer by electrochemistry while highlighting an even–odd generation behavior.

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