Carbodiimides are electrophilic functional groups that
react with
select nucleophiles under mild conditions. However, their potential
as platforms for postpolymerization modification has been relatively
underexplored. We describe the synthesis and radical polymerization
of a styrenic carbodiimide which undergoes rapid nucleophilic addition
with primary and secondary alkyl amines under ambient conditions,
even in the presence of other protic nucleophiles. The monomer is
amenable to both free and controlled radical (co)polymerization, and
we further demonstrate the utility of this approach by preparing covalent
adaptable networks through guanylation of the styrenic carbodiimide
with difunctional amines. These materials exhibit a variation in relaxation
times according to both the guanidine structure and concentration,
providing a facile means for tuning dynamic behavior.