I've got a question regarding the functionalization of polyallylamine. I am not much of a polymer chemist, so please treat me with leniency.
As part of my PhD project I would like to functionalize the amines of polyallylamine (or any similar polymer that consists of a aliphatic backbone and has amines in the side-chains). Specifically I would like to react the amine with an Acylchloride, actually with a Fmoc-chloride derivative I synthesized. The reaction I try to achieve can be depicted as something like: https://imgur.com/a/0tHf73S
What would be a proper synthetic strategy to go about it? I know I can usually react amines with Fmoc-chloride in DCM in the presence of DIPEA as a base. But I can not really apply this procedure here, since the polymer behaves weirdly in DCM, as soon as it touches DCM it becomes a gum-like, insoluble, unusable blop.
I've got two formulations of the polyallylamine: on the one hand the hydrochloride (which of course is not nucleophilic) as a solid https://www.sigmaaldrich.com/NL/en/product/aldrich/283223
and on the other hand I have a watery solution (which is messing with Acylchlorides) https://www.sigmaaldrich.com/NL/en/product/aldrich/479136
I just naively tried to react the watery polymer solution with sulfonated Fmoc-Cl in water/dioxane with Na2Co3 as a base, but under these conditions the Fmoc-Cl would already start cleaving and causing troubles, also I had no proof the desired reaction actually took place.
Does anyone of you know a good strategy on how to functionalize polyallyamine side-chain amines? I would not need to react every single active site on the polymer, I think it would be sufficient if only like 20-40mol% of the amines would be reacted. But how to achieve that? How to access the active sites of these kind of polymers? I am grateful for any suggestion on how to go about it, as well as for any literature on the topic (I could not find lots of useful literature).