<br/>Guanidine is frequently employed as a nucleophilic reagent and catalyst in various reactions. In terms of nitrogen-based nucleophiles, guanidines share similar reactivity with amines in many cases. In this regard, various guanidine derivatives which can be prepared by nucleophilic reactions of guanidine compounds have been reported.<br/>In this work, we report unique chemical structures derived from guanidines which are degradable under specific conditions. Those structures could be readily prepared from corresponding guanidines under mild reaction conditions. Structural analysis was conducted by NMR, mass spectroscopy and the exact structure was also confirmed by SC-XRD analysis. Interestingly, such compounds were rapidly decomposed into original guanidines in presence of various nucleophiles unlike amine-based analogs. Inspired by these results, degradable polymers with guanidine backbones were also prepared. According to GPC analysis, significant decrease in molecular weight was observed in nucleophilic solvents implying degradation of guanidine backbones.

Unique degradable guanidine derivatives and their polymers

2019 Fall National Meeting

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