RNA-inspired phosphate diester dynamic covalent networks
POLYMER CHEMISTRY(2023)
Abstract
Neighboring group assisted rearrangement substantially increases relaxation rates in dynamic covalent networks, allowing easier (re)processing of these materials. In this work, we introduce a dynamic covalent network with anionic phosphate diesters as the sole dynamic group, incorporating & beta;-hydroxy groups as a neighboring group, mimicking the self-cleaving backbone structure of RNA. The diester-based networks have slightly slower dynamics, but significantly better hydrolytic (and thermal) stability than analogous phosphate triester-based networks. Catalysis by the & beta;-hydroxy group is vital for fast network rearrangement to occur, while the nature of the counterion has a negligible effect on the relaxation rate. Variable temperature 31P solid-state NMR demonstrated a dissociative bond rearrangement mechanism to be operative. Phosphate diesters were used as reactive moieties in dynamic covalent networks, harnessing internal catalysis by a neighboring & beta;-hydroxy group. These networks are more hydrolytically stable than their phosphate triester counterpart.
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Key words
phosphate,rna-inspired
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