Abstract
Novel poly(allylaminocarboxylate) ligands, which have a carboxylate and the neighboring amide group in the same side-chain, were synthesized as model ligands for crystalline CaCO3 biominerals. Poly{N-allyl-malonamate}, poly{N-allyl-succinamate} and poly{4-allylcarbamoyl-butyrate} form 6-, 7- or 8-membered ring intra-side-chain NHO hydrogen bonds, respectively, between the carboxylate and the neighboring amide NH in the carboxylate anion state, although the formation of each intra-side-chain NHO hydrogen bond is independent on the stereoisomers of the polymer main-chain. In the polymer ligand–CaCO3 composites, strong binding of polymer ligands to CaCO3 crystals is caused by stabilizing a Ca–O (carboxylate) bond due to the pKa shift of carboxylic acid by the NHO hydrogen bond. Furthermore, the strong Ca binding in CaCO3 composites stabilizes the meta-stable morphology of CaCO3 vaterite crystals.
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