Copolymerization of an indazole ligand into the self-polymerization of dopamine for enhanced binding with metal ions

Abstract

5,6-Dihydroxy-1H-indazole (DHI) is able to self-polymerize through the same mussel-inspired chemistry responsible for generating poly(dopamine) (PDA), demonstrating the potential to expand this class of catecholamine-exclusive chemistry onto heterocyclic catechol derivatives for the preparation of functional materials. Although DHI exhibits slower polymerization kinetics compared to dopamine, the two chemical species are compatibly polymerizable under the same reaction conditions and allow the preparation of copolymer coatings in different molar ratios. Of these copolymers, the 1 : 3-copolymer (DHI-to-dopamine ratio) has demonstrated adequate structural stability as a polymer coating. While PDA performs as an intact framework, the incorporated DHI enhances the colloidal stability and provides additional coordinating functionality through the pyrazole moieties. The 1 : 3-copolymer was fabricated into polymer capsules which exhibit negligible cytotoxicity towards murine dermal fibroblasts (L929) and enhanced binding behaviour towards copper(II). This represents a new channel for fabricating cargo carriers for biomedical applications that involve the use of transition metal-based species.