Synthesis and characterization of nucleic base functionalized molecules as potential precursors for stimuli-responsive hydrogels and a computational study of sequential amine substitution on cyanuric chloride

Abstract

Hydrogels, being highly absorbent materials, have been widely recognized for their applications in tissue engineering and as artificial skin. Particularly important are the stimuli responsive hydrogels that respond to external stimuli. Magnetic responsive hydrogels are an example of such type of hydrogels that are affected by an alternating magnetic field. Several ferrogels have been synthesized and investigated for various applications. However, the use of the hydrogen bonding ability of nucleic bases have not been considered. Thus, it is imperative to start with designing nucleic base functionalized molecules as precursors for these magnetic responsive hydrogels with a catechol source to incorporate the use of iron oxide nanoparticles. Herein, we report the synthesis and characterization of an 3-(6-amino-9H-purin-9-yl)propanehydrazide functionalized polymer and a trisubstituted 1,3,5-triazines 3-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanehydrazide and dopamine substituents as potential precursors for the development of magnetic responsive hydrogels. This is achieved via the selective nucleophilic substitution reaction of cyanuric chloride which is also thoroughly theoretically investigated. The presence of the nucleic bases is expected to promote hydrogen bonding between the two synthesized precursors while the dopamine is used as an anchoring group for iron oxide nanoparticles.