Development of star-shaped benzoxazine supramolecule

Abstract

Synthesis of star-shaped structure with four-arm benzoxazine dimers through the reaction between tetra-tosylated pentaerythritol as a core molecule and benzoxazine dimers as arm molecules is focused. A model reaction of phenol with core molecule suggests that the reaction for four-arm substitution is prohibited, and only two-arm star product substituted with phenols was obtained. In case of the reactions between benzoxazine dimers and core molecule, surprisingly, it does not give only two-arm star product, but also show the formation of cyclic benzoxazine dimers when the amount of case catalyst is excess. Furthermore, the mechanism related to this reaction was proposed as a model for substitution reaction of multi-tosylated core molecule and phenolic derivatives.