Self-Complementary Dimers of Oxalamide-Functionalized Resorcinarene Tetrabenzoxazines

Abstract

Self-complementarity is a useful concept in supramolecular chemistry, molecular biology and polymeric systems. Two resorcinarene tetrabenzoxazines decorated with four oxalamide groups are synthesized and characterized. The oxalamide groups possessed self-complementary hydrogen bonding sites between the carbonyls and amide groups. The self-complementary nature of the oxalamide groups resulted in self-included dimeric assemblies. The hydrogen bonding interactions within the tetrabenzoxazines give rise to the formation of dimers, which are confirmed by single crystal Xray diffractions analysis and supported by NMR spectroscopy and mass spectrometry. The self-included dimers are connected by numerous and strong intermolecular N-H···O and C-H···O hydrogen bonds supplemented with C-H···p interactions, forming one-dimensional polymers, which are then further linked into threedimensional networks.