Synthesis and application of structurally controlled benzoxazine as a host-guest compound

Abstract

Three types of benzoxazine dimer derivatives were successfully prepared, i.e., 2-hydroxyl benzyl type (4), (5), and (6), 2-benzoyl benzyl type (7), (9), and (11), and 2-acetyl benzyl type (8), (10), and (12). In the case of 2hydroxyl benzyl type, N,N-Bis (3,5-dimethyl-2-hydroxybenzyl) methylamine (5) exhibits the highest potassium picrate extraction for 31% and 58% at the host concentration of 7x10⁻²M and 7x10⁻¹M, respectively. The benzoyl benzyl and acetyl benzyl types compounds ((7)-(12)) show significant extraction ability up to 90%, for potassium picrate at the host concentration 7x10⁻²M. Qualitative analysis by ¹H-NMR technique shows picrate salt at δ = 8.8 ppm clarifying the stability of the complex formation.