Molecular design of benzoxazines:|ban approach for inclusion compounds

Abstract

A series of benzoxazine dimer, esterified dimer, and cyclic oligobenzoxazine derivatives having different phenol rings and electron donor groups were designed and successfully prepared as structural characterized by FTIR, 'H-NMR, EA, and MS. The inclusion phenomena with metal ions were studied by Pedersen’s technique using metal (sodium, and potassium) picrate salts, and the prepared dimers at the concentrations of 5.6x102 and 7x10 5 M, respectively. Benzoxazine dimers showed ion extraction ability at 43-62% while that of esterified dimers at 75-94%. The ion extraction ability depended on the type of benzoxazine dimer implies the effect of hydrogen bonding network and the electron rich area in each benzoxazine dimer structure. For cyclic oligobenzoxazine, unexpectedly, the ion interaction could not be observed which implies that the cavity size was not proper for the sodium and potassium metal ions.