Molecular Recognition Properties of p-Phenylenediamine-Imprinted Polymers / 分析化学

ABSTRACT

Two p-phenylenediamine (p-PD)-imprinted polymers, P (MAA) and P (AA), were synthesized using methacrylic acid (MAA) and acrylamide(AA) as functional monomer, respectively, in order to prepare molecular recognition material with high selectivity for p-PD and explore the feasibility of methods such as molecular spectrometry and computational approach of quantum chemistry for the selection of functional mono mer with high imprinting efficiency.The molecular recognition properties of the imprinted polymers were evaluated by high performance liquid chromatography.The results indicated that P(AA) exhibited no imprint ing effect for p-PD, while P(MAA) can bind p-PD selectively(k' =3.57), which showed remarkable imprint ing effect (IF=2.95), and p-PD and its analogues o-phenylenediamine and p-aminobenzoic acid can almost realize baseline separation on P (MAA) column in the mobile phase of methanol.Furthermore, we made a comparative study on the interaction of p-PD with MAA and AA by spectroscopic techniques such as UV and fluorometry as well as HF/6-31G~* computational approach.The results demonstrated that the complex of p-PD-MAA was more stable than that of p-PD-AA, which can give a good explanation for the molecular recog nition properties of P (MAA) and P (AA).The study indicated that both molecular spectrometry (UV and fluorometry)and computational approach of quantum chemistry can be employed as efficient means for the selection of efficient functional monomer.The results showed that fluorometry is sensitive and convenient for the choice of functional monomer if the template molecule is fluorescent.