Study On Synthetic Of BINOL, Amino Acid And Derivatives Molecularly Imprinted Polymers And Their Application In The Chiral Resolution

Molecularly imprinted polymer (MIPs) is a new kind of macromolecular material with high molecular recognition characteristics. It has been developed quickly in recent years. Molecular imprinting technology (MIT) has been a hot issue to be investigated because it can provide the polymers that have high recognization and selectivity properties to objective molecule. Three kinds of MIPs were synthesized by R-BINOL, animo acid and their derivatives. On the basis of the review to the progress of MIT, the following experiments were carried on:1. R-(+)-1,1'-bi-2-naphthol imprinted polymers were prepared, and the MIPs were used as HPLC solid phase for resolutions of bi-naphthyl compounds. The self-assembly between template and functional monomer were studied by 1H NMR. The SEM characteristic formulations of the MIPs further indicated that it is a polymer with multihole structure which provides good diffusion channels for the solutes. The results suggested that the dissociation constant for the R-enantiomer, the imprinting molecule, was lower than that for the S-enantiomer (3.28mmol/L and 12.18mmol/L, respectively). The chromatographic conditions such as flow rate, mobile phase, load amount and column temperature were investigated, and the chiral separation mechanism was disscussed.2. Using functional monomer (acrylamide) and crosslinker (EDMA), MIPs with recognition properties to L-phenylalanine (L-Phe) were prepared by photo polymerization method in the presence of template (L-Phe). The experimental results indicated that the MIPs had higher L-Phe binding ability than D-Phe. On the basis of isothermal binding thermodynamic investigation, the recognition mechanism between L-Phe and MIPs recognition group was described by Langmuir isothermal binding. Therefore, some thermodynamic parameters were obtained:ΔH= 3.75kJ/mol,ΔS= 28.27J/(mol-K),ΔG298.15=-4.67kJ/mol and the apparent activation energy was 3.75kJ/mol.3. In the presence of amino acid derivatives, MIPs were synthesized and evaluated by HPLC. All the MIPs made in this investigation exhibited good enantiomeric recognition of the imprinted species when evaluated by HPLC. The separation factor is 2.86. The specificities of MIPs in terms of size, shape, and hydrogen-bonding selectivity were also investigated in detail.