Preaparation And Evaluation Of Imidazolyl-Phenyl-Propanol And Derivation-based HPLC Stationary Phase

Chiral ionic liquids with both chiral centre and characteristics of ionic liquid moiety canprovide a new approach for chiral separation, chiral synthesis and chiral catalyst. Theobjective of this thesis is to prepare and evaluate chromotography mechanism of new HPLCstationary phases based on imidzolyl-phenyl-propanol or it’s derivatives.Using L-phenylalanine as the starting material, through reduction and condensation,chiral imidazolyl-phenyl propanol, L-2-（1-imidazolyl）-3-phenyl-1-propanol]（ImPh-PrOH）was synthesized. The structure of ImPh-PrOH was confirmed by¹H NMR,¹³C NMR, IRand MS. To improve chiral separation ability: ImPh-PrOH was coupled withmethylenediphenyl diisocyanate and the new compound, diphenylmethane4,4′-bis[2-（1-imidazolyl）-3-phenyl-1-propanol carbamate]（ImPh-Carb） was obtained. Thestructure of ImPh-Carb was also confirmed by¹H NMR,¹³C NMR, IR and MS. Meanwhile,the optimal reaction conditions was obtained as following: n（ImPh-PrOH）:n（MDI）=2.01:1,the reaction was refluxed in toluene for10h under argon, which gives a yields of41%.ImPh-PrOH and ImPh-Carb were bonded to silica respectively to prepareSil-ImPh-PrOH and Sil-ImPh-Carb stationary phase. Both stationary phase were characteredby EA and TG-DSC, and evaluated by a limited set of neutral aromatic probe solutes utilizingthe LSER methodology under reversed-phase. The comparison reveals Sil-ImPh-Carbstationary phase exhibited difference in the hydrogen bond acceptance, cavity effects anddispersive interaction properties, besides the similar interaction properties of hydrophobic andÏ€-Ï€ interactions, which also certify the appropriate application of Sil-ImPh-Carb stationaryphase under normal phase.Sil-ImPh-Carb stationary phase was evaluated by using different solute probes includingaromatic compounds, phenols, carbamate pesticides and amino acids under reverser phase. thenew stationary phase interacts with analytes by multiple mechanisms but mainly byhydrophobic. Carbamate pesticides, amino acids and organophosphorus pesticides wereselected as analytes to evaluate the chromatographic performance of Sil-ImPh-Carb stationaryphase under normal phase.The results indicated the existance of multiple interactions, such as Ï€-Ï€, hydrogen bond, charge transfer interaction, dipole/dipole and ion/dipole interactions. Theexistence of multiple mechanisms and better separation results indicated the potentialapplication of Sil-ImPh-Carb phase in both reversed-phase （RP） and normal-phase （NP）modes.