The Synthesis Of Optically Active Poly-3-[9-(3-pyridyl)fluoren-9-yl] Propene Oxides And Their Application In Gas Chromatography

Gas chromatography is becoming increasingly important in medicine analysisand environmental monitoring. The resolution of chiral drugs is the focos of researchand gas chromatography plays an irreplaceable role in this field. Exploiting andutilizing chiral stationary phases that possess comprehensive chiral recognition abilityrepresents the tendency of the development of current chiral gas chromatography.Recent years, researchers have been greatly interested in chiral resolution basedon helical polymers because of their unique space structures. Our group havesynthetized poly-3-(9-alklyfuoren-9-yl) propene oxides and proved this polymerskeep sigle-handed helical conformation in solution. Liu Dexian used these helicalpolymers as HPLC chiral stationary phases and many racemic compounds such asbenzoin and DL-Methyl mandelate were separated successfully. So we apply thispolymers to chiral gas chromatography separation and expect a desirable outcomeWith the purpose of improving the ability of chiral resolution of this kind ofpolyether, we designed and synthesized (R)-(-)/(S)-(+)-3-[9-(3-pyridyl)fluoren-9-yl]propene oxide. These monomers were polymerized in bulky or solution, helicalpolyether were obtained. There is a pyridyl in the side chain of helical polyether. Thestructure of polymers was proved by nuclear magnetic resonance and MALDI-TOF MSand the polymers were confirmed to keep sigle-handed helical conformation byoptical rotation. As there are N atoms in the side chain of the polyether, thehydrogen-bond between the polymer and racemic compound can be strengthened, andthe ability of chiral resolution could be enhanced. In addition, with existence of Natoms, it is benefit for the polymer to coordinate with other metal atoms, so it shouldhave application in chiral catalysis field.In this paper, we prepared chiral capillary columns by coating helical polyethersinto capillary columns with dynamic or static method, and then we carried out thechiral resolution for some racemic compounds such as2-hexanol and citronellal usingthe prepared chiral capillary columns, but the results were not perfect, the main reasonwas that the polymerization degree of polyethers were not large enough or the racemiccompounds we selected were not fit for this kind of chiral stationary phases to beresolved. The coming research works are to try to enhance the molecule weight ofpoly[3-(9-(3-pyridyl)fluoren-9-yl) propene oxide] so that the chiral recognizing abilityto racemate can be enhance and to undergo study of the polymer’s application in the asymmetric catalysis.