Helicity induction and memory effect in poly(biphenylylacetylene)s bearing various functional groups and their use as switchable chiral stationary phases for HPLC

摘要: A series of poly(biphenylylacetylene)s (PBPAs) bearing various functional groups at the 4′-position biphenyl pendants were synthesized. The effects pendant on their macromolecular helicity induction and subsequent memory behaviors as well chiral recognition abilities stationary phases (CSPs) for high-performance liquid chromatography (HPLC) investigated. Both axial chirality PBPAs ester, acyloxy or carbamate induced by noncovalent interactions with an optically active alcohol more stably memorized compared to those in ether when was completely removed. a showed different toward racemates depending difference achiral used CSPs HPLC under normal phase conditions. PBPA exhibited excellent ability resolved many including axially compounds metal acetylacetonate complexes. Since obtained are soluble alcohol, it almost impossible switch enantioselectivities treatment coated-type solution column. By immobilizing chains onto silica gel, reversible control column could be achieved through alternate containing (R)- (S)-enantiomer thereby enabling repeated switching enantiomer elution order.