(1) Institute of Organic Chemistry, University of Tuebingen, Auf der Morgenstelle 18, 72076 Tuebingen, Germany
Abstract:
Three poly(ethylene-co-acrylic) acid copolymers (–CH2CH2–)xCH2CH(CO2H)–]y with different chain lengths and mass fractions of acrylic acid were covalently immobilized as stationary phases on silica via two variants of spacer molecules (3-aminopropyltriethoxysilane and 3-glycidoxypropyltrimethoxysilane). Different mobilities of the alkyl chains in the stationary phases were observed using 13C solid-state NMR spectroscopy. The stationary phases with more rigid trans-ordered alkyl chains had better selectivity for geometric -carotene and xanthophyll isomers (provitamin A derivatives). Also, all the separations of the analytes were affected by polar interactions with the chromatographic sorbent. This was further proved by separating more polar cis/trans retinoic acid isomers (vitamin A derivatives). 13C high-resolution/magic-angle spinning (HR/MAS) NMR measurements of the chromatographic sorbents suspended in the mobile phase confirmed a dependence of molecular shape recognition ability on alkyl chain conformation.