Immobilization of a cellulose carbamate-type chiral selector onto silica gel by alkyne-azide click chemistry for the preparation of chiral stationary chromatography phases

Abstract A new synthesis strategy for the preparation of cellulose derivative-based chiral selectors and subsequent mild immobilization onto pre-functionalized silica gel are introduced, utilizing Cu(I)-catalyzed alkyne-azide Huisgen cycloaddition (“ click ”) chemistry. 3,5-dimethylphenyl carbamate derivative carrying propynyl groups was prepared by a combination carbonate aminolysis isocyanate For immobilization, 3-azidopropyl-functionalized as an inert carrier used, synthesized via 3-chloropropyl intermediate. The selector, well inorganic/organic hybrid materials (silica gel/chiral selector), were comprehensively characterized ATR-FTIR, solid-state 13 C 29 Si NMR, liquid-state GPC, TGA, elemental analysis. enantioseparation performance immobilized-type stationary phase evaluated HPLC with set representative test analytes different eluents compared to respective coated-type (=non-covalently bound) same selector quality quantity on matrix. did not adversely affect separation performance; contrary, in some chromatographic separations surprisingly even surpassed coated reference material. Graphical abstract