Abstract
A new synthesis strategy for the preparation of cellulose derivative-based chiral selectors and the subsequent mild immobilization onto pre-functionalized silica gel are introduced, utilizing Cu(I)-catalyzed alkyne-azide Huisgen cycloaddition (“click”) chemistry. A cellulose 3,5-dimethylphenyl carbamate derivative carrying propynyl carbamate groups was prepared by a combination of carbonate aminolysis and isocyanate chemistry. For immobilization, 3-azidopropyl-functionalized silica gel as an inert carrier was used, synthesized via a 3-chloropropyl intermediate. The chiral selector, as well as the inorganic/organic hybrid materials (silica gel/chiral selector), were comprehensively characterized by ATR-FTIR, solid-state 13C and 29Si NMR, liquid-state NMR, GPC, TGA, and elemental analysis. The enantioseparation performance of the immobilized-type chiral stationary phase was evaluated by HPLC with a set of representative chiral test analytes and different eluents and compared to a respective coated-type (=non-covalently bound) chiral stationary phase carrying the same selector quality and quantity on the same silica gel matrix. The immobilization did not adversely affect the chiral separation performance; on the contrary, in some chromatographic separations the immobilized-type chiral stationary phase surprisingly even surpassed the coated reference material. Graphical abstract: [Figure not available: see fulltext.].
Original language | English |
---|---|
Pages (from-to) | 915-932 |
Number of pages | 18 |
Journal | Cellulose |
Volume | 30 |
Issue number | 2 |
DOIs | |
Publication status | Published - Jan 2023 |
MoE publication type | A1 Journal article-refereed |
Keywords
- Carbonate aminolysis
- Cellulose derivatization
- Chiral chromatography
- Chiral stationary phase
- Click chemistry
- Enantioseparation
- Inorganic/organic hybrid materials