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Số người truy cập: 112,298,152

 Immobilization of A Cellulose Carbamate‑type Chiral Selector onto Silica Gel by Alkyne‑azide Click Chemistry for The Preparation of Chiral Stationary Chromatography Phases
Tác giả hoặc Nhóm tác giả: Cuong Viet Bui, Thomas Rosenau, Hubert Hettegger
Nơi đăng: Cellulose; Số: None;Từ->đến trang: 1-18;Năm: 2022
Lĩnh vực: Khoa học công nghệ; Loại: Bài báo khoa học; Thể loại: Quốc tế
TÓM TẮT
A new synthesis strategy for the preparation of cellulose derivative-based chiral selectors
and the subsequent mild immobilization onto prefunctionalized 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, liquidstate NMR, GPC, TGA, and elemental analysis. The enantioseparation performance of the immobilizedtype chiral stationary phase was evaluated by HPLC with a set of representative chiral test analytes and different eluents and compared to a respective coatedtype (=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.
ABSTRACT
A new synthesis strategy for the preparation of cellulose derivative-based chiral selectors
and the subsequent mild immobilization onto prefunctionalized 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, liquidstate NMR, GPC, TGA, and elemental analysis. The enantioseparation performance of the immobilizedtype chiral stationary phase was evaluated by HPLC with a set of representative chiral test analytes and different eluents and compared to a respective coatedtype (=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.
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