Covalent anchoring of a cellulose per(phenyl carbamate) chiral selector onto silica gel through alkyne-azide click chemistry and its utilization in HPLC

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F25%3A43933728" target="_blank" >RIV/60461373:22310/25:43933728 - isvavai.cz</a>

Result on the web

<a href="https://link.springer.com/article/10.1007/s10570-025-06497-9?utm_source=getftr&utm_medium=getftr&utm_campaign=getftr_pilot&getft_integrator=clarivate" target="_blank" >https://link.springer.com/article/10.1007/s10570-025-06497-9?utm_source=getftr&utm_medium=getftr&utm_campaign=getftr_pilot&getft_integrator=clarivate</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1007/s10570-025-06497-9" target="_blank" >10.1007/s10570-025-06497-9</a>

Result language

angličtina

Original language name

Covalent anchoring of a cellulose per(phenyl carbamate) chiral selector onto silica gel through alkyne-azide click chemistry and its utilization in HPLC

Original language description

High-performance liquid chromatography is a powerful tool for enantioseparation, based on chiral stationary phases as separation media. Cellulose-based chiral selectors are among the most successful ones used for the preparation of chiral separation materials, exploiting the inherent chirality of the homopolymer. Compared to initial coating-type chiral stationary phases solely deposited onto silica as the chromatographic support, covalently immobilized selectors exhibit a significantly broader scope of applicable eluents, but appropriate synthetic strategies are still scarce. In this work, we present the application of the Cu(I)-catalyzed Huisgen alkyne-azide click reaction as a means to covalently immobilize a cellulose 3,5-dichlorophenyl carbamate-type chiral selector to a silica-based chromatographic support. Cellulose was first functionalized with 3,5-dichlorophenyl carbamate groups (DS = 2.35) and 4-propargyloxy-3,5-dichlorophenyl carbamate groups (propargyl carbamate DS = 0.45, overall DS = 2.80), then clicked to 3-azidopropyl-functionalized silica gel as the chromatographic support affording a 9 wt.% covalently functionalized chiral stationary phase. The chiral selector was comprehensively characterized by means of ATR-FTIR and NMR spectroscopy, and elemental analysis. The degrees of substitution of both, overall functionalization and propargyl-anchor substitution, were estimated by NMR spectroscopy. Additionally, coating-type chiral stationary phases with 9 and 20 wt.% loadings were prepared. All chiral phases were tested with regard to their separation performance using a representative set of racemic analytes under usual normal-phase conditions. Solvent compatibility and thus the chemical robustness of the immobilized stationary phase was studied using higher shares of stronger, more polar solvents in the eluent, i.e., ethyl acetate, tetrahydrofuran and chloroform. The covalently linked selectors performed very favorably with regard to separation performance and stability.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

—

OECD FORD branch

10406 - Analytical chemistry

Project

—

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2025

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

CELLULOSE

ISSN

0969-0239

e-ISSN

1572-882X

Volume of the periodical

32

Issue of the periodical within the volume

9

Country of publishing house

NL - THE KINGDOM OF THE NETHERLANDS

Number of pages

15

Pages from-to

5247-5261

UT code for WoS article

001461165400001

EID of the result in the Scopus database

2-s2.0-105002162982