Separation of enantiomers by open‐tubular capillary electrochromatography using (R)‐1,1′‐bi‐2‐naphthol derivatives as chiral stationary phases

Abstract

Bi-2-naphthol is a kind of commonly used chiral molecule that has been widely applied in the fields of molecular recognition, materials, and asymmetric synthesis. Since there are few examples of utilizing (R)-1,1′-bi-2-naphthol derivatives used as stationary phases to resolve chiral compounds by capillary electrochromatography, three The (R)-1,1′-bi-2-naphthol derivatives were synthesized and used as stationary phases to fabricate capillary columns for chiral separation. Some of the experimental parameters for enantiomer separations were optimized. the columns exhibited good enantioselectivity for chiral alcohols, amines, ketones, and so forth. The relative standard deviation of enantiomer retention time in run-to-run, day-to-day and column-to-column experiments were 1.02, 4.45 and 5.60% using the (R)-(3,3′-di-p-cyanophenyl)-2,2′-dimethoxyl-1,1′-binaphthalene coated column, and 2.38, 3.20 and 4.94% using the (R)-(3,3′-dip-acetylphenyl)-2,2′-dimethoxy-1,1′-binaphthalene coated column. The results indicated that the (R)-1,1′-bi-2-naphthol derivatives may have utility in capillary electrochromatography.

Recent applications and chiral separation development based on stationary phases in open tubular capillary electrochromatography (2019–2022)

“…This column has chiral recognition ability and can separate three basic drugs. 1,1′-bi-2-naphthol (BINOL), the guest molecule for assessing the separation ability, was used as the SP of the OT column [ 43 ], being able to separate chiral alcohols, amines, ketones, etc. This suggests that some analytes with chiral recognition properties, such as some drugs, antibiotics, proteins, and non-pathogenic bacteria, can be used as SPs for enantiomeric separation.…”

“…Overall, we provide readers interested in OT-CEC with the most up-to-date overview of this field, and the related new SPs from 2019 to 2022 are listed in Table 1 [ 3 , [5] , [6] , [7] , [8] , [9] , [10] , [11] , [12] , [13] , [14] , [15] , [16] , [17] , [18] , [19] , [20] , [21] , [22] , [23] , [24] , [25] , [26] , [27] , [28] , [29] , [30] , [31] , [32] , [33] , [34] , [35] , [36] , [37] , [38] , [39] , [40] , [41] , [42] , [43] , [44] , [45] , [46] , [47] , [48] , [49] , [50] , [51] , [52] , [53] , [54] , [55] , [56] , [57] , [58] , [59] , [60] , [61] , [62] , [63] , [64] , [65] ]. PubMed and Web of Science were used to search the following characters (also their acronyms) alone or in combination: “Open tubular”, “Capillary electrochromatography”, “Chiral separation”, “Stationary phase”, and “Coating” for relevant literature to analyze recent OT-CEC developments.…”