Solid‐phase extraction with metal–organic frameworks for the analysis of chiral compounds

Abstract

Metal-organic frameworks (MOFs) are excellent porous materials with nanoscale cavities and high surface areas, which make them promising as novel adsorbents in solid-phase extraction (SPE). In this article we report a new application of the chiral MOF [Zn (D-Cam) (4,4'-bpy)] in SPE used for the measurement of the enantiomeric excess (ee) of (±)-1,1'-bi-2-naphthol. Several important experimental parameters that may influence the extraction efficiency were investigated and optimized. Under the optimum conditions, a good linearity (R > 0.999) was found between the ee value and the reciprocal of the peak areas. When compared with the actual ee measured using chiral HPLC, the SPE-based assay also showed good accuracy and precision. The results showed that SPE based on chiral MOFs as adsorbents is a simple and effective method for the determination of the ee values of chiral compounds.

Metal–organic frameworks in chiral separation of pharmaceuticals

“…151 Therefore, selecting sorbent material and elution solvent plays a crucial role in determining separation efficiency. 152 The MOF has emerged as a new sorbent class due to its large surface area, pore size, high sensitivity, good chemical selectivity, and diversity in its chemical structure. 153 This section discusses different MOFs as sorbents and their applications in SPE.…”

“…Analysis of (±)-1,1 0bi-2-naphthol was performed with a 5% error. 152 A new MOF [Co(L-tyr)] n (L-tyrCo) was synthesized and utilized as a sorbent to determine ee of (±)-1,1 0 -bi-2-naphthol using SPE. 163 [Zn 2 (D-Cam) 2 (4,4 0 -bpy)] n and [Co(Ltyr)] n (L-tyrCo) MOFs showed good accuracy and promising results for determination of ee of chiral compounds.…”

“…163 [Zn 2 (D-Cam) 2 (4,4 0 -bpy)] n and [Co(Ltyr)] n (L-tyrCo) MOFs showed good accuracy and promising results for determination of ee of chiral compounds. 152,163 A chiral Cu-II 3D-MOF-based on tripeptide Gly-L-His-Gly (GHG) was developed for chiral selective separation of ephedrine and methamphetamine. The developed MOF [Cu (GHG)] was used as sorbent in SPE and isolated 50% of (+)-ephedrine enantiomer in 4 min from a racemic mixture.…”

“…The retained analyte is extracted using a solvent having more affinity for the analyte 151 . Therefore, selecting sorbent material and elution solvent plays a crucial role in determining separation efficiency 152 . The MOF has emerged as a new sorbent class due to its large surface area, pore size, high sensitivity, good chemical selectivity, and diversity in its chemical structure 153 .…”

Determination of Enantiomeric Excess by Solid-Phase Extraction Using a Chiral Metal-Organic Framework as Sorbent

“…These unique features make MOFs attractive as advanced media for separation [ 14 , 15 ], gas adsorption and storage [ 16 , 17 ], catalysis [ 18 , 19 ], sensing [ 20 , 21 ], imaging [ 22 ], and other applications. To date, a number of MOFs, such as MIL-53 [ 23 , 24 ], MIL-100 [ 23 ], MIL-101 [ 23 , 25 , 26 ], MOF-199 [ 27 , 28 ], ZIF-8 [ 29 , 30 ], ZIF-67 [ 31 ], ZIF-90 [ 32 ], MIL-88B [ 33 ], MAF-X8 [ 34 ], MOF-5 [ 35 ], UIO-66 [ 36 ], and UIO-67 [ 37 ], have been used as adsorbents for SPE or solid-phase microextraction (SPME) and shown much promise [ 14 , 38 , 39 ].…”