Metal oxide-based Nanoparticles in the identification and separation of enantiomers.

Core/Shell	Chiral selector	Chiral compound(s)	Separation/detection	Remarks	Ref.
Fe3O4	β-CD	Alanine (Ala), Trp, tyr	Optical polarimetry	β-CD modified Fe3O4 nanoparticles mostly absorbed (l)-Trp more than (d)-Trp	68
Fe3O4/SiO2	Carboxymethyl-β-CD (CM-β-CD)	Tryptophan (Trp), phenylalanine (Phe), tyrosine (Tyr)	UV-vis	Qualitatively the resolution predicts from the absorption capacity: (l)-Trp > (l)-Phe > (l)-tyr and (d)-Trp > (d)-Phe > (d)-tyr	69
GO/Fe3O4	β-CD	Trp	OT-CE	Av size about 8 nm. Trp enantiomers resolution was 1.65 and was achieved within 50 s	70
Fe3O4-PS	Helical substituted polyacetylene	1-Phenylethylamine	Optical rotation measurement	Adsorption of the (R)-form was much higher than the (S)-form of 1-phenylethylamine, e.g., 24.60% at 12 h, compared to 1.76%	76
Fe3O4/SiO2	CM-β-CD	Trp, Phe, Tyr	HPLC-UV	ee for separation (d,l)-Trp, (d,l)-Phe, and (d,l)-Tyr racemic were 94%, 73%, and 58%, respectively	71
Fe3O4/SiO2	Amine functionalized derivatives β-CD (AmCD)	N-(3,5-Dinitrobenzoyl) phenlglycine, N-(1-phenylethyl) phthalamic acid	HPLC-UV	Am-CD-MNPs preferred to adsorb (S)-form enantiomer, i.e., about 50% for (S)-phenylglycine and 30% for (S)-phthalamic acid, while the (R)-form was not carried	72
Fe3O4	BSA	Ibuprofen, ofloxacin	HPLC-UV	Av size ∼13.3 nm. At single-stage operation, ee value of racemic ibuprofen and ofloxacin was 13% and 14%, respectively. The multistage process enhances the ee value up to 54% and 39%, respectively	81
GO/Fe3O4	BSA	Trp, threonine, propranolol	OT-CE	Rs of Trp, threonine, and propranolol were 1.22, 1.9, and 2.1, respectively	82
Fe3O4@Au	BSA	Tryptophan, threonine, ofloxacin	MCE	The size of Fe3O4 NPs and Fe3O4@Au NPs were about 8–10 nm and 25–30 nm, and the thickness of the Au shell was 9 nm. Rs were 1.67 (Trp). 1.79 (threonine) and 2.15 (ofloxacin)	83
Fe3O4@SiO2@PAMAM	BSA	Tryptophan, phenylalanine, histidine	HPLC-PDA	The mean diameter of Fe3O4 was 400 nm, thickness silica layer was 60 nm. BSA–PMNPs gave stronger interactions the (−)-enantiomers than the (+)-enantiomers	84
Fe3O4@SiO2@PAMAM	HSA	Trp, warfarin, ibuprofen	CD and CE	Av diameter of a core–shell structure was 600 nm. HSA–PMSM preferred to interact with the (−)-enantiomers than (+)-enantiomers for (d,l)-Trp and warfarin. In contrast, ibuprofen was the other way around	85
Fe3O4/SiO2	Cationic β-CD	Dansyl (d,l)-valine, dansyl (d,l)-leucine, dansyl (d,l)-phenylalanine	CE	Av particle size was about 580 nm. Cationic-β-CD-modified Fe3O4/SiO2 interacted better with the (l)-enantiomer. Enantiomeric excess for Phe, Leu, and Val are 12.3, 10.0, and 9.6, respectively	73
Fe3O4/SiO2	Maleic anhydride-β-CD (MAH-β-CD)	Trp, Phe, 2-phenylglycine, chlorpheniramin	CE	Av. size of 550 nm. MAH-β-CD-modified Fe3O4 microspheres interacted better with (−)-enantiomers than (+)-enantiomers. It was obtained ee of 12.6% and 13.7% for enantioseparation of (d,l)-trp and chlorpheniramine, respectively	74
Fe3O4@PDA	MIP	Tryp, tyrosine, Gly–Phe, ofloxacin	OT-CE	Fe3O4@PDA NPs have an average diameter of 146 nm. ∼8 nm in thickness of MIP. The resolution factor was about 1.65, 1.76, 3.15, and 2.16 for (d,l)-Trp, (d,l)-tyrosine, Gly- (d,l)-Phe, and racemic ofloxacin, respectively	126
Fe3O4	Helical substituted polyacetylene	Alanine	SEM, XRD, CD spectra	(R)-PSA-based microspheres give strong interaction to (d)-ala with an ee of 79%. Whereas (S)-PSA-based microspheres is the other way around with the ee of 62%	78
Fe3O4	Helical substituted polyacetylene	Alanine	SEM, XRD, CD spectra	After three rounds of enantioselective crystallization, the obtained ee is up to 89%	79
Fe3O4/SiO2	β-CD-epichlorohydrin polymers (β-CD-EP)	Trp	CE	β-CD-EP-modified Fe3O4 absorbs more (l)-Trp. The supernatant ee of (d,l)-Trp reached up to 44.2% after interaction with 300 mg of β-CDEP-modified Fe3O4	127
iFe3O	Metal–organic frameworks (MOFs) i.e. [Zn2(bdc)(l-lac)(dmf)](DMF), (ZnBLD)	Phenyl methyl sulfoxide, phenyl vinyl sulfoxide, 4-chlorophenyl methyl sulfoxide	HPLC	The best ee was obtained for the separation of phenyl methyl sulfoxide, e.g., 85.2%	128
Fe3O4@PNE (polynorepinephrine)	MIP	Tryptophan, valine, threonine, Gly–Phe, ofloxacin, binaphthol	PDMS microchip device	Particle diameter size is 100 nm on average. PNE coats NPs in 6 nm of thickness. For trp, val, thre, ofloxacin, Gly-(d,l)-Phe, and binaphthol obtained Rs of 1.84, 1.54, 2.17, 3.33, 3.53, and 1.66, respectively	77
Fe3O4	Helical substituted polyacetylene	Threonine	SEM, XRD, CD spectra	The complex particles mostly induced (l)-threonine to form rectangular-shaped crystals with an ee up to 90% after two times of enantioselective crystallization	80
Fe3O4@SiO2	Chiral amino acid ionic liquid, HMDI-EMIMLpro	Cysteine (Cys), arginine (Arg), leucine (Leu), glutamine (Glu), tryptophan (Trp)	Automatic digital polarimeter and centrifugal chiral chromatography	Av diameter of the cluster was 80 nm with average nanoparticles size of about 13 nm. Fe3O4@SiO2@HMDI-EMIMLpro nanospheres preferred to interact with the (+)-enantiomers than that with the (−)-enantiomers cys, arg, and glu. Whereas for Leu and Trp is the other way around	129
Fe3O4@SiO2	Cellulose-2,3-bis(3,5-dimethylphenylcarbamat) (CBDMPC)	Benzoin methyl ether, promethazine hydrochloride, (±)-2-phenoxypropinionic acid, 4-phenyl-1,3-dioxane, dl-sec-phenethyl alcohol	Automatic digital polarimeter	The mean diameter of Fe3O4@SiO2@CBDMPC was 545 ± 20 nm. Fe3O4@SiO2@CBDMPC preferred to interact with the (−)-isomer than the (+)-isomer	130
Fe3O4@SiO2	CBDMPC	Benzoin	Chiral microsphere magnetic chromatography	The mean diameter of the microspheres was 240 ± 20 nm. (l)-benzoin has a high affinity to the chiral selector. The Rs is 1.5	131
Fe3O4@ZrO3	Cellulose tris(3,5-dimethylphenylcarbamate) (CDMPC)	Propronolol, alprenolol, pindolol, metoprolol, atenolol, carvedolol, ibuprofen, ketoprofen	Automatic Polarimeter	The average particle size is 340 nm. The synthesized particle preferred to bind with (−)-enantiomer of propronolol, alprenolol, pindolol, metoprolol, and atenolol. It is the other way around for carvedolol, ibuprofen, and ketoprofen	132
Fe3O4	Cellulose tris-(4-methylbenzoate) (CTMB)	Ibuprofen	HPLC	Fe3O4@CTMB interacted stronger with the (S)-enantiomer than the (R)-enantiomer of ibuprofen. At the single stage, ee was 4.7%. At four steps, the ee was 26.3%	89
TiO2@SiO2	Cellulose tris(3,5-dimethylphenylcarbamate) (CDMPC)	Eight basic indole ring derivatives	HPLC	From eight indole rings compound, at optimized conditions, only two obtained Rs > 1.5. The best Rs up to 2.89 was achieved	90
TiO2@SiO2	(CDMPC)	2-Hydroxyl-phenylacetonitrile, α-phenylethanol, matalaxyl, and diclofop-methyl	HPLC	Chromatogram shows qualitatively CSP could separate 2-hydroxyl phenylacetonitrile and α phenylethanol well. Rs matalaxyl up to 3.75. RS diclofopmethyl up to 1.67	91
SCMNSs (silica-coated magnetite nanospheres)	Bovine hemoglobin	Tryptophan	Spectrofluorometric	Av size of nanospheres (Hb-SCMNSs) was about 94 nm, with the thickness of the coating layer being about 29 nm. Hb-SCMNSs effectively adsorb the (l)-trp in the presence of (d)-Trp	86
SCMNSs	Tryptophan	Naproxen and phenylglycine	Resonance light scatterings measurements	Av diameter of Try-SCMNSs was 130 nm. –MNSs are very sensitive towards + NAP and +PHY enantiomers and, on the other way around	88
MNPs, i.e., hydroxyl group-modified superparamagnetic nanospheres	MIP	Ofloxacin	Microfluidic channel	The Av diameter of nanoparticles was 200 nm. The obtained Rs of ofloxacin was 1.46	133
Mesoporous silica-coated MNPs (MSMNPs)	Teicoplanin	(d,l)-Tryptophan, (d,l)-phenylalanine, (d,l)-mandelic acid, (d,l)-1-phenyl-1,2-ethanediol, N-benzoyl-(d,l)-alanine	CE	Av diameter was about 600 nm, and the mean pore size was 3.9 nm. Optical purity for Trp, Phe, MA, Phe-e, and benzoyl-ala was obtained at 35.4, 27.8, 8.0, 13.7, and 34.2%, respectively	87
MSNPs	(R)- and (S)-N-(2,2-dimethyl-4-pentanoyl)-proline-3,5-dimethylanilide	N-(3,5-Dinitrobenzoyl)alanine, valine and leucine, N-propylamide	HPLC-UV	Av size MSNPs: 300 nm. (S)-enantiomer was preferred to adsorb by MSNPs/(S)-CS. The ee using MSNPs/(S)-CS was 38.2% in (S) for ala, 29.3% in (S) for Val, and 13.8% in (S) for Leu. Whereas for propylamide, the Rs using MSNPs/(S)-CS was 68.1% ee in (S) and using NMSPs/(R)-CS 80.1% ee in (R)	134