A chiral stationary phase coated by surface molecularly imprinted polymer for separating 1,1'-binaphthalene-2,2'-diamine enantiomer by high performance liquid chromatography

Journal of Chromatography A

Volumn 1376, Issue , 2015, Pages 172-176

  Dong, Hongxing ^a   Zheng, Meixia ^a   Ou, Yiling ^a   Zhang, Chunhong ^a   Liu, Lijia ^a   Li, Junqing ^a   Yang, Xiaoguang ^a  

^a HARBIN ENGINEERING UNIVERSITY   (China)

Author keywords

1,1' Binaphthalene 2,2' diamine; Chiral separation; Coating; Surface molecularly imprinted polymers

Indexed keywords

AMINES; CHIRALITY; COATINGS; ETHYLENE; ETHYLENE GLYCOL; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUIDS; MONOMERS; POLYMERS; SEPARATION; SILICA; SILICA GEL; STEREOCHEMISTRY;

BINAPHTHALENES; CHIRAL SEPARATIONS; CHIRAL STATIONARY PHASE; ETHYLENE GLYCOL DIMETHACRYLATE; MOLECULARLY IMPRINTED POLYMER; PRETREATMENT TEMPERATURE; SILICA GEL PARTICLES; SURFACE MOLECULARLY IMPRINTED POLYMERS;

PLASTIC COATINGS;

1,1' BINAPHTHALENE 2,2' DIAMINE; DIAMINE DERIVATIVE; ETHYLENE GLYCOL DIMETHACRYLATE; METHACRYLIC ACID; MOLECULARLY IMPRINTED POLYMER; MONOMER; SILICA GEL; UNCLASSIFIED DRUG; 2,2'-DIAMINO-1,1'-BINAPHTHALENE; CROSS LINKING REAGENT; METHACRYLIC ACID DERIVATIVE; NAPHTHALENE DERIVATIVE; POLYMETHACRYLIC ACID; POLYMETHACRYLIC ACID DERIVATIVE; SILICON DIOXIDE;

ARTICLE; CHIRALITY; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MATERIAL COATING; POLYMERIZATION; SURFACE PROPERTY; TEMPERATURE; CHEMISTRY; ISOLATION AND PURIFICATION; MOLECULAR IMPRINTING; PROCEDURES; STEREOISOMERISM;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CROSS-LINKING REAGENTS; METHACRYLATES; MOLECULAR IMPRINTING; NAPHTHALENES; POLYMETHACRYLIC ACIDS; SILICON DIOXIDE; STEREOISOMERISM; TEMPERATURE;

EID: 84920778103     PISSN: 00219673     EISSN: 18733778     Source Type: Journal    
DOI: 10.1016/j.chroma.2014.12.009     Document Type: Article

References (25)

1. Zhang Z.H., Mo L.P., Liu Q.B., Li T.S. Preparation and application in asymmetrical synthesis of 2,2'-diamino-1,1'-binaphthalene. Chin. J. Org. Chem. 2003, 23:37-43.
2. Telfer S.G., Kuroda R. 1,1'-Binaphthyl-2,2'-diol and 2,2'-diamino-1,1'-binaphthyl: versatile frameworks for chiral ligands in coordination and metallosupramolecular chemistry. Coord. Chem. Rev. 2003, 242:33-46.
3. Guillena G., Hita M.C., Najera C., Viozquez S.F. Solvent-free asymmetric direct aldol reactions organocatalysed by recoverable (Sa)-binam-l-prolinamide. Tetrahedron: Asymm. 2007, 18:2300-2304.
4. Wang C.J., Xu Z.P., Wang X., Teng H.L. Axial [6,6'-(2,4-pentadioxy)]-1,1'-biphenyl-2,2'-diamine (PD-BIPHAM): practical synthesis and applications in asymmetric hydrogenation. Tetrahedron 2010, 66:3702-3706.
5. 2 symmetric diamines as chiral ligands. Tetrahedron: Asymm. 1995, 6:705-718.
6. 2-symmetrical chiral nucleophilicm organocatalysts via Pd-catalyzed coupling. Tetrahedron: Asymm. 2012, 23:1694-1699.
7. Zabihi O. Modeling of phenomenological mechanisms during thermal formation and degradation of an epoxy-based nanocomposite. Thermochim. Acta 2012, 543:239-245.
8. Zabihi O., Mostafavi S.M., Ravari F., Khodabandeh A., Hooshafza A., Zare K., Shahizadeh M. The effect of zinc oxide nanoparticles on thermo-physical properties of diglycidyl ether of bisphenol A/2,2-diamino-1,1-binaphthalene nanocomposites. Thermochim. Acta 2011, 521:49-58.
9. Gullotti M., Santagostini L., Pagliarin R., Granata A., Casella L. Synthesis and characterization of new chiral octadentate nitrogen ligands and related copper(II) complexes as catalysts for stereoselective oxidation of catechols. J. Mol. Catal. A: Chem. 2005, 235:271-284.
10. Yao N., Song R.J., Fu Y., Shi H.Y., Long Y.D., Huang T.B. Preparation of (R)-(+)-1,1'-binaphthyl-2,2'-diamine polymer as a novel chiral stationary phase by surface-initiated polymerization and chromatographic evaluation. Chem. J. Chin. Univ. 2008, 29:1102-1106.
11. Shi J.H., Cheng X.W., Yan W. J. Instrum. Anal. 2008, 27:772.
12. Nishi H., Nakamura K., Nakai H., Sato T. Separation of optical isomers of 2,2'-dihydroxy-1,1'-binaphthyl and 2,2'-diamino-1,1'-binaphthyl by reversed-phase high performance liquid chromatography on (S)-hydroxypropyl-β-cyclodextrin chiral column. J. Chromatogr. A 1997, 757:225-235.
13. Monser L.I., Greenway G.M., Ewing D.F. Novel 2-chrysenyl- and 1-pyrenyl-tartaramide derivatives as liquid chromatographic chiral phases for enantiomeric separation on porous graphitic carbon. Tetrahedron: Asymm. 1996, 7:1189-1198.
14. Jiang J.B., Song K.S., Chen Z., Zhou Q., Tang Y.W., Gu F.L., Zuo X.J., Xu Z.G. Novel molecularly imprinted microsphere using a single chiral monomer and chirality-matching (S)-kotoprofen template. J. Chromatogr. A 2011, 1218:3763-3770.
15. Dong H.X., Wang Y.H., Ou Y.L., She J., Shen X.D., Li J., Zhang C.H., Liu L.J. Preparation of molecularly imprinted polymer for chiral recognition of racemic 1,1'-binaphthalene-2,2'-diamine by HPLC. Acta Chromatogr. 2014, 26:1-11.
16. Gao B.J., Lu J.H., Chen Z.P., Guo J.F. Preparation and recognition performance of cholic acid-imprinted material prepared with novel surface-imprinting technique. Polymer 2009, 50:3275-3284.
17. Pan J.M., Zou X.H., Wang X., Guan W., Yan Y.S., Han J. Selective recognition of 2,4-dichlorophenol from aqueous solution by uniformly sized molecularly imprinted microspheres with β-cyclodextrin/attapulgite composites as support. Chem. Eng. J. 2010, 162:910-918.
18. Zhang W., Qin L., He X.W., Li W.Y., Zhang Y.K. Novel surface modified molecularly imprinted polymer using acryloyl-β-cyclodextrin and acrylamide as monomers for selective recognition of lysozyme in aqueous solution. J. Chromatogr. A 2009, 1216:4560-4567.
19. Gao F.X., Ma X.T., He X.W., Li W.Y., Zhang Y.K. Smart surface imprinting polymer nanospheres for selective recognition and separation of glycoprotein. Colloids Surf. A 2013, 433:191-199.
20. Chen H.J., Zhang Z.H., Luo L.J., Yao S.Z. Surface-imprinted chitosan-coated magnetic nanoparticles modified multi-walled carbon nanotubes biosensor for detection of bovine serum albumin. Sens. Actuators B 2012, 163:76-83.
21. Gao B.J., Wang J., An F.Q., Liu Q. Molecular imprinted material prepared by novel surface imprinting technique for selective adsorption of pirimicarb. Polymer 2008, 49:1230-1238.
22. He H.Y., Fu G.Q., Wang Y., Chai Z.H., Jiang Y.Z., Chen Z.L. Imprinting of protein over silica nanoparticles via surface graft copolymerization using low monomer concentration. Biosens. Bioelectron. 2010, 26:760-765.
23. Fan H.T., Li J., Li Z.C., Sun T. An ion-imprinted amino-functionalized silica gel sorbent prepared by hydrothermal assisted surface imprinting technique for selective removal of cadmium (II) from aqueous solution. Appl. Surf. Sci. 2012, 258:3815-3822.
24. Okamoto Y., Kawashima M., Hatada K. Chromatographic resolution: XI. Controlled chiral recognition of cellulose triphenylcarbamate derivatives supported on silica gel. J. Chromatogr. 1986, 363:173-186.
25. Shen J., Zhao Y.Q., Inagakib S., Yamamotob C., Shen Y., Liu S.Y., Okamotoa Y. Enantioseparation using ortho- or meta-substituted phenylcarbamates of amylose as chiral stationary phases for high-performance liquid chromatography. J. Chromatogr. A 2013, 1286:41-46.