title: In-situ functionalized monolithic polysiloxane-polymethacrylate composite materials from polythiol-ene double click reaction in capillary column format for enantioselective nano-high-performance liquid chromatography.
abstract: This work reports on the proof-of-principle of preparation of novel one step in-situ functionalized monolithic polysiloxane-polymethacrylate composite materials in capillary columns for enantioselective nano-HPLC using a thiol-ene click reaction. Quinine carbamate as functional monomer and ethylene dimethacrylate as crosslinker were both used as ene components in a thermally initiated double click-type polymerization reaction with poly(3-mercaptopropyl)methylsiloxane as thiol component in presence of 1-propanol as porogenic solvent. Elemental analysis and on-capillary fluorescence measurement proved the successful incorporation of the functional chiral monomer into the polymer. Scanning electron microscopy images revealed a macroporous polymer morphology which is typical for a nucleation and growth mechanism of pore formation. The individual microglobules appear relatively spherical and smooth indicating a non-porous nature. Nano-HPLC experiments of the chiral monolithic capillary column provided successful enantiomer separation of N-3,5-dinitrobenzoylleucine as test compound in polar organic elution mode clearly documenting the successful implementation of the proposed concept towards new functionalized monolithic composite materials.
authors.affiliation: Institute of Pharmaceutical Sciences, Pharmaceutical (Bio-)Analysis, University of Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany.
authors.forename: Marc
authors.initials: M
authors.lastname: Wolter
authors.affiliation: Institute of Pharmaceutical Sciences, Pharmaceutical (Bio-)Analysis, University of Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany. Electronic address: Michael.laemmerhofer@uni-tuebingen.de.
authors.forename: Michael
authors.initials: M
authors.lastname: Lämmerhofer
mesh_terms: D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation / Q000379:methods*; D057930:Click Chemistry; D004136:Dinitrobenzenes / Q000032:analysis / Q000302:isolation & purification; D007930:Leucine / Q000031:analogs & derivatives / Q000032:analysis / Q000302:isolation & purification; D008689:Methacrylates / Q000737:chemistry; D008855:Microscopy, Electron, Scanning; D011109:Polymethacrylic Acids / Q000737:chemistry*; D016062:Porosity; D012833:Siloxanes / Q000737:chemistry*; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000737:chemistry
chemical_list: D004136:Dinitrobenzenes; D008689:Methacrylates; D011109:Polymethacrylic Acids; D012833:Siloxanes; D013438:Sulfhydryl Compounds; C465293:dinitrobenzoyl leucine; C030613:polymethacrylic acid; C004919:ethylene dimethacrylate; D007930:Leucine
keywords: Chiral separation; Click polymerization; Composite material; Monolithic capillary column; Nano-HPLC; Thiol-ene click reaction