Synthesis and characterization of a novel resorcinarene-based stationary phase bearing polar headgroups for use in reversed-phase high-performance liquid chromatography.
A novel silica-bonded stationary phase containing a functionalized resorcinarene selector was prepared by a straightforward synthesis. The complete modification of all resorcinic hydroxyl groups was achieved by reaction with isopropyl isocyanate. The derivatized resorcinarene selector was subsequently immobilized via the four alkenyl chains containing a terminal double bond by a free radical-induced reaction on mercaptopropyl-functionalized silica. A comprehensive characterization of the resulting bonded stationary phase was carried out by solid state NMR, IR and elemental analysis. The resulting selector is defined as a "polar headed" reversed phase since the highly ordered polar carbamate groups of the new stationary phase are located, compared to conventional polar embedded stationary phases, at a greater distance from the silica surface. Thus a new concept is introduced in the field of polar modified reversed-phase HPLC. The properties of the novel stationary phase are demonstrated by comparison with commercially available reversed phases.
Ruderisch
Alexander
A
Institute of Organic Chemistry, Tübingen, Germany.
Iwanek
Waldemar
W
Pfeiffer
Jens
J
Fischer
Gert
G
Albert
Klaus
K
Schurig
Volker
V
D000873:Anthracenes / Q000302:isolation & purification; D047250:Calixarenes; D002851:Chromatography, High Pressure Liquid / Q000295:instrumentation / Q000379:methods*; D007554:Isotopes; D009281:Naphthalenes / Q000302:isolation & purification; D019906:Nuclear Magnetic Resonance, Biomolecular; D019800:Phenol / Q000302:isolation & purification; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D012825:Silicon; D012822:Silicon Dioxide; D013055:Spectrophotometry, Infrared; D017550:Spectroscopy, Fourier Transform Infrared
D000873:Anthracenes; D007554:Isotopes; D009281:Naphthalenes; C466160:resorcinarene; D047250:Calixarenes; C031721:naphthalene; D019800:Phenol; D010649:Phenylalanine; D012822:Silicon Dioxide; C034020:anthracene; D012825:Silicon