Recent analytical applications of fluorinated hydrocarbon-based stationary phases in HPLC

References

• Zhang, W. Fluorocarbon Stationary Phases for Liquid Chromatography Applications. J. Fluorine Chem. 2008, 129, 910–919.
   Web of Science ®Google Scholar
• Przybyciel, M. Fluorinated HPLC Phases – Looking Beyond C18 for Reversed-Phase HPLC. LCGC North Am. 2005, 23, 554–565.
   Web of Science ®Google Scholar
• Varughese, P.; Gangoda, M. E.; Gilpin, R. K. Applications of Fluorinated Compounds as Phases and Additives in Chromatography and Their Uses in Pharmaceutical Analysis. J. Chromatogr. Sci. 1988, 26, 401–405.
   PubMed Web of Science ®Google Scholar
• Hayama, T.; Yoshida, H.; Yamaguchi, M.; Nohta, H. Fluorous Affinity-Based Separation Techniques for the Analysis of Biogenic and Related Molecules. J. Pharm. Biomed. Anal. 2014, 101, 151–160.
   PubMed Web of Science ®Google Scholar
• Berendsen, G. E.; Pikaart, K. A.; De Galan, L.; Olieman, C. (Heptadecafluorodecyl)dimetylsilyl Bonded Phase for Reversed-Phase Liquid Chromatography. Anal. Chem. 1980, 52, 1990–1993.
   Web of Science ®Google Scholar
• Billiet, H. A. H.; Schoenmakers, P. J.; de Galan, L. Retention and Selectivity Characteristics of a Non-polar Perfluorinated Stationary Phase for Liquid Chromatography. J. Chromatogr. 1981, 218, 443–454.
   Web of Science ®Google Scholar
• Bicking, M. K. L.; Bicking, M. L.; Longman, W. E. Direct Fluorination of Silica for Use in Liquid Chromatography. Anal. Chem. 1986, 58, 499–501.
   Web of Science ®Google Scholar
• Kamiusuki, T.; Monde, T.; Yano, K.; Yoko, T.; Konakahara, T. Preparation of Branched-Polyfluoroalkylsilane-Coated Silica Gel Columns and Their HPLC Separation Characteristics. Chromatograhia. 1999, 49, 649–656.
   Web of Science ®Google Scholar
• Williams, D. E.; Kabra, P. M. Extended Life for Blood Serum Analysis Columns Using Dual Zone Chromatographic Materials. Anal. Chem. 1990, 62, 807–810.
   PubMed Web of Science ®Google Scholar
• Csato, E.; Fulop, N.; Szabo, G. Preparation and Comparison of a Pentafluorophenyl Stationary Phase for Reversed-Phase Liquid Chromatography. J. Chromatogr. 1990, 511, 79–88.
   Web of Science ®Google Scholar
• Danielson, N. D.; Ahmed, S.; Huth, J. A.; Targrove, M. A. Characterization of Organomagnesium Modified Kel-F Polymers as Column Packings. J. Liq. Chromatogr. 1986, 9, 727–743.
   Web of Science ®Google Scholar
• Williams, R. C.; Vasta-Russell, J. F.; Glajch, J. L.; Golebiowski, K. Separation of Proteins on a Polymeric Fluorocarbon High-Performance Liquid Chromatography Column Packing. J. Chromatogr. 1986, 371, 63–70.
   PubMed Web of Science ®Google Scholar
• Hirayama, C.; Ihara, H.; Nagaoka, S.; Hamada, K. Totally Organic Stationary Phase from Perfluoroalkyl Acrylate for Liquid Chromatography. J. Chromatogr. 1989, 465, 241–248.
   Web of Science ®Google Scholar
• Danielson, N. D.; Beaver, L. G.; Wangsa, J. Fluoropolymers and Fluorocarbon Bonded Phases as Column Packings for Liquid Chromatography. J. Chromatogr. 1991, 544, 187–199.
   Web of Science ®Google Scholar
• Daley, A. B.; Oleschuk, R. D. Development of Fluorinated, Monolith Columns for Improved Chromatographic Separations of Fluorous-Tagged Analytes. J. Chromatogr. A. 2009, 1216, 772–780.
   PubMed Web of Science ®Google Scholar
• http://www.agilent.com/cs/library/primers/Public/LC-Handbook-Complete-2.pdf.
   Google Scholar
• http://www.sigmaaldrich.com/content/dam/sigma-aldrich/docs/Supelco/General_Information/1/supelco-1-hplc.pdf
   Google Scholar
• Curran, D. P. Separation with Fluorous Silica Gel and Related Materials. In Handbook of Fluorous Chemistry; Gladysz, J. A.; Curran, D. P.; Horvath, I. T., Eds. Chapter 7, Weinheim: Wiley, 2004; 594 pp.
   Google Scholar
• Pesek, J. J.; Matyska, M. T.; Prajapati, K. V. Synthesis and Evaluation of Silica Hydride-Based Fluorinated Stationary Phases. J. Sep. Sci. 2010, 33, 2908–2916.
   PubMed Web of Science ®Google Scholar
• Pesek, J. J.; Matyska, M. T.; Natekar, H. Evaluation of the Dual Retention Properties of Stationary Phases Based on Silica Hydride: Perfluorinated Bonded Material. J. Sep. Sci. 2016, 39, 1050–1055.
   PubMed Web of Science ®Google Scholar
• Andre, C.; Aljhni, R.; Lethier, L.; Guillaume, Y. Development and Evaluation of a New Fluorinated Double-Wall Carbon Nanotube HPLC Stationary Phase. Chromatograhia. 2014, 77, 1257–1265.
   Web of Science ®Google Scholar
• Haky, J. E.; Blauvelt, T. M.; Wieserman, L. F. Perfluorooctyl and Perfluorobutyl Bonded Alumina Stationary Phases for High Performance Liquid Chromatography. J. Liq. Chromatogr. Rel. Technol. 1996, 19, 307–332.
   Web of Science ®Google Scholar
• Maldaner, L.; Jardin, I. C. S. F. A New Thermally Immobilized Fluorinated Stationary Phase for RP-HPLC. J. Sep. Sci. 2010, 33, 174–181.
   PubMed Web of Science ®Google Scholar
• Maldaner, L.; Jardim, I. C. S. F. Preparation and Characterization of a Microwave-Immobilized Fluorinated Stationary Phase for RP-LC. Chromatographia. 2010, 72, 617–626.
   Web of Science ®Google Scholar
• Jardin, I. C. S. F.; Maldaner, L.; Lourenco, J.; Fioravanti, L. M. A.; Collins, C. H. Some New Selective Stationary Phases for RP-HPLC. J. Sep. Sci. 2010, 33, 2917–2929.
   PubMed Web of Science ®Google Scholar
• Shearer, J. W.; Ding, L.; Olesik, S. V. Solvation Parameter Models for Retention of Perfluorinated and Fluorinated Low Temperature Glassy Carbon Stationary Phases in Reversed-Phase Liquid Chromatography. J. Chromatogr. A. 2007, 1141, 73–80.
   PubMed Web of Science ®Google Scholar
• Moldoveanu, S. C.; David, V. Essentials in Modern HPLC Separations. Elsevier: Amsterdam, 2013.
   Google Scholar
• Biffinger, J. C.; Kim, H. W.; DiMagno, S. G. The Polar Hydrophobicity of Fluorinated Compounds. ChemBioChem. 2004, 5, 622–627.
   PubMed Web of Science ®Google Scholar
• Marchetti, N.; Guzzinati, R.; Catani, M.; Massi, A.; Pasti, L.; Cavazzini, A. New Insights into Perfluorinated Adsorbents for Analytical and Bioanalytical Applications. Anal. Bionanal. Chem. 2015, 407, 17–21.
   PubMed Web of Science ®Google Scholar
• Sadek, P. C.; Carr, P. W. Study of Solute Retention in Reversed-Phase High Performance Liquid Chromatography on Hydrocarbonaceous and Three Fluorinated Bonded Phases. J. Chromatogr. 1984, 288, 25–41.
   Web of Science ®Google Scholar
• Felix, G.; Bertrand, C. HPLC on Pentafluorophenethyl Silica Gel. J. High Res. Chromatogr. Chrom. Commun. 1987, 10, 411–412.
   Google Scholar
• Kruger, D. G.; Rajan, S.; Kingsbury, C. A. Segregation in Fluorocarbon-Hydrocarbon Solutions. J. Sol. Chem. 1982, 11, 719–728.
   Web of Science ®Google Scholar
• Bell, D. S.; Cramer, H. M.; Jones, A. D. Rational Method Development Strategies on a Fluorinated Liquid Chromatography Stationary Phase: Mobile Phase Ion Concentration and Temperature Effects on the Separation of Ephedrine Alkaloids. J. Chromatogr. A. 2005, 1095, 113–118.
   PubMed Web of Science ®Google Scholar
• Dolfinger, R.; Locke, D. C. Dependence of Selectivity on Eluent Composition and Temperature in the HPLC Separation of Taxanes Using Fluorinated and Hydrocarbon Phases. Anal. Chem. 2003, 75, 1355–1364.
   PubMed Web of Science ®Google Scholar
• Santasania, C. T.; Bell, D. S. Mechanism of Interaction Responsible for Alternative Selectivity of Fluorinated Stationary Phases. LCGC North Am. 2016, 34, 92–105.
   Web of Science ®Google Scholar
• Petruczynik, A. Effect of Ionic Liquid Additives to Mobile Phase on Separation and System Efficiency for HPLC of Selected Alkaloids on Different Stationary Phases. J. Chromatogr. Sci. 2012, 50, 287–293.
   PubMed Web of Science ®Google Scholar
• Nichthauser, J.; Stepnowski, P. Retention Mechanism of Selected Ionic Liquids on a Pentafluorophenylpropyl Polar Phase: Investigation Using RP-HPLC. J. Chromatogr. Sci. 2009, 47, 247–253.
   PubMed Web of Science ®Google Scholar
• Bell, D. S.; Jones, A. D. Solute Attributes and Molecular Interactions Contributing to “U-Shape” Retention on a Fluorinated High-Performance Liquid Chromatography Stationary Phase. J. Chromatogr. A. 2005, 1073, 99–109.
   PubMed Web of Science ®Google Scholar
• Bacalum, E.; Galaon, T.; David, V.; Aboul-Enein, H. Y. Retention Behavior of Some Compounds Containing Polar Functional Groups on Perfluorophenyl Silica-Based Stationary Phase. Chromatographia. 2014, 77, 543–552.
   Web of Science ®Google Scholar
• Valko, K.; Espinosa, S.; Du, C. M.; Bosch, E.; Roses, M.; Bevan, C.; Abraham, M. H. Unique Selectivity of Perfluorinated Stationary Phases with 2,2,2-Trifluoroethanol as Organic Mobile Phase Modifier. J. Chromatogr. A. 2001, 933, 73–81.
   PubMed Web of Science ®Google Scholar
• Jinno, K.; Nakamura. H. Retention Characteristics of Fluorinated Bonded Silica Phase in Reversed-Phase Liquid Chromatography. Chromatographia. 1994, 39, 285–293.
   Web of Science ®Google Scholar
• Euerby, M. R.; McKeown, A. P.; Petersson, P. Chromatographic Classification and Comparison of Commercially Available Perfluorinated Stationary Phases for Reversed-Phase Liquid Chromatography Using Principal Component Analysis. J. Sep. Sci. 2003, 26, 295–306.
   Web of Science ®Google Scholar
• Reta, M.; Carr, P. W.; Sadek, P. C.; Rutan, S. C. Comparative Study of Hydrocarbon, Fluorocarbon, and Aromatic Bonded RP-HPLC Stationary Phases by Linear Solvation Energy Relationships. Anal. Chem. 1999, 71, 3484–3496.
   PubMed Web of Science ®Google Scholar
• Ciogli, A.; Simone, P.; Villani, C.; Gasparrini, F.; Lagana, A.; Capitani, D.; Marchetti, N.; Pasti, L.; Massi, A.; Cavazzini, A. Revealing the Fine Details of Functionalized Silica Surfaces by Solid-State NMR and Adsorption Isotherm Measurements: The Case of Fluorinated Stationary Phases for Liquid Chromatography. Chem. Eur. J. 2014, 20, 8138–8148.
   PubMed Web of Science ®Google Scholar
• Mountain, R. D.; Lippa, K. A. Solvation of Perfluorooctane and Octane in Water, Methanol, Acetonitrile, and Aqueous Mixtures of Methanol and Acetonitrile. J. Phys. Chem. B. 2008, 112, 7785–7793.
   PubMed Web of Science ®Google Scholar
• Mao, K.; Kobayashi, T.; Wiench, J. W.; Chen, H.-T.; Tsai, C.-H.; Lin, V. S.-Y.; Pruski, M. Conformations of Silica-Bound (Pentafluorophenyl)propyl Groups Determined by Solid-State NMR Spectroscopy and Theoretical Calculations. J. Am. Chem. Soc. 2010, 132, 12452–12457.
   PubMed Web of Science ®Google Scholar
• Xu, Z.; Oleschuk, R. D. A Study of the Methylene/Perfluoromethylene Selectivity of Porous Polymer Monolithic Stationary Phases Exhibiting Different Fluorous/Hydrophobic Content. J. Chromatogr. A. 2014, 1329, 61–70.
   PubMed Web of Science ®Google Scholar
• Catani, M.; Guzzinati, R.; Marchetti, N.; Pasti, L.; Cavazzini, A. Exploring Fluorous Affinity by Liquid Chromatography. Anal. Chem. 2015, 87, 6854–6860.
   PubMed Web of Science ®Google Scholar
• Luo, Z.; Zhang, Q.; Oderaotoshi, Y.; Curran, D. P. Fluorous Mixture Synthesis: A Fluorous-Tagging Strategy for the Synthesis and Separation of Mixtures of Organic Compounds. Science. 2001, 291, 1766–1769.
   PubMed Web of Science ®Google Scholar
• Zhang, Z.; Luo, Z.; Chen, C. H.-T.; Curran, D. P. Solution-Phase Preparation of a 560-Compound Library of Individual Pure Mappicine Analogues by Fluorous Mixture Synthesis. J. Am. Chem. Soc. 2002, 124, 10443–10450.
   PubMed Web of Science ®Google Scholar
• Curran, D. P. Fluorous Reverse Phase Silica Gel. A New Tool for Preparative Separations in Synthetic Organic and Organofluorine Chemistry. Synlett. 2011, 9, 1488–1496.
   Google Scholar
• Yamazaki, O.; Hao, X.; Yoshida, A.; Nishikido, J. Fluorous Reverse-Phase Silica Gel-Supported Lewis Acids as Recyclable Catalysts in Water. Tetrahedron Lett. 2003, 44, 8791–8795.
   Web of Science ®Google Scholar
• Regalado, E. L.; Zhuang, P.; Chen, Y.; Makarov, A. A.; Schafer, W. A.; McGachy, N.; Welch, C. J. Chromatographic Resolution of Closely Related Species in Pharmaceutical Chemistry: Dehalogenation Impurities and Mixtures of Halogen Isomers. Anal. Chem. 2014, 86, 805–813.
   PubMed Web of Science ®Google Scholar
• Regalado, E. L.; Makarov, A. A.; McClain, R.; Przybyciel, M.; Welch, C. J. Search for Improved Fluorinated Stationary Phases for Separation of Fluorine-Containing Pharmaceuticals from Their Desfluoro Analogs. J. Chromatogr. A. 2015, 1380, 45–54.
   PubMed Web of Science ®Google Scholar
• Xindu, G.; Carr, P. W. Use of Fluorinated Bonded Phases in Reversed-Phase High-Performance Liquid Chromatography of Proteins. J. Chromatogr. 1983, 269, 96–102.
   Web of Science ®Google Scholar
• Richheimer, S. L.; Tinnermeier, D. M.; Timmons, D. W. High-Performance Liquid Chromatographic Assay of Taxol. Anal. Chem. 1992, 64, 2323–2326.
   PubMed Web of Science ®Google Scholar
• Kopycki, W. J.; Elsohly, H. N.; McChesney, J. D. HPLC Determination of Taxol and Related Compounds in Taxus Plant Extracts. J. Liq. Chromatogr. 1994, 17, 2569–2591.
   Web of Science ®Google Scholar
• Itoh, H.; Kinoshita, T.; Nimura, N. High-Performance Liquid Chromatographic Separation of Nucleic Acids on a Fluorocarbon-Bonded Silica Gel Column. J. Chromatogr. 1994, 662, 95–99.
   Web of Science ®Google Scholar
• Richheimer, S. L.; Kent, M. C.; Bernart, M. W. Reversed-Phase High Performance Liquid Chromatographic Method Using a Pentafluorophenyl Bonded Phase for Analysis of Tocopherols. J. Chromatogr. A. 1994, 677, 75–80.
   Web of Science ®Google Scholar
• Monde, T.; Kamiusuki, T.; Kuroda, T.; Mikumo, K.; Ohkawa, T.; Fukube, H. High-Performance Liquid Chromatographic Separation of Phenols on a Fluorocarbon-Bonded Silica Gel Column. J. Chromatogr. A. 1996, 72, 273–280.
   Web of Science ®Google Scholar
• Kamiusuki, T.; Monde, T.; Nemoto, F.; Konakahara, T.; Takahashi, Y. Separation and Characterization of Octylphenol Ethoxylate Surfactants Used in Reversed-Phase High-Performance Liquid Chromatography on Branched Fluorinated Silica Gel Columns. J. Chromatogr. A. 1999, 852, 475–485.
   PubMed Web of Science ®Google Scholar
• De Miguel, I.; Roueche, A.; Betbeder, D. Separation of Dipalmitoyl Phosphatidyl Choline, Cholesterol and Their Degradation Products by High-Performance Liquid Chromatography on a Perfluorinated Stationary Bonded Phase. J. Chromatogr. A. 1999, 840, 31–38.
   Web of Science ®Google Scholar
• Needham, S. R.; Brown, P. R.; Duff, K.; Bell, D. Optimized Stationary Phases for the High-Performance Liquid Chromatography-Electrospray Ionization Mass Spectrometric Analysis of Basic Pharmaceuticals. J. Chromatogr. A. 2000, 869, 159–170.
   PubMed Web of Science ®Google Scholar
• Yamamoto, F. M.; Rokushika, S. Retention Properties of the Fluorinated Bonded Phase on Liquid Chromatography of Aromatic Hydrocarbons. J. Chromatogr. A. 2000, 898, 141–151.
   PubMed Web of Science ®Google Scholar
• Andre, C.; Ismaili, L.; Millet, J.; Thomassin, M.; Guillaume, Y. C. Effect of Sodium Chloride on Herbicide-Fluorinated Stationary Phase Association-Evidence of a Dual Mechanism. Chromatographia. 2003, 57, 771–776.
   Web of Science ®Google Scholar
• Vybiralova, Z.; Nobilis, M.; Zoulova, J.; Kvetina, J.; Petr, P. High-Performance Liquid Chromatographic Determination of Ciprofloxacin in Plasma Samples. J. Pharm. Biomed. Anal. 2005, 37, 851–858.
   PubMed Web of Science ®Google Scholar
• Maia, A. S.; Ribeiro, A. R.; Amorim, C. L.; Barreiro, J. C.; Cass, Q. B.; Castro, P. M. L.; Tiritan, M. E. Degradation of Fluoroquinolone Antibiotics and Identification of Metabolites/Transformation Products by Liquid Chromatography-Tandem Mass Spectrometry. J. Chromatogr. A. 2014, 1333, 87–98.
   PubMed Web of Science ®Google Scholar
• Langlois, I.; Oehme, M. Structural Identification of Isomers Present in Technical Perfluorooctane Sulfonate by Tandem Mass Spectrometry. Rapid Commun. Mass Spectrom. 2006, 20, 844–850.
   PubMed Web of Science ®Google Scholar
• Benskin, J. P.; Bataineh, M.; Martin, J. W. Simultaneous Characterization of Perfluoroalkyl Carboxylate, Sulfonate, and Sulfonamide Isomers by Liquid Chromatography-Tandem Mass Spectrometry. Anal. Chem. 2007, 79, 6455–6464.
   PubMed Web of Science ®Google Scholar
• Pellati, F.; Benvenuti, S. Determination of Ephedrine Alkaloids in Ephedra Natural Products Using HPLC on a Pentafluorophenylpropyl Stationary Phase. J. Pharm. Biomed. Anal. 2008, 48, 254–263.
   PubMed Web of Science ®Google Scholar
• Havlikova, L.; Matysova, L.; Hajkova, R.; Satinsky, D.; Solich, P. Advantages of Pentafluorophenylpropyl Stationary Phase over Conventional C18 Stationary Phase – Application to Analysis of Triamcinolone Acetonide. Talanta. 2008, 76, 597–601.
   PubMed Web of Science ®Google Scholar
• de Villiers, A.; Venter, P.; Pasch, H. Recent Advances and Trends in the Liquid Chromatography-Mass Spectrometry Analysis of Flavonoids. J. Chromatogr. A. 2016, 1430, 16–78.
   PubMed Web of Science ®Google Scholar
• Baba, K.; Arao, T.; Yamaguchi, N.; Watanabe, E.; Eun, H.; Ishizaka, M. Chromatographic Separation of Arsenic Species with Pentafluorophenyl Column and Application to Rice. J. Chromatogr. A. 2014, 1354, 109–116.
   PubMed Web of Science ®Google Scholar
• Lanina, S. A.; Toledo, P.; Sampels, S.; Kamal-Eldin, A.; Jastrebova, J. A. Comparison of Reversed-Phase Liquid Chromatography-Mass Spectrometry with Electrospray and Atmosferic Pressure Chemical Ionization for Analysis of Dietary Tocopherols. J. Chromatogr. A. 2007, 1157, 159–170.
   PubMed Web of Science ®Google Scholar
• Nazario, C. E. D.; Silva, M. R.; Franco, M. S.; Lancas, F. M. Evolution in Minituarized Column Liquid Chromatography Instrumentation and Applications: An Overview. J. Chromatogr. A. 2015, 1421, 18–37.
   PubMed Web of Science ®Google Scholar
• Dohnal, V.; Musilek, K.; Kuca, K. Retention Behavior of Pyridinium Oximes on PFP Stationary Phase in High-Performance Liquid Chromatography. J. Chromatogr. Sci. 2014, 52, 246–251.
   PubMed Web of Science ®Google Scholar
• Medvedovici, A.; Sora, I. D.; Radulescu, M.; David, V. Discontinuous Double Mechanism for the Retention of Some Cation-Type Oximes on Hydrophilic Stationary Phases in Liquid Chromatography. Anal. Methods 2011, 3, 241–244.
   Web of Science ®Google Scholar
• Needham, S. R.; Brown, P. R. The High-Performance Liquid Chromatography Electrospray Ionization Mass Spectrometry Analysis of Diverse Basic Pharmaceuticals on Cyanopropyl and Pentafluorophenylpropyl Stationary Phases. J. Pharm. Biomed. Anal. 2000, 23, 597–605.
   PubMed Web of Science ®Google Scholar
• Needham, S. R.; Jeanville, P. M.; Brown, P. R.; Estape, E. S. Performance of a Pentafluorophenylpropyl Stationary Phase for the Electrospray Ionization High-Performance Liquid Chromatography-Mass Spectrometry-Mass Spectrometry Assay of Cocaine and Its Metabolite Ecgonine Methyl Ester in Human Urine. J. Chromatogr. B. 2000, 748, 77–87.
   PubMed Web of Science ®Google Scholar
• Gilar, M.; Olivova, P.; Daly, A. E.; Gebler, J. C. Orthogonality of Separation in Two-Dimensional Liquid Chromatography. Anal. Chem. 2005, 77, 6426–6434.
   PubMed Web of Science ®Google Scholar
• Blahova, E.; Jandera, P.; Cacciola, F.; Mondello, L. Two Dimensional and Serial Column Reversed-Phase Separation of Phenolic Antioxidants on Octadecyl-, Polyethyleneglycol-, and Pentafluorophenylpropyl-Silica Columns. J. Sep. Sci. 2006, 29, 555–566.
   PubMed Web of Science ®Google Scholar
• Neue, U. D.; O’Gara, J. E.; Mendez, A. Selectivity in Reversed-Phase Separations Influence of the Stationary Phase. J. Chromatogr. A. 2006, 1127, 161–174.
   PubMed Web of Science ®Google Scholar
• Jandera, P. Stationary and Mobile Phases in Hydrophilic Interaction Chromatography: A Review. Anal. Chim. Acta. 2011, 692, 1–25.
   PubMed Web of Science ®Google Scholar