, Volume 52, Issue 1–2, pp 51–57 | Cite as

Synthesis and characterization of new organometallic complexes bonded stationary phases for high-performance liquid chromatography

  • O. Bordelanne
  • M. H. Delville
  • G. Félix
  • C. Labrugère
  • A. Thienpont
  • C. Vidal
Originals Column Liquid Chromatography


The preparation, characterization and potential liquid chromatographic applications of various organometallic iron complexes silica stationary phases are presented. These new supports are synthesized by covalently linking ferrocene, as well as some of its cationic derivatives, to appropriately derivatized silica support matrices. These columns exhibit moderate to high selectivity towards the separation of polycyclic aromatic hydrocarbons (PAHs). A charge transfer retention mechanism has been proposed. A comparison with a reference stationary phase, 3,5-dinitrobenzamide (DNB), to quantify the acceptor power of the new stationary bonded phases, is also reported. Finally, the effect of varying the derivatives of the bonded metallocene on PAHs retention is discussed.

Key Words

Column liquid chromatography Synthesis of bonded stationary phases Organometallic complexes Charge-transfer interactions PAHs 


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. [1]
    Kirkland, J.J.,Modern Practice of Liquid Chromatography 1971, John Wiley J.J. & Sons, New York.Google Scholar
  2. [2]
    Snyder, L.R.; Kirkland, J.J.Introduction to Modern Liquid Chromatography 1971, John Wiley & Sons, New York.Google Scholar
  3. [3]
    Kibbey, C.E.; Meyerhoff, M.E.J. Chromatogr. 1974,641, 49.CrossRefGoogle Scholar
  4. [4]
    Forster, R.Organic Charge-Transfer Complexes 1966, Academic Press, London, New York.Google Scholar
  5. [5]
    Person, W.B.; Mulliken, R.S.Molecular Complexes 1969, Wiley & Sons, New York.Google Scholar
  6. [6]
    Forster, R.Molecular Association 1979, Academic Press, London, New York, San Francisco.Google Scholar
  7. [7]
    Paetzold, R.Zeit. Chem. 1975,15, 377.Google Scholar
  8. [8]
    Morokura, K.Acc. Chem. Res. 1977,10, 294.CrossRefGoogle Scholar
  9. [9]
    Holstein, W.; Hemetsberger, H.Chromatographia 1982,15, 186.CrossRefGoogle Scholar
  10. [10]
    Holstein, W.; Hemetsberger, H.Chromatographia 1982,15, 251.CrossRefGoogle Scholar
  11. [11]
    Félix, G.; Bertrand, C.;Analusis 1989,17, 326.Google Scholar
  12. [12]
    Félix, G.; Thienpont, A.; Dentraygues, P.Chromatographia 1992,34, 177.CrossRefGoogle Scholar
  13. [13]
    Cagniant, D.; Davankov, V.A.; Félix, G.; Nondek, L. inComplexation Chromatography. Cagniant, D., Ed.,Chromatogr. Sci. Ser.,1991,57.Google Scholar
  14. [14]
    Mifune, M.; Kanai, T.; Urabe, M.; Iwado, A., Haginaka, J.; Motohashi, N.; Saito, Y.Anal. Sci. 1999,15, 581; b) Mifune, M.; Onoda, M.; Takatsuki, T.; Kanai, T.; Iwado, A.; Motohashi, N.; Haginaka, J.; Saito, Y.Chem. Pharm. Bull. 1999,47, 346; c) Mifune, M.; Mori, Y.; Onoda, M.; Iwado, A.; Motohashi, N.; Haginaka, J.; Saito, Y.Anal. Sci. 1998,14, 1127.CrossRefGoogle Scholar
  15. [15]
    Xiao, J.; Kibbey, C.E.; Coutant, D.E.; Martin, G.B.; Meyerhoff, M.E.,J. Liq. Chrom. Rel. Technol. 1996,19, 2901.Google Scholar
  16. [16]
    Deeming, A.J. InComprehensive Organometallic Chemistry 1982,4, 377. Wilkinson, G.; Stone, F.L.; Abel, E. Eds, Pergamon Press, Oxford.Google Scholar
  17. [17]a)
    Green, M.L.H.,Organometallic Compounds 1968,II: The Transition Elements, Methuen, London; b) Collman, J.P.: Hedegus, L.S.Principles and Applications of Organotransition Metal Chemistry, University Science Books, Mill Valley, 1980; c) Cotton, F.A.; Wilkinson, G.Advanced Inorganic Chemistry 1980, 4th ed., John & Sons Wiley, New York.Google Scholar
  18. [18]
    Marr, G.; Rockett, B.W.J. Organomet. Chem. 1982,227, 373.CrossRefGoogle Scholar
  19. [19]
    Cass, A.E.G.; Davis, G.; Francis, G.D.; Hill, H.A.O.; Higgins, I.J.; Aston, W.J.; Plotkin, E.V.; Scott, L.D.; Turner, A.P.F.Anal. Chem. 1984,56, 667.Google Scholar
  20. [20]
    Cass, A.E.G.; Davis, G.; Hill, H.A.O.; Higgins, I.J.; Plotkin, E.V.; Turner, A.P.F.; Aston, W.J. InCharge and Field Effects in Biosystems 1984, 475; Allen, N.J.; Usherwood, P.N.R., Eds, Abacus Press, Tumbridge Wells.Google Scholar
  21. [21]
    Astruc, D.Tetrahedron 1983,39, 4027.CrossRefGoogle Scholar
  22. [22]
    Astruc, D.Top. Curr. Chem. 1991,160, 49.Google Scholar
  23. [23]a)
    Nicholls, B.; Whiting, M.C.J. Chem. Soc. 1959,551; b) Semmelack, M.F.Annals, N.Y. Acad. Sci. 1977,295, 26; c) Jaouen, G.Annals, N.Y. Acad. Sci. 1977,295, 59; d) Bunnett, J.F.; Hermann, H.J. Org. Chem. 1971,36, 4081.Google Scholar
  24. [24]a)
    Khand, I.U.; Pauson, P.L.; Watts, W.F.J. Chem. Soc. C 1968, 2261; b) Piorko, A.; Abd-El-Aziz, A.S.; Lee, C.C.; Sutherland, R.G.J. Chem. Soc. 1989,Perkin Trans. 1, 469; c) Lee, C.C.; Gill, U.S.; Iqbal, M.; Azogu, C.I.; Sutherland, R.G.J. Organometal. Chem. 1982,231, 151; d) Sutherland, R.G.J. Organometal. Chem. Libr. 1977,3, 311; e) Sutherland, R.G.; Iqbal, M.; Piorko, A.J. Organometal. Chem. 1986,302, 307; f) Abd-El-Aziz, A.S.; Lee, C.C.; Piorko, A.; Sutherland, R.G.J. Organometal. Chem. 1988,348, 95.Google Scholar
  25. [25]a)
    Nesmeyanov, A.N.; Reutov, O.A.Dokl. Akad. Nauk SSSR 1957,115, 518; Lau, H.H.; Hart, H.J. Org. Chem. 1959,24, 280; b) Katada, T.; Nishida, M.; Kato, S.; Mizuta, M.J. Organomet. Chem. 1977,129, 189; c) Rosenblum, M.Chemistry of the Iron Group Metallocenes;1965, John Wiley & Sons, New York, Part. I; d) Nesmeyanov, A.N.; Vol’kenau, N.A.; Bolesova, I.N.Dokl. Akad. Nauk SSSR 1963,149, 615 and1966,166, 607; e) Nesmeyanov, A.N.Adv. Organomet. Chem. 1972,10, 1; f) Nesmeyanov, A.N.; Vol’kenau, N.A.; Bolesova, I.N.Dokl. Akad. Nauk SSSR 1967,1975, 606; g) Nesmeyanov, A.N.; Vol’kenau, N.A.; Isaeva, L.S.; Bolesova, I.N.Dokl. Akad. Nauk SSSR 1968,183, 354 and1967,176, 106; h) Nesmeyanov, A.N.; Vol’kenau, N.A.; Sirotkina, E.I.; Deryabin, V.V.Dokl. Akad. Nauk SSSR 1967,177, 1110.Google Scholar
  26. [26]
    Rosset, R.; Caude, M.; Jardy, A.Chromatographies en Phases Liquide et Supercritique 1991, ed. Masson, Paris, Milan, Barcelonne, Bonn.Google Scholar
  27. [27]
    Shriver, D.F.The manipulation of Air-Sensitive Compounds 1969, McGraw-Hill, New-York.Google Scholar
  28. [28]
    Coffield, T.H.; Sandel, V.; Closson, R.D.J. Am. Chem. Soc. 1957,79, 5826.CrossRefGoogle Scholar
  29. [29]
    Guerchais, V.; Roman, E.; Astruc, D.Organometallics 1986,5, 2505.CrossRefGoogle Scholar
  30. [30]a)
    Linton, R.W.; Miller, M.L.; Maciel, G.E.; Hawkins, B.L.Surf. Interface Anal. 1985,7, 196; b) Miller, M.L.; Linton, R.W.; Bush, S.G.; Jorgenson, J.W.Anal. Chem. 1984,56, 2204; c) Miller, M.L.; Linton, R.W.Anal. Chem. 1985,57, 2314.CrossRefGoogle Scholar
  31. [31]a)
    Buszewski, B.Chromatographia 1990,29, 233; b) Brown, V.A.; Barrett, D.A.; Shaw, P.A.; Davies, M.C.; Ritchie, H.J.; Ross, P.; Paul, A.J.; Watts, J.F.Surf. Interface Anal. 1994,21, 263.CrossRefGoogle Scholar
  32. [32]
    Mose, P.R.; Murray, R.M.J. Electroanal. Chem. 1977,77, 393.Google Scholar
  33. [33]
    Bordelanne, O.; Delville, M.H.; Labrugère, C. work in progress.Google Scholar
  34. [34]a)
    Mifune, M.; Shimomura, Y.; Mori, Y.; Onoda, M.; Iwado, A.; Motohashi, N.; Haginaka, J.; Saito, Y.Bull. Chem. Soc. Jpn. 1998,71, 1825; b) Silva, C.R.; Jardim, I.C.S.F.; Airoldi, C.J. High Resol. Chromatogr. 1999,22, 103.CrossRefGoogle Scholar
  35. [35]
    Félix, G.; Bertrand, C.HRC & CC 1984,7, 160.Google Scholar
  36. [36]
    Bordelanne, O.; Delville, M.H.; Félix, G. unpublished results.Google Scholar
  37. [37]
    Togni, A.; Hayashi, T.Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Sciences 1995, VCH-Wiley, Weinheim, New-York.Google Scholar
  38. [38]
    Davies, S.G.; Green, M.L.H.; Mingos, D.M.P.,Tetrahedron 1978,34, 3047.CrossRefGoogle Scholar
  39. [39]a)
    Warren, K.D.Struct. Bond. 1976,27, 45; b) Clark, D.W.; Warren, K.D.Struct. Bond. 1980,27, 45; c) Anderson, S.F. Jr; Drago, R.S.J. Am. Chem. Soc. 1970,92, 4244;Inorg. Chem. 1972,11, 1564.Google Scholar
  40. [40]
    Bertrand-Motard, C.Thesis 1988, University of Bordeaux I.Google Scholar

Copyright information

© Friedr. Vieweg & Sohn Verlagsgesellschaft mbH 2000

Authors and Affiliations

  • O. Bordelanne
    • 1
    • 2
  • M. H. Delville
    • 2
  • G. Félix
    • 1
  • C. Labrugère
    • 3
  • A. Thienpont
    • 1
  • C. Vidal
    • 1
  1. 1.Laboratoire d’Analyse Chimique par Reconnaissance MoléculaireEcole Nationale Supérieure de Chimie et de Physique de BordeauxTalenceFrance
  2. 2.Institut de Chimie de la Matière Condensée de Bordeaux-CNRSFrance
  3. 3.Centre de Caractérisation des Matériaux AvancésICMCB-CNRSPessacFrance

Personalised recommendations