Skip to main content
SpringerLink
Log in

Synthesis, Crystal Structure, and Electrochemical Analysis of 1,4-diferrocenyl-tetrafluorobenzene. Effects of Linker Perfluorination on Intermetallic Electronic Communication

  • Published:
Transition Metal Chemistry Aims and scope Submit manuscript

Abstract

The reaction of monolithioferrocene (prepared from ferrocene and n-butyllithium) and 0.25 equiv of hexafluorobenzene afforded 1,4-diferrocenyl-tetrafluorobenzene (1) in 15 % isolated yield. Complex (1) was characterized crystallographically. The molecule adopts a conformation in which the cyclopentadienyl-arylene torsion angle is about 14 deg, suggesting typical biaryl electronic conjugation. However, solution voltammetric data reveal very little electronic communication between the two iron centers. Thus the p-tetrafluorophenylene linker exhibits insulating behavior.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. A.S. Abd-El-Aziz E.K. Todd (2003) Coord. Chem. Rev. 246 3 Occurrence Handle10.1016/S0010-8545(03)00107-3 Occurrence Handle1:CAS:528:DC%2BD3sXpt1Gisbw%3D

    Article  CAS  Google Scholar 

  2. I. Manners (2001) Science 294 1664 Occurrence Handle10.1126/science.1066321 Occurrence Handle1:CAS:528:DC%2BD3MXoslequrw%3D

    Article  CAS  Google Scholar 

  3. R.P. Hughes X. Zheng R.L. Ostrander A.L. Rheingold (1994) Organometallics 13 1567 Occurrence Handle1:CAS:528:DyaK2cXktV2ltbw%3D

    CAS  Google Scholar 

  4. P. Nguyen P. Gómez-Elipe I. Manners (1999) Chem. Rev. 99 1515 Occurrence Handle10.1021/cr960113u Occurrence Handle1:CAS:528:DyaK1MXislyju70%3D

    Article  CAS  Google Scholar 

  5. I. Manners, in Advances in Organometallic Chemistry, F.G.A. Stone and R. West (eds), Academic Press, New York, 1995, Vol. 37, pp. 131–168.

  6. R.W. Heo J.S. Park J.T. Goodson G.C. Claudio M. Takenaga T.A. Albright R.T. Lee (2004) Tetrahedron 60 7225 Occurrence Handle10.1016/j.tet.2004.06.067 Occurrence Handle1:CAS:528:DC%2BD2cXmtVWht7Y%3D

    Article  CAS  Google Scholar 

  7. C.E. Stanton T.R. Lee R.H. Grubbs N.S. Lewis J.K. Pudelski M.R. Callstrom M.S. Erickson M.L. McLaughlin (1995) Macromolecules 28 8713 Occurrence Handle10.1021/ma00130a002 Occurrence Handle1:CAS:528:DyaK2MXpsFWqtLY%3D

    Article  CAS  Google Scholar 

  8. D.L. Compton T.B. Rauchfuss (1994) Organometallics 13 4367 Occurrence Handle10.1021/om00023a045 Occurrence Handle1:CAS:528:DyaK2cXmsFKntb0%3D

    Article  CAS  Google Scholar 

  9. R.D.A. Hudson (2001) J. Organometal. Chem 637–639 47

    Google Scholar 

  10. T.Y. Dong C.H. Huang C.K. Chang H.C. Hsieh S.M. Peng G.H. Lee (1995) Organometallics 14 1776 Occurrence Handle10.1021/om00004a034 Occurrence Handle1:CAS:528:DyaK2MXks1Gru74%3D

    Article  CAS  Google Scholar 

  11. A. Hradsky B. Bildstein N. Schuler H. Schottenberger P. Jaitner K.H. Ongania K. Wurst J.P. Launay (1997) Organometallics 16 392 Occurrence Handle10.1021/om960676w Occurrence Handle1:CAS:528:DyaK2sXktFOrtQ%3D%3D

    Article  CAS  Google Scholar 

  12. A.C. Ribou J.P. Launay M.L. Sachtleben H. Li C.W. Spangler (1996) Inorg. Chem. 35 3735 Occurrence Handle10.1021/ic951376u Occurrence Handle1:CAS:528:DyaK28Xjt1emsrc%3D

    Article  CAS  Google Scholar 

  13. R. Rulkens A.J. Lough I. Manners (1994) J. Am. Chem. Soc. 116 797 Occurrence Handle1:CAS:528:DyaK2cXnvVSltg%3D%3D

    CAS  Google Scholar 

  14. T. Hirao, M. Kurashina, K. Aramaki and H. Nishihara, J. Chem. Soc., Dalton Trans., 2929 (1996)

  15. J. Alvarez A.E. Kaifer (1999) Organometallics 18 5733 Occurrence Handle1:CAS:528:DyaK1MXns1Sisbo%3D

    CAS  Google Scholar 

  16. E.E. Bunel P. Campos J. Ruz L. Valle I. Chadwick M. Santa Ana G. Gonzalez J.M. Manriquez (1988) Organometallics 7 474 Occurrence Handle1:CAS:528:DyaL1cXhtFaltbk%3D

    CAS  Google Scholar 

  17. P.A. Deck M.J. Lane J.L. Montgomery C. Slebodnick F.R. Fronczek (2000) Organometallics 19 1013 Occurrence Handle1:CAS:528:DC%2BD3cXht1yjt7c%3D

    CAS  Google Scholar 

  18. F.C. Krebs H. Spanggaard (2002) J. Org. Chem. 67 7185 Occurrence Handle1:CAS:528:DC%2BD38XmvF2nu7g%3D

    CAS  Google Scholar 

  19. R.D.A. Hudson B.M. Foxman M. Rosenblum (2000) Organometallics 19 469 Occurrence Handle10.1021/om990750l Occurrence Handle1:CAS:528:DC%2BD3cXmsFKq

    Article  CAS  Google Scholar 

  20. C.B. Hollandsworth W.G.J. Hollis C. Slebodnick P.A. Deck (1999) Organometallics 18 3610 Occurrence Handle10.1021/om990321n Occurrence Handle1:CAS:528:DyaK1MXltVGgsbk%3D

    Article  CAS  Google Scholar 

  21. M.I. Bruce and M.J. Melvin, J. Chem. Soc. C, 2107 (1969).

  22. H. Rosenberg, US Patent No. 3422130 (1969), to United States Air Force.

  23. S.I. Goldberg L.H. Keith T.S. Prokopov (1963) J. Org. Chem. 28 850 Occurrence Handle1:CAS:528:DyaF3sXms1GrtQ%3D%3D

    CAS  Google Scholar 

  24. M.D. Rausch D.J. Ciappenelli (1967) J. Organometal. Chem. 10 127 Occurrence Handle10.1016/S0022-328X(00)81725-8 Occurrence Handle1:CAS:528:DyaF2sXltVShsL0%3D

    Article  CAS  Google Scholar 

  25. D.M. Heinekey (1991) J. Am. Chem. Soc. 113 6074 Occurrence Handle10.1021/ja00016a022 Occurrence Handle1:CAS:528:DyaK3MXltFClu7k%3D

    Article  CAS  Google Scholar 

  26. M. Rausch M. Vogel H. Rosenberg (1957) J. Org. Chem. 22 900 Occurrence Handle10.1021/jo01359a012 Occurrence Handle1:CAS:528:DyaG1cXitFSrug%3D%3D

    Article  CAS  Google Scholar 

  27. R. Sanders U.T. Mueller-Westerhoff (1996) J. Organometal. Chem. 512 219 Occurrence Handle10.1016/0022-328X(95)05914-B Occurrence Handle1:CAS:528:DyaK28XivFOnsL4%3D

    Article  CAS  Google Scholar 

  28. D.W. Slocum T.R. Engelmann C. Ernst C.A. Jennings W. Jones B. Koonsvitsky J. Lewis P. Shenkin (1969) J. Chem. Educ. 46 144 Occurrence Handle1:CAS:528:DyaF1MXksFSitbo%3D

    CAS  Google Scholar 

  29. D. Guillaneux H.B. Kagan (1995) J. Org. Chem. 60 2502 Occurrence Handle10.1021/jo00113a033 Occurrence Handle1:CAS:528:DyaK2MXkvFGiu7g%3D

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Roanoke College, Salem, VA, 24153, U.S.A

    W. Gary Hollis Jr., Troy F. Bonsall & Valerie L. Cuba

  2. Department of Chemistry, Virginia Tech, Blacksburg, VA, 24061, U.S.A

    Paul A. Deck

  3. Department of Chemistry, Louisiana State University, Baton Rouge, LA, 70803, U.S.A

    Frank R. Fronczek

Authors
  1. W. Gary Hollis Jr.
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Troy F. Bonsall
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Valerie L. Cuba
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Paul A. Deck
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Frank R. Fronczek
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to W. Gary Hollis Jr..

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gary Hollis, W., Bonsall, T.F., Cuba, V.L. et al. Synthesis, Crystal Structure, and Electrochemical Analysis of 1,4-diferrocenyl-tetrafluorobenzene. Effects of Linker Perfluorination on Intermetallic Electronic Communication. Transition Met Chem 31, 246–249 (2006). https://doi.org/10.1007/s11243-005-6295-1

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11243-005-6295-1

Keywords

Search

Navigation