Paramagnetic and semiconducting 1:1 salts of 1,1′-disubstituted ferrocenes and [Ni(mnt)2]-. Synthesis, structure, and physical properties

Organometallics

Volumn 15, Issue 25, 1996, Pages 5342-5346

  Hobi, Markus ^a   Zürcher, Stefan ^a   Gramlich, Volker ^a   Burckhardt, Urs ^a   Mensing, Christian ^a   Spahr, Michael ^a   Togni, Antonio ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000947288     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9603981     Document Type: Article

References (46)

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13. See, for example: (a) Aumüller, A.; Erk, P.; Klebe, G.; Hünig, S.; von Schütz, J.-U.; Werner, H.-P. Angew. Chem. 1986, 98, 759-761; Angew. Chem., Int. Ed. Engl. 1986, 25, 740-741. (b) Hünig, S.; Erk, P. Adv. Mater. 1991, 3, 225-236.
14. See, for example: (a) Magnetic Molecular Materials; Gatteschi, D., Kahn, O., Miller, J. S., Palacio F., Eds.; NATO ASI Series, Series E: Applied Sciences, Vol. 198; Kluwer: Dordrecht, The Netherlands, 1991. (b) Davison, A.; Edelstein, N.; Holm, R.; Maki, A. H. J. Am. Chem. Soc. 1963, 85, 2029-2030. (c) Davison, A.; Edelstein, N.; Holm, R. H.; Maki, A. H. Inorg. Chem. 1963, 2, 1227-1232. For the preparation of mnt complexes, see: (d) Davison, A.; Holm, R. H. Inorg. Synth. 1967, 10, 8-26. (e) Hoyer, E.; Olk, R.-M.; Olk, B.; Dietzsch, W.; Kirmse, R. Coord. Chem. Rev. 1992, 117, 99-131.
15. See, for example: (a) Magnetic Molecular Materials; Gatteschi, D., Kahn, O., Miller, J. S., Palacio F., Eds.; NATO ASI Series, Series E: Applied Sciences, Vol. 198; Kluwer: Dordrecht, The Netherlands, 1991. (b) Davison, A.; Edelstein, N.; Holm, R.; Maki, A. H. J. Am. Chem. Soc. 1963, 85, 2029-2030. (c) Davison, A.; Edelstein, N.; Holm, R. H.; Maki, A. H. Inorg. Chem. 1963, 2, 1227-1232. For the preparation of mnt complexes, see: (d) Davison, A.; Holm, R. H. Inorg. Synth. 1967, 10, 8-26. (e) Hoyer, E.; Olk, R.-M.; Olk, B.; Dietzsch, W.; Kirmse, R. Coord. Chem. Rev. 1992, 117, 99-131.
16. See, for example: (a) Magnetic Molecular Materials; Gatteschi, D., Kahn, O., Miller, J. S., Palacio F., Eds.; NATO ASI Series, Series E: Applied Sciences, Vol. 198; Kluwer: Dordrecht, The Netherlands, 1991. (b) Davison, A.; Edelstein, N.; Holm, R.; Maki, A. H. J. Am. Chem. Soc. 1963, 85, 2029-2030. (c) Davison, A.; Edelstein, N.; Holm, R. H.; Maki, A. H. Inorg. Chem. 1963, 2, 1227-1232. For the preparation of mnt complexes, see: (d) Davison, A.; Holm, R. H. Inorg. Synth. 1967, 10, 8-26. (e) Hoyer, E.; Olk, R.-M.; Olk, B.; Dietzsch, W.; Kirmse, R. Coord. Chem. Rev. 1992, 117, 99-131.
17. See, for example: (a) Magnetic Molecular Materials; Gatteschi, D., Kahn, O., Miller, J. S., Palacio F., Eds.; NATO ASI Series, Series E: Applied Sciences, Vol. 198; Kluwer: Dordrecht, The Netherlands, 1991. (b) Davison, A.; Edelstein, N.; Holm, R.; Maki, A. H. J. Am. Chem. Soc. 1963, 85, 2029-2030. (c) Davison, A.; Edelstein, N.; Holm, R. H.; Maki, A. H. Inorg. Chem. 1963, 2, 1227-1232. For the preparation of mnt complexes, see: (d) Davison, A.; Holm, R. H. Inorg. Synth. 1967, 10, 8-26. (e) Hoyer, E.; Olk, R.-M.; Olk, B.; Dietzsch, W.; Kirmse, R. Coord. Chem. Rev. 1992, 117, 99-131.
18. See, for example: (a) Magnetic Molecular Materials; Gatteschi, D., Kahn, O., Miller, J. S., Palacio F., Eds.; NATO ASI Series, Series E: Applied Sciences, Vol. 198; Kluwer: Dordrecht, The Netherlands, 1991. (b) Davison, A.; Edelstein, N.; Holm, R.; Maki, A. H. J. Am. Chem. Soc. 1963, 85, 2029-2030. (c) Davison, A.; Edelstein, N.; Holm, R. H.; Maki, A. H. Inorg. Chem. 1963, 2, 1227-1232. For the preparation of mnt complexes, see: (d) Davison, A.; Holm, R. H. Inorg. Synth. 1967, 10, 8-26. (e) Hoyer, E.; Olk, R.-M.; Olk, B.; Dietzsch, W.; Kirmse, R. Coord. Chem. Rev. 1992, 117, 99-131.
19. For a review on ferrocene derivatives, see: (a) Togni, A. In Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science; Togni, A., Hayashi, T., Eds.; VCH: Weinheim, Germany, 1995; pp 433-469. For scattered reports, see, for example: (b) Müller-Westerhoff, U. T.; Eilbracht, P. J. Am. Chem. Soc. 1972, 94, 9272-9274. (c) Goldberg, S. Z.; Spivack, B.; Stanley, G.; Eisenberg, R.; Braitsch, D. M.; Miller, J. S.; Abkowitz, M. J. Am. Chem. Soc. 1977, 99, 110-117. (d) Ueno, Y.; Sano, H.; Okawara, M. J. Chem. Soc., Chem. Commun. 1980, 28-30. (e) Bolinger, C. M.; Darkwa, J.; Gammie, G.; Gammon, S. D.; Lyding, J. W.; Rauchfuss, T. B.; Wilson, S. R. Organometallics 1986, 5, 2386-2388.
20. For a review on ferrocene derivatives, see: (a) Togni, A. In Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science; Togni, A., Hayashi, T., Eds.; VCH: Weinheim, Germany, 1995; pp 433-469. For scattered reports, see, for example: (b) Müller-Westerhoff, U. T.; Eilbracht, P. J. Am. Chem. Soc. 1972, 94, 9272-9274. (c) Goldberg, S. Z.; Spivack, B.; Stanley, G.; Eisenberg, R.; Braitsch, D. M.; Miller, J. S.; Abkowitz, M. J. Am. Chem. Soc. 1977, 99, 110-117. (d) Ueno, Y.; Sano, H.; Okawara, M. J. Chem. Soc., Chem. Commun. 1980, 28-30. (e) Bolinger, C. M.; Darkwa, J.; Gammie, G.; Gammon, S. D.; Lyding, J. W.; Rauchfuss, T. B.; Wilson, S. R. Organometallics 1986, 5, 2386-2388.
21. For a review on ferrocene derivatives, see: (a) Togni, A. In Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science; Togni, A., Hayashi, T., Eds.; VCH: Weinheim, Germany, 1995; pp 433-469. For scattered reports, see, for example: (b) Müller-Westerhoff, U. T.; Eilbracht, P. J. Am. Chem. Soc. 1972, 94, 9272-9274. (c) Goldberg, S. Z.; Spivack, B.; Stanley, G.; Eisenberg, R.; Braitsch, D. M.; Miller, J. S.; Abkowitz, M. J. Am. Chem. Soc. 1977, 99, 110-117. (d) Ueno, Y.; Sano, H.; Okawara, M. J. Chem. Soc., Chem. Commun. 1980, 28-30. (e) Bolinger, C. M.; Darkwa, J.; Gammie, G.; Gammon, S. D.; Lyding, J. W.; Rauchfuss, T. B.; Wilson, S. R. Organometallics 1986, 5, 2386-2388.
22. For a review on ferrocene derivatives, see: (a) Togni, A. In Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science; Togni, A., Hayashi, T., Eds.; VCH: Weinheim, Germany, 1995; pp 433-469. For scattered reports, see, for example: (b) Müller-Westerhoff, U. T.; Eilbracht, P. J. Am. Chem. Soc. 1972, 94, 9272-9274. (c) Goldberg, S. Z.; Spivack, B.; Stanley, G.; Eisenberg, R.; Braitsch, D. M.; Miller, J. S.; Abkowitz, M. J. Am. Chem. Soc. 1977, 99, 110-117. (d) Ueno, Y.; Sano, H.; Okawara, M. J. Chem. Soc., Chem. Commun. 1980, 28-30. (e) Bolinger, C. M.; Darkwa, J.; Gammie, G.; Gammon, S. D.; Lyding, J. W.; Rauchfuss, T. B.; Wilson, S. R. Organometallics 1986, 5, 2386-2388.
23. For a review on ferrocene derivatives, see: (a) Togni, A. In Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science; Togni, A., Hayashi, T., Eds.; VCH: Weinheim, Germany, 1995; pp 433-469. For scattered reports, see, for example: (b) Müller-Westerhoff, U. T.; Eilbracht, P. J. Am. Chem. Soc. 1972, 94, 9272-9274. (c) Goldberg, S. Z.; Spivack, B.; Stanley, G.; Eisenberg, R.; Braitsch, D. M.; Miller, J. S.; Abkowitz, M. J. Am. Chem. Soc. 1977, 99, 110-117. (d) Ueno, Y.; Sano, H.; Okawara, M. J. Chem. Soc., Chem. Commun. 1980, 28-30. (e) Bolinger, C. M.; Darkwa, J.; Gammie, G.; Gammon, S. D.; Lyding, J. W.; Rauchfuss, T. B.; Wilson, S. R. Organometallics 1986, 5, 2386-2388.
24. For reviews, see: (a) Miller, J. S.; Epstein, A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 385-416. (b) Miller, J. S.; Epstein, A. J.; Reiff, W. M. Chem. Rev. 1988, 88, 201-220. (c) Miller, J. S.; Epstein, A. J.; Reiff, W. M. Acc. Chem. Res. 1988, 21, 114-120. (d) Miller, J. S.; Epstein, A. J.; Reiff, W. M. Science 1988, 240, 40-47. (e) Miller, J. S.; Epstein, A. J. In Research Frontiers in Magnetochemistry; O'Connor, C. J., Ed.; World Scientific: Singapore, 1993; pp 283-302.
25. For reviews, see: (a) Miller, J. S.; Epstein, A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 385-416. (b) Miller, J. S.; Epstein, A. J.; Reiff, W. M. Chem. Rev. 1988, 88, 201-220. (c) Miller, J. S.; Epstein, A. J.; Reiff, W. M. Acc. Chem. Res. 1988, 21, 114-120. (d) Miller, J. S.; Epstein, A. J.; Reiff, W. M. Science 1988, 240, 40-47. (e) Miller, J. S.; Epstein, A. J. In Research Frontiers in Magnetochemistry; O'Connor, C. J., Ed.; World Scientific: Singapore, 1993; pp 283-302.
26. For reviews, see: (a) Miller, J. S.; Epstein, A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 385-416. (b) Miller, J. S.; Epstein, A. J.; Reiff, W. M. Chem. Rev. 1988, 88, 201-220. (c) Miller, J. S.; Epstein, A. J.; Reiff, W. M. Acc. Chem. Res. 1988, 21, 114-120. (d) Miller, J. S.; Epstein, A. J.; Reiff, W. M. Science 1988, 240, 40-47. (e) Miller, J. S.; Epstein, A. J. In Research Frontiers in Magnetochemistry; O'Connor, C. J., Ed.; World Scientific: Singapore, 1993; pp 283-302.
27. For reviews, see: (a) Miller, J. S.; Epstein, A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 385-416. (b) Miller, J. S.; Epstein, A. J.; Reiff, W. M. Chem. Rev. 1988, 88, 201-220. (c) Miller, J. S.; Epstein, A. J.; Reiff, W. M. Acc. Chem. Res. 1988, 21, 114-120. (d) Miller, J. S.; Epstein, A. J.; Reiff, W. M. Science 1988, 240, 40-47. (e) Miller, J. S.; Epstein, A. J. In Research Frontiers in Magnetochemistry; O'Connor, C. J., Ed.; World Scientific: Singapore, 1993; pp 283-302.
28. For reviews, see: (a) Miller, J. S.; Epstein, A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 385-416. (b) Miller, J. S.; Epstein, A. J.; Reiff, W. M. Chem. Rev. 1988, 88, 201-220. (c) Miller, J. S.; Epstein, A. J.; Reiff, W. M. Acc. Chem. Res. 1988, 21, 114-120. (d) Miller, J. S.; Epstein, A. J.; Reiff, W. M. Science 1988, 240, 40-47. (e) Miller, J. S.; Epstein, A. J. In Research Frontiers in Magnetochemistry; O'Connor, C. J., Ed.; World Scientific: Singapore, 1993; pp 283-302.
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36. 8 Their formal electrode Potentials for the one-electron oxidation step are lower by 0.1-0.2 V than for ferrocene.
37. -, see: (b) Reith, W.; Polborn, K.; Amberger, E. Angew. Chem., Int. Ed. Engl. 1988, 27, 699-700. (c) Colpas, G. J.; Kumar, M.; Day, R. O.; Maroney, M. J. Inorg. Chem. 1990, 29, 4779-4788. (d) Mahadevan, C. J. Cryst. Spectrosc, 1986, 16, 159-167. (e) Brunn, K.; Endres, H.; Weiss, J. Z. Naturforsch. 1987, 42B, 1222-1226.
38. -, see: (b) Reith, W.; Polborn, K.; Amberger, E. Angew. Chem., Int. Ed. Engl. 1988, 27, 699-700. (c) Colpas, G. J.; Kumar, M.; Day, R. O.; Maroney, M. J. Inorg. Chem. 1990, 29, 4779-4788. (d) Mahadevan, C. J. Cryst. Spectrosc, 1986, 16, 159-167. (e) Brunn, K.; Endres, H.; Weiss, J. Z. Naturforsch. 1987, 42B, 1222-1226.
39. -, see: (b) Reith, W.; Polborn, K.; Amberger, E. Angew. Chem., Int. Ed. Engl. 1988, 27, 699-700. (c) Colpas, G. J.; Kumar, M.; Day, R. O.; Maroney, M. J. Inorg. Chem. 1990, 29, 4779-4788. (d) Mahadevan, C. J. Cryst. Spectrosc, 1986, 16, 159-167. (e) Brunn, K.; Endres, H.; Weiss, J. Z. Naturforsch. 1987, 42B, 1222-1226.
40. -, see: (b) Reith, W.; Polborn, K.; Amberger, E. Angew. Chem., Int. Ed. Engl. 1988, 27, 699-700. (c) Colpas, G. J.; Kumar, M.; Day, R. O.; Maroney, M. J. Inorg. Chem. 1990, 29, 4779-4788. (d) Mahadevan, C. J. Cryst. Spectrosc, 1986, 16, 159-167. (e) Brunn, K.; Endres, H.; Weiss, J. Z. Naturforsch. 1987, 42B, 1222-1226.
41. -, see: (b) Reith, W.; Polborn, K.; Amberger, E. Angew. Chem., Int. Ed. Engl. 1988, 27, 699-700. (c) Colpas, G. J.; Kumar, M.; Day, R. O.; Maroney, M. J. Inorg. Chem. 1990, 29, 4779-4788. (d) Mahadevan, C. J. Cryst. Spectrosc, 1986, 16, 159-167. (e) Brunn, K.; Endres, H.; Weiss, J. Z. Naturforsch. 1987, 42B, 1222-1226.
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44. See also: (b) Weiher, J. F.; Melby, L. R.; Benson, R. E. J. Am. Chem. Soc. 1964, 86, 4329-4333. (c) Davison, A.; Edelstein, N.; Holm, R. H.; Maki, A. H. Inorg. Chem. 1963, 2, 1227-1232.
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46. For a detailed theoretical account on structure and mechanism of conductivity of metal bis(dithiolene) derivatives, see: Alvarez, S.; Vicente, R.; Hoffmann, R. J. Am. Chem. Soc. 1985, 107, 6253-6277.