Parallel and perpendicular stacking of ferrocene rings. Syntheses, X-ray structures, and electrochemistry of 1,8-bis-[1-(1′-phenylthio)ferrocenyl] naphthalene and 8,8′-bis-[1-(1′-phenylthio)ferrocenyl]-1,1′- binaphthyl

Inorganica Chimica Acta

Volumn 350, Issue , 2003, Pages 259-265

  Hua, Duy H ^a   McGill, James W ^a   Lou, Kaiyan ^a   Ueki, Akiharu ^a   Helfrich, Brian ^a   Desper, John ^a   Zanello, Piero ^b   Cinquantini, Arnaldo ^b   Corsini, Maddalena ^b   Fontani, Marco ^b  

^a KANSAS STATE UNIVERSITY   (United States)

^b UNIVERSITY OF SIENA   (Italy)

Author keywords

Crystal structures; Electrochemistry; Face to face ferrocene triads; Intramolecular electronic communication; Perpendicular stacking ferrocenes

Indexed keywords

CRYSTAL STRUCTURE; DICHLOROMETHANE; DIHEDRAL ANGLE; ELECTROCHEMISTRY; ELECTROLYTES; NAPHTHALENE; ORGANIC POLYMERS; ORGANOMETALLICS; SINGLE CRYSTALS; X RAYS;

DICHLOROMETHANE SOLUTIONS; ELECTROCHEMICAL BEHAVIOUR; ELECTRON DELOCALIZATION; ELECTROSTATIC REPULSION; FERROCENES; INTRAMOLECULAR ELECTRONIC COMMUNICATION; SINGLE CRYSTAL X-RAY ANALYSIS; THROUGH-SPACE INTERACTION;

IRON COMPOUNDS;

1,8 BIS[1 (1' PHENYLTHIO)FERROCENYL]NAPHTHALENE; 1,8 DIIODO 1,1' BINAPHTHYL; 1,8 DIIODONAPHTHALENE; 2,4,6 TRIS(1' PHENYLTHIO 1 FERROCENYL)BOROXIN; 8,8' BIS[1 (1' PHENYLTHIO)FERROCENYL] 1,1' BINAPHTHYL; ANION; CYCLOPENTADIENE DERIVATIVE; DICHLOROMETHANE; ELECTROLYTE; FERROCENE DERIVATIVE; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; ELECTROCHEMISTRY; OXIDATION REDUCTION REACTION; X RAY CRYSTALLOGRAPHY;

EID: 0142248994     PISSN: 00201693     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0020-1693(02)01573-6     Document Type: Article

References (42)

1. For a few recent literature data: (a) A.-C. Ribou, J.-P. Launay, M.L. Sachtleben, H. Li, C.W. Spangler, Inorg. Chem. 35 (1996) 3735; (b) S. Barlow, D. O'Hare, Chem. Rev. 97 (1997) 637; (c) M. Kurosawa, T. Nankawa, T. Matsuda, K. Kubo, M. Kurihara, H. Nishihara, Inorg. Chem. 38 (1999) 5113; (d) T.-Y. Dong, P.-H. Ho, X.-Q. Lai, Z.-W. Lin, K.-J. Lin, Organometallics 19 (2000) 1096; (e) L.-A. Hore, J. McAdam, J.L. Kerr, N.W. Duffy, B.H. Robinson, J. Simpson, Organometallics 19 (2000) 5039; (f) G.E. Southard, M.D. Curtis, Organometallics, 20 (2001) 508; (g) R.D. Adams, B. Qu, J. Organomet. Chem. 619 (2001) 271; (h) A. Tárraga, P. Molina, D. Curiel, M.D. Velasco, Organometallics, 20 (2001) 2145; (i) J.A. Mata, E. Peris, J. Chem. Soc., Dalton Trans. (2001) 3634.
2. For a few recent literature data: (a) A.-C. Ribou, J.-P. Launay, M.L. Sachtleben, H. Li, C.W. Spangler, Inorg. Chem. 35 (1996) 3735; (b) S. Barlow, D. O'Hare, Chem. Rev. 97 (1997) 637; (c) M. Kurosawa, T. Nankawa, T. Matsuda, K. Kubo, M. Kurihara, H. Nishihara, Inorg. Chem. 38 (1999) 5113; (d) T.-Y. Dong, P.-H. Ho, X.-Q. Lai, Z.-W. Lin, K.-J. Lin, Organometallics 19 (2000) 1096; (e) L.-A. Hore, J. McAdam, J.L. Kerr, N.W. Duffy, B.H. Robinson, J. Simpson, Organometallics 19 (2000) 5039; (f) G.E. Southard, M.D. Curtis, Organometallics, 20 (2001) 508; (g) R.D. Adams, B. Qu, J. Organomet. Chem. 619 (2001) 271; (h) A. Tárraga, P. Molina, D. Curiel, M.D. Velasco, Organometallics, 20 (2001) 2145; (i) J.A. Mata, E. Peris, J. Chem. Soc., Dalton Trans. (2001) 3634.
3. For a few recent literature data: (a) A.-C. Ribou, J.-P. Launay, M.L. Sachtleben, H. Li, C.W. Spangler, Inorg. Chem. 35 (1996) 3735; (b) S. Barlow, D. O'Hare, Chem. Rev. 97 (1997) 637; (c) M. Kurosawa, T. Nankawa, T. Matsuda, K. Kubo, M. Kurihara, H. Nishihara, Inorg. Chem. 38 (1999) 5113; (d) T.-Y. Dong, P.-H. Ho, X.-Q. Lai, Z.-W. Lin, K.-J. Lin, Organometallics 19 (2000) 1096; (e) L.-A. Hore, J. McAdam, J.L. Kerr, N.W. Duffy, B.H. Robinson, J. Simpson, Organometallics 19 (2000) 5039; (f) G.E. Southard, M.D. Curtis, Organometallics, 20 (2001) 508; (g) R.D. Adams, B. Qu, J. Organomet. Chem. 619 (2001) 271; (h) A. Tárraga, P. Molina, D. Curiel, M.D. Velasco, Organometallics, 20 (2001) 2145; (i) J.A. Mata, E. Peris, J. Chem. Soc., Dalton Trans. (2001) 3634.
4. For a few recent literature data: (a) A.-C. Ribou, J.-P. Launay, M.L. Sachtleben, H. Li, C.W. Spangler, Inorg. Chem. 35 (1996) 3735; (b) S. Barlow, D. O'Hare, Chem. Rev. 97 (1997) 637; (c) M. Kurosawa, T. Nankawa, T. Matsuda, K. Kubo, M. Kurihara, H. Nishihara, Inorg. Chem. 38 (1999) 5113; (d) T.-Y. Dong, P.-H. Ho, X.-Q. Lai, Z.-W. Lin, K.-J. Lin, Organometallics 19 (2000) 1096; (e) L.-A. Hore, J. McAdam, J.L. Kerr, N.W. Duffy, B.H. Robinson, J. Simpson, Organometallics 19 (2000) 5039; (f) G.E. Southard, M.D. Curtis, Organometallics, 20 (2001) 508; (g) R.D. Adams, B. Qu, J. Organomet. Chem. 619 (2001) 271; (h) A. Tárraga, P. Molina, D. Curiel, M.D. Velasco, Organometallics, 20 (2001) 2145; (i) J.A. Mata, E. Peris, J. Chem. Soc., Dalton Trans. (2001) 3634.
5. For a few recent literature data: (a) A.-C. Ribou, J.-P. Launay, M.L. Sachtleben, H. Li, C.W. Spangler, Inorg. Chem. 35 (1996) 3735; (b) S. Barlow, D. O'Hare, Chem. Rev. 97 (1997) 637; (c) M. Kurosawa, T. Nankawa, T. Matsuda, K. Kubo, M. Kurihara, H. Nishihara, Inorg. Chem. 38 (1999) 5113; (d) T.-Y. Dong, P.-H. Ho, X.-Q. Lai, Z.-W. Lin, K.-J. Lin, Organometallics 19 (2000) 1096; (e) L.-A. Hore, J. McAdam, J.L. Kerr, N.W. Duffy, B.H. Robinson, J. Simpson, Organometallics 19 (2000) 5039; (f) G.E. Southard, M.D. Curtis, Organometallics, 20 (2001) 508; (g) R.D. Adams, B. Qu, J. Organomet. Chem. 619 (2001) 271; (h) A. Tárraga, P. Molina, D. Curiel, M.D. Velasco, Organometallics, 20 (2001) 2145; (i) J.A. Mata, E. Peris, J. Chem. Soc., Dalton Trans. (2001) 3634.
6. For a few recent literature data: (a) A.-C. Ribou, J.-P. Launay, M.L. Sachtleben, H. Li, C.W. Spangler, Inorg. Chem. 35 (1996) 3735; (b) S. Barlow, D. O'Hare, Chem. Rev. 97 (1997) 637; (c) M. Kurosawa, T. Nankawa, T. Matsuda, K. Kubo, M. Kurihara, H. Nishihara, Inorg. Chem. 38 (1999) 5113; (d) T.-Y. Dong, P.-H. Ho, X.-Q. Lai, Z.-W. Lin, K.-J. Lin, Organometallics 19 (2000) 1096; (e) L.-A. Hore, J. McAdam, J.L. Kerr, N.W. Duffy, B.H. Robinson, J. Simpson, Organometallics 19 (2000) 5039; (f) G.E. Southard, M.D. Curtis, Organometallics, 20 (2001) 508; (g) R.D. Adams, B. Qu, J. Organomet. Chem. 619 (2001) 271; (h) A. Tárraga, P. Molina, D. Curiel, M.D. Velasco, Organometallics, 20 (2001) 2145; (i) J.A. Mata, E. Peris, J. Chem. Soc., Dalton Trans. (2001) 3634.
7. For a few recent literature data: (a) A.-C. Ribou, J.-P. Launay, M.L. Sachtleben, H. Li, C.W. Spangler, Inorg. Chem. 35 (1996) 3735; (b) S. Barlow, D. O'Hare, Chem. Rev. 97 (1997) 637; (c) M. Kurosawa, T. Nankawa, T. Matsuda, K. Kubo, M. Kurihara, H. Nishihara, Inorg. Chem. 38 (1999) 5113; (d) T.-Y. Dong, P.-H. Ho, X.-Q. Lai, Z.-W. Lin, K.-J. Lin, Organometallics 19 (2000) 1096; (e) L.-A. Hore, J. McAdam, J.L. Kerr, N.W. Duffy, B.H. Robinson, J. Simpson, Organometallics 19 (2000) 5039; (f) G.E. Southard, M.D. Curtis, Organometallics, 20 (2001) 508; (g) R.D. Adams, B. Qu, J. Organomet. Chem. 619 (2001) 271; (h) A. Tárraga, P. Molina, D. Curiel, M.D. Velasco, Organometallics, 20 (2001) 2145; (i) J.A. Mata, E. Peris, J. Chem. Soc., Dalton Trans. (2001) 3634.
8. For a few recent literature data: (a) A.-C. Ribou, J.-P. Launay, M.L. Sachtleben, H. Li, C.W. Spangler, Inorg. Chem. 35 (1996) 3735; (b) S. Barlow, D. O'Hare, Chem. Rev. 97 (1997) 637; (c) M. Kurosawa, T. Nankawa, T. Matsuda, K. Kubo, M. Kurihara, H. Nishihara, Inorg. Chem. 38 (1999) 5113; (d) T.-Y. Dong, P.-H. Ho, X.-Q. Lai, Z.-W. Lin, K.-J. Lin, Organometallics 19 (2000) 1096; (e) L.-A. Hore, J. McAdam, J.L. Kerr, N.W. Duffy, B.H. Robinson, J. Simpson, Organometallics 19 (2000) 5039; (f) G.E. Southard, M.D. Curtis, Organometallics, 20 (2001) 508; (g) R.D. Adams, B. Qu, J. Organomet. Chem. 619 (2001) 271; (h) A. Tárraga, P. Molina, D. Curiel, M.D. Velasco, Organometallics, 20 (2001) 2145; (i) J.A. Mata, E. Peris, J. Chem. Soc., Dalton Trans. (2001) 3634.
9. For a few recent literature data: (a) A.-C. Ribou, J.-P. Launay, M.L. Sachtleben, H. Li, C.W. Spangler, Inorg. Chem. 35 (1996) 3735; (b) S. Barlow, D. O'Hare, Chem. Rev. 97 (1997) 637; (c) M. Kurosawa, T. Nankawa, T. Matsuda, K. Kubo, M. Kurihara, H. Nishihara, Inorg. Chem. 38 (1999) 5113; (d) T.-Y. Dong, P.-H. Ho, X.-Q. Lai, Z.-W. Lin, K.-J. Lin, Organometallics 19 (2000) 1096; (e) L.-A. Hore, J. McAdam, J.L. Kerr, N.W. Duffy, B.H. Robinson, J. Simpson, Organometallics 19 (2000) 5039; (f) G.E. Southard, M.D. Curtis, Organometallics, 20 (2001) 508; (g) R.D. Adams, B. Qu, J. Organomet. Chem. 619 (2001) 271; (h) A. Tárraga, P. Molina, D. Curiel, M.D. Velasco, Organometallics, 20 (2001) 2145; (i) J.A. Mata, E. Peris, J. Chem. Soc., Dalton Trans. (2001) 3634.
10. Manners I. Angew. Chem., Int. Ed. Engl. 35:1996;1602. and references therein.
11. Yamamoto T., Morikita T., Maruyama T. Macromolecules. 30:1997;5390.
12. Cardona C.M., Kaifer A.E. J. Am. Chem. Soc. 120:1998;4023.
13. Lee M.-T., Foxman B.M., Rosenblum M. Organometallics. 4:1985;539.
14. Arnold R., Foxman B.M., Rosenblum M., Euler W.B. Organometallics. 7:1988;1253.
15. Iyoda M., Okabe T., Katada M., Kuwatani Y. J. Organomet. Chem. 569:1998;225.
16. McAdam C.J., Brunton J.J., Robinson B.H., Simpson J. J. Chem. Soc., Dalton Trans. 1999;2487.
17. Hudson R.D.A., Foxman B.M., Rosenblum M. Organometallics. 19:2000;469.
18. Alfonso G., Chávez I., Arancibia V., Manríquez J.M., Garland M.T., Roig A., Molins E., Baggio R.F. J. Organomet. Chem. 620:2001;32.
19. Herber R.H., Nowik I., Rosenblum M. Organometallics. 21:2002;846.
20. Rosenblum M., Nugent H.M., Jang K.-S., Labes M.M., Cahalane W., Klemarzyk P., Reigg W.M. Macromolecules. 28:1995;6330.
21. Hua D.H., McGill J.W., Ueda M., Stephany H.A. J. Organomet. Chem. 637-639:2001;832.
22. House H.O., Koepsell D.G., Campbell W.J. J. Org. Chem. 37:1972;1003.
23. Dyker G. J. Org. Chem. 58:1993;234.
24. SMART v5.060, © 1997-1999, Bruker Analytical X-ray Systems, Madison, WI.
25. SAINT v6.02, © 1997-1999, Bruker Analytical X-ray Systems, Madison, WI.
26. SHELXTL v5.10, © 1997, Bruker Analytical X-ray Systems, Madison, WI.
27. Fabrizi de Biani F., Laschi F., Zanello P., Ferguson G., Trotter J., O'Riordan G.M., Spalding T.R. J. Chem. Soc., Dalton Trans. 2001;1520.
28. LeSuer R., Geiger W.E. Angew. Chem., Int. Ed. Engl. 39:2000;248.
29. Camire N., Mueller-Westerhoff U.T., Geiger W.E. J. Organomet. Chem. 637-639:2001;823.
30. For reviews of Suzuki coupling reactions: (a) N. Miyaura, Advances in Metal-Organic Chemistry, vol. 6, JAI Press Inc., Connecticut, 1998, pp. 187-243; (b) N. Miyaura, A. Suzuki, Chem. Rev. 95 (1995) 2457; (c) S.P. Stanforth, Tetrahedron 54 (1998) 263; (d) A. Suzuki, J. Organomet. Chem. 576 (1999) 147. Coupling of ferrocenylboronic acids with phenyl halides: (e) R. Knapp, M. Rehahn, J. Organomet. Chem. 452 (1993) 235.
31. For reviews of Suzuki coupling reactions: (a) N. Miyaura, Advances in Metal-Organic Chemistry, vol. 6, JAI Press Inc., Connecticut, 1998, pp. 187-243; (b) N. Miyaura, A. Suzuki, Chem. Rev. 95 (1995) 2457; (c) S.P. Stanforth, Tetrahedron 54 (1998) 263; (d) A. Suzuki, J. Organomet. Chem. 576 (1999) 147. Coupling of ferrocenylboronic acids with phenyl halides: (e) R. Knapp, M. Rehahn, J. Organomet. Chem. 452 (1993) 235.
32. For reviews of Suzuki coupling reactions: (a) N. Miyaura, Advances in Metal-Organic Chemistry, vol. 6, JAI Press Inc., Connecticut, 1998, pp. 187-243; (b) N. Miyaura, A. Suzuki, Chem. Rev. 95 (1995) 2457; (c) S.P. Stanforth, Tetrahedron 54 (1998) 263; (d) A. Suzuki, J. Organomet. Chem. 576 (1999) 147. Coupling of ferrocenylboronic acids with phenyl halides: (e) R. Knapp, M. Rehahn, J. Organomet. Chem. 452 (1993) 235.
33. For reviews of Suzuki coupling reactions: (a) N. Miyaura, Advances in Metal-Organic Chemistry, vol. 6, JAI Press Inc., Connecticut, 1998, pp. 187-243; (b) N. Miyaura, A. Suzuki, Chem. Rev. 95 (1995) 2457; (c) S.P. Stanforth, Tetrahedron 54 (1998) 263; (d) A. Suzuki, J. Organomet. Chem. 576 (1999) 147. Coupling of ferrocenylboronic acids with phenyl halides: (e) R. Knapp, M. Rehahn, J. Organomet. Chem. 452 (1993) 235.
34. For reviews of Suzuki coupling reactions: (a) N. Miyaura, Advances in Metal-Organic Chemistry, vol. 6, JAI Press Inc., Connecticut, 1998, pp. 187-243; (b) N. Miyaura, A. Suzuki, Chem. Rev. 95 (1995) 2457; (c) S.P. Stanforth, Tetrahedron 54 (1998) 263; (d) A. Suzuki, J. Organomet. Chem. 576 (1999) 147. Coupling of ferrocenylboronic acids with phenyl halides: (e) R. Knapp, M. Rehahn, J. Organomet. Chem. 452 (1993) 235.
35. Hua D.H., McGill J.W., Robinson P.D., Meyers C.Y. Acta Crystallogr., Sect. E. 57:2001;m413.
36. Compound 8 was prepared from the monolithiation of ferrocene in THF with n-BuLi followed by the reaction with diphenyl disulfide. (a) N.M. Lagneau, Y. Chen, P.M. Robben, H.-S. Sin, K. Takasu, J.-S. Chen, P.D. Robinson, D.H. Hua, Tetrahedron, 54 (1998) 7301, and references cited therein; (b) A.J. Adebanjo, Y.W. Yu, L.K. Liu, Organometallics, 11 (1992) 2543.
37. Compound 8 was prepared from the monolithiation of ferrocene in THF with n-BuLi followed by the reaction with diphenyl disulfide. (a) N.M. Lagneau, Y. Chen, P.M. Robben, H.-S. Sin, K. Takasu, J.-S. Chen, P.D. Robinson, D.H. Hua, Tetrahedron, 54 (1998) 7301, and references cited therein; (b) A.J. Adebanjo, Y.W. Yu, L.K. Liu, Organometallics, 11 (1992) 2543.
38. Richardson D.E., Taube H. Inorg. Chem. 20:1981;1278.
39. Bott A.W. Current Separations (Bioanalytical Systems). 16:1997;61.
40. Astruc D. Electron Transfer and Radical Processes in Transition-Metal Chemistry. 1995;Wiley-VCH, New York.
41. Palaniappan V., Singru R.M., Agarwala U.C. Inorg. Chem. 27:1988;181.
42. Brunschwig B.S., Sutin N. Coord. Chem. Rev. 187:1999;233.