Electron delocalization in vinyl ruthenium substituted cyclophanes: Assessment of the through-space and the through-bond pathways

Journal of Organometallic Chemistry

Volumn 696, Issue 20, 2011, Pages 3186-3197

  Mücke, Philipp ^a   Zabel, Manfred ^b   Edge, Ruth ^c   Collison, David ^c   Clément, Sébastien ^d,f   Záliš, Stanislav ^e   Winter, Rainer F ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

^b UNIVERSITY OF REGENSBURG   (Germany)

^c UNIVERSITY OF MANCHESTER   (United Kingdom)

^d UNIVERSITÉ DE FRANCHE COMTÉ   (France)

^e J HEYROVSKÝ INSTITUTE OF PHYSICAL CHEMISTRY   (Czech Republic)

^f UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

Cyclophanes; Electrochemistry; Mixed valent; Ruthenium; Spectroelectrochemistry; Vinyl complexes

Indexed keywords

[2.2]PARACYCLOPHANE; BAND SHIFT; CLASS II; COMPLEX 1; CYCLOPHANES; DELOCALIZATIONS; DICATIONS; DIRUTHENIUM COMPLEX; ELECTROACTIVE; ELECTRON DELOCALIZATION; ELECTRONIC COUPLING; INTERVALENCE CHARGE-TRANSFER; IR BANDS; MIXED-VALENT; NEUTRAL COMPLEXES; ONE-ELECTRON OXIDATION; PARACYCLOPHANE; RADICAL CATIONS; SIMPLIFIED MODELS; SPIN DENSITY DISTRIBUTIONS; VINYL COMPLEXES;

CHARGE TRANSFER; POSITIVE IONS; RUTHENIUM; SPECTROELECTROCHEMISTRY; STYRENE;

RUTHENIUM COMPOUNDS;

EID: 84860390486     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2011.06.028     Document Type: Article

References (98)

1. J.W. Steed, J.L. Atwood, Supramolecular Chemistry, Wiley, Chichester, 2000.
2. Z. Chen, A. Lohr, C.R. Saha-Moeller, and F. Würthner Chem. Soc. Rev. 38 2009 564 584
3. H. Roesky, and M. Andruh Coord. Chem. Rev. 236 2003 91 119
4. C. Janiak J. Chem. Soc., Dalton Trans. 2000 3885 3896
5. P. Douglas, and F.J. Stoddart Angew. Chem. Int. Ed. Engl. 35 1996 1155 1196
6. N.W. Alcock, P.R. Barker, J.M. Haider, M.J. Hannon, C.L. Painting, Z. Pikramenou, E.A. Plummer, K. Rissanen, and P. Saarenketo Dalton Trans. 2000 1447 1462
7. A.S. Ionkin, W.J. Marshall, and Y. Wang Organometallics 24 2005 619 627
8. J.W. Hong, H.Y. Woo, B. Liu, and G.C. Bazan J. Am. Chem. Soc. 127 2005 7435 7443
9. S.R. Amrutha, and M. Jayakannan J. Phys. Chem. B 110 2006 4083 4091
10. P. Shen, G. Sang, J. Lu, B. Zhao, M. Wan, Y. Zou, Y. Li, and S. Tan Macromolecules 41 2008 5716 5722
11. Y. Yamauchi, M. Yoshizawa, and M. Fujita J. Am. Chem. Soc. 130 2008 5832 5833
12. L.-L. Li, K.-J. Lin, C.-J. Ho, C.-P. Sun, and H.-D. Yang Chem. Commun. 2006 1286 1288
13. C. Elschenbroich, M. Wolf, O. Schiemann, K. Harms, O. Burghaus, and J. Pebler Organometallics 21 2002 5810 5819
14. T. Cauchy, E. Ruiz, O. Jeannin, M. Nomura, and M. Formigué Chem. Eur. J. 13 2007 8858 8866
15. C. Elschenbroich, B. Kanellakopulos, F.H. Köhler, B. Metz, R. Lescouëzec, N. Mitzel, and W. Strauß Chem. Eur. J. 13 2007 1191 1200
16. K.M. Knoblock, C.J. Silvestri, and D.M. Collard J. Am. Chem. Soc. 128 2006 13680 13681
17. C. Hou, J.-M. Shi, Y.-M. Sun, W. Shi, P. Cheng, and L.-D. Liu Dalton Trans. 2008 5970 5976
18. D.L. Reger, A. Debreczeni, B. Reinecke, V. Rassolov, and M.D. Smith Inorg. Chem. 58 2009 8911 8924
19. I.V. Fedyanin, K.A. Lyssenko, Z.A. Starikova, and M.Y. Antipin Russ. Chem. Bulletin 53 2004 1153 1158
20. P.J. Ball, T.R. Shtoyko, J.A. Krause Brauer, W.J. Oldham, and W.B. Connick Inorg. Chem. 43 2004 622 632
21. J. Casado, K. Takimiya, T. Otsubo, F.J. Ramírez, J.J. Quirante, R.P. Ortiz, S.R. González, and J.T. López Navarrete J. Am. Chem. Soc. 130 2008 14028 14029
22. M.E. Stoll, S.R. Lovelace, W.E. Geiger, H. Schimanke, I. Hyla-Kryspin, and R. Gleiter J. Am. Chem. Soc. 121 1999 9343 9351
23. S. Gath, R. Gleiter, F. Rominger, and C. Bleiholder Organometallics 26 2007 644 650
24. S.F. Nelsen, G. Li, K.P. Schultz, H.Q. Tran, and I.A. Guzei J. Am. Chem. Soc. 130 2008 11620 11622
25. D.-L. Sun, S.V. Rosokha, S.V. Lindeman, and J.K. Kochi J. Am. Chem. Soc. 125 2003 15950 15963
26. A. Fürstner, M. Alcarazo, H. Krause, and C.W. Lehmann J. Am. Chem. Soc. 129 2007 12676 12677
27. G.B. Bartholomew, and G.C. Bazan Acc. Chem. Res. 34 2001 30 39
28. Y. Tanaka, T. Ozawa, A. Inagaki, and M. Akita Dalton Trans. 2007 928 933
29. M.R. Arkin, E.D.A. Stemp, R.E. Holmlin, J.K. Barton, A. Hörmann, E.J.C. Olson, and P.F. Barbara Science 273 1996 475 480
30. S.O. Kelly, and K.K. Barton Chem. Biol. 5 1998 413 425
31. T.T. Tashica, and J.K. Barton M. Demeunynck, C. Bailly, W.D. Wilson, Small Molecule DNA and RNA Binders 2003 Wiley-VCH Weinheim, Germany 146 177
32. A. Tirosi Mol. Simulat. 32 2006 707 716
33. A. van de Craats, N. Stutzmann, O. Bunk, M.N. Nielsen, M. Watson, K. Müllen, H.D. Chanzy, H. Sirringhaus, and R.H. Friend Adv. Mater. 15 2003 495 499
34. L. Li, S.-W. Kang, J. Harden, Q. Sun, X. Zhu, L. Dai, A. Jakli, S. Kumar, and Q. Li Liquid Crystals 35 2008 233 239
35. S. Laschat, A. Baro, N. Steinke, F. Giesselmann, C. Hägele, G. Scalia, R. Judele, E. Kapatsina, S. Sauer, A. Schreivogel, and M. Tosoni Angew. Chem. Int. Ed. Engl. 46 2007 4832 4887
36. S. Sergeyev, W. Pisula, and Y.H. Geerts Chem. Soc. Rev. 36 2007 1902 1929
37. S. Rathgeber, D. Bastos de Toledo, E. Birckner, H. Hoppe, and D.A.M. Egbe Macromolecules 43 2010 306 315
38. P.H. Dinolfo, M.E. Williams, C.L. Stern, and J.T. Hupp J. Am. Chem. Soc. 126 2004 12989 13001
39. P.H. Dinolfo, and J.T. Hupp J. Am. Chem. Soc. 126 2004 16814 16819
40. P.H. Dinolfo, S.J. Lee, V. Coropceanu, J.-L. Brédas, and J.T. Hupp Inorg. Chem. 44 2005 5789 5797
41. F. Gerson Top. Curr. Chem. 115 1983 57 105
42. S. Amthor, and C. Lambert J. Phys. Chem. A 110 2006 1177 1189
43. S.F. Nelsen, A.E. Konradsson, and J.P. Telo J. Am. Chem. Soc. 127 2005 920 925
44. Y. Morisaki, and Y. Chujo Angew. Chem. Int. Ed. Engl. 45 2006 6430 6437
45. A. Wartini, J. Valenzuela, H.A. Staab, and F.A. Neugebauer Eur. J. Org. Chem. 1998 139 148
46. A. Wartini, H.A. Staab, and F.A. Neugebauer Eur. J. Org. Chem. 1998 1161 1170
47. D.R. Kattnig, B. Mladenova, G. Grampp, C. Kaiser, A. Heckmann, and C. Lambert J. Phys. Chem. C 113 2009 2983 2995
48. M. Krejcik, M. Danek, and F. Hartl J. Electroanal. Chem. 317 1991 179 187
49. P.R. Murray, and L.J. Yellowlees W. Kaim, A. Klein, Spectroelectrochemistry 2008 RSC Publishing Cambridge 207 231
50. M.A. Esteruelas, and H. Werner J. Organomet. Chem. 303 1986 221 231
51. S. Clément, L. Guyard, M. Knorr, S. Dilsky, C. Strohmann, and M. Arroyo J. Organomet. Chem. 692 2007 839 850
52. M. Holzapfel, and C. Lambert J. Phys. Chem. C 112 2008 1227 1243
53. M.J. Frisch, G. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Blonio, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr. , J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, J.B. ÖFarkasForesman, J.V. Ortiz, J. Cioslowski, and D.J. Fox Gaussion 09, Revision A.02 2009 Gaussian, Inc Wallingford CT
54. G. te Velde, F.M. Bickelhaupt, S.J.A. van Gisbergen, C. Fonseca Guerra, E.J. Baerends, J.G. Snijders, and T. Ziegler J. Comput. Chem. 22 2001 931 967
55. ADF 2010.01. in: V.U. SCM, Amsterdam (Ed.), edition 2005 ed., http://www.scm.com, Amsterdam, The Netherlands.
56. D. Andrae, U. Haeussermann, M. Dolg, H. Stoll, and H. Preuss Theor. Chim. Acta 77 1990 123
57. P.H. Hariharan, and J.A. Pople Theor. Chim. Acta 28 1973 213 222
58. J.P. Perdew, K. Burke, and M. Ernzerhof Phys. Rev. Lett. 77 1996 3865 3868
59. C. Adamo, and V. Barone J. Chem. Phys. 110 1999 6158 6170
60. Y. Zhao, N.E. Schultz, and D.G. Truhlar J. Chem. Theory Comput. 2 2006 364 382
61. M. Cossi, N. Rega, G. Scalmani, and V. Barone J. Comput. Chem. 24 2003 669 681
62. E. van Lenthe, A. van der Avoird, and P.E.S. Wormer J. Chem. Phys. 107 1997 2488 2498
63. E. van Lenthe, A. van der Avoird, and P.E.S. Wormer J. Chem. Phys. 108 1998 4783 4796
64. A.D. Becke Phys. Rev. A 38 1988 3098 3100
65. J.P. Perdew Phys. Rev. B 33 1986 8822 8824
66. E. van Lenthe, A.E. Ehlers, and E.J. Baerends J. Chem. Phys. 110 1999 8943 8953
67. S. Clément, L. Guyard, M. Knorr, C. Däschlein, and C. Strohmann Acta Cryst. E65 2009 o528 u1861
68. H. Werner, M.A. Esteruelas, and H. Otto Organometallics 5 1986 2295
69. D. Huang, W.E. Streib, J.C. Bollinger, K.G. Caulton, R.F. Winter, and T. Scheiring J. Am. Chem. Soc. 121 1999 8087 8097
70. S. Jung, K. Ilg, C.D. Brandt, J. Wolf, and H. Werner Eur. J. Inorg. Chem. 2004 469 480
71. N.W. Alcock, J. Cartwright, A.F. Hill, M. Marcellin, and H.M. Rawles J. Chem. Soc., Chem. Commun. 1995 369 370
72. Y. Maruyama, K. Yamamura, T. Sagawa, H. Katayama, and F. Ozawa Organometallics 19 2000 1308 1318
73. M. Pichlmaier, R.F. Winter, M. Zabel, and S. Záli J. Am. Chem. Soc. 131 2009 4892 4903
74. J. Maurer, M. Linseis, B. Sarkar, B. Schwederski, M. Niemeyer, W. Kaim, S. Záliš, C. Anson, M. Zabel, and R.F. Winter J. Am. Chem. Soc. 130 2008 259 268
75. K. Kowalski, M. Linseis, R.F. Winter, M. Zabel, S. Záliš, H. Kelm, H.-J. Krüger, B. Sarkar, and W. Kaim Organometallics 28 2009 4196 4209
76. D.E. Richardson, and H. Taube Coord. Chem. Rev. 60 1984 107 129
77. R.J. Crutchley Adv. Inorg. Chem. 41 1994 273 325
78. Y.-C. Lin, W.-T. Chen, J. Tai, D. Su, S.-Y. Huang, I. Lin, J.-L. Lin, M.M. Lee, M.F. Chiou, Y.-H. Liu, K.-S. Kwan, and Y.-J. Chen Inorg. Chem. 48 2009 1857 1870
79. F. Barrire, N. Camire, W.E. Geiger, U.T. Mueller-Westerhoff, and R. Sanders J. Am. Chem. Soc. 124 2002 7262 7263
80. D.M. D'Alessandro, and F.R. Keene Dalton Trans. 2004 3950 3954
81. J. Maurer, R.F. Winter, B. Sarkar, J. Fiedler, and S. Záliš Chem. Commun. 2004 1900 1901
82. F. Hartl, D.J. Stufkens, and A. Vlček Inorg. Chem. 31 1992 1687 1695
83. F. Hartl, A.K. Renfrew, F. Lafolet, T. Mahabiersing, M.J. Calhorda, S. Chardon-Noblat, and A. Deronzier Inorg. Chem. 48 2009 8233 8244
84. S.J. Sherlock, D.C. Boyd, B. Moasser, and W.L. Gladfelter Inorg. Chem. 20 1991 3626 3632
85. J. Maurer, B. Sarkar, B. Schwederski, W. Kaim, R.F. Winter, and S. Záliš Organometallics 25 2006 3701 3712
86. X.H. Wu, S. Jin, J.H. Liang, Y.Y. Li, G.-ao Yu, and S.H. Liu Organometallics 28 2009 2450 2459
87. W.Y. Man, J.-L. Xia, N.J. Brown, J.D. Farmer, D.S. Yufit, J.A.K. Howard, S.H. Liu, and P.J. Low Organometallics 30 2011 1852 1858
88. M.A. Fox, R.L. Roberts, T.E. Baines, B. Le Guennic, J.-F. Halet, F. Hartl, D.S. Yufit, D. Albesa-Jové, J.A.K. Howard, and P.J. Low J. Am. Chem. Soc. 130 2008 3566 3578
89. S. Záliš, R.F. Winter, and W. Kaim Coord. Chem. Rev. 254 2010 1383 1396
90. M. Renz, K. Theilacker, C. Lambert, and M. Kaupp J. Am. Chem. Soc. 131 2009 16292 16302
91. J. Maurer, B. Sarkar, W. Kaim, R.F. Winter, and S. Záliš Chem. Eur. J. 13 2007 10257 10272
92. J. Maurer, B. Sarkar, S. Zalis, and R.F. Winter J. Solid State Electrochem. 9 2005 738 749
93. M. Linseis, R.F. Winter, B. Sarkar, W. Kaim, and S. Záliš Organometallics 27 2008 3321 3324
94. M. Rudolph, and S. Feldberg DigiSim3, Version 3.03 1994 Bioanalytical Systems, Inc
95. C.G. Atwood, and W.E. Geiger J. Am. Chem. Soc. 122 2000 5477 5485
96. S.V. Lindemann, S.V. Rosokha, and J.K. Kochi J. Am. Chem. Soc. 124 2002 843 855
97. W. Weng, T. Bartik, M. Brady, B. Bartik, J.A. Ramsden, A.M. Arif, and J.A. Gladysz J. Am. Chem. Soc. 117 1995 11922 11931
98. G.F. Caramori, and S.E. Galembeck J. Phys. Chem. A 111 2007 1705 1712