Polynuclear carbon-rich organometallic complexes: clarification of the role of the bridging ligand in the redox properties. Karine Costuas, St´ ephane Rigaut To cite this version: Karine Costuas, St´ ephane Rigaut. Polynuclear carbon-rich organometallic complexes: clarifi- cation of the role of the bridging ligand in the redox properties.. Dalton Transactions, Royal Society of Chemistry, 2011, 40 (21), pp.5643-58. <10.1039/c0dt01388a>. <hal-00860419> HAL Id: hal-00860419 https://hal.archives-ouvertes.fr/hal-00860419 Submitted on 10 Sep 2013 HAL is a multi-disciplinary open access archive for the deposit and dissemination of sci- entific research documents, whether they are pub- lished or not. The documents may come from teaching and research institutions in France or abroad, or from public or private research centers. L’archive ouverte pluridisciplinaire HAL, est destin´ ee au d´ epˆ ot et ` a la diffusion de documents scientifiques de niveau recherche, publi´ es ou non, ´ emanant des ´ etablissements d’enseignement et de recherche fran¸cais ou ´ etrangers, des laboratoires publics ou priv´ es.
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Polynuclear carbon-rich organometallic complexes:
clarification of the role of the bridging ligand in the
redox properties.
Karine Costuas, Stephane Rigaut
To cite this version:
Karine Costuas, Stephane Rigaut. Polynuclear carbon-rich organometallic complexes: clarifi-cation of the role of the bridging ligand in the redox properties.. Dalton Transactions, RoyalSociety of Chemistry, 2011, 40 (21), pp.5643-58. <10.1039/c0dt01388a>. <hal-00860419>
HAL Id: hal-00860419
https://hal.archives-ouvertes.fr/hal-00860419
Submitted on 10 Sep 2013
HAL is a multi-disciplinary open accessarchive for the deposit and dissemination of sci-entific research documents, whether they are pub-lished or not. The documents may come fromteaching and research institutions in France orabroad, or from public or private research centers.
L’archive ouverte pluridisciplinaire HAL, estdestinee au depot et a la diffusion de documentsscientifiques de niveau recherche, publies ou non,emanant des etablissements d’enseignement et derecherche francais ou etrangers, des laboratoirespublics ou prives.
C(R1) C C Ru(dppe)2Cl][BF4] (16) (R1 = Me, Ph; R2 = H,
Me) have been reported. These studies provide a picture of the
electron delocalisation between the two ruthenium termini in
the reduced and oxidized states by means of EPR, IR, UV-vis,
and NIR spectroscopies, and computational studies (DFT). All
together, the results demonstrate that the C7 bridging ligand
spanning the metal centres by almost 12 A is implicated in
both redox processes, with no tendency for spin localisation on
one of the halves (Fig. 1).58 For example, with the “W” shaped
adduct 16 with R1 = H, R2 = H, it was first established that in
the reduced state the single electron is delocalised mainly over
the carbon chain with very little metal contribution. Only the
isotropic g-value in fluid solution could be estimated for this
reduced neutral species (2.0032), and is very close to that of the
free electron. Furthermore, the hyperfine splitting illustrates the
electron delocalisation (the active set of nuclei being considered
is: 8 P, 2 Ru, and 1 H). Within the oxidized form, the odd
electron is fully delocalised over the chain and the metal centres.
The rhombic EPR spectra recorded at 77 K and 4 K exhibit
quite low g anisotropy (0.160) and the average <g> factor of
2.0064 is not strongly shifted from the free electron g-value.
Accordingly, computed spin densities on simplified models show
full localisation of the unpaired electron on the carbon chain in
the reduced state, and half of the unpaired electron lies on the
Ru centres and half on the bridging ligand in the oxidized form
(Fig. 1). The low energy bands observed are rather ascribed to
p to p* transitions in this extended system than to intervalence
transfer (IT) bands.
Fig. 1 Contour plots of the calculated spin density of simplified models (with dpe ligands) 15-H0/2+, and 16-H0/2+. Contour values are ±0.0045 e bohr-3.
studies and physical measurements. The complementarities of
the experimental and theoretical approaches will definitely help
in improving the level of knowledge in this domain.3b,14 We
do believe that organometallic systems containing carbon-rich
conjugated bridges are particularly well-suited for improving
this knowledge particularly because, as illustrated above, their
electronic properties can be smoothly tuned by slight structural
modifications (ancillary ligands, bridging ligands, metal atoms,
geometrical arrangements) providing an infinite number of objects
for research. In addition, these metal complexes potentially offer
numerous addressable functionalities in one molecular compo-
nent, owing to these unique easily tuneable electronic properties.
Therefore, they are also well-suited systems to bring molecular
electronics knowledge to a further stage of development.
Acknowledgements
The authors wish to thank Dr Jean-Francois Halet for helpful
discussions.
References
1 A. Aviram and M. A. Ratner, Chem. Phys. Lett., 1974, 29, 277; R. L.Carroll and C. B. Gorman, Angew. Chem., Int. Ed., 2002, 41, 437; J. A.Nitzan and M. A. Ratner, Science, 2003, 300, 1384; R. L. McCreery,Chem. Mater., 2004, 16, 4477; C. Joachim and M. A. Ratner, Proc. Natl.Acad. Sci. U. S. A., 2005, 102, 8801; R. M. Metzger, J. Mater. Chem.,2008, 18, 4364; S. H. Choi, B.-S. Kim and C. D. Frisbie, Science, 2008,320, 1382; V. Balzani, A. Credi, and M. Venturi, in Molecular Devicesand Machines. Concepts and Perspectives for the Nanoword, Wiley-VCH,Weinheim, 2nd edn, 2008, and references therein.
2 J.-M. Lehn, in Supramolecular Chemistry: Concepts and Perspectives,Wiley-VCH, Weinheim, 1995.
3 (a) K. D. Demadis, C. M. Harshorn and T. J. Meyer, Chem. Rev.,2001, 101, 2655; (b) P. Chen and T. J. Meyer, Chem. Rev., 1998, 98,1439; (c) D. M. D’Alessandro and R. F. Keene, Chem. Rev., 2006, 106,2270; (d) F. Paul and C. Lapinte, Coord. Chem. Rev., 1998, 178–180,431; (e) P. Aguirre-Etchevery and D. O’Hare, Chem. Rev., 2010, 110,4839; (f) P. J. Low and N. J. Brown, J. Cluster Sci., 2010, 21, 235,DOI: 10.1007/s10876-010-0328-4; (g) A. Ceccon, S. Santi, L. Oian andA. Bisello, Coord. Chem. Rev., 2004, 248, 683; (h) M. H. Chisholm andN. J. Patmoore, Acc. Chem. Res., 2007, 40, 19; (i) J.-P. Launay, Chem.Soc. Rev., 2001, 30, 386.
4 S. F. Nelsen, Chem.–Eur. J., 2000, 6, 581; D.-L. Sun, V. Rosokha andJ. K. Kochi, J. Am. Chem. Soc., 2003, 125, 15950; S. Barlow, C. Risko,S.-J. Chung, N. M. Tucker, V. Coropceanu, S. C. Jones, Z. Levi, J.-L.Bredas and S. R. Marder, J. Am. Chem. Soc., 2005, 127, 16900; D. R.Kattnig, B. Mladenova, G. Grampp, C. Kaiser, A. Heckmann and C.Lambert, J. Phys. Chem. C, 2009, 113, 2983and references therein; J.Bonvoisin, J.-P. Launay, W. Verbouwe, M. Van, der Auweraer and F. C.De Schryver, J. Phys. Chem., 1996, 100, 17079.
5 D. Astruc, in Electron Transfer and Radical Processes in Transition-Metal Chemistry, VCH-Publishers, Inc., New York, 1995.
6 W. Kaim and G. K. Lahiri, Angew. Chem., Int. Ed., 2007, 46, 1778;M. D. Ward and J. A. McClaverty, J. Chem. Soc., Dalton Trans., 2002,275; S. Zalis, R. F. Winter and W. Kaim, Coord. Chem. Rev., 2010, 254,1383.
7 C. Lambert, S. Althor and J. Schelter, J. Phys. Chem. A, 2004, 108,6474.
8 C. E. B. Evans, M. L. Naklicki, A. R. Rezvani, C. A. White, V. V.Kondratiev and R. J. Crutchley, J. Am. Chem. Soc., 1998, 120, 13096.
9 P. Day, N. S. Hush and R. J. H. Clark, Philos. Trans. R. Soc. London,Ser. A, 2008, 366, 5.
10 R. A. Marcus, Annu. Rev. Phys. Chem., 1964, 15, 155.11 R. S. Mulliken, J. Am. Chem. Soc., 1952, 64, 811; R. S. Mulliken, and
W. B. Person, in Molecular complexes, Wiley, New York, 1969; N. S.Hush, Prog. Inorg. Chem., 1967, 8, 391; N. S. Hush, Electrochim. Acta,1968, 13, 1005.
12 Robin and Day’s classification established that (1) Class I systemscorrespond to a trapped valence on one of the two sites; (2) If the‘mixed-valent’ atoms are completely undistinguishable the compoundis classified as class III with a genuine non-integral valence; (3) Class IIlies between the two previous cases with an accessible thermal electrontransfer and the presence of an intervalence transfer optical transition,see: M. B. Robin and P. Day, Adv. Inorg. Chem., 1967, 10, 247.
13 D. M. D’Alessandro and F. R. Keene, Chem. Soc. Rev., 2006, 35, 424.14 J. R. Reimers, B. B. Wallace and N. S. Hush, Philos. Trans. R. Soc.
London, Ser. A, 2008, 366, 15.15 rab = |(mb-ma)/e|; ma and mb are the dipole moments of the diabatic
states a and b, respectively.16 J. T. Hupp, Y. Dong, R. L. Blackbourn and H. Lu, J. Phys. Chem.,
1993, 97, 3278; G. U. Bublitz, W. M. Laidlaw, R. G. Denning and S. G.Boxer, J. Am. Chem. Soc., 1998, 120, 6068.
17 R. J. Cave and M. D. Newton, Chem. Phys. Lett., 1996, 249, 15.18 H. M. McConnell, J. Chem. Phys., 1961, 35, 508; M. A. Ratner, J. Phys.
Chem., 1990, 94, 4877; S. D. Glover, J. C. Goeltz, B. J. Lear and C. P.Kubiak, Coord. Chem. Rev., 2010, 254, 331.
19 S. F. Nelsen, R. F. Ismagilov and D. R. Powell, J. Am. Chem. Soc.,1998, 120, 1924; A. El-ghayoury, A. Harriman, A. Khatyr and R.Ziessel, J. Phys. Chem. A, 2000, 104, 1512; S. Fraysse, C. Coudretand J.-P. Launay, J. Am. Chem. Soc., 2003, 125, 5888; C. Lambert, S.Amthor and J. Schelter, J. Phys. Chem. A, 2004, 108, 6474; M. Fabre,J. Jaud, M. Hliwa, J.-P. Launay and J. Bonvoisin, Inorg. Chem., 2006,45, 9332–9345; F. de Montiny, G. Argouarch, K. Costuas, J.-F. Halet,L. Toupet and C. Lapinte, Organometallics, 2005, 24, 4558; M. Fabreand J. Bonvoisin, J. Am. Chem. Soc., 2007, 129, 1434; M. H. Chisholm,J. S. D’Achioli, C. M. Hadad and N. J. Patmore, Inorg. Chem., 2006,45, 11035.
20 B. S. Brunschwig, C. Creutz and N. Sutin, Chem. Soc. Rev., 2002, 31,168; J.-P. Launay, C. Coudret and C. Hortholary, J. Phys. Chem. B,2007, 111, 6788.
21 (a) J. J. Conception, D. M. Dattelbaum, T. J. Meyer and R. C. Rocha,Philos. Trans. R. Soc. London, Ser. A, 2008, 366, 163; (b) R. G. Rocha,F. N. Rein, H. Jude, A. P. Scheve, J. J. Conception and T. J. Meyer,Angew. Chem., Int. Ed., 2008, 47, 503.
22 Other parameters should be taken into account as well as temperaturedependence, particularly because of vibrational evolution and vibroniccoupling, interaction with the electrolyte, ion-pairing possibilities orpolarisability effects.
23 (a) A. Zheludev, V. Barone, M. Bonnet, B. Delley, A. Grand, E.Ressouche, P. Rey, R. Subra and J. Schweizer, J. Am. Chem. Soc., 1994,116, 2019; (b) A. S. Wills, E. Lelievre-Berna, F. Tasset, J. Schweizer andR. Ballou, Phys. B, 2005, 356, 254; (c) J. Luzon, J. Campo, F. Palacio,G. J. McIntyre and A. Millan, Phys. Rev. B: Condens. Matter Mater.Phys., 2008, 78, 054414; (d) E. Lelievre-Berna, A. S. Wills, E. Bourgeat-Lami, A. Dee, T. Hansen, P. F. Henry, A. Poole, M. Thomas, X. Tonon,J. Torregrossa, K. Andersen, F. Bordenave, D. Jullien, P. Mouveau, B.Guerard and G. Manzin, Meas. Sci. Technol., 2010, 21, 055106.
24 H. M. McConnell, J. Chem. Phys., 1961, 35, 508.25 DFT results were indeed shown to be in good agreement with the
experimental spin-densities, see ref. 23a,c.26 M. Reiher, Faraday Discuss., 2007, 135, 97.27 M. Renz, K. Theilacker, C. Lambert and M. Kaupp, J. Am. Chem. Soc.,
2009, 131, 16292.28 (a) For a recent application in the focus of this paper and published
during the referring process see: Y. Lu, R. Quardokus, C. S. Lent, F.Justaud, C. Lapinte and S. A. Kandel, J. Am. Chem. Soc., 2010, 132,13519; (b) The electronic asymmetry resulting from localization of theelectron on one side of the oxidized molecule was confirmed throughSTM images and comparison to theoretical STM images calculatedusing constrained density-functional theory (CDFT): see ref. 28a.
29 A. Pedone, M. Biczysko and V. Barone, ChemPhysChem, 2010, 11,1812.
30 For illustrations with examples used in the discussion, see ref. 37c and82.
31 F. Barriere and W. E. Geiger, J. Am. Chem. Soc., 2006, 128, 3980.32 C. Lapinte, J. Organomet. Chem., 2008, 693, 793.33 (a) P. Hapiot, L. D. Kispert, V. V. Konovalov and J.-M. Saveant, J. Am.
Chem. Soc., 2001, 123, 6669; (b) See also D. H. Evans, Chem. Rev.,2008, 108, 2113.
34 J. E. Sutton, P. M. Sutton and H. Taube, Inorg. Chem., 1979, 18, 1017.35 K. Kay, T. Petrenko, K. Wieghardt and F. Neese, Dalton Trans., 2007,
36 F. Paul, B. J. Ellis, M. I. Bruce, L. Toupet, T. Roisnel, K. Costuas, J.-H.Halet and C. Lapinte, Organometallics, 2006, 25, 649.
37 (a) F. Paul, L. Toupet, J.-Y. Thepot, K. Costuas, J.-H. Halet and C.Lapinte, Organometallics, 2005, 24, 5464; (b) F. Paul, G. da Costa, A.Bondon, N. Gauthier, S. Sinbandhit, L. Toupet, K. Costuas, J.-H. Haletand C. Lapinte, Organometallics, 2007, 26, 874; (c) F. Paul, F. Malvolti,G. da Costa, S. Le Stang, F. Justaud, G. Argouarch, A. Bondon, S.Sinbandhit, K. Costuas, L. Toupet and C. Lapinte, Organometallics,2010, 29, 2491; (d) V. Guillaume, P. Thominot, F. Coat, A. Mari and C.Lapinte, J. Organomet. Chem., 1998, 565, 75.
38 (a) C. E. Powell, M. P. Cifuentes, J. P. Morrall, R. Stranger, M. G.Humphrey, M. Samoc, B. Luther-Davies and G. A. Heath, J. Am.Chem. Soc., 2003, 125, 602; (b) N. Gauthier, N. Tchouar, F. Justaud,G. Argouarch, M. P. Cifuentes, L. Toupet, D. Touchard, J.-F. Halet,S. Rigaut, M. G. Humphrey, K. Costuas and F. Paul, Organometallics,2009, 28, 2253.
39 (a) W. Kaim, S. Ernst and V. Kasack, J. Am. Chem. Soc., 1990, 112,173; (b) V. Kasack, W. Kaim, H. Binder, J. Jordanov and E. Roth, Inorg.Chem., 1995, 34, 1924; (c) S. Patra, B. Sarkar, S. Ghumaan, J. Fiedler,W. Kaim and G. K. Lahiri, Dalton Trans., 2004, 754.
40 O. F. Koentjoro, R. Rousseau and P. J. Low, Organometallics, 2001, 20,4502; M. A. Fox, R. L. Roberts, W. M. Khairul, F. Hartl and P. J. Low,J. Organomet. Chem., 2007, 692, 3277.
41 For further information of the effect of the ligand system on thestructure of the Ru complexes see C.-Y. Wong, C.-M. Che, M. C. W.Chan, J. Han, K.-H. Leung, D. L. Phillips, K.-Y. Wong and N. Zhu,J. Am. Chem. Soc., 2005, 127, 13997.
42 N. J. Brown, D. Collison, R. Edge, E. C. Fitzgerald, M. Helliwell,J. A. K. Howard, H. N. Lancashire, P. J. Low, J. J. W. McDouall, J.Raftery, C. A. Smith, D. S. Yufit and M. W. Whiteley, Organometallics,2010, 29, 1261.
43 N. J. Brown, D. Collison, R. Edge, E. C. Fitzgerald, P. J. Low, M.Helliwell, Y. T. Ta and M. W. Whiteley, Chem. Commun., 2010, 46,2253.
44 J. Maurer, M. Linseis, B. Sarkar, B. Schwederski, M. Niemeyer, W.Kaim, S. Zalis, C. Anson, M. Zabel and R. F. Winter, J. Am. Chem.Soc., 2008, 130, 259.
45 V. Cardieno and J. Gimeno, Chem. Rev., 2009, 109, 3512.46 S. Rigaut, O. Maury, D. Touchard and P. H. Dixneuf, Chem. Commun.,
2001, 373(a) N. Auger, D. Touchard, S. Rigaut, J.-F. Halet and J.-Y.Saillard, Organometallics, 2003, 22, 1638; (b) S. Rigaut, K. Costuas,D. Touchard, J.-Y. Saillard, S. Golhen and P. H. Dixneuf, J. Am.Chem. Soc., 2004, 126, 4072; (c) R. F. Winter and K.-W. Klinkhammer,Organometallics, 2001, 20, 1317; (d) M. P. Cifuentes, M. G. Humphrey,G. A. Koutsantonis, N. A. Lengkeek, S. Petrie, V. Sanford, P. A. Schauer,B. W. Skelton, R. Stranger and A. H. White, Organometallics, 2008, 27,1716; (e) C.-Y. Wong, C.-M. Che, M. C. W. Chan, K.-H. Leung, D. L.Phillips and N. Zhu, J. Am. Chem. Soc., 2004, 126, 2501.
47 K. Venkatesan, O. Blacque, T. Fox, M. Alfonso, H. W. Schmalleand Heinz Berke, Organometallics, 2004, 23, 1183; K. Venkatesan,O. Blacque, T. Fox, M. Alfonso, H. W. Schmalle and H. Berke,Organometallics, 2004, 23, 4661.
48 S. Le Stang, F. Paul and Claude Lapinte, Organometallics, 2000, 19,103; F. de Montigny, G. Argouarch, K. Costuas, J.-F. Halet, T. Roisnel,L. Toupet and C. Lapinte, Organometallics, 2005, 24, 4558; S. I.Ghazala, F. Paul, L. Toupet, T. Roisnel, P. Hapiot and C. Lapinte,J. Am. Chem. Soc., 2006, 128, 2463; Y. Tanaka, J. A. Shaw-Taberlet, F.Justaud, O. Cador, T. Roisnel, M. Akita, J.-R. Hamon and C. Lapinte,Organometallics, 2009, 28, 4656.
49 M.-C. Chung, X. Gu, B. A. Etzenhouser, A. M. Spuches, P. T.Rye, S. K. Seetharaman, D. J. Rose, J. Zubieta and M. B. Sponsler,Organometallics, 2003, 22, 3485.
50 M. Brady, W. Weng, Y. Zhou, J. W. Seyler, A. J. Amoroso, A. M. Arif, M.Bo1hme, G. Frenking and J. A. Gladysz, J. Am. Chem. Soc., 1997, 119,775; R. Dembinski, T. Bartik, B. Bartik, M. Jaeger and J. A. Gladysz,J. Am. Chem. Soc., 2000, 122, 810; C. Herrmann, J. Neugebauer, J. A.Gladysz and M. Reiher, Inorg. Chem., 2005, 44, 6174.
51 H. Jiao, K. Costuas, J. A. Gladysz, J.-F. Halet, M. Guillemot, L. Toupet,F. Paul and C. Lapinte, J. Am. Chem. Soc., 2003, 125, 9511.
52 F. Zhuravlav and J. A. Gladysz, Chem.–Eur. J., 2004, 10, 6510.53 M. I. Bruce, P. J. Low, K. Costuas, J.-F. Halet, S. P. Best and G. A.
Heath, J. Am. Chem. Soc., 2000, 122, 1949; M. I. Bruce, K. Costuas,T. Davin, B. G. Ellis, J.-F. Halet, C. Lapinte, P. J. Low, M. E. Smith,B. W. Skelton, Loic Toupet and A. H. White, Organometallics, 2005,24, 3864.
54 M. I. Bruce, K. Costuas, B. G. Ellis, J.-F. Halet, P. J. Low, B. Moubaraki,K. S. Murray, N. Ouddaı, G. J. Perkins, B. W. Skelton and A. H. White,Organometallics, 2007, 26, 3735.
55 M. I. Bruce, K. Costuas, T. Davin, J.-F. Halet, K. A. Kramarczuk, P. J.Low, B. K. Nicholson, G. J. Perkins, R. L. Roberts, B. W. Skelton, M. E.Smith and A. H. White, Dalton Trans., 2007, 5387.
56 M. A. Fox, J. D. Farmer, R. L. Roberts, M. G. Humphrey and P. J.Low, Organometallics, 2009, 28, 5266.
57 A. Klein, O. Lavastre and J. Fiedler, Organometallics, 2006, 25, 635.58 S. Rigaut, C. Olivier, K. Costuas, S. Choua, O. Fadhel, J. Massue, P.
Turek, J.-Y. Saillard, P. H. Dixneuf and D. Touchard, J. Am. Chem.Soc., 2006, 128, 5859.
59 G.-L. Xu, G. Zu, Y.-H. Ni, M. C. DeRosa, R. J. Crutchley and T. Ren,J. Am. Chem. Soc., 2003, 125, 10057.
60 G.-L. Xu, R. J. Crutchley, M. C. DeRosa, Q.-J. Pan, H.-X. Zhang, X.Wang and T. Ren, J. Am. Chem. Soc., 2005, 127, 13354.
61 J. Maurer, R. F. Winter, B. Sarkar, J. Fiedler and S. Zalis, Chem.Commun., 2004, 1900; J. Maurer, B. Sarkar, B. Schwederski, W. Kaim,R. F. Winter and S. Zalis, Organometallics, 2006, 25, 3701; S. Zalis,R. F. Winter and W. Kaim, Coord. Chem. Rev., 2010, 254, 1383.
62 S. Kheradmandan, K. Heinze, H. W. Schmalle and H. Berke, Angew.Chem., Int. Ed., 1999, 38, 2270; S. Kheradmandan, K. Venkatesan, O.Blacque, H. W. Schmalle and H. Berke, Chem.–Eur. J., 2004, 10, 4872;K Vkatesan, O. Blacque and H. Berke, Dalton Trans., 2007, 1091.
63 G. R. Owen, J. Stahl, F. Hampel and J. A. Gladysz, Chem.–Eur. J., 2008,14, 73; W. Mohr, J. Stahl, F. Hampel and J. A. Gladysz, Chem.–Eur. J.,2003, 9, 3324; G. R. Owen, S. Gauthier, N. Weisbach, F. Hampel, N.Bhuvanesh and J. A. Gladysz, Dalton Trans., 2010, 39, 5260.
64 (a) D. S. Frohnapfel, B. E. Woodworth, H. H. Thorp and J. L.Templeton, J. Phys. Chem. A, 1998, 102, 5665; (b) J. Sun, S. E. Shaner,M. K. Jones, D. C. O’Hanlon, J. S. Mugridge and M. D. Hopkins,Inorg. Chem., 2010, 49, 1687; (c) S. N. Semenov, O. Blacque, T. Fox, K.Venkatesan and H. Berke, J. Am. Chem. Soc., 2010, 132, 3115.
65 S. Rigaut, J. Perruchon, S. Guesmi, C. Fave, D. Touchard and P. H.Dixneuf, Eur. J. Inorg. Chem., 2005, 447; N. Mantovani, M. Brugnati,L. Gonsalvi, E. Grigiotti, F. Laschi, L. Marvelli, M. Peruzzini, G.Reginato, R. Rossi and P. Zanello, Organometallics, 2005, 24, 405.
66 M. Linseis, R. F. Winter, B. Sarkar, W. Kaim and S. Zalis,Organometallics, 2008, 27, 3321.
67 L. D. Field, A. M. Magill, T. K. Shearer, S. B. Colbran, S. T. Lee, S. J.Dalgarno and M. M. Bhadbhade, Organometallics, 2010, 29, 957; C.Olivier, B.-S. Kim, D. Touchard and S. Rigaut, Organometallics, 2008,27, 509.
68 C. Olivier, K. Costuas, S. Choua, V. Maurel, P. Turek, J.-Y. Saillard, D.Touchard and S. Rigaut, J. Am. Chem. Soc., 2010, 132, 5683; C. Olivier,S. Choua, P. Turek, D. Touchard and S. Rigaut, Chem. Commun., 2007,3100.
69 J.-W. Ying, I. Po-Chun Liu, B. Xi, Y. Song, C. Campana, J.-L. Zuo andT. Ren, Angew. Chem. Int. Ed., 2010, 49, 954.
70 S. N. Semenov, S. F. Taghipourian, O. Blacque, T. Fox, K. Venkatesanand H. Berke, J. Am. Chem. Soc., 2010, 132, 7584.
71 M. Mayor, C. von Honisch, H. B. Weber, J. Reichert and D. Beckmann,Angew. Chem., Int. Ed., 2002, 41, 1183.
72 T. L. Schull, J. G. Kushmerick, C. H. Patterson, C. George, M. H.Moore, S. K. Pollack and R. Shashidhar, J. Am. Chem. Soc., 2003, 125,3202.
73 A. S. Blum, T. Ren, D. A. Parish, S. A. Trammell, M. H. Moore,J. G. Kushmerick, J.-L. Xu, J. R. Deschamps, S. K. Pollack and R.Shashidhar, J. Am. Chem. Soc., 2005, 127, 10010.
74 A. K. Mahapatro, J. Ying, T. Ren and D. B. Janes, Nano Lett., 2008, 8,2131.
75 J.-W. Ying, A. Cordova, T. Y. Ren, G.-L. Xu and T. Ren, Chem.–Eur. J.,2007, 13, 6874.
76 B.-S. Kim, J. M. Beebe, C. Olivier, S. Rigaut, D. Touchard, J. G.Kushmerick, X.-Y. Zhu and C. D. Frisbie, J. Phys. Chem. C, 2007,111, 7521.
77 K. Liu, X. Wang and F. Wang, ACS Nano, 2008, 2, 2315.78 H. Qi, A. Gupta, B. C. Noll, G. L. Snider, Y. Lu, C. S. Lent and T. P.
Fehlner, J. Am. Chem. Soc., 2005, 127, 15218; H. Qi, S. Sharma, Z. Li,G. L. Snider, A. O. Orlov, C. S. Lent and T. P. Fehlner, J. Am. Chem.Soc., 2003, 125, 15250.
79 F. Paul, K. Costuas, I. Ledoux, S. Deveau, J. Zyss, J.-F. Halet and C.Lapinte, Organometallics, 2002, 21, 5229.
80 M. P. Cifuentes, M. G. Humphrey, J. P. Morrall, M. Samoc, F. Paul, C.Lapinte and T. Roisnel, Organometallics, 2005, 24, 4280; M. Samoc, N.
Gauthier, M. P. Cifuentes, F. Paul, C. Lapinte and M. G. Humphrey,Angew. Chem., Int. Ed., 2006, 45, 7376.
81 N. Gauthier, G. Argouarch, F. Paul, M. G. Humphrey, L. Toupet, S.Ababou-Girard, H. Sabbah, P. Hapiot and B. Fabre, Adv. Mater., 2008,20, 1952.
82 K. M.-C. Wong, S. C.-F. Lam, C.-C. Ko, N. Zhu, V. W.-W. Yam, S.Roue, C. Lapinte, S. Fathallah, K. Costuas, S. Kahlal and J.-F. Halet,Inorg. Chem., 2003, 42, 7086.
83 Y. Liu, C. Lagrost, K. Costuas, N. Tchouar, H. Le Bozec and S. Rigaut,Chem. Commun., 2008, 6117.
84 K. Motoyama, T. Koike and M. Akita, Chem. Commun., 2008,5812.
85 Y. Tanaka, T. Ishisaka, A. Inagaki, T. Koike, C. Lapinte and M. Akita,Chem.–Eur. J., 2010, 16, 4762.
86 Y. Lin, J. Yuan, M. Hu, J. C. Cheng, J. Yin, S. Jin and S. H. Liu,Organometallics, 2009, 28, 6402.
87 Y. Tanake, A. Inagaki and M. Akita, Chem. Commun., 2007,1169.
88 K. A. Green, M. P. Cifuentes, T. C. Corkery, M. Samoc and M. G.Humphrey, Angew. Chem., Int. Ed., 2009, 48, 7867.