Synthesis, UV/vis spectra and electrochemical characterisation of arylthio and styryl substituted ferrocenes

• Autorzy: Thomas Sørensen , Merete Nielsen
• Języki publikacji: EN

Abstrakty

EN

Two series of substituted ferrocenes were synthesised using either the Horner-Wadsworth-Emmons reaction or monolithiation of ferrocene. The series consist of arylthio- and styryl-ferrocenes with different substituents in the para position of the aryl rings of the systems. The electronic communication was investigated by comparing the substituent effects in absorption spectroscopy and in cyclic voltammetry. A small substituent effect was found in the electronic transitions of the styryl substituted ferrocenes. The oxidation of the ferrocene derivatives showed clear substituent effects as illustrated by the linear Hammett plots. The effect was shown to be an order of magnitude larger in the arylthio-systems than in the styryl systems. It is suggested that the reason behind the large effect is a direct sulfur-iron orbital overlap. [...]

Słowa kluczowe

EN

Electrochemistry; Lithiation; Ligand effects; Ferrocene

• Czasopismo: Open Chemistry
• Rocznik: 2011
• Tom: 9
• Numer: 4
• Strony: 610-618

Daty

wydano

2011-08-01

online

2011-06-04

Twórcy

autor

Thomas Sørensen

• Nano-Science Center and Department of Chemistry, University of Copenhagen, 2100, København Ø, Denmark,

autor

Merete Nielsen

• Nano-Science Center and Department of Chemistry, University of Copenhagen, 2100, København Ø, Denmark

Bibliografia

• [1] C.E.D. Chidsey, C.R. Bertozzi, T.M. Putvinski, A.M. Mujsce, J. Am. Chem. Soc. 112, 4301 (1990) http://dx.doi.org/10.1021/ja00167a028[Crossref]
• [2] A. Anne, A. Bouchardon, J. Moiroux, J. Am. Chem. Soc. 125, 1112 (2003) http://dx.doi.org/10.1021/ja028640k[Crossref]
• [3] D.R. van Staveren, N. Metzler-Nolte, Chem. Rev. 104, 5931 (2004) http://dx.doi.org/10.1021/cr0101510[Crossref]
• [4] D.B. Ge, R. Levicky, Chem. Comm. 46, 7190 (2010) http://dx.doi.org/10.1039/c0cc02044c[Crossref]
• [5] T. Hayashi, M. Konishi, Y. Kobori, M. Kumada, T. Higuchi, K. Hirotsu, J. Am. Chem. Soc. 106, 158 (1984) http://dx.doi.org/10.1021/ja00313a032[Crossref]
• [6] B.M. Trost, D.L. VanVranken, Chem. Rev. 96, 395 (1996) http://dx.doi.org/10.1021/cr9409804[Crossref]
• [7] F. Rebiere, O. Samuel, H.B. Kagan, Tetrahedron Lett. 31, 3121 (1990) http://dx.doi.org/10.1016/S0040-4039(00)94710-5[Crossref]
• [8] B. Bildstein, M. Malaun, H. Kopacka, K. Wurst, M. Mitterboeck, K.-H. Ongania, G. Opromolla, P. Zanello, Organometallics, 18, 4325 (1999) http://dx.doi.org/10.1021/om990377h[Crossref]
• [9] D.L. Lichtenberger, H.J. Fan, N.E. Gruhn, J. Organomet. Chem. 666, 75 (2003) http://dx.doi.org/10.1016/S0022-328X(02)02035-1[Crossref]
• [10] U.T. Mueller-Westerhoff, Z. Yang, G. Ingram, J. Organomet. Chem. 463, 163 (1993) http://dx.doi.org/10.1016/0022-328X(93)83414-Q[Crossref]
• [11] M. Herberhold, Ferrocene Compounds Containing Heteroelements, In: A. Togni, T. Hayashi (Eds.), Ferrocenes (VCH, Weinheim, 1994)
• [12] A.K. Bhattacharya, G. Thyagarajan, Chem. Rev. 81, 415 (1981) http://dx.doi.org/10.1021/cr00044a004[Crossref]
• [13] B.E. Maryanoff, A.B. Reitz, Chem. Rev. 89, 863 (1989) http://dx.doi.org/10.1021/cr00094a007[Crossref]
• [14] M. Hirano, S. Yakabe, N. Uraoka, T. Morimoto, Org. Prep. Proced. Int. 30, 360 (1998) http://dx.doi.org/10.1080/00304949809355298[Crossref]
• [15] J.A. Adeleke, Y.W. Chen, L.K. Liu, Organometallics, 11, 2543 (1992) http://dx.doi.org/10.1021/om00043a043[Crossref]
• [16] S. Miniere, V. Reboul, R.G. Arrayas, P. Metzner, J.C. Carretero, Synthesis 2249 (2003)
• [17] C. Pichon, B. Odell, J.M. Brown, Chem. Comm. 598 (2004) [Crossref]
• [18] X. Li, D. Zhang, H. Pang, F. Shen, H. Fu, Y. Jiang, Y. Zhao, Org. Lett. 7, 4919 (2005) http://dx.doi.org/10.1021/ol051871m[Crossref]
• [19] G. Laven, J. Stawinski, Synlett. 225 (2009)
• [20] P.J. Hotchkiss, H. Li, P.B. Paramonov, S.A. Paniagua, S.C. Jones, N.R. Armstrong, J.-L. Bredas, S.R. Marder, Adv. Mater. 21, 4496 (2009) http://dx.doi.org/10.1002/adma.200900502[Crossref]
• [21] S.-R. Jang, C. Lee, H. Choi, J.J. Ko, J. Lee, R. Vittal, K.-J. Kim, Tetrahedron Lett. 45, 125 (2004) http://dx.doi.org/10.1016/j.tetlet.2003.10.099[Crossref]
• [22] V. Cardile, R. Chillemi, L. Lombardo, S. Sciuto, C. Spatafora, C. Tringali, Z. Naturforsch., C: J. Biosci. 62, 189 (2007)
• [23] S. Das, N. Gopinathan, S. Abraham, N. Jayaraman, M.K. Singh, S.K. Prasad, D.S.S. Rao, Adv. Funct. Mater. 18, 1632 (2008) http://dx.doi.org/10.1002/adfm.200701181[Crossref]
• [24] A.S. Khartulyari, M. Kapur, M.E. Maier, Org. Lett. 8, 5833 (2006) http://dx.doi.org/10.1021/ol062479r[Crossref]
• [25] C. Bellucci, F. Gualtieri, A. Chiarini, Eur. J. Med. Chem. 22, 473 (1987) http://dx.doi.org/10.1016/0223-5234(87)90039-0[Crossref]
• [26] N. Stuhr-Hansen, J.B. Christensen, N. Harrit, T. Bjørnholm, J. Org. Chem. 68, 1275 (2003) http://dx.doi.org/10.1021/jo0263770[Crossref]
• [27] R. Frantz, J.-O. Durand, G.F. Lanneau, J. Organomet. Chem. 689, 1867 (2004) http://dx.doi.org/10.1016/j.jorganchem.2004.03.007[Crossref]
• [28] A.J. Moore, A. Chesney, M.R. Bryce, A.S. Batsanov, J.F. Kelly, J.A.K. Howard, I.F. Perepichka, D.F. Perepichka, G. Meshulam, G. Berkovic, Z. Kotler, R. Mazor, V. Khodorkovsky, Eur. J. Org. Chem. 2671 (2001) [Crossref]
• [29] W.-y. Liu, Q.-h. Xu, Y.-x. Ma, Y.-m. Liang, N.-l. Dong, D.-p. Guan, J. Organomet. Chem. 625, 128 (2001) http://dx.doi.org/10.1016/S0022-328X(00)00927-X[Crossref]
• [30] T. Yasuda, J. Abe, H. Yoshida, T. Iyoda, T. Kawai, Adv. Synth. Catal. 344, 705 (2002) http://dx.doi.org/10.1002/1615-4169(200208)344:6/7<705::AID-ADSC705>3.0.CO;2-O[Crossref]
• [31] D. Plazuk, J. Zakrzewski, J. Organomet. Chem. 691, 287 (2006) http://dx.doi.org/10.1016/j.jorganchem.2005.03.057[Crossref]
• [32] N. Tsuboya, R. Hamasaki, M. Ito, M. Mitsuishi, T. Miyashita, Y. Yamamoto, J. Mater. Chem. 13, 511 (2003) http://dx.doi.org/10.1039/b211019a[Crossref]
• [33] B. Koenig, H. Zieg, P. Bubenitschek, P.G. Jones, Chem. Ber. 127, 1811 (1994) http://dx.doi.org/10.1002/cber.19941270935[Crossref]
• [34] C. Amatore, S. Gazard, E. Maisonhaute, C. Pebay, B. Schollhorn, J.-L. Syssa-Magale, J. Wadhawan, Eur. J. Inorg. Chem. 4035 (2007)
• [35] P. Diter, O. Samuel, S. Taudien, H.B. Kagan, Tetrahedron: Asymmetry 5, 549 (1994) http://dx.doi.org/10.1016/0957-4166(94)80015-4[Crossref]
• [36] S. Toma, A. Gáplovský, P. Elecko, Chem. Papers. 39, 115 (1985)
• [37] M.A. Carrol, A.J.P. White, D.A. Widdowson, D.J. Williams, J. Chem. Soc. Perkin Trans. 1, 1551 (2000) http://dx.doi.org/10.1039/b000833h[Crossref]
• [38] R.J. Kloetzing, M. Lotz, P. Knochel, Tetrahedron Lett. 14, 255 (2003) [Crossref]
• [39] D. Guillaneux, H.B. Kagan, J. Org. Chem. 60, 2502 (1995) http://dx.doi.org/10.1021/jo00113a033[Crossref]
• [40] Y.S. Sohn, Hendrick. Dn, H.B. Gray, J. Am. Chem. Soc. 93, 3603 (1971) http://dx.doi.org/10.1021/ja00744a011[Crossref]
• [41] A.J. Bard, L.R. Faulkner, Electrochemical Medthods, Fundamentals and Application, 2nd edition (Wiley, Hoboken, 2001)
• [42] A.G. Nagy, S. Toma, J. Organomet. Chem. 266, 257 (1984) http://dx.doi.org/10.1016/0022-328X(84)80138-2[Crossref]
• [43] W.E. Britton, R. Kashyap, M. El-Hashash, M. El-Kady, M. Herberhold, Organometallics 5, 1029 (1986) http://dx.doi.org/10.1021/om00136a033[Crossref]
• [44] D. Osella, A. Carretta, C. Nervi, M. Ravera, R. Gobetto, Organometallics 19, 2791 (2000) http://dx.doi.org/10.1021/om0001366[Crossref]
• [45] Z.I. Niazimbetova, D.H. Evans, I.A. Guzei, C.D. Incarvito, A.L. Rheingold, J. Electrochem. Soc. 146, 1492 (1999) http://dx.doi.org/10.1149/1.1391792[Crossref]
• [46] L. Engman, J. Persson, C.M. Andersson, M. Berglund, J. Chem. Soc., Perkin Transactions 2, 1309 (1992) http://dx.doi.org/10.1039/p29920001309[Crossref]
• [47] C. Hansch, A. Leo, R.W. Taft, Chem. Rev. 91, 165 (2002) http://dx.doi.org/10.1021/cr00002a004[Crossref]

Identyfikatory

DOI

10.2478/s11532-011-0040-8