Citation: CAO Qian-Yong, LU Xin, KUANG Ren-Yun, LI Zhi-Hua, YANG Zhen-Yu. Optical and Electrochemical Properties of Ethynyl-Bridged Ferrocenes with Electron Donor Groups[J]. Acta Physico-Chimica Sinica, ;2010, 26(08): 2158-2162. doi: 10.3866/PKU.WHXB20100822
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We present the synthesis, optical and electrochemical properties of three ethynyl-bridged ferrocenes with electron donor groups, Fc—C≡C—Ph-(p-OMe) (3a), Fc—C≡C—Ph-(p-NMe2) (3b) and Fc—C≡C—Ph—(p-NPh2) (3c). All three compounds show a Fe(II)Cp—C≡C—Ph—(p-R) (Cp=cyclopentadienyl) metal to ligand charge transition (MLCT) in 400-550 nm. Upon oxidation, 3a and 3c show a Cp—C≡C—Ph—(p-R)Fe(III) ligand to metal charge transition (LMCT) in the near-IR range (946 and 1044 nm). A reversible Fc+/Fc potential for 3a-3c and an irreversible Ph—NR+2/Ph—NR2 potential for 3b and 3c are observed by in the cyclic and differential pulse voltammetry. Finally, 3b shows an optical and electrochemical response upon protonation, with a red shift of the MLCT transition, an anodic shift of the Fc+/Fc potential, and disappearance of the Ph—NR+2/Ph—NR2 peak.
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Keywords:
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Ferrocene
, - Protonation,
- Absorption spectrum,
- Oxidation,
- Electrochemistry
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[1]
[1]. Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res., 2001, 34: 40
-
[2]
[2]. Sauvage, J. P.; Collin, J. P.; Chambron, J. C.; Guillerez, S.; Coudret, C.; Balzani, V.; Barigelletti, F.; Cola, L. D.; Flamigni, L. Chem. Rev., 1994, 94: 993
-
[3]
[3]. Bella, S. D. Chem. Soc. Rev., 2001, 30: 355
-
[4]
[4]. Fery-Forgues, S.; Delavaux-Nicot, B. J. Photochem. Photobiol. A: Chem., 2000, 132: 137
-
[5]
[5]. Debroy, P.; Roy, S. Coord. Chem. Rev., 2007, 251: 203
-
[6]
[6]. Peris, E. Coord. Chem. Rev., 2004, 248: 279
-
[7]
[7]. Liao, Y.; Eichinger, B. E.; Firestone, K. A.; Haller, M.; Luo, J. D.; Kaminsky, W.; Benedict, J. B.; Reid, P. J.; Jen, A. K. Y.; Dalton, L. R.; Robinson, B. H. J. Am. Chem. Soc., 2005, 127: 2758
-
[8]
[8]. Delavaux-Nicot, B.; Maynadie, J.; Lavabre, D.; Fery-Forgues, S. Inorg. Chem., 2006, 45: 5691
-
[9]
[9]. Guldi, D. M.; Maggini, M.; Scorrano, G.; Prato, M. J. Am. Chem. Soc., 1997, 119: 974
-
[10]
[10]. Ceccon, A.; Santi, S.; Orian, L.; Bisello, A. Coord. Chem. Rev., 2004, 248: 683
-
[11]
[11]. Cuffe, L.; Hudson, R. D. A.; Gallagher, J. F.; Jennings, S.; McAdam, C. J.; Connelly, R. B. T.; Manning, A. R.; Robinson, B. H.; Simpson, J. Organometallics, 2005, 24: 2051
-
[12]
[12]. Chawdhury, N.; Long, N. J.; Mahon, M. F.; Ooi, L.; Raithby, P. R.; Rooke, S.; White, A. J. P.; Williams, D. J.; Younus, M. J. Organomet. Chem., 2004, 689: 840
-
[13]
[13]. Chen, Y. J.; Pan, D. S.; Chiu, C. F.; Su, J. X.; Lin, S. J.; Kwan, K. S. Inorg. Chem., 2000, 39: 953
-
[14]
[14]. Polin, J.; Schottenberger, H. Org. Synth., 1998, 9: 411
-
[15]
[15]. Xiao, H. B.; Shen, H.; Lin, Y. G.; Su, J. H.; Tian, H. Dyes Pigments, 2007, 73: 224
-
[16]
[16]. Perrin, D. D.; Armare , W. L. F.; Perrin, D. R. Purification of laboratory chemicals. 2th ed. Oxford: Pergamon Press, 1980
-
[17]
[17]. Muthiah, C.; Kumar, K. P.; Mani, C. A.; Swamy, K. K. C. J. Org. Chem., 2000, 65: 3733
-
[18]
[18]. Kocher, S.; Lang, H. J. Organomet. Chem., 2001, 637-639: 198
-
[19]
[19]. Barlow, S.; Marder, S. R. Chem. Commun., 2000: 1555
-
[20]
[20]. Ju, H. D.; Tao, X. T.; Wan, Y.; Shi, J. H.; Yang J. X.; Xin, Q.; Zou, D. C.; Jiang, M. H. Chem. Phys. Lett., 2006, 432: 321
-
[21]
[21]. Barlow, S.; O′ahare, D. Chem. Rev., 1997, 637-669: 97
-
[22]
[22]. Martinez, R.; Ratera, I.; Tarraga, A.; Molina, P.; Veciana, J. Chem. Commun., 2006: 3809
-
[23]
[23]. McGale, E. M.; Robinson, B. H.; Simpson, J. Organometallics, 2003, 22: 931
-
[24]
[24]. Zucchero, A. J.; Wilson, J. N.; Bunz, U. H. F. J. Am. Chem. Soc., 2006, 128: 11872
-
[25]
[25]. García-Acosta, B.; Martínez-Mánez, R.; Sancenon, F.; Soto, J.; Rurack, K.; Spieles, M.; García-Breijo, E.; Gil, L. Inorg. Chem., 2007, 46: 3123
-
[26]
[26]. odall, W.; Williams, J. A. G. Chem. Commun., 2001: 2514
-
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