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Acta Physico-Chimica Sinica  2010, Vol. 26 Issue (08): 2158-2162    DOI: 10.3866/PKU.WHXB20100822
Optical and Electrochemical Properties of Ethynyl-Bridged Ferrocenes with Electron Donor Groups
CAO Qian-Yong1, LU Xin1, KUANG Ren-Yun2, LI Zhi-Hua1, YANG Zhen-Yu1
1. Department of Chemistry, Nanchang University, Nanchang 330031, P. R. China;
2. College of Chemistry and Chemical Engineering, Jinggangshan University, Ji'an 343009, Jiangxi Province, P. R. China
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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.

Key wordsFerrocene      Protonation      Absorption spectrum      Oxidation      Electrochemistry     
Received: 05 January 2010      Published: 25 June 2010
MSC2000:  O646  

The project was supported by the National Natural Science Foundation of China (20963007), Bureau of Education of Jiangxi Province, China (GJJ09074) and Program for Innovative Research Team of Nanchang University, China.

Corresponding Authors: CAO Qian-Yong     E-mail:
Cite this article:

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. Acta Physico-Chimica Sinica, 2010, 26(08): 2158-2162.

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[1]. Gust, D.; Moore, T. A.; Moore, A. L. Acc. Chem. Res., 2001, 34: 40
[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]. Bella, S. D. Chem. Soc. Rev., 2001, 30: 355
[4]. Fery-Forgues, S.; Delavaux-Nicot, B. J. Photochem. Photobiol. A: Chem., 2000, 132: 137
[5]. Debroy, P.; Roy, S. Coord. Chem. Rev., 2007, 251: 203
[6]. Peris, E. Coord. Chem. Rev., 2004, 248: 279
[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]. Delavaux-Nicot, B.; Maynadie, J.; Lavabre, D.; Fery-Forgues, S. Inorg. Chem., 2006, 45: 5691
[9]. Guldi, D. M.; Maggini, M.; Scorrano, G.; Prato, M. J. Am. Chem. Soc., 1997, 119: 974
[10]. Ceccon, A.; Santi, S.; Orian, L.; Bisello, A. Coord. Chem. Rev., 2004, 248: 683
[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]. 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]. Chen, Y. J.; Pan, D. S.; Chiu, C. F.; Su, J. X.; Lin, S. J.; Kwan, K. S. Inorg. Chem., 2000, 39: 953
[14]. Polin, J.; Schottenberger, H. Org. Synth., 1998, 9: 411
[15]. Xiao, H. B.; Shen, H.; Lin, Y. G.; Su, J. H.; Tian, H. Dyes Pigments, 2007, 73: 224
[16]. Perrin, D. D.; Armarego, W. L. F.; Perrin, D. R. Purification of laboratory chemicals. 2th ed. Oxford: Pergamon Press, 1980
[17]. Muthiah, C.; Kumar, K. P.; Mani, C. A.; Swamy, K. K. C. J. Org. Chem., 2000, 65: 3733
[18]. Kocher, S.; Lang, H. J. Organomet. Chem., 2001, 637-639: 198
[19]. Barlow, S.; Marder, S. R. Chem. Commun., 2000: 1555
[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]. Barlow, S.; O′ahare, D. Chem. Rev., 1997, 637-669: 97
[22]. Martinez, R.; Ratera, I.; Tarraga, A.; Molina, P.; Veciana, J. Chem. Commun., 2006: 3809
[23]. McGale, E. M.; Robinson, B. H.; Simpson, J. Organometallics, 2003, 22: 931
[24]. Zucchero, A. J.; Wilson, J. N.; Bunz, U. H. F. J. Am. Chem. Soc., 2006, 128: 11872
[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]. Goodall, W.; Williams, J. A. G. Chem. Commun., 2001: 2514

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