Application: SAM preparation, electrochemical reaction

Chemical Name: 11-Ferrocenyl-1-undecanethiol
CAS: 127087-36-9

Appearance: Yellow or yellowish-orange solid
Purity: ≥95.0% (HPLC)
MW: 372.39, C21H32FeS

Storage Condition: -20ºC, protect from metal
Shipping Condition: with blue ice


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Structural Formula

Product Description of Ferrocenyl Alkanethiols
Ferrocenyl alkanethiols are utilized for the modification of gold surfaces to introduce electrochemically active molecules. The modified gold surface can be utilized for the development of sensitive electrochemical analyses. Rubin and others fabricated mixed SAMs of aminoalkanethiols and ferrocenyl alkanethiols with various chain lengths on a gold electrode surface. They immobilized glucose oxidase on aminoalkanethiol sites and used ferrocenyl-alkanethiol sites as electron mediators. They reported the relationship between electrical response and chain length of mixed SAMs. Uosaki and co-workers reported the results of structural changes and the number of absorbed ferrocenyl alkanethiols during redox reaction of 11-ferrocenyl-1-undecanethiol SAMs on a gold electrode using Fourier transform infrared reflection adsorption spectroscopy (FT-IRRAS) and electrochemical quartz crystal microbalance (EQCM) method. They suggested the possibility of orientation change of the monolayer during the redox reaction of the ferrocene moiety. They also estimated this change using voltammograms and ellipsometry.

When it is difficult to take out all the powder from the container,
please add the solvent into a container and dissolve it before its use.

1) M. D. Porter, T. B. Bright, D. L. Allara and C. E. D. Chidsey, Spontaneously Organized Molecular Assemblies.4.Structural Characterization of n-Alkyl Thiol Monolayers on Gold by Optical Ellipsometry, Infrared Spectroscopy, and Electrochemistry, J. Am. Chem. Soc., 1987, 109, 3559.
2) C. E. D. Chidsey, C. R. Bertozzi, T. M. Putvinski and A. M. Mujsce, Coadsorption of Ferrocene-Terminated and Unsubstituted Alkanethiols on Gold: Electroactive Self-Assembled Monolayers, J. Am. Chem. Soc., 1990, 112, 4301.
3) J. J. Hickman, D. Ofer, P. E. Laibinis, G. M. Whitesides and M. S. Wrighton, Molecular Self-Assembly of Two-Terminal, Voltammetric Microsensors with Internal references, Science, 1991, 252, 688.
4) C. E. D. Chidsey, C. R. Bertozzi, T. M. Putvinski and A. M. Mujsce, Coadsorption of Ferrocene-Terminated and Unsubstituted Alkanethiols on Gold:Electroactive Self-Assembled Monolayers, Chemtracts, 1991, 3, 27.
5) K. Uosaki, Y. Sato and H. Kita, Electrochemical Characteristics of a Gold Electrode Modified with a Self-Assembled Monolayer of Ferrocenylalkanethiols, Langmuir, 1991, 7, 1510.
6) Y. Kajiya, T. Okamoto and H. Yoneyama, Glucose Sensitivity of Thiol-modified Gold Electrodes Having Immobilized Glucose Oxidase and 2-Aminoethylferrocene, Chem. Lett., 1993, 2107.
7) T. Ohtsuka, Y. Sato and K. Uosaki, Dynamic Ellipsometry of a Self-Assembled Monolayer of a Ferrocenylalkanethiol during Oxidation-Reduction Cycles, Langmuir, 1994, 10, 3658.
8) K. Shimazu, I. Yagi, Y. Sato and K. Uosaki, Electrochemical Quartz Crystal Microbalance Studies of Self-Assembled Monolayers of 11-ferrocenyl-1-undecanethiol: Structure-dependent Ion-pairing and Solvent Uptake, J. Electroanal. Chem., 1994, 372, 117.
9) T. Kondo, M. Takechi, Y. Sato and K. Uosaki, Absorption Behavior of Functionalized Ferrocenylalkane Thiol and Disulfide onto Au and ITO and Electrochemical Properties of Modified Electrodes: Effects of Acyl and Alkyl Groups Attached to the Ferrocene Ring, J. Electroanal. Chem., 1995, 381, 203.
10) J. l. Anderson, E. F. Bowden and P. G. Pickup, Dynamic Electrochemistry : Methodology and Application E Anal. Chem., 1996, 68, 379R.
11) K. Chen, F. Xu and C. A. Mirkin, Do Alkanethiols Adsorb onto the Surfaces of Tl-Ba-Ca-Cu-O-Based High-Temperature Superconductors? The Critical Role of H2O Contact on the Adsorption Process, Langmuir, 1996, 12, 2622.
12) S. Rubin, G. Bar, R. W. Cutts, J. T. Chow, J. P. Ferraris and T. A. Zawodzinski Jr., Electrical Communication Between Glucose Oxidase and Different Ferrocenylalkanethiol Chain Lengths, Mat. Res. Soc. Symp. Proc., 1996, 413, 377.
13) R. C. Sabapathy, S. Bhattacharyya, W. E. Cleland Jr. and C. L. Hussey, Host-Guest Complexation in Self-Assembled Monolayers: Inclusion of a Monolayer-Anchored Cationic Ferrocene-Based Guest by Cyclodextrin Hosts, Langmuir, 1998, 14, 3797.

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