Diverse Redox-Active Molecules Bearing O-, S-, or Se-Terminated Tethers for Attachment to Silicon in Studies of Molecular Information Storage

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• 作者：Arumugham Balakumar ; Andrey B. Lysenko ; Carole Carcel ; Vladimir L. Malinovskii ; Daniel T. Gryko ; Karl-Heinz Schweikart ; Robert S. Loewe ; Amir A. Yasseri ; Zhiming Liu ; David F. Bocian ; and Jonathan S.
• 刊名：Journal of Organic Chemistry
• 出版年：2004
• 出版时间：March 5, 2004
• 年：2004
• 卷：69
• 期：5
• 页码：1435 - 1443
• 全文大小：227K
• 年卷期：v.69,no.5(March 5, 2004)
• ISSN：1520-6904

文摘

A molecular approach to information storage employs redox-active molecules tethered to anelectroactive surface. Attachment of the molecules to electroactive surfaces requires control overthe nature of the tether (linker and surface attachment group). We have synthesized a collectionof redox-active molecules bearing different linkers and surface anchor groups in free or protectedform (hydroxy, mercapto, S-acetylthio, and Se-acetylseleno) for attachment to surfaces such assilicon, germanium, and gold. The molecules exhibit a number of cationic oxidation states, includingone (ferrocene), two [zinc(II)porphyrin], three [cobalt(II)porphyrin], or four (lanthanide triple-deckersandwich compound). Electrochemical studies of monolayers of a variety of the redox-activemolecules attached to Si(100) electrodes indicate that molecules exhibit a regular mode of attachment(via a Si-X bond, X = O, S, or Se), relatively homogeneous surface organization, and robust reversibleelectrochemical behavior. The acetyl protecting group undergoes cleavage during the surfacedeposition process, enabling attachment to silicon via thio or seleno groups without handling freethiols or selenols.