Rapid Proton-coupled Electron-transfer of Hydroquinone through Phenylenevinylene Bridges
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- 作者：Scott A. Trammell ; Dwight S. Seferos ; Martin Moore ; Daniel A. Lowy ; Guillermo C. Bazan ; James G. Kushmerick ; Nikolai Lebedev
- 刊名：Langmuir
- 出版年：2007
- 出版时间：January 16, 2007
- 年：2007
- 卷：23
- 期：2
- 页码：942 - 948
- 全文大小：151K
- 年卷期：v.23,no.2(January 16, 2007)
- ISSN：1520-5827
文摘
We describe the synthesis of two oligo(phenylene vinylene)s (OPVs) with a hydroquinone moiety and a thiol anchorgroup: 4-(2',5'-dihydroxystyryl)benzyl thioacetate and 4-[4'-(2' ',5' '-dihydroxystyryl)styryl]benzyl thioacetate. Monolayers on gold of these molecules were examined by electrochemical techniques to determine the electron transferkinetics of the hydroquinone functionality (H2Q) through these delocalized tethers ("molecular wires") as a functionof pH. Between pH 4 and 9, rate constants were ca. 100-fold faster than for the same H2Q functionality confined tothe surface via alkane tethers. Also, in this same pH range rate constants were independent of the length of the OPVbridge. These new electroactive molecules in which the hydroquinone functionality is wired to the gold surface bymeans of OPV tethers should be useful platforms for constructing bioelectronic devices such as biosensors, biofuelcells, and biophotovoltaic cells with a fast response time.