Rapid Proton-coupled Electron-transfer of Hydroquinone through Phenylenevinylene Bridges
| Autor: | Daniel A. Lowy, Dwight S. Seferos, Martin H. Moore, James G. Kushmerick, Nikolai Lebedev, Guillermo C. Bazan, Scott A. Trammell |
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| Rok vydání: | 2006 |
| Předmět: |
Time Factors
Vinyl Compounds Electrons Photochemistry Electron transfer Molecular wire chemistry.chemical_compound Phenylene Electrochemistry Moiety Organic chemistry Molecule General Materials Science Electrodes Spectroscopy Biophotovoltaic Hydroquinone Chemistry Physical Chemistry Surfaces and Interfaces Hydrogen-Ion Concentration Condensed Matter Physics Hydroquinones Kinetics Models Chemical Polyvinyls Gold Protons Proton-coupled electron transfer |
| Zdroj: | Langmuir. 23:942-948 |
| ISSN: | 1520-5827 0743-7463 |
| DOI: | 10.1021/la061555w |
| Popis: | We describe the synthesis of two oligo(phenylene vinylene)s (OPVs) with a hydroquinone moiety and a thiol anchor group: 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 transfer kinetics of the hydroquinone functionality (H2Q) through these delocalized tethers (“molecular wires”) as a function of pH. Between pH 4 and 9, rate constants were ca. 100-fold faster than for the same H2Q functionality confined to the surface via alkane tethers. Also, in this same pH range rate constants were independent of the length of the OPV bridge. These new electroactive molecules in which the hydroquinone functionality is wired to the gold surface by means of OPV tethers should be useful platforms for constructing bioelectronic devices such as biosensors, biofuel cells, and biophotovoltaic cells with a fast response time. |
| Databáze: | OpenAIRE |
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