Oxidative electrochemical switching in dithienylcyclopentenes, part 2: Effect of substitution and asymmetry on the efficiency and direction of molecular switching and redox stability
| Autor: | Browne, WR, de Jong, JJD, Kudernac, T, Walko, M, Lucas, LN, Uchida, K, van Esch, JH, Feringa, BL, Lucas, Linda N. |
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| Přispěvatelé: | Stratingh Institute of Chemistry, Synthetic Organic Chemistry, Physics of Nanodevices, Molecular Energy Materials |
| Jazyk: | angličtina |
| Rok vydání: | 2005 |
| Předmět: |
cyclization
LUMINESCENT METAL-COMPLEXES Electrochemistry Photochemistry RUTHENIUM(II) Redox Catalysis DITHIENYLETHENE chemistry.chemical_compound Photochromism Electron transfer redox chemistry CHEMISTRY 2'-BIPYRIDYLS Moiety Cyclopentene UV/Vis spectroscopy DERIVATIVES Organic Chemistry Intermolecular force General Chemistry 2 2'-BIPYRIDYLS photochromism CHIRALITY PHOTOCHROMIC DIARYLETHENES LIGHT chemistry electrochemistry MEMORIES Chirality (chemistry) |
| Zdroj: | Chemistry, 11(21), 6430-6441. Wiley-VCH Verlag GmbH & Co. KGaA |
| ISSN: | 0947-6539 |
| Popis: | The electrochemical and spectroelectrochernical properties of a series of C5-substituted dithienylhexahydro- and dithienylhexafluorocyclopentenes are reported. The effect of substitution at C5 of the thienyl moiety on the redox properties is quite dramatic, in contrast to the effect on their photochemical properties. The efficiency of electrochemical switching is dependent both on the central cyclopentene unit and on the nature of the substituents, whereby electron-donating moieties favour oxidative electrochemical ring-closure and vice versa. Asymmetrically substituted dithienylcyclopentenes were investigated to explore the ring-closure process in more detail. The results indicate that electrochemically induced ring-closure occurs via the monocation of the open form. In the presence of electroactive groups at C5 of the thienyl ring (e.g., methoxyphenyl) initial oxidation of these groups is followed by intermolecular electron transfer, which drives ring-closure of the open forms. |
| Databáze: | OpenAIRE |
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