Photoinduced charge separation in cyclohexylidene-based donor-(σ-Bridge)-acceptor compounds: building blocks for materials
We describe the syntheses and properties of five semi-rigid donor−(σ-bridge)−acceptor (D−σ−A) compounds. These compounds, which are candidates for incorporation in materials, have aniline-type donors and (mixed) cyano- and alkoxycarbonyl-1,1-difunctionalized vinyl acceptors that are separated by a f...
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| Hauptverfasser: | , , , , , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
23 July 2003
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| In: |
European journal of organic chemistry
Year: 2003, Heft: 16, Pages: 3117-3130 |
| ISSN: | 1099-0690 |
| DOI: | 10.1002/ejoc.200200693 |
| Online-Zugang: | Resolving-System, lizenzpflichtig, Volltext: https://doi.org/10.1002/ejoc.200200693 Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.200200693 
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| Verfasserangaben: | Wibren D. Oosterbaan, Paul C.M. van Gerven, Cornelis A. van Walree, Mattijs Koeberg, Jacob J. Piet, Remco W.A. Havenith, Jan W. Zwikker, Leonardus W. Jenneskens, and Rolf Gleiter |
MARC
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| 520 | |a We describe the syntheses and properties of five semi-rigid donor−(σ-bridge)−acceptor (D−σ−A) compounds. These compounds, which are candidates for incorporation in materials, have aniline-type donors and (mixed) cyano- and alkoxycarbonyl-1,1-difunctionalized vinyl acceptors that are separated by a four-σ-bond bridge. Their electronic properties were studied by means of photoelectron spectroscopy in combination with ab initio MO calculations, cyclic voltammetry, UV-Vis absorption spectroscopy, (time-resolved) fluorescence spectroscopy, and time-resolved microwave conductivity (TRMC). We found that these D−σ−A compounds exhibit a weak intramolecular charge-transfer absorption band that borrows its intensity from local transitions. Upon photoexcitation, a charge-separated state is generated in virtually quantitative yield. Conformational contraction or “folding” of this state takes place for the two D−σ−A compounds with a dicyanovinyl acceptor in apolar solvents. The absence of folding in compounds with an alkoxycarbonyl-functionalized acceptor is attributed to a reduced lifetime of the charge-separated state. | ||
| 650 | 4 | |a Donor−acceptor systems | |
| 650 | 4 | |a Electron transfer | |
| 650 | 4 | |a Photochemistry | |
| 650 | 4 | |a Solvatochromism | |
| 700 | 1 | |a van Gerven, Paul C. M. |e VerfasserIn |4 aut | |
| 700 | 1 | |a van Walree, Cornelis A. |e VerfasserIn |4 aut | |
| 700 | 1 | |a Koeberg, Mattijs |e VerfasserIn |4 aut | |
| 700 | 1 | |a Piet, Jacob J. |e VerfasserIn |4 aut | |
| 700 | 1 | |a Havenith, Remco W. A. |e VerfasserIn |4 aut | |
| 700 | 1 | |a Zwikker, Jan W. |e VerfasserIn |4 aut | |
| 700 | 1 | |a Jenneskens, Leonardus W. |e VerfasserIn |4 aut | |
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