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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: Oosterbaan, Wibren (VerfasserIn) , van Gerven, Paul C. M. (VerfasserIn) , van Walree, Cornelis A. (VerfasserIn) , Koeberg, Mattijs (VerfasserIn) , Piet, Jacob J. (VerfasserIn) , Havenith, Remco W. A. (VerfasserIn) , Zwikker, Jan W. (VerfasserIn) , Jenneskens, Leonardus W. (VerfasserIn) , Gleiter, Rolf (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 23 July 2003
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
Volltext
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
Beschreibung
Zusammenfassung: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.
Beschreibung:Gesehen am 27.10.2020
Beschreibung:Online Resource
ISSN:1099-0690
DOI:10.1002/ejoc.200200693

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