Twisted Push–Pull Alkenes Bearing Geminal Cyclicdiamino and Difluoroaryl Substituents
The systematic combination of N-heterocyclic olefins (NHOs) with fluoroarenes resulted in twisted push–pull alkenes. These alkenes carry electron-donating cyclicdiamino substituents and two electron-withdrawing fluoroaryl substituents in the geminal positions. The synthetic method can be extended to...
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Veröffentlicht in: | Journal of organic chemistry 2021-09, Vol.86 (18), p.12683-12692 |
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Hauptverfasser: | , , , , , , , , , , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | The systematic combination of N-heterocyclic olefins (NHOs) with fluoroarenes resulted in twisted push–pull alkenes. These alkenes carry electron-donating cyclicdiamino substituents and two electron-withdrawing fluoroaryl substituents in the geminal positions. The synthetic method can be extended to a variety of substituted push–pull alkenes by varying the NHO as well as the fluoroarenes. Solid-state molecular structures of these molecules reveal a notable elongation of the central C–C bond and a twisted geometry in the alkene motif. Absorption properties were investigated with UV–vis spectroscopy. The redox properties of the twisted push–pull alkenes were probed with electrochemistry as well as UV–vis/NIR and EPR spectroelectrochemistry, while the electronic structures were computationally evaluated and validated. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.1c01201 |