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
Hauptverfasser: Kundu, Abhinanda, Chandra, Shubhadeep, Mandal, Debdeep, Neuman, Nicolás I, Mahata, Alok, Anga, Srinivas, Rawat, Hemant, Pal, Sudip, Schulzke, Carola, Sarkar, Biprajit, Chandrasekhar, Vadapalli, Jana, Anukul
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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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c01201