Twisted Push?Pull Alkenes Bearing Geminal Cyclicdiamino and Difluoroaryl Substituents

ABHINANDA KUNDU; SHUBHADEEP CHANDRA; DEBDEEP MANDAL; NEUMAN, NICOLÁS I; ALOK MAHATA; SRINIVAS ANGA; HEMANT RAWAT; SUDIP PAL; CAROLASCHULZKE; BIPRAJIT SARKAR; VADAPALLI CHANDRASEKHAR; ANUKUL JANA

JOURNAL OF ORGANIC CHEMISTRY

AMER CHEMICAL SOC

Lugar: Washington; Año: 2021 vol. 86 p. 12683 - 12692

0022-3263

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.