Air and moisture stable para- and ortho-quinodimethane derivatives derived from bis-N-Heterocyclic olefins
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Tarih
2023
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
American Chemical Society
Erişim Hakkı
info:eu-repo/semantics/closedAccess
Özet
Herein we report the development of a new methodology for the synthesis of various quinodimethane derivatives under two-electron oxidation of bis-Nheterocyclic olefins linked by different pi-conjugated aromatic spacers. In case of paraand ortho-phenylene bridge, we obtained air and moisture stable diimidazolium paraand ortho-quinodimethane derivatives. Analogues of the para-phenylene spacer such as tetrafluoro-p-phenylene and p-anthracene also led to the corresponding air and moisture stable quinodimethane derivatives. This emphasizes the influence of imidazolium substituents which facilitate the air and moisture stability of the quinodimethane derivatives. Differences were observed for the electron transfer processes: two one-electron vs one two-electron redox transitions between bis-N-heterocyclic olefins and diimidazolium-quinodimethanes depending on the employed pi-conjugated aromatic spacer. The formation of the pi-conjugated radical-cations, transient redox intermediates between bis-N-heterocyclic olefins and diimidazolium-quinodimethanes, was addressed by an EPR investigation.
Açıklama
Anahtar Kelimeler
Electrolytic Oxidation
Kaynak
Organic Letters
WoS Q Değeri
Q1
Scopus Q Değeri
Q1
