The Biomimetic Synthesis of Polyarylated Fluorenes, Relevant to Selaginellaceae Polyphenols, Leading to the Spontaneous Formation of Stable Radicals
Yükleniyor...
Tarih
2023
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
John Wiley and Sons Inc
Erişim Hakkı
info:eu-repo/semantics/openAccess
Attribution 3.0 United States
Attribution 3.0 United States
Özet
This work reports a biomimetic synthesis of polyarylated fluorene derivatives. The molecules are formed via intramolecular electrophilic aromatic substitution, resembling a cyclization leading towards the natural selaginpulvilins from selaginellins. The scope of the reaction was investigated, and the products were obtained in 60–95 % yields. Some of the compounds decompose to a stable radical. We investigated the nature and the origin of the radical using experimental methods, including EPR or electrochemical measurements, as well as theoretical methods, such as DFT calculations. Based on our observations, we hypothesize, that phenoxy radicals are formed in the first instance, which however undergo internal rearrangement to thermodynamically more stable carbon-centered radicals. The preliminary data also show the cytotoxic properties of some of the molecules.
Açıklama
Anahtar Kelimeler
Biomimetic synthesis, Cytotoxicity, Radicals, Selaginellacea polyphenols, Spin density distribution
Kaynak
ChemPlusChem
WoS Q Değeri
Q2
Scopus Q Değeri
Cilt
Sayı
Künye
Nallappan, S., Lapinskaite, R., Hájíček, J., Kunák, D., Čambal, P., Nečas, D., … Rycek, L. (2023). The Biomimetic Synthesis of Polyarylated Fluorenes, Relevant to Selaginellaceae Polyphenols, Leading to the Spontaneous Formation of Stable Radicals. ChemPlusChem. https://doi.org/10.1002/cplu.202300410
