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Helically Chiral NHC‐Gold(I) Complexes: Synthesis, Chiroptical Properties and Electronic Features of the [5]Helicene‐Imidazolylidene Ligand
Author(s) -
Gauthier Etienne S.,
Cordier Marie,
Dorcet Vincent,
Vanthuyne Nicolas,
Favereau Ludovic,
Williams J. A. Gareth,
Crassous Jeanne
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100722
Subject(s) - helicene , enantiopure drug , carbene , chemistry , circular dichroism , ligand (biochemistry) , phosphorescence , singlet state , conjugated system , photochemistry , crystallography , fluorescence , organic chemistry , polymer , enantioselective synthesis , molecule , biochemistry , physics , receptor , quantum mechanics , nuclear physics , excited state , catalysis
We describe the preparation of helically chiral gold(I) complexes bearing a [5]helicenic‐N‐heterocyclic carbene ligand. They were successfully obtained as enantiopure compounds by semi‐preparative chiral HPLC and their structural, chiroptical, and photophysical properties were subsequently investigated. Notably, strong electronic circular dichroism, dual emission from singlet and triplet states, with the timescale of the latter up to the millisecond range at room temperature, and moderate circularly phosphorescence were observed. The σ‐donating and π‐accepting properties of the constituent helical ortho ‐fused π‐conjugated carbene were investigated by classical quantitative analysis of the IR stretching frequencies and NMR characteristics of the corresponding Ir(CO) 2 Cl complex and selenourea.