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Azo‐MICs: Redox‐Active Mesoionic Carbene Ligands Derived from Azoimidazolium Dyes
Author(s) -
Chadwick F. Mark,
Curchod Basile F. E.,
Scopelliti Rosario,
Fadaei Tirani Farzaneh,
Solari Euro,
Severin Kay
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201813780
Subject(s) - mesoionic , carbene , cyclic voltammetry , chemistry , singlet state , redox , photochemistry , homo/lumo , metal , stereochemistry , electrochemistry , medicinal chemistry , organic chemistry , molecule , catalysis , physics , electrode , nuclear physics , excited state
Azoimidazolium dyes were used as precursors for mesoionic carbene ligands (Azo‐MICs). The properties of these ligands were examined by synthesizing Rh I , Au I , and Pd II complexes. Experimental (NMR, IR) and theoretical investigations show that Azo‐MICs are potent σ‐donor ligands. Yet, they feature a small singlet–triplet gap and very low‐lying LUMO levels. The unique electronic properties of Azo‐MICs allow for reversible one‐electron reductions of the metal complexes, as evidenced by cyclic voltammetry.