Azo-MICs: Redox-Active Mesoionic Carbene Ligands Derived from Azoimidazolium Dyes

F. Mark Chadwick; Basile F.E. Curchod; Rosario Scopelliti; Farzaneh Fadaei Tirani; Euro Solari; Kay Severin

doi:10.1002/anie.201813780

Azo-MICs: Redox-Active Mesoionic Carbene Ligands Derived from Azoimidazolium Dyes

F. Mark Chadwick
, Basile F.E. Curchod
, Rosario Scopelliti
, Farzaneh Fadaei Tirani
, Euro Solari
, Kay Severin^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

19 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	1764-1767
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	58
Issue number	6
DOIs	https://doi.org/10.1002/anie.201813780
Publication status	Published - 4 Feb 2019

Bibliographical note

Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Research Groups and Themes

Physical & Theoretical

Keywords

azoimidazolium dyes
gold
mesoionic carbenes
N-heterocyclic carbenes
rhodium

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10.1002/anie.201813780

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Cite this

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title = "Azo-MICs: Redox-Active Mesoionic Carbene Ligands Derived from Azoimidazolium Dyes",

abstract = " 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. ",

keywords = "azoimidazolium dyes, gold, mesoionic carbenes, N-heterocyclic carbenes, rhodium",

author = "Chadwick, \{F. Mark\} and Curchod, \{Basile F.E.\} and Rosario Scopelliti and \{Fadaei Tirani\}, Farzaneh and Euro Solari and Kay Severin",

note = "Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2019",

month = feb,

day = "4",

doi = "10.1002/anie.201813780",

language = "English",

volume = "58",

pages = "1764--1767",

journal = "Angewandte Chemie - International Edition",

issn = "1433-7851",

publisher = "John Wiley \& Sons, Ltd.",

number = "6",

}

TY - JOUR

T1 - Azo-MICs

T2 - Redox-Active Mesoionic Carbene Ligands Derived from Azoimidazolium Dyes

AU - Chadwick, F. Mark

AU - Curchod, Basile F.E.

AU - Scopelliti, Rosario

AU - Fadaei Tirani, Farzaneh

AU - Solari, Euro

AU - Severin, Kay

PY - 2019/2/4

Y1 - 2019/2/4

N2 - 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.

AB - 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.

KW - azoimidazolium dyes

KW - gold

KW - mesoionic carbenes

KW - N-heterocyclic carbenes

KW - rhodium

UR - https://www.scopus.com/pages/publications/85060004170

U2 - 10.1002/anie.201813780

DO - 10.1002/anie.201813780

M3 - Article (Academic Journal)

C2 - 30561125

AN - SCOPUS:85060004170

SN - 1433-7851

VL - 58

SP - 1764

EP - 1767

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 6

ER -

Azo-MICs: Redox-Active Mesoionic Carbene Ligands Derived from Azoimidazolium Dyes

Abstract

Bibliographical note

Research Groups and Themes

Keywords

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