Silver and Gold Complexes with a New 1,10‐Phenanthroline Analogue N‐Heterocyclic Carbene: A Combined Structural, Theoretical, and Photophysical Study

Kriechbaum, Margit; List, Manuela; Berger, Raphael J. F.; Patzschke, Michael; Monkowius, Uwe

doi:10.1002/chem.201200465

Cited by 52 publications

(57 citation statements)

References 31 publications

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“…[29] This coordination geometry was also found for the corresponding Au III complex bearing ligand A. [17] Electronic Spectra…”

Section: Wwweurjicorg Full Papermentioning

confidence: 71%

“…13 C NMR resonances of the carbene carbon atoms appear at 175.6 (NHC-Au I complex 5) and 148.1 ppm (NHC-Au III complex 6), which are very similar to the analogous complexes bearing ligand A. [17] The corresponding carbon atom of the imidazolium chloride 3 resonates at δ = 148.7 ppm.…”

Section: Synthesis and Characterizationmentioning

confidence: 94%

“…[7,17,30,31] Despite the high atomic number of gold, the spin-orbit coupling promoted by the gold atom is comparably low and leads to relatively long phosphorescence lifetimes at 77 K, but it is high enough to allow for efficient S 1 -T 1 intersystem crossing. This behaviour can be traced back to the low-lying d orbitals, which are not involved in low-energy electronic transitions.…”

Section: Wwweurjicorg Full Papermentioning

confidence: 97%

“…As reported recently, NHC-Au III bromides undergo photoreductive elimination of Br 2 to form the corresponding NHC-Au I bromide. [17,23] Figure 9 illustrates the spectral changes of complex 6 upon irradiation for 10 min. Initially, the spectrum shows LE bands at 330, 315, 304, 285 and…”

Section: /Kap1mentioning

confidence: 99%

“…We have recently reported a 1,10-phenanthroline analogue NHC ligand (A) and the emissive properties of its Au I and Au III complexes. [17] In this contribution we present a similar NHC with an ether oxygen atom as the second binding site that forms a potential chelating ligand (B) similar to 10-hydroxybenzo[h]quinoline (C, Scheme 1). Scheme …”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Characterization and Luminescence of Gold Complexes Bearing an NHC Ligand Based on the Imidazo[1,5‐a]quinolinol Scaffold

et al. 2013

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We report on the synthesis and characterization of an NHC ligand based on the imidazo[1,5‐a]quinolinol scaffold. The benzyl‐protected NHC precursor was used for the preparation of the corresponding AgI, AuI and AuIII complexes. The molecular structures of the AuI and AuIII halide complexes determined by single‐crystal X‐ray diffraction reveal considerable distortion of the rigid NHC moiety due to steric repulsion between the gold and oxygen atoms. At ambient temperature, the complexes are weakly fluorescent from an intraligand excited state, whereas at 77 K the emission spectra are dominated by intraligand phosphorescence.

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“…[29] This coordination geometry was also found for the corresponding Au III complex bearing ligand A. [17] Electronic Spectra…”

Section: Wwweurjicorg Full Papermentioning

confidence: 71%

Section: Synthesis and Characterizationmentioning

confidence: 94%

Section: Wwweurjicorg Full Papermentioning

confidence: 97%

Section: /Kap1mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, Characterization and Luminescence of Gold Complexes Bearing an NHC Ligand Based on the Imidazo[1,5‐a]quinolinol Scaffold

et al. 2013

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The Chemistry of Gold– NHC Carbene Complexes

Zhang

Chen

et al. 2015

Patai's Chemistry of Functional Groups

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Au‐NHC chemistry has received much attention in the last 10 years, mainly due to straightforward synthetic routes to Au(I)‐NHC complexes and their catalytic interest. Now Au‐NHC complexes have been employed, not only as highly selective catalysts in directed organic synthetic strategies, but also as dynamic intermediates to promote constructive chemical steps at the metal active center. Some very recent examples have described the stabilization imparted by NHC which allows to isolate otherwise “unstable” intermediates, such as vinylgold derivatives. Another important property shown by Au‐NHC complexes is their luminescence. The lower energy excitation and emission bands in some Au‐NHCs are of suitable wavelengths for cellular distribution studies allowing to investigate the uptake and distribution in cancer cells using fluorescence confocal microscopy. The strong Au–carbene bonds also permit stable Au‐NHC complexes immune to biologically important thiol groups, and thus Au‐NHCs have also been found to have potential in medicinal and biochemical applications.

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L‐Shaped Heterobidentate Imidazo[1,5‐a]pyridin‐3‐ylidene (N,C)‐Ligands for Oxidant‐Free Au^I/Au^III Catalysis

Gao

Zhou

et al. 2023

Angewandte Chemie

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In the last decade, major advances have been made in homogeneous gold catalysis. However, Au I / Au III catalytic cycle remains much less explored due to the reluctance of Au I to undergo oxidative addition and the stability of the Au III intermediate. Herein, we report activation of aryl halides at gold(I) enabled by NHC (NHC=N-heterocyclic carbene) ligands through the development of a new class of L-shaped heterobidentate ImPy (ImPy = imidazo[1,5-a]pyridin-3-ylidene) N,C ligands that feature hemilabile character of the amino group in combination with strong σ-donation of the carbene center in a rigid conformation, imposed by the ligand architecture. Detailed characterization and control studies reveal key ligand features for Au I /Au III redox cycle, wherein the hemilabile nitrogen is placed at the coordinating position of a rigid framework. Given the tremendous significance of homogeneous gold catalysis, we anticipate that this ligand platform will find widespread application.

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Silver and Gold Complexes with a New 1,10‐Phenanthroline Analogue N‐Heterocyclic Carbene: A Combined Structural, Theoretical, and Photophysical Study

Cited by 52 publications

References 31 publications

Synthesis, Characterization and Luminescence of Gold Complexes Bearing an NHC Ligand Based on the Imidazo[1,5‐a]quinolinol Scaffold

Synthesis, Characterization and Luminescence of Gold Complexes Bearing an NHC Ligand Based on the Imidazo[1,5‐a]quinolinol Scaffold

The Chemistry of Gold– NHC Carbene Complexes

L‐Shaped Heterobidentate Imidazo[1,5‐a]pyridin‐3‐ylidene (N,C)‐Ligands for Oxidant‐Free Au^I/Au^III Catalysis

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Silver and Gold Complexes with a New 1,10‐Phenanthroline Analogue N‐Heterocyclic Carbene: A Combined Structural, Theoretical, and Photophysical Study

Cited by 52 publications

References 31 publications

Synthesis, Characterization and Luminescence of Gold Complexes Bearing an NHC Ligand Based on the Imidazo[1,5‐a]quinolinol Scaffold

Synthesis, Characterization and Luminescence of Gold Complexes Bearing an NHC Ligand Based on the Imidazo[1,5‐a]quinolinol Scaffold

The Chemistry of Gold– NHC Carbene Complexes

L‐Shaped Heterobidentate Imidazo[1,5‐a]pyridin‐3‐ylidene (N,C)‐Ligands for Oxidant‐Free AuI/AuIII Catalysis

Contact Info

Product

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L‐Shaped Heterobidentate Imidazo[1,5‐a]pyridin‐3‐ylidene (N,C)‐Ligands for Oxidant‐Free Au^I/Au^III Catalysis