Electrogenerated chemiluminescence from newly synthesized α-diimine-ligated heteroleptic iridium(III) complexes

Kang, Tae Kyeong; Kang, Chang Hoon; Lee, Jihoon; Kim, Shin Han; Kim, Byeong Hyo; Lee, Won Yong

doi:10.1016/j.jelechem.2016.05.027

Cited by 5 publications

(3 citation statements)

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“…1 H NMR is consistent with the literature. 29 N-Benzyl-4-(trimethylsilyl)benzamide (31). Purification of 31 by flash column chromatography (petroleum ether/ethyl acetate: 5/1) afforded the desired product as a white solid (49.…”

Section: -Methyl-1-(4-(trimethylsilyl)phenyl)mentioning

confidence: 99%

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Revisiting the Mg/TMSCl/Dipolar Solvent System for Dearomatic Silylation of Aryl Carbonyl Compounds: Substrate Scope, Transformations, and Mechanistic Studies

Gao

et al. 2022

J. Org. Chem.

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Dearomatic silylation of arene derivatives is an intriguing synthetic target, which represents an elegant extension of Birch reduction and produces silylated cyclohexene derivatives with great potential of further transformation. Herein, we report a systematic study on dearomatic silylation of aryl carbonyl compounds with Mg and the TMSCl/NMP adduct. The protocol displays a wide range of substrate scope, including alkyl aryl ketones, aromatic amides, benzonitriles, tert-butyl benzoates, and even 2,2′-bipyridines. Synthetic utility is demonstrated using the products as versatile substrate in various transformations. The detailed mechanism is presented with both control experimental analyses and theoretical calculations. An unusual five-coordinated silicon dianion intermediate is first proposed and described here. The selectivity is influenced by the relative rates of single electron reductions (the TMSCl/NMP adduct versus the substrate) and the steric effects.

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Section: -Methyl-1-(4-(trimethylsilyl)phenyl)mentioning

confidence: 99%

“…4-(Trimethylsilyl)benzoic acid (27) could also be obtained from benzonitrile in 65% yield. Aromatic amides were suitable substrates as well (29−36), including the N−H substrate (31).…”

Section: ■ Introductionmentioning

confidence: 99%

Revisiting the Mg/TMSCl/Dipolar Solvent System for Dearomatic Silylation of Aryl Carbonyl Compounds: Substrate Scope, Transformations, and Mechanistic Studies

Gao

et al. 2022

J. Org. Chem.

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“…Finally, the stronger Ir–N bond would be expected, which is favorable to facilitating and refining the phosphorescent process. Besides alteration of the primary ligands, the incorporation of substituents into the primary ligand or development of various ancillary ligands , is an alternative express pathway to shift emissive wavelength. However, introduction of the substituent into ancillary ligand is rarely reported.…”

Section: Introductionmentioning

confidence: 99%

Comprehension of the Effect of a Hydroxyl Group in Ancillary Ligand on Phosphorescent Property for Heteroleptic Ir(III) Complexes: A Computational Study Using Quantitative Prediction

Wang¹,

Yang²,

Wen³

et al. 2017

Inorg. Chem.

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A new Ir(III) complex (dfpypya)Ir(pic-OH) (2) is theoretically designed by introduction of a simple hydroxyl group into the ancillary ligand on the basis of (dfpypya)Ir(pic) (1) with the aim to get the high-efficiency and stable blue-emitting phosphors, where dfpypya is 3-methyl-6-(2',4'-difluoro-pyridinato)pyridazine, pic is picolinate, and pic-OH is 3-hydroxypicolinic acid. The other configuration (dfpypya)Ir(pic-OH)' (3) is also investigated to compare with 2. The difference between 2 and 3 is whether the intramolecular hydrogen bond is formed in the (dfpypya)Ir(pic-OH). The quantum yield is determined by three different methods including the semiquantitative and quantitative methods. To quantitatively determine the quantum yield is still not an easy task to be completed. This work would provide some useful advices to select the suitable method to reliably evaluate the quantum yield. Complex 2 has larger quantum yield and more stability as compared with 1 and 3. The formation of intramolecular hydrogen bond would become a new method to design new phosphor with the desired properties.

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Highly efficient electrochemiluminescence labels comprising iridium(iii) complexes

et al. 2017

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Improving the performance of labeling agents is crucial to the further development of electrochemiluminescence (ECL) related technologies. Although a large number of ECL luminophores beyond ruthenium complexes have been reported so far, there is still a scarcity of studies involving novel ECL labeling agents. Herein, five novel iridium ECL labels and one control label comprising a ruthenium complex have been rationally designed and thoroughly characterized using photophysical techniques, theoretical calculations and electrochemical characterization to assess the ECL properties in this work. Both in coreactant-assisted potential scan experiments and through an annihilation approach, most of these novel iridium labels exhibit equivalent or even-stronger ECL signals than tri-2,2'-bipyridylruthenium(ii) [abbreviated as Ru(bpy)] under the same experimental conditions. Most importantly, using the same labeling protocol, bovine serum albumin (BSA) labeled with an iridium label (label 3 in this work) exhibits a much more intense ECL signal (1.9 times) than the same amount labeled with a traditional ruthenium complex (Ru-based Label in this work) in ProCell buffer solution. In addition to the advantage of exhibiting various emission colors, the novel iridium labels reported in this work may offer insight for the further development of ECL-based analytical technology.

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Electrogenerated chemiluminescence from newly synthesized α-diimine-ligated heteroleptic iridium(III) complexes

Cited by 5 publications

References 50 publications

Revisiting the Mg/TMSCl/Dipolar Solvent System for Dearomatic Silylation of Aryl Carbonyl Compounds: Substrate Scope, Transformations, and Mechanistic Studies

Revisiting the Mg/TMSCl/Dipolar Solvent System for Dearomatic Silylation of Aryl Carbonyl Compounds: Substrate Scope, Transformations, and Mechanistic Studies

Comprehension of the Effect of a Hydroxyl Group in Ancillary Ligand on Phosphorescent Property for Heteroleptic Ir(III) Complexes: A Computational Study Using Quantitative Prediction

Highly efficient electrochemiluminescence labels comprising iridium(iii) complexes

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