Synthesis, optical and theoretical characterization of heteroleptic Iridium(III) Imidazo[1,5-a]pyridine and -quinoline complexes

Herr, Jasmin; Rössiger, Carina; Locke, Harald; Wilhelm, Mikko; Becker, Jonathan; Heimbrodt, W.; Schlettwein, Derck; Göttlich, Richard

doi:10.1016/j.dyepig.2020.108512

Cited by 14 publications

(18 citation statements)

References 52 publications

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“…The electrochemical behavior of cationic iridium cyclometalated complexes is well known: one electron ligand-based reduction and one electron metal-based oxidation are typically observed for this type of molecules [ 36 , 37 , 38 , 39 ].…”

Section: Resultsmentioning

confidence: 99%

Dipyridylmethane Ethers as Ligands for Luminescent Ir Complexes

et al. 2021

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This work reports two new cationic heteroleptic cyclometalated iridium complexes, containing ether derivatives of di(pyridin-2-yl)methanol. The new ligands are based on dipyridin-2-ylmethane and are designed to obtain ether-based intermediates with extended electronic conjugation by insertion of π system such as phenyl, allyl and ethynyl. Different synthetic strategies were employed to introduce these units, as molecular wires, between the dipyridin-2-ylmethane chelating portion and the terminal N-containing functional group, such as amine and carbamide. The corresponding complexes show luminescence in the blue region of the spectrum, lifetimes between 0.6 and 2.1 μs, high quantum yield and good electrochemical behavior. The computational description (DFT) of the electronic structure highlights the key role of the conjugated π systems on optical and electrochemical properties of the final products.

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Section: Resultsmentioning

confidence: 99%

Dipyridylmethane Ethers as Ligands for Luminescent Ir Complexes

et al. 2021

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“…The emission lifetime values, compatible with a fluorescence emission mechanism from a singlet excited state, have been reported from 1 to 10 ns, [13,119,19] these values could be strongly modified after complexation reactions. The presence of transition metal ions (chelated by the impy nucleus) typically increases the lifetime from ns to ms due to intersystem crossing and consequent phosphorescence emission (eventually quenched by molecular oxygen) [17,28,67] …”

Section: Discussionmentioning

confidence: 99%

“…The presence of transition metal ions (chelated by the impy nucleus) typically increases the lifetime from ns to ms due to intersystem crossing and consequent phosphorescence emission (eventually quenched by molecular oxygen). [17,28,67] The electrochemical properties of a new luminescent scaffold are of paramount importance for possible applications. The reported impy compounds display mono-electronic oxidation (generally reversible), characterized by half-wave potential E 1/2 of about 400 mV (versus ferrocene/ferrocenium reference, Fc/Fc + ), as previously reported for impy derivatives and corresponding complexes.…”

Section: Optical Behaviours and Reported Applications Of Impy Derivat...mentioning

confidence: 99%

“…[12][13][14][15] To obtain these structural modifications it is of paramount importance to know the available different synthetic approaches to introduce functional groups, spacers or additional conjugated systems (such as imidazo-quinoline). [16][17][18][19][20][21] The distinctive emission of the impy moiety typically lies in the 450-530 nm range, with a large Stokes shift (up to 150 nm) and good quantum yield (ranging from 10% to 50%). Due to their structural flexibility and tuneable optical behaviours, impy luminescent products represent excellent candidates to be widely employed for different applications such as downshifting [22][23][24] and optoelectronic devices.…”

Section: Introductionmentioning

confidence: 99%

“…In general, impy skeleton could be designed to obtain luminescent ligands from transition metal complexes, to connect other fluorophores (as BODIPY or rhodamine), [8–11] or to act as a fluorogenic centre itself [12–15] . To obtain these structural modifications it is of paramount importance to know the available different synthetic approaches to introduce functional groups, spacers or additional conjugated systems (such as imidazo‐quinoline) [16–21] …”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Luminescent Imidazo[1,5‐a]pyridine Scaffold: Synthetic Heterocyclization Strategies‐Overview and Promising Applications

Volpi

2022

Asian J Org Chem

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In the last few years, imidazo[1,5‐a]pyridine derivatives have attracted growing attention due to their remarkable emissive behaviours, structural modification and biological properties. Previously published works emphasize the possible technological applications of this luminescent scaffold and demonstrate the stringent relationship between chemical substituents and optical properties. The main goal of this work is to provide a complete list of the reported achievements concerning these promising heterocyclization reactions obtained starting from a huge variety of reagents, catalysts, oxidants, dehydrating agents involved in various reaction conditions. Particular attention is focused on the final possible substitutions, conjugations and structural modifications of the reported synthetic approaches, a powerful aspect to design innovative and employable new luminescent imidazo[1,5‐a]pyridine products.

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Highly Versatile Preparation of Imidazo[1,5‐a]quinolines and Characterization of Their Photoluminescent Properties

Kulhanek,

Martin,

Göttlich

2023

Eur J Org Chem

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In this work, we describe a simple and robust synthetic approach for the formation of 1,3‐substituted imidazo[1,5‐a]quinolines. This was achieved by developing a mild and selective bromination with N‐bromosuccinimide (NBS) in 3‐position of the imidazole ring. This was followed by a Negishi coupling, which we performed with various coupling partners, resulting in a wide range of different combinations, usually unattainable by other approaches and similar coupling reactions. Fluorescence measurements identified beneficial substitution patterns for the future use of imidazo[1,5‐a]quinolines in optical applications, such as organic light‐emitting diodes (OLEDs).

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Synthesis, optical and theoretical characterization of heteroleptic Iridium(III) Imidazo[1,5-a]pyridine and -quinoline complexes

Cited by 14 publications

References 52 publications

Dipyridylmethane Ethers as Ligands for Luminescent Ir Complexes

Dipyridylmethane Ethers as Ligands for Luminescent Ir Complexes

Luminescent Imidazo[1,5‐a]pyridine Scaffold: Synthetic Heterocyclization Strategies‐Overview and Promising Applications

Highly Versatile Preparation of Imidazo[1,5‐a]quinolines and Characterization of Their Photoluminescent Properties

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