Structure–property–function relationships of stabilized and persistent <i>C</i>- and <i>N</i>-based triaryl radicals

Vasiļevska, Anna; Slanina, Tomáš

doi:10.1039/d3cc05706b

Chem. Commun.

2024

DOI: 10.1039/d3cc05706b

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Structure–property–function relationships of stabilized and persistent C- and N-based triaryl radicals

Anna Vasiļevska,

Tomáš Slanina

Abstract: Triaryl amine radical cations and trityl radicals use two completely orthogonal stabilization strategies. The former delocalize both the spin and charge density over the π-system, while the latter isolate the spin density by persistent barriers.

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Cited by 4 publications

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Molecular Electro(Photo)Catalysis: Triarylamine and Triarylimidazole Derivatives Mediated Oxidation Systems in Organic Electrosynthesis

Liu,

Ma,

Hao

et al. 2024

Adv Synth Catal

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Organic electrosynthesis has become a green, efficient and sustainable alternative to traditional organic transformation for the redox reactions. In this connection, indirect electrolysis employing redox mediators is attaining increasing significance as it offers a chance to improve reaction selectivity and avoids the over‐oxidation/reduction issues encountered in direct electrolysis. Triarylamines and triarylimidazoles, as representative organic molecular mediators, have attracted widespread attention in recent years due to the advantages of well‐defined easy structural modification and tunable redox ability. Hence, in this minireview, the recent growth of triarylamine and triarylimidazole derivatives mediated electrochemical oxidation reactions were presented, highlighting the structural optimization, electrochemical performance and reaction mechanism of these organic mediators. Moreover, the photocatalytic and photoelectrocatalytic cases with these molecular mediators were also highlighted. To conclude, the current challenges and future prospects of this field are also discussed.

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Molecular Electro(Photo)Catalysis: Triarylamine and Triarylimidazole Derivatives Mediated Oxidation Systems in Organic Electrosynthesis

Liu,

Ma,

Hao

et al. 2024

Adv Synth Catal

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Ein Stabiles Chichibabin Diradikaloid mit Nahinfraroter Emission

Chang,

Arnold,

Blinder

et al. 2024

Angewandte Chemie

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Conjugated molecules with multiple radical centers such as the iconic Chichibabin diradicaloid hold promise as building blocks in materials for quantum sensing and quantum information processing. However, it is a considerable challenge to design simple analogues of the Chichibabin hydrocarbon that are chemically inert, exhibit high diradical character and emit light at a distinct wavelength that may offer an optical readout of the spin state in functional ensembles. Here we describe the serendipitous discovery of the stable TTM‐TTM diradicaloid, which exhibits high diradical character, a striking sky‐blue color and near‐infrared (NIR) emission (in solution). This combination of properties is unique among related diradicaloids and is due to the presence of hydrogen and chlorine atoms in “just the right positions”, allowing a perfectly planar, yet predominantly benzenoid bridge to connect the two sterically stabilized radical centers. In‐depth studies of the optical and magnetic properties suggest that this structural motif could become a mainstay building block of organic spin materials.

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A Stable Chichibabin Diradicaloid with Near‐Infrared Emission

Chang,

Arnold,

Blinder

et al. 2024

Angew Chem Int Ed

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Structure–property–function relationships of stabilized and persistent C- and N-based triaryl radicals

Abstract: Triaryl amine radical cations and trityl radicals use two completely orthogonal stabilization strategies. The former delocalize both the spin and charge density over the π-system, while the latter isolate the spin density by persistent barriers.

Cited by 4 publications

References 98 publications

Molecular Electro(Photo)Catalysis: Triarylamine and Triarylimidazole Derivatives Mediated Oxidation Systems in Organic Electrosynthesis

Molecular Electro(Photo)Catalysis: Triarylamine and Triarylimidazole Derivatives Mediated Oxidation Systems in Organic Electrosynthesis

Ein Stabiles Chichibabin Diradikaloid mit Nahinfraroter Emission

A Stable Chichibabin Diradicaloid with Near‐Infrared Emission

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