A Stable Chichibabin Diradicaloid with Near‐Infrared Emission

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 a...

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Vydáno v:Angewandte Chemie International Edition Ročník 63; číslo 29; s. e202404853 - n/a
Hlavní autoři: Chang, Xingmao, Arnold, Mona E., Blinder, Rémi, Zolg, Julia, Wischnat, Jonathan, Slageren, Joris, Jelezko, Fedor, Kuehne, Alexander J. C., Delius, Max
Médium: Journal Article
Jazyk:angličtina
Vydáno: Germany Wiley Subscription Services, Inc 15.07.2024
Vydání:International ed. in English
Témata:
Chlorine
conjugated materials
Data processing
Emissions
EPR spectroscopy
Information processing
Magnetic properties
Near infrared radiation
NIR emission
Optical properties
Quantum phenomena
radical chemistry
stable diradicaloid
NIR emission
conjugated materials
stable diradicaloid
EPR spectroscopy
radical chemistry
ISSN:1433-7851, 1521-3773, 1521-3773
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Popis
Shrnutí: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. A stable analogue of the iconic Chichibabin hydrocarbon was synthesized by Ullmann coupling from a readily available, chlorinated trityl radical (TTM‐I). Thanks to its planar bridge, which exhibits hydrogen and chlorine atoms in just the right positions, the TTM‐TTM diradicaloid has skyblue color in solution, emits in the NIR range but nevertheless has significant diradical character at room temperature.
Bibliografie:These authors contributed equally to this work.
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.202404853