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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Abstract	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.
AbstractList	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. 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.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. 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. 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.
Author	Delius, Max Arnold, Mona E. Jelezko, Fedor Kuehne, Alexander J. C. Chang, Xingmao Blinder, Rémi Zolg, Julia Slageren, Joris Wischnat, Jonathan
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BackLink	https://www.ncbi.nlm.nih.gov/pubmed/38695271$$D View this record in MEDLINE/PubMed
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CitedBy_id	crossref_primary_10_1021_acsami_5c13020 crossref_primary_10_1016_j_chempr_2025_102621 crossref_primary_10_1002_anie_202512691 crossref_primary_10_1021_jacs_4c08876 crossref_primary_10_1002_anie_202414406 crossref_primary_10_1002_anie_202424128 crossref_primary_10_1038_s41467_025_59317_w crossref_primary_10_3762_bjoc_21_80 crossref_primary_10_1002_ange_202414406 crossref_primary_10_1021_acs_jpclett_5c02104 crossref_primary_10_1038_s41557_025_01875_z crossref_primary_10_1016_j_chempr_2025_102628 crossref_primary_10_1002_adma_202511877 crossref_primary_10_1038_s41377_025_01993_w crossref_primary_10_1021_acscentsci_4c01632 crossref_primary_10_1002_chem_202500749 crossref_primary_10_1002_ange_202424128 crossref_primary_10_1002_cplu_202500033 crossref_primary_10_3390_molecules30061191 crossref_primary_10_1039_D5CC01805F crossref_primary_10_1039_D5QM00328H crossref_primary_10_1002_ange_202512691 crossref_primary_10_1021_jacs_5c02672 crossref_primary_10_3390_chemistry7010021 crossref_primary_10_1039_D5SC03673A crossref_primary_10_1002_agt2_70100 crossref_primary_10_1021_jacs_4c08167 crossref_primary_10_1021_jacs_4c11549 crossref_primary_10_1002_chem_202403372
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Keywords	NIR emission conjugated materials stable diradicaloid EPR spectroscopy radical chemistry
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Snippet	Conjugated molecules with multiple radical centers such as the iconic Chichibabin diradicaloid hold promise as building blocks in materials for quantum sensing...
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StartPage	e202404853
SubjectTerms	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
Title	A Stable Chichibabin Diradicaloid with Near‐Infrared Emission
URI	https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.202404853 https://www.ncbi.nlm.nih.gov/pubmed/38695271 https://www.proquest.com/docview/3076685478 https://www.proquest.com/docview/3050174802
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