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Perchlorotrityl radical (PTM), tris (2,4,6-trichlorophenyl) methyl radical (TTM), (3,5-dichloro-4-pyridyl) bis (2,4,6 trichlorophenyl) methyl radical (PyBTM), (N-carbazolyl) bis (2,4,6-trichlorophenyl) methyl radical (CzBTM), and their derivatives are stable organic radicals that exhibit light emissions at room temperature. Since these triarylmethyl radicals have an unpaired electron, their electron spins at the lowest excited state and ground state are both doublets, and the transition from the lowest excited state to the ground state does not pose the problem of a spin-forbidden reaction. When used as OLED layers, these triarylmethyl radicals exhibit unique light-emitting properties, which can increase the theoretical upper limit of the OLED's internal quantum efficiency (IQE) to 100%. In recent years, research on the luminescent properties of triarylmethyl radicals has attracted increasing attention. In this review, recent developments in these triarylmethyl radicals and their derivatives in OLED devices are introduced.
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http://dx.doi.org/10.3390/molecules27051632 | DOI Listing |
Angew Chem Int Ed Engl
September 2025
Department of Chemistry, McGill University, Montreal, QC, Canada.
Luminescent radicals are of significant recent interest because of the unique quantum properties of the doublet excited state. Control of the energy level of the singly-occupied molecular orbital (SOMO) is essential for the design and application of open-shell materials, but most triarylmethyl radicals are very electron-poor and exhibit similar SOMO values. In this work, we show how a combination of chlorine and methoxy substituents in triarylmethyl radicals allows tuning of their SOMO level over a wide range of -5.
View Article and Find Full Text PDFBeilstein J Org Chem
May 2025
OC III - Institute of Organic and Macromolecular Chemistry, Ulm University, Albert-Einstein-Allee 11, 89081 Ulm, Germany.
Organic radicals with light-emitting properties and exceptional stability offer exciting opportunities to address spin-statistical limitations in organic electronics and advance quantum technologies. These radicals, acting as small molecular magnets, exhibit sensitivity to minute magnetic fields and can be tailored with diverse spin centers, making them ideal for spin-optical interfaces, representing key components in quantum communication systems. Furthermore, their ability to form organized, higher-dimensional assemblies presents a promising avenue for overcoming scalability challenges in quantum technologies.
View Article and Find Full Text PDFOrg Lett
April 2025
Department of Chemistry, School of Science, The University of Tokyo, Tokyo 113-0033, Japan.
We have developed a novel photocatalytic system using readily available triarylmethyl cations for radical-mediated (4 + 2) and (2 + 2) cycloaddition reactions. A variety of substituted triarylmethyl cations were investigated, and the optimal catalyst exhibited high efficiency and broad substrate scope, affording the desired cycloadducts in good to excellent yields with high regio- and diastereoselectivities. Furthermore, the catalyst could be immobilized on a polymer support and reused multiple times without a significant loss of activity.
View Article and Find Full Text PDFChemistry
April 2025
Division of Materials Science, Nara Institute of Science and Technology, 8916-5 Takayama, Ikoma, 630-0192, Japan.
Two units of a highly stable luminescent triarylmethyl radical (PyBTM) were bridged using a chiral octahydrobinaphthyl moiety, resulting in a diradical with sufficient stability to enable the measurement of its chiroptical properties. To synthesize this diradical, a novel boronic ester radical precursor, αH-PyBTM-B(Epin), was designed. The use of this precursor significantly improved the yield and streamlined the preparation of stable luminescent radical-substituted molecules.
View Article and Find Full Text PDFChem Biomed Imaging
January 2025
In Vivo Multifunctional Magnetic Resonance Center, Robert C. Byrd Health Sciences Center, West Virginia University, Morgantown, West Virginia 26506, United States.
Enzyme catalytic activities are critical biomarkers of tissue states under physiological and pathophysiological conditions. However, the direct measurement and imaging of enzyme activity remains extremely challenging. We report the synthesis and characterization of the first stable triarylmethyl (TAM) radical substrate of alkaline phosphatase (TAM-ALPs).
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