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Luminescence of doublet molecular systems

COORDINATION CHEMISTRY REVIEWS (2022)

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Amplification of luminescence of stable radicals by coordination to NHC-gold(i) complex

Yohei Hattori et al.

Summary: The luminescence of stable radicals can be enhanced by coordination to metal complexes. The fluorescence quantum yield of F2PyBTM radical in dichloromethane was increased from 4% to 36% by coordination to Au-I metal complex with N-heterocyclic carbene ligand, setting a record for metal-radical complexes.

CHEMICAL COMMUNICATIONS (2022)

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Article Chemistry, Multidisciplinary

Stable Diarylamine-Substituted Tris(2,4,6-trichlorophenyl)methyl Radicals: One-Step Synthesis, Near-Infrared Emission, and Redox Chemistry

Chuan Yan et al.

Summary: A mild one-step synthesis strategy has been developed to produce a new family of TTM radical derivatives. By introducing different diarylamine substituents on the TTM radicals, the photoluminescence properties and structures can be controlled. The oxidation of the diarylamine-substituted TTM radicals reveals their unusual structures and slow valence tautomerization process.

CCS CHEMISTRY (2022)

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Article Chemistry, Multidisciplinary

Highly Efficient Multifunctional Luminescent Radicals

Yihan Zhao et al.

Summary: Stable organic luminescent radicals are a special class of compounds with potential applications in various fields. This study reports two luminescent radicals with high efficiency and less dependence on solvent polarity, showing promise as fluorescent probes and electroluminescent emitters in fluorescence sensing and OLEDs.

CCS CHEMISTRY (2022)

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Article Multidisciplinary Sciences

Efficient rare earth cerium(III) complex with nanosecond d-f emission for blue organic light-emitting diodes

Zifeng Zhao et al.

Summary: The blue emissive rare earth cerium(III) complex Ce-2 demonstrated high photoluminescence quantum yield and a short excited state lifetime, making it a promising candidate for efficient and stable blue OLEDs with significantly improved performance compared to typical phosphorescence or delayed fluorescence emitters.

NATIONAL SCIENCE REVIEW (2021)

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Article Chemistry, Multidisciplinary

Controlling Spin-Correlated Radical Pairs with Donor-Acceptor Dyads: A New Concept to Generate Reduced Metal Complexes for More Efficient Photocatalysis

Svenja Neumann et al.

Summary: The study investigates a molecular dyad capable of producing reduced metal complexes through an indirect pathway, demonstrating the potential of novel photocatalysts with unprecedented quantum yields. By optimizing this approach, the generation of reduced metal complexes via this pathway could outperform the conventional direct metal complex photoreduction. This research provides valuable evidence for the indirect mechanism of reduced metal complex generation and its advantages over direct pathways.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

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Article Chemistry, Inorganic & Nuclear

Highly Efficient Heteroleptic Cerium(III) Complexes with a Substituted Pyrazole Ancillary Ligand and Their Application in Blue Organic Light-Emitting Diodes

Wenchao Yan et al.

Summary: Compared to red and green OLEDs, blue OLEDs face bottleneck issues. Ce(III) complexes show promising properties as emitters in OLEDs, with Ce(Tp(Me2))(2)(dppz) exhibiting the best performance in terms of brightness and efficiency.

INORGANIC CHEMISTRY (2021)

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Article Multidisciplinary Sciences

Crystallization-induced mechanofluorescence for visualization of polymer crystallization

Sota Kato et al.

Summary: By introducing tetraarylsuccinonitrile (TASN) into crystalline polymers, researchers were able to visualize and evaluate the stress caused by micro-mechanical forces during polymer crystallization using fluorescence microscopy and electron paramagnetic resonance. This study provides a new method for studying residual stress in polymeric materials.

NATURE COMMUNICATIONS (2021)

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Article Chemistry, Multidisciplinary

Stable Boron-Containing Blue-Photoluminescent Radicals

Zhongtao Feng et al.

Summary: The study focuses on developing synthetic strategies to create new stable luminescent radicals with desired emission wavelengths. Two dioxoborocyclic radicals were isolated and characterized with UV, EPR spectroscopy, and SQUID measurements. Both radicals produced blue photoluminescence through radiative decay from higher excited states to the ground state, breaking Kasha rule. This work presents a new kind of radical emitters and the first stable radicals with blue emission bands.

CHINESE JOURNAL OF CHEMISTRY (2021)

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Article Physics, Applied

Efficient light-emitting diodes from organic radicals with doublet emission

John M. Hudson et al.

Summary: Organic light-emitting diodes (OLEDs) with doublet-spin radical emitters have shown highly efficient performance, breaking through the efficiency limits imposed on typical OLED devices with organic semiconductors.

JOURNAL OF APPLIED PHYSICS (2021)

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Article Chemistry, Multidisciplinary

An Open-shell, Luminescent, Two-Dimensional Coordination Polymer with a Honeycomb Lattice and Triangular Organic Radical

Shun Kimura et al.

Summary: In this study, a novel triangular organic radical, tris(3,5-dichloro-4-pyridyl)methyl radical (trisPyM), was synthesized and used to form stable 2D coordination polymers with luminescent and high photostability properties. The complexation of trisPyM with Zn-II resulted in the formation of a honeycomb lattice with graphene-like spin topology. This radical demonstrates better chemical stability and luminescent properties compared to conventional radicals, making it a promising building block for new 2D coordination polymers with unique properties.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Chemistry, Multidisciplinary

Radical-Based Coordination Polymers as a Platform for Magnetoluminescence

Shun Kimura et al.

Summary: The study explores the magnetoluminescence properties of organic radicals and introduces a novel method for achieving radical magnetoluminescence through coordination polymers. Reducing radical-radical interactions in polymers is found to be a key method for modulating magnetoluminescence.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Article Polymer Science

Visualization of the Necking Initiation and Propagation Processes during Uniaxial Tensile Deformation of Crystalline Polymer Films via the Generation of Fluorescent Radicals

Sota Kato et al.

Summary: By introducing TASN moieties into crystalline polymers, the necking behavior during uniaxial stretching can be visualized and quantified. The yellow fluorescence from the dissociated TASN radicals in the stretching direction reveals the orientation of polymer chains. Comparison between linear and star-shaped TASN-centered crystalline polymers shows a higher dissociation ratio in the star-shaped polymer, indicating more chains connected to the lamellar crystal.

ACS MACRO LETTERS (2021)

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Article Chemistry, Physical

Solid-State Room-Temperature Near-Infrared Photoluminescence of a Stable Organic Radical

Ryota Matsuoka et al.

Summary: While the electronic structures and photophysical properties of metaPyBTM and its analogues in solution are similar, metaPyBTM exhibits distinctive near-infrared photoluminescence in the pure crystalline state at room temperature. The solid-state luminescence properties of metaPyBTM strongly depend on temperature and the degree of aggregation, with an external magnetic field also modulating the emission spectrum in the moderately aggregated state.

CHEMPHOTOCHEM (2021)

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Article Nanoscience & Nanotechnology

Lanthanide Cerium(III) Tris(pyrazolyl)borate Complexes: Efficient Blue Emitters for Doublet Organic Light-Emitting Diodes

Peiyu Fang et al.

Summary: This research achieved efficient bright blue emission by tuning the structure of complexes. Using the Ce(III) complex as emitter, the OLED showed high external quantum efficiency and luminance. The study demonstrated that lanthanide complexes can serve as important emitters for blue OLEDs, offering new insights for improving OLED performance.

ACS APPLIED MATERIALS & INTERFACES (2021)

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Article Chemistry, Multidisciplinary

Photoinduced Radical Emission in a Coassembly System

Yiran Li et al.

Summary: Developing radical emission at ambient conditions poses a challenge due to the instability of radical species in air. The study demonstrated that coassembling tricarbonyl-substituted benzene molecules with polyvinyl alcohol (PVA) can protect free radicals and lead to strong solid state free radical emission. Quantum-chemical calculations predicted the origin of such fluorescence and the photoinduced radical emission was successfully utilized for information encryption application.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Review Chemistry, Multidisciplinary

Photostable Luminescent Triarylmethyl Radicals and Their Metal Complexes: Photofunctions Unique to Open-shell Electronic States

Tetsuro Kusamoto et al.

Summary: Stable organic radicals with unpaired electrons have distinctive physical characteristics such as magnetic and electron-conducting properties, and they also exhibit luminescence properties which can expand the utility of radicals in molecular photonics.

CHEMISTRY LETTERS (2021)

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Article Chemistry, Multidisciplinary

Expansion of Photostable Luminescent Radicals by Meta-Substitution

Yohei Hattori et al.

Summary: The synthesis and fluorescence properties of polychlorinated pyridyldiphenylmethyl radicals with substituents meta to the alpha-carbon have been studied. Different substituents showed varied effects on the fluorescence behavior of the radicals in different solvents. DFT calculations revealed that the fluorescence properties were related to the nature of the excited states of the radicals.

CHEMISTRY-AN ASIAN JOURNAL (2021)

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Article Chemistry, Multidisciplinary

Luminescent First-Row Transition Metal Complexes

Christina Wegeberg et al.

Summary: Recent developments in the field of inorganic photophysics and photochemistry indicate a shift towards cheaper and more abundant metals, away from traditional precious and rare elements. Conceptual breakthroughs have expanded the range of elements, particularly those in different oxidation states, that can be used for emissive complexes. New design strategies have led to the discovery of fundamentally new types of 3d-metal-based luminophores and photosensitizers operating in solution at room temperature.

JACS AU (2021)

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Article Chemistry, Multidisciplinary

A stable triplet diradical emitter

Zhongtao Feng et al.

Summary: This study isolated two borocyclic diradicals with different substituents, one of which was identified as an open shell singlet diradical, while the other was found to be a triplet ground state diradical with a large singlet-triplet energy gap. Both diradicals showed multiple fluorescence peaks and have potential applications in material design and organic semiconductors.

CHEMICAL SCIENCE (2021)

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Article Materials Science, Multidisciplinary

First demonstration of the use of open-shell derivatives as organic luminophores for transparent luminescent solar concentrators

Sara Mattiello et al.

Summary: Luminescent solar concentrators (LSCs) are crucial for achieving zero-energy buildings, and the development of new efficient and sustainable luminophores is key for further improving their performance. LSCs based on the best performing luminescent radicals show little reabsorption losses, providing better performance than literature standards on active areas exceeding 400 cm².

MATERIALS ADVANCES (2021)

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Article Chemistry, Multidisciplinary

Red-to-NIR emissive radical cations derived from simple pyrroles

Lihua Zheng et al.

Summary: A new strategy for preparing red-to-NIR fluorophores from electron-rich 2,5-dimethylpyrroles through air oxidation and stabilization has been proposed, showing promising potential for biomedical applications in bio-imaging.

MATERIALS HORIZONS (2021)

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Article Chemistry, Multidisciplinary

Mixed-halide triphenyl methyl radicals for site-selective functionalization and polymerization

Lisa Chen et al.

Summary: Derivatives of the stable, luminescent TTM radical with mixed halides can be obtained through simple Friedel-Crafts alkylation, showing higher stability and site-specific reactivity. These radicals serve as powerful building blocks for the synthesis of stable luminescent molecules.

RSC ADVANCES (2021)

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Review Chemistry, Multidisciplinary

Circularly polarized luminescence in chiral nematic liquid crystals: generation and amplification

Xuefeng Yang et al.

Summary: Circularly polarized luminescent materials have great potential in research fields, but the most important parameter, luminescence dissymmetry factor (g(lum)), has not been satisfactory, especially for organic small molecules. Therefore, finding ways to obtain high g(lum) values has become an urgent challenge in the CPL research field, leading to various strategies being proposed.

MATERIALS CHEMISTRY FRONTIERS (2021)

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Article Chemistry, Inorganic & Nuclear

Luminescence from open-shell, first-row transition metal dipyrrin complexes

Austin B. Scharf et al.

Summary: In this study, several first-row transition metal complexes with 1,9-bis(2',4',6'-triphenylphenyl)-5-mesityl dipyrrinato ligand and its tetrahalogenated analogues were synthesized, and their luminescence spectra were obtained. The protonated ligands, as well as the Li(i), Mn(ii), Cu(i), Cu(ii), and Zn(ii) chelates exhibited appreciable luminescence, with zinc complex showing the highest fluorescence quantum yields. The introduction of heavy halogens to the ligand backbone and paramagnetic metal ions partially quenched luminescence. Room-temperature, solution state phosphorescence was observed from the halogenated dipyrrinato lithium salts, as well as from the non-halogenated Mn(ii) complex.

DALTON TRANSACTIONS (2021)

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Facile construction of well-defined radical metallacycles through coordination-driven self-assembly

Qian Tu et al.

Summary: This study successfully synthesized two discrete radical metallacycles by designing and synthesizing a new organic radical ligand and utilizing a coordination-driven self-assembly approach. The open-shell nature of the organic radical was preserved under mild coordination conditions, and a chiral self-sorting behavior was observed during the self-assembly process. The photophysical properties of the radicals changed significantly after coordination, leading to different color and emission characteristics of the resulting metallacycles.

MATERIALS CHEMISTRY FRONTIERS (2021)

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Review Chemistry, Multidisciplinary

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Yoshio Teki

CHEMISTRY-A EUROPEAN JOURNAL (2020)

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An Enantiopure Propeller-Like Trityl-Brominated Radical: Bringing Together a High Racemization Barrier and an Efficient Circularly Polarized Luminescent Magnetic Emitter

Paula Mayorga-Burrezo et al.

CHEMISTRY-A EUROPEAN JOURNAL (2020)

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Broad-Band Near-Infrared Doublet Emission in a Tetrathiafulvalene-Based Metal-Organic Framework

Feifan Wang et al.

JOURNAL OF PHYSICAL CHEMISTRY LETTERS (2020)

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Open-Shell Effects on Optoelectronic Properties: Antiambipolar Charge Transport and Anti-Kasha Doublet Emission from a N-Substituted Bisphenalenyl

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Shuqi Ma et al.

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Nils W. Rosemann et al.

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A Pure-Red Doublet Emission with 90 % Quantum Yield: Stable, Colorless, Iodinated Triphenylmethane Solid

Cheng-Hao Liu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Understanding the luminescent nature of organic radicals for efficient doublet emitters and pure-red light-emitting diodes

Alim Abdurahman et al.

NATURE MATERIALS (2020)

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Deep-blue organic light-emitting diodes based on a doubletd-ftransition cerium(III) complex with 100% exciton utilization efficiency

Liding Wang et al.

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Photofunctionality of iron(III) N-heterocyclic carbenes and related d transition metal complexes

Pavel Chábera et al.

COORDINATION CHEMISTRY REVIEWS (2020)

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Triplet-triplet annihilation based near infrared to visible molecular photon upconversion

Pankaj Bharmoria et al.

CHEMICAL SOCIETY REVIEWS (2020)

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Excimer emission and magnetoluminescence of radical-based zinc(II) complexes doped in host crystals

Shun Kimura et al.

CHEMICAL COMMUNICATIONS (2020)

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Richard Barre et al.

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Christoph Foerster et al.

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Zhiyuan Cui et al.

CCS CHEMISTRY (2020)

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NIR Emission and Acid-Induced Intramolecular Electron Transfer Derived from a SOMO-HOMO Converted Non-Aufbau Electronic Structure

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Introducing static cross-linking points into dynamic covalent polymer gels that display freezing-induced mechanofluorescence: enhanced force transmission efficiency and stability

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POLYMER CHEMISTRY (2019)

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DFT/MRCI-R2018 study of the photophysics of the zinc(ii) tripyrrindione radical: non-Kasha emission?

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Effects of substituents on luminescent efficiency of stable triaryl methyl radicals

Shengzhi Dong et al.

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Four new rare-earth nitronyl nitroxide radical complexes: Magnetic and luminescent properties

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Effective photosensitized, electrosensitized, and mechanosensitized luminescence of lanthanide complexes

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Freezing-Induced Mechanoluminescence of Polymer Gels

Sota Kato et al.

ACS MACRO LETTERS (2018)

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A pure red luminescent beta-carboline-substituted biphenylmethyl radical: photophysics, stability and OLEDs

Alim Abdurahman et al.

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Paramagnetism and Fluorescence of Zinc(II) Tripyrrindione: A Luminescent Radical Based on a Redox-Active Biopyrrin

Ritika Gautam et al.

INORGANIC CHEMISTRY (2018)

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Radical-Based Organic Light-Emitting Diodes with Maximum External Quantum Efficiency of 10.6%

Zhiyuan Cui et al.

JOURNAL OF PHYSICAL CHEMISTRY LETTERS (2018)

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Efficient radical-based light-emitting diodes with doublet emission

Xin Ai et al.

NATURE (2018)

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Solvent-Controlled Doublet Emission of an Organometallic Gold(I) Complex with a Polychlorinated Diphenyl(4-pyridyl)methyl Radical Ligand: Dual Fluorescence and Enhanced Emission Efficiency

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INORGANIC CHEMISTRY (2017)

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Low-Energy and Long-Lived Emission from Polypyridyl Ruthenium(II) Complexes Having A Stable-Radical Substituent

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A low-spin Fe(III) complex with 100-ps ligand-to-metal charge transfer photoluminescence

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Georgina Karecla et al.

NEW JOURNAL OF CHEMISTRY (2017)

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A family of lanthanide compounds based on nitronyl nitroxide radicals: synthesis, structure, magnetic and fluorescence properties

Xue-Hui Lv et al.

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A fluorescent dithiadiazolyl radical: structure and optical properties of phenanthrenyl dithiadiazolyl in solution and polymer composites

Yassine Beldjoudi et al.

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Luminescent solar concentrators for building-integrated photovoltaics

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Tetraarylsuccinonitriles as mechanochromophores to generate highly stable luminescent carbon-centered radicals

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Spin-state-correlated optical properties of copper(II)-nitroxide based molecular magnets

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Multicarbazolyl substituted TTM radicals: red-shift of fluorescence emission with enhanced luminescence efficiency

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Ablikim Obolda et al.

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Synergistic luminescence enhancement of a pyridyl-substituted triarylmethyl radical based on fluorine substitution and coordination to gold

Yohei Hattori et al.

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Daniela M. Arias-Rotondo et al.

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Lisa A. Fredin et al.

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Cerium Photosensitizers: Structure-Function Relationships and Applications in Photocatalytic Aryl Coupling Reactions

Haolin Yin et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

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Enhanced Luminescent Properties of an Open-Shell (3,5-Dichloro-4-pyridyl) bis(2,4,6-trichlorophenyl)methyl Radical by Coordination to Gold

Yohei Hattori et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

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Organic Light-Emitting Diodes Using a Neutral π Radical as Emitter: The Emission from a Doublet

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Review Chemistry, Inorganic & Nuclear

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Iron sensitizer converts light to electrons with 92% yield

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Highly photostable luminescent open-shell (3,5-dihalo-4-pyridyl)bis(2,4,6-trichlorophenyl)methyl radicals: significant effects of halogen atoms on their photophysical and photochemical properties

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Coordination-driven nanosized lanthanide 'Molecular Lanterns' as luminescent chemosensors for the selective sensing of magnesium ions

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Terbium(III) and Yttrium(III) Complexes with Pyridine-Substituted Nitronyl Nitroxide Radical and Different β-Diketonate Ligands. Crystal Structures and Magnetic and Luminescence Properties

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Three-Dimensional Porous Metal-Radical Frameworks Based on Triphenylmethyl Radicals

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Highly efficient organic light-emitting diodes from delayed fluorescence

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Thirty Years of Luminescent Solar Concentrator Research: Solar Energy for the Built Environment

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Ultrafast Intersystem Crossing and Spin Dynamics of Zinc meso-Tetraphenylporphyrin Covalently Bound to Stable Radicals

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Distance-Dependent Fluorescence Quenching and Binding of CdSe Quantum Dots by Functionalized Nitroxide Radicals

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Highly Fluorescent Open-Shell NIR Dyes: The Time-Dependence of Back Electron Transfer in Triarylamine-Perchlorotriphenylmethyl Radicals

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Nanosized trigonal prismatic and antiprismatic CuII coordination cages based on tricarboxylate linkers

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Taking advantage of the radical character of tris(2,4,6-trichlorophenyl)methyl to synthesize new paramagnetic glassy molecular materials

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Light-emitting persistent radicals for efficient sensor devices of solvent polarity

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TETRAHEDRON LETTERS (2008)

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Red organic light-emitting radical adducts of carbazole and tris(2,4,6-trichlorotriphenyl)methyl radical that exhibit high thermal stability and electrochemical amphotericity

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Coordination complexes exhibiting room-temperature phosphorescence: Evaluation of their suitability as triplet emitters in organic light emitting diodes

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COORDINATION CHEMISTRY REVIEWS (2006)

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COORDINATION CHEMISTRY REVIEWS (2006)

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[4-(N-carbazolyl)-2,6-dichlorophenyl]bis(2,4,6-trichlorophenyl)methyl radical an efficient red light-emitting paramagnetic molecule

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TETRAHEDRON LETTERS (2006)

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Non-linear effects in the quenching of fluorescent quantum dolts by nitroxyl free radicals

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First observation of NIR 4f-4f luminescence through the energy transfer from the SOMO π* doublet in nitronyl nitroxide radical lanthanide(III) complexes

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Luminescence from lanthanide(3+) ions in solution

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The emitting state of the imino nitroxide radical

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CHEMICAL PHYSICS LETTERS (2005)

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Designing tridentate ligands for ruthenium(II) complexes with prolonged room temperature luminescence lifetimes

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Cerium phosphate nanotubes: Synthesis, valence state, and optical properties

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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2005)

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Dual fluorophore-nitronyl probe for investigation of superoxide dynamics and antioxidant status of biological systems

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Tuning the fluorescence of 1-imino nitroxide pyrene with two chemical inputs: mimicking the performance of an AND gate

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White organic light-emitting devices for solid-state lighting

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Bond dissociation energies for radical dimers derived from highly stabilized carbon-centered radicals

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ORGANIC LETTERS (2004)

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Unusual enlargment of magnetic interactions in the lowest excited states of nitroxide radical chromium(III) complexes as revealed by magnetic circular dichroism and luminescence

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Captodative modification in polymer science

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PROGRESS IN POLYMER SCIENCE (2003)

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Solid-state absorption and luminescence spectroscopy of nitronyl nitroxide radicals

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NEW JOURNAL OF CHEMISTRY (2003)

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Investigations of the heavy atom effect occurring in bianthryl and 10,10 '-dibromobianthryl. Fluorescence, cyclovoltamperometric and actinometric studies

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Synthesis, structures, and magnetic and optical properties of a series of europium(III) and gadolinium(III) complexes with chelating nitronyl and imino nitroxide free radicals

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Optical metal-to-ligand charge transfer in tris(pyrazine-2-carboxylato)cerium(III) - Absorption and emission

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Synthesis, spectroscopic and magnetic properties of lanthanide(III) complexes with a chelated imino nitroxide radical

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Nearly 100% internal phosphorescence efficiency in an organic light-emitting device

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Relationship between electron spin polarization, electron exchange interaction, and lifetime: The excited multiplet states of phthalocyaninatosilicon covalently linked to one nitroxide radical

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A fluorescent probe for monitoring nitric oxide production using a novel detection concept

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ANALYST (2001)

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Ligand-centered near-infrared luminescence from lanthanide complexes with chelating nitronyl nitroxide free radicals

C Lescop et al.

INORGANIC CHEMISTRY (2000)

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Review Chemistry, Inorganic & Nuclear

Luminescent sensor molecules based on coordinated metals: a review of recent developments

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COORDINATION CHEMISTRY REVIEWS (2000)

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