Violet-blue- or pure-blue-emitting triphenylamine derivatives: synthesis and properties

2013 ◽  
Vol 91 (11) ◽  
pp. 1043-1047
Author(s):  
Zhi-Ping Wu ◽  
Gui-Jun Liu ◽  
Cai-Cai Zhu ◽  
Zhi-Mei Li ◽  
Xi-Cun Gao ◽  
...  
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Fluorescence Spectra ◽  
Cross Coupling ◽  
Quantum Yields ◽  
Coupling Reactions ◽  
Visible Absorption ◽  
Fluorescence Quantum Yields ◽  
Cross Coupling Reactions ◽  
Deep Blue ◽  
High Fluorescence

We report the synthesis and optoelectronic properties of a series of nine triphenylamine derivatives. They were synthesized by Suzuki cross-coupling reactions and characterized by elemental analysis, nuclear magnetic resonance, ultraviolet visible absorption spectra, fluorescence spectra, and cyclic voltammetry. All compounds exhibit reversibly electrochemical behavior. In solid state, compounds 5 and 9 emit near violet blue and compounds 1, 2, 4, 6, 7, and 8 emit deep blue or pure blue and compound 3 emits green. Of all of these compounds, compounds 1, 3, 4, and 8 exhibit high fluorescence quantum yields (44%–68%) with the best coplanarity. Compared with them, compounds 5 and 9 have the lowest fluorescence quantum yields due to the least coplanarity. With the similarity in structure with those reported in literature, these compounds can be potentially useful for blue-emitting, host, and up-converting materials.

Regioselective Oxidative Cross-Coupling Reaction: Synthesis of Imidazo[1,2-a]pyridine Fluorophores

Synthesis ◽  
2021 ◽  
Author(s):  
Xianglong Chu ◽  
Yadi Niu ◽  
Chen Ma ◽  
Xiaodong Wang ◽  
Yunliang Lin ◽  
...  
Keyword(s):  
Photophysical Properties ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Quantum Yields ◽  
Fluorescence Quantum Yields ◽  
Cross Coupling Reaction ◽  
Color Tunable ◽  
Palladium Catalyzed ◽  
Structure Relationship ◽  
High Fluorescence

AbstractA rapid access to a series of N-heteroarene fluorophores has been developed on the basis of the palladium-catalyzed direct oxidative C–H/C–H coupling of imidazo[1,2-a]pyridines with thiophenes/furans. The photophysical properties–structure relationship was systematically investigated. The resulting N-heteroarene fluorophores present color-tunable emissions (λem: 431–507 nm in CH2Cl2) and high fluorescence quantum yields (up to 91% in CH2Cl2).

scholarly journals Efficient Synthesis of Novel 1,3,4-Oxadiazoles Bearing a 4-N,N-Dimethylaminoquinazoline Scaffold via Palladium-Catalyzed Suzuki Cross-Coupling Reactions

Molecules ◽  
2020 ◽  
Vol 25 (21) ◽  
pp. 5150
Author(s):  
Barbara Wołek ◽  
Mateusz Werłos ◽  
Magdalena Komander ◽  
Agnieszka Kudelko
Keyword(s):  
Phase Transfer ◽  
Tetrabutylammonium Bromide ◽  
Fluorescence Emission ◽  
Cross Coupling ◽  
Solvent System ◽  
Quantum Yields ◽  
Coupling Reactions ◽  
Two Phase ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

Two series of novel (symmetrical and unsymmetrical) quinazolinylphenyl-1,3,4-oxadiazole derivatives were synthesized using palladium-catalyzed Suzuki cross-coupling reactions. The presented synthetic methodology is based on the use of bromine-substituted 2-phenyl-4-N,N-dimethylaminoquinazolines and either a boronic acid pinacol ester or a diboronic acid bis(pinacol) ester of 2,5-diphenyl-1,3,4-oxadiazole. The reactions are conducted in a two-phase solvent system in the presence of catalytic amounts of [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II), sodium carbonate, and tetrabutylammonium bromide, which plays the role of a phase-transfer catalyst. The luminescence properties of the obtained compounds are discussed in the context of applying these compounds in optoelectronics. Specifically, two highly-conjugated final products: N,N-dimethyl-2-phenyl-6-(4-(5-phenyl-1,3,4-oxadiazol-2-yl)phenyl)quinazolin-4-amine (8f) and 6,6′-(4,4′-(1,3,4-oxadiazole-2,5-diyl)bis(4,1-phenylene))bis(N,N-dimethylquinazolin-4-amine (9f), which contain a 1,3,4-oxadiazole moiety connected to a quinazoline ring by a 1,4-phenylene linker at the 6 position, exhibit strong fluorescence emission and high quantum yields.

Luminescent tetraphenylethene-substituted silanes

2010 ◽  
Vol 82 (4) ◽  
pp. 863-870 ◽  
Author(s):  
Zujin Zhao ◽  
Shuming Chen ◽  
Jacky W. Y. Lam ◽  
Carrie Y. K. Chan ◽  
Cathy K. W. Jim ◽  
...  
Keyword(s):  
Thin Films ◽  
Thermal Stability ◽  
Weight Loss ◽  
High Thermal Stability ◽  
Quantum Yields ◽  
Maximum Luminance ◽  
Amorphous Films ◽  
Fluorescence Quantum Yields ◽  
Deep Blue ◽  
High Fluorescence

Tetraphenylethene (TPE)-substitued silanes [(Ph4C=C)mSi(Ph)n, m = 3–1, n = 3–1] are designed and synthesized, and their optical, thermal, and electrochemical properties are studied. Whereas they are nonluminescent in solutions, they become highly emissive when aggregated in poor solvents (such as water) or fabricated into thin films, demonstrating a novel phenomenon of aggregation-induced emission (AIE). Their amorphous films exhibit high fluorescence quantum yields (54.6–63.7 %). They enjoy high thermal stability with 5 % weight loss occurring at 320–420 °C. Multilayer electroluminescence (EL) devices (ITO/NPB/emitter/TPBi/LiF/Al) utilizing the silanes as emitting layers are fabricated, which give deep blue EL with maximum luminance and external quantum efficiency of 5672 cd/m2, and 1.6 %, respectively.

scholarly journals Mixed-Halide Triphenyl Methyl Radicals for Site-Selective Functionalization and Polymerization

2021 ◽  
Author(s):  
Lisa Chen ◽  
Mona Arnold ◽  
Rémi Blinder ◽  
Fedor Jelezko ◽  
Alexander Kuehne
Keyword(s):  
Cross Coupling ◽  
Open Shell ◽  
Quantum Yields ◽  
Coupling Reactions ◽  
Methyl Radicals ◽  
Cross Coupling Reactions ◽  
Donor Acceptor ◽  
Metal Catalyzed ◽  
Derivatives Of ◽  
Acceptor Molecules

<p>Derivatives of the stable, luminescent tris-2,4,6-trichlorophenylmethyl (TTM) radical exhibit unique doublet spin properties that are of interest for applications in optoelectronics, spintronics, and energy storage. However, the synthesis and variety of TTM-type donor-acceptor molecules with high quantum yields are limited by the symmetric chloride decoration and poor reactivity of chlorides in metal-catalyzed C-C cross-coupling reactions. Therefore, only few donor-acceptor molecules have been successfully coupled to the TTM radical motif. Here, we present a synthetic pathway to obtain mixed-halide derivatives of TTM, partly carrying bromo- instead of chloro-substituents, leading to improved reactivity and enabling site-specific cross-coupling reactions. These highly stable mixed-halide triphenyl methyl radicals represent a powerful tool to obtain complex, and so far inaccessible open-shell small molecules, as well as polymers.</p>

scholarly journals Mixed-Halide Triphenyl Methyl Radicals for Site-Selective Functionalization and Polymerization

2021 ◽  
Author(s):  
Lisa Chen ◽  
Mona Arnold ◽  
Rémi Blinder ◽  
Fedor Jelezko ◽  
Alexander Kuehne
Keyword(s):  
Cross Coupling ◽  
Open Shell ◽  
Quantum Yields ◽  
Coupling Reactions ◽  
Methyl Radicals ◽  
Cross Coupling Reactions ◽  
Donor Acceptor ◽  
Metal Catalyzed ◽  
Derivatives Of ◽  
Acceptor Molecules

<p>Derivatives of the stable, luminescent tris-2,4,6-trichlorophenylmethyl (TTM) radical exhibit unique doublet spin properties that are of interest for applications in optoelectronics, spintronics, and energy storage. However, the synthesis and variety of TTM-type donor-acceptor molecules with high quantum yields are limited by the symmetric chloride decoration and poor reactivity of chlorides in metal-catalyzed C-C cross-coupling reactions. Therefore, only few donor-acceptor molecules have been successfully coupled to the TTM radical motif. Here, we present a synthetic pathway to obtain mixed-halide derivatives of TTM, partly carrying bromo- instead of chloro-substituents, leading to improved reactivity and enabling site-specific cross-coupling reactions. These highly stable mixed-halide triphenyl methyl radicals represent a powerful tool to obtain complex, and so far inaccessible open-shell small molecules, as well as polymers.</p>

Dual Nickel/Palladium-Catalyzed Reductive Cross-Coupling Reactions Between Two Phenol Derivatives

2020 ◽  
Author(s):  
Baojian Xiong ◽  
Yue Li ◽  
Yin Wei ◽  
Søren Kramer ◽  
Zhong Lian
Keyword(s):  
Functional Group ◽  
Low Cost ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Phenol Derivatives ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
One Step ◽  
Aryl Tosylates ◽  
Low Sensitivity

Cross-coupling between substrates that can be easily derived from phenols is highly attractive due to the abundance and low cost of phenols. Here, we report a dual nickel/palladium-catalyzed reductive cross-coupling between aryl tosylates and aryl triflates; both substrates can be accessed in just one step from readily available phenols. The reaction has a broad functional group tolerance and substrate scope (>60 examples). Furthermore, it displays low sensitivity to steric effects demonstrated by the synthesis of a 2,2’disubstituted biaryl and a fully substituted aryl product. The widespread presence of phenols in natural products and pharmaceuticals allow for straightforward late-stage functionalization, illustrated with examples such as Ezetimibe and tyrosine. NMR spectroscopy and DFT calculations indicate that the nickel catalyst is responsible for activating the aryl triflate, while the palladium catalyst preferentially reacts with the aryl tosylate.

An Iron-Based Catalyst Enables The Enantioconvergent Synthesis of Chiral 1,1-Diarylalkanes Through a Suzuki-Miyaura Cross-Coupling Reaction

2020 ◽  
Author(s):  
Chet Tyrol ◽  
Nang Yone ◽  
Connor Gallin ◽  
Jeffery Byers
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Radical Intermediates ◽  
Cross Coupling Reactions ◽  
Cross Coupling Reaction ◽  
Boronic Esters ◽  
Carbon Centered Radical ◽  
Iron Based ◽  
High Yields

By using an iron-based catalyst, access to enantioenriched 1,1-diarylakanes was enabled through an enantioselective Suzuki-Miyaura crosscoupling reaction. The combination of a chiral cyanobis(oxazoline) ligand framework and 1,3,5-trimethoxybenzene additive were essential to afford high yields and enantioselectivities in cross-coupling reactions between unactivated aryl boronic esters and a variety of benzylic chlorides, including challenging ortho-substituted benzylic chloride substrates. Mechanistic investigations implicate a stereoconvergent pathway involving carbon-centered radical intermediates.

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