Three new carbazole derivatives with high thermal stability as host for efficient green phosphorescent organic-light emitting diodes

Ji, Jun; Li, Pengfei; Tian, Qifeng; Wang, Feng; Wu, Changjiang

doi:10.1016/j.dyepig.2019.107670

Cited by 13 publications

(8 citation statements)

References 24 publications

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“…Meanwhile, the standard conditions were suitable for the coupling of naphthalene boronic acids with SA, and naphthalen‐2‐ylboronic acid performed better than naphthalen‐1‐ylboronic acid ( 3 ay and 3 ax , respectively). Interestingly, (9‐phenyl‐9 H ‐carbazol‐3‐yl)boronic acid serving as an intermediate of OLED materials, [18] could be used to generate the desired product 3 az in moderate yield.…”

Section: Figurementioning

confidence: 99%

“…It was worth note that the reactionh ighly depended on the ligand. Thus, the yield of 3aa dropped significantly using other typical nitrogen-containing ligandso rw ithout the ligand (Table 1, entries [14][15][16][17][18][19]. In addition, the omission of TEMPO (2,2,6,6-tetra-methylpiperidine-N-oxyl) andt he change of TEMPO equivalent resultedi nl ower yields of 3aa (Table 1, entries 20-23).…”

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confidence: 99%

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Aerobic Copper‐Catalyzed Salicylaldehydic C_formyl−H Arylations with Arylboronic Acids

Lin

Lang

Jiang

et al. 2021

Chemistry A European J

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We report a challenging copper‐catalyzed Cformyl−H arylation of salicylaldehydes with arylboronic acids that involves unique salicylaldehydic copper species that differ from reported salicylaldehydic rhodacycles and palladacycles. This protocol has high chemoselectivity for the Cformyl−H bond compared to the phenolic O−H bond involving copper catalysis under high reaction temperatures. This approach is compatible with a wide range of salicylaldehyde and arylboronic acid substrates, including estrone and carbazole derivatives, which leads to the corresponding arylation products. Mechanistic studies show that the 2‐hydroxy group of the salicylaldehyde substrate triggers the formation of salicylaldehydic copper complexes through a CuI/CuII/CuIII catalytic cycle.

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Section: Figurementioning

confidence: 99%

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confidence: 99%

Aerobic Copper‐Catalyzed Salicylaldehydic C_formyl−H Arylations with Arylboronic Acids

Lin

Lang

Jiang

et al. 2021

Chemistry A European J

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“…Due to their good solubility, they are widely used in production of organic photoconductors and photorefractive materials in OLEDs [ 23 ]. Carbazole is characterized by high structural rigidity and high thermal stability [ 24 ]. In addition, it has good hole transporting properties [ 25 , 26 , 27 ], and due to its intense blue luminescence, it is used as a building block for the production of various optoelectronic devices [ 28 , 29 , 30 ].…”

Section: Introductionmentioning

confidence: 99%

Effect of the Chloro-Substitution on Electrochemical and Optical Properties of New Carbazole Dyes

et al. 2021

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Carbazole derivatives are the structural key of many biologically active substances, including naturally occurring and synthetic ones. Three novel (E)-2-(2-(4-9H-carbazol-9-yl)benzylidene)hydrazinyl)triazole dyes were synthesized with different numbers of chlorine substituents attached at different locations. The presented research has shown the influence of the number and position of attachment of chlorine substituents on electrochemical, optical, nonlinear, and biological properties. The study also included the analysis of the use of the presented derivatives as potential fluorescent probes for in vivo and in vitro tests. Quantum-chemical calculations complement the conducted experiments.

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“…One of the most effective techniques to make it is the modification of metal-free organic sensitizers, mainly by varying the chemical groups in the donor moiety, π-bridge and anchorage moiety [25]. In relation to donor moiety, carbazole has been used, for its donor capacity [26][27][28][29], in the development of diodes [30], organic field-effect transistors [31], solar cells [32], sensors [33] and OLEDs [34]. Carbazole has good electron delocalization [35] and it is planar with an electron-rich aromatic heterocycle [36].…”

Section: Introductionmentioning

confidence: 99%

Theoretical Study of the Effect of π-Bridge on Optical and Electronic Properties of Carbazole-Based Sensitizers for DSSCs

et al. 2020

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Eight novel metal-free organic sensitizers were proposed for dye-sensitized solar cells (DSSCs), theoretically calculated and studied via density functional theory with D-π-A structure. These proposals were formed to study the effect of novel π-bridges, using carbazole as the donor group and cyanoacrylic acid as the anchorage group. Through the M06/6-31G(d) level of theory, ground state geometry optimization, vibrational frequencies, the highest occupied molecular orbital, the lowest unoccupied molecular orbital, and their energy levels were calculated. Further, chemical reactivity parameters were obtained and analyzed, such as chemical hardness (η), electrophilicity index (ω), electroaccepting power (ω+) and electrodonating power (ω-). Free energy of electron injection (ΔGinj) and light-harvesting efficiency (LHE) also were calculated and discussed. On the other hand, absorption wavelengths, oscillator strengths, and electron transitions were calculated through time-dependent density functional theory with the M06-2X/6-31G(d) level of theory. In conclusion, the inclusion of thiophene groups and the Si heteroatom in the π-bridge improved charge transfer, chemical stability, and other optoelectronic properties of carbazole-based dyes.

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Three new carbazole derivatives with high thermal stability as host for efficient green phosphorescent organic-light emitting diodes

Cited by 13 publications

References 24 publications

Aerobic Copper‐Catalyzed Salicylaldehydic C_formyl−H Arylations with Arylboronic Acids

Aerobic Copper‐Catalyzed Salicylaldehydic C_formyl−H Arylations with Arylboronic Acids

Effect of the Chloro-Substitution on Electrochemical and Optical Properties of New Carbazole Dyes

Theoretical Study of the Effect of π-Bridge on Optical and Electronic Properties of Carbazole-Based Sensitizers for DSSCs

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Three new carbazole derivatives with high thermal stability as host for efficient green phosphorescent organic-light emitting diodes

Cited by 13 publications

References 24 publications

Aerobic Copper‐Catalyzed Salicylaldehydic Cformyl−H Arylations with Arylboronic Acids

Aerobic Copper‐Catalyzed Salicylaldehydic Cformyl−H Arylations with Arylboronic Acids

Effect of the Chloro-Substitution on Electrochemical and Optical Properties of New Carbazole Dyes

Theoretical Study of the Effect of π-Bridge on Optical and Electronic Properties of Carbazole-Based Sensitizers for DSSCs

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Aerobic Copper‐Catalyzed Salicylaldehydic C_formyl−H Arylations with Arylboronic Acids

Aerobic Copper‐Catalyzed Salicylaldehydic C_formyl−H Arylations with Arylboronic Acids