The Construction of H-shaped Fluorescent Materials Based on Building Blocks Consisting of Triphenylamine and Fluorene

Zhang, Cheng; Zhang, Yu Jian; Xiang, Wenqin; Hu, Bin; Ouyang, Mi; Xu, Ying; Ma, Chao

doi:10.1246/cl.2010.520

Cited by 10 publications

(5 citation statements)

References 17 publications

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“…The mixture was heated to reflux for 10 h. After the reaction mixture was cooled to room temperature, it was extracted with chloroform (CHCl 3 ). The product was purified by column chromatography (EA/Hexane = 1/5) to obtain 3 (2.1 g, 71% General procedure for synthesis of compound 4 [30]: compound 3 (2.28 g, 4.6mmol), CF 3 SO 3 H (0.72 mL, 8.0 mmol), MTPA (0.52 g, 2.0 mmol) reacted at 75 °C for 3 h, and then stirred at room temperature. The resulting solution was poured into methanol, followed by washing with water and filtration to afford the crude product which was further purified by column chromatography (CH 2 Cl 2 /hexane = 1/2) to get 4 (2.18 g, 90% General procedure for the Pd-catalyzed amination of 4 with diarylamines to get compounds 5a-5c [32]: compound 4 (0.61 g, 0.5 mmol), diarylamines (4,4-dimethy-diphenylamine, diphenylamine N-Phenyl-1-naphthylamine (2.0 mmol) ), and sodium tert-butoxide (0.38 g, 4 mmol) were mixed in a flask.…”

Section: Methodsmentioning

confidence: 99%

“…On one hand, high solubility and excellent thermal stability were obtained by the introduction of aromatic imide (N-phthalimide) [23] acted as the electron-acceptor; On the other hand, the 2-donor-7-acceptor-9-fluorenone and the MTPA moieties were connected through sp3-hybridized C-9 carbon atom [24], which not only hinder close packing and crystallization, but also lead to pronounced morphological stability of amorphous materials. The existence of MTPA group could improve the hole injection and solubility of the compounds [25][26][27][28][29][30].…”

Section: Introductionmentioning

confidence: 99%

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Studies on Donor-Acceptor Substituted with Triphenylamine-Core Fluorescent Derivatives

Zhou

et al. 2011

AMR

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A series of donor-acceptor (D-A) substituted with triphenylamine-core fluorescent derivatives have been synthesized via nucleophilic addition of Grignard reagent to 2,7-dibromo-9-fluorenone, CF3SO3H-promoted Friedel-Crafts reaction, Ullmann coupling reaction, and Pd-catalyzed Suzuki cross-coupling reaction in turn. Aromatic imide (N-phthalimide) group was firstly introduced as electron acceptor in the donor-π-acceptor (D-π-A) opto-electronic materials. Hole-injection capability of the fluorene derivatives were promoted by introducing 4-methyl-triphenylamine (MTPA) group at the 9-position. All these compounds present excellent solubility and thermal stability (with glass transition temperature of 191-279 °C), thermo gravimetric analysis (TGA) indicated that 5% or 10% weight losses occurred at about 415-463 °C or 427-498 °C respectively. The relationship of the solvent polarity or the conjugation length of the D-A structure with the luminescent properties has been studied by the UV-vis spectra and the fluorescent spectra. The CV data revealed that these fluorescent derivatives are possessed low-lying HOMO energy levels ranging from -5.19 to -5.37 eV and are exhibited strong blue-green luminance around 448-546 nm.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Studies on Donor-Acceptor Substituted with Triphenylamine-Core Fluorescent Derivatives

Zhou

et al. 2011

AMR

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“…4-甲酰基苯硼酸, 9,9-二甲基-2-芴硼酸, 2-溴芴酮, 2,7-二溴芴酮 , 三氟甲烷磺酸 , 四 ( 三苯基膦 ) 钯 [Pd(PPh 3 ) 4 ], 四丁基溴化铵等试剂购于阿拉丁. 2-溴-9-(4'-甲基苯)-9-芴醇与 2,7-二溴-9-(4'-甲基苯)-9-芴醇根据文献 [27]合成.…”

Section: 实验部分unclassified

Synthesis and Properties of 9,9'-Diarylspriofluorene with Substituted Group at 2,7-Position of Fluorene

Ouyang¹,

Zhang²,

Xiang³

et al. 2012

Chin. J. Org. Chem.

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A series of novel 2-/2,7-(di)arylfluorene building-blocks were synthesized and utilized to prepare novel organic blue-emitting oligomers via Suzuki reaction and Friedel-Crafts reaction. The desired oligomers contained the 4-methyltriphenylamine core and fluorene derivatives peripheries. Their structures were confirmed by NMR and MS techniques and elemental analysis. The maximum photoluminescence (PL) emission wavelengths of the compounds ranged from 442 to 466 nm. Cyclic voltammetry (CV) showed that the highest occupied molecular orbital (HOMO) energy level of the compounds was located between-5.15 and-5.19 eV. The results of differential scanning calorimeter (DSC) and thermogravimetric (TG) indicated that these materials had excellent thermal stability with glass transition temperature of higher than 166 ℃ and thermal-decomposition temperature over 398 ℃.

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“…Another is the difficulty of purification of the polymer material. The oligomers with star-shaped molecules structure, avoiding the above intractable issue, are being widely used in optoelectronic materials [5].…”

Section: Introductionmentioning

confidence: 99%

New Usage for Cyclotrimerization Reaction: A Facile Synthesis of 1,3,5-Triazine Derivatives

Ouyang

Zhang

et al. 2012

KEM

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Series of star-shaped molecules based on 1,3,5-triazine core have been synthesized via CF3SO3H-mediated cyclotrimerization reaction, and then characterized by 1H-NMR, 13C-NMR, MALDI-TOF-MS, and elemental analysis. The effects of different factors, such as the steric hindrance and electronegativity on the reaction efficiency, are systematically studied. The results indicate that the steric hindrance plays an important role in the reaction, while electronegativity has little impact on this reaction. In addition, the bridges including ethylene group and carbon atom between 1,3,5-triazine core and peripherals are firstly studied in this work, which expands the application of CF3SO3H-mediated cyclotrimerization reaction. Moreover, we have successfully broadened the cyclotrimerization reaction to the preparation of 1,3,5-triazine derivatives with different substituents as the peripheral, which is promising for preparation of single-layer multi-functional optoelectronic materials.

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The Construction of H-shaped Fluorescent Materials Based on Building Blocks Consisting of Triphenylamine and Fluorene

Cited by 10 publications

References 17 publications

Studies on Donor-Acceptor Substituted with Triphenylamine-Core Fluorescent Derivatives

Studies on Donor-Acceptor Substituted with Triphenylamine-Core Fluorescent Derivatives

Synthesis and Properties of 9,9'-Diarylspriofluorene with Substituted Group at 2,7-Position of Fluorene

New Usage for Cyclotrimerization Reaction: A Facile Synthesis of 1,3,5-Triazine Derivatives

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