Tetrahedral silicon-centered imidazolyl derivatives: Promising candidates for OLEDs and fluorescence response of Ag (I) ion

Wang, Dengxu; Niu, Yuzhong; Wang, Yike; Han, Jianjun; Feng, Shengyu

doi:10.1016/j.jorganchem.2010.06.026

Cited by 30 publications

(23 citation statements)

References 47 publications

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“…2,2 0 ,7,7 0 -Tetraethynyl-9,9 0 -spirobiuorene (TESF), 24 tetrakis(4bromophenyl)silane (p-Si) 25 and tetrakis(3-bromophenyl)silane (m-Si) 26 were synthesized by the previous reports. 2,2 0 ,7,7 0 -Tetraethynyl-9,9 0 -spirobiuorene (TESF), 24 tetrakis(4bromophenyl)silane (p-Si) 25 and tetrakis(3-bromophenyl)silane (m-Si) 26 were synthesized by the previous reports.…”

Section: Methodsmentioning

confidence: 99%

Porous organic polymers derived from tetrahedral silicon-centered monomers and a stereocontorted spirobifluorene-based precursor: synthesis, porosity and carbon dioxide sorption

Yang

2015

RSC Adv.

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Sonogashira-Hagihara coupling reactions of tetrahedral silicon-centered monomers, i.e., tetrakis(4bromophenyl)silane (p-Si) and tetrakis(3-bromophenyl)silane (m-Si), and stereocontorted 2,2 0 ,7,7 0tetraethynyl-9,9 0 -spirobifluorene (TESF) result in two novel porous organic polymers, POP-1 and POP-2.Compared with other porous polymers, these materials show high thermal stability and comparable specific surface areas with Brunauer-Emmer-Teller surface areas of up to 983 m 2 g À1 , and total pore volumes of up to 0.81 cm 3 g À1 (POP-1). The N 2 isotherm analysis reveals that their porosities could be tuned by changing the structure geometry of the silicon-centered monomers. Further porosity comparison with other porous polymers indicates that the introduction of silicon-centered units in the porous networks could increase the porosity and copolymerization, i.e., changing the second monomer, is an efficient strategy to tune the porosity of the final materials. For applications, the resulting materials show moderate carbon dioxide uptakes of up to 1.92 mmol g À1 (8.45 wt%) at 273 K and 1.03 bar, and 1.12 mmol g À1 (4.93 wt%) at 298 K and 1.01 bar (POP-1), and also a comparably high binding ability with CO 2 with an isostreic heat of 26.8 kJ mol À1 (POP-1). Moreover, the materials exhibited moderate selectivity of CO 2 over other gases, including N 2 , O 2 and CH 4 . These results reveal that these materials could be potentially applied as promising candidates for storing and capturing CO 2 . † Electronic supplementary information (ESI) available: CO 2 adsorption and desorption isotherms of POP-1 and POP-2 at 273 K and 298 K, isosteric heat of CO 2 adsorption of POP-1 and POP-2, Toth model tting of CO 2 , N 2 , CH 4 and O 2 adsorption isotherms of POP-1 and POP-2. See Scheme 1 Synthetic routes of porous organic polymers, POP-1 and POP-2. (i): Pd(PPh 3 )/CuI, DMF/i-Pr 2 NH, 90 C, 72 h. The fragments of these porous polymers are shown as examples. 64164 | RSC Adv., 2015, 5, 64163-64169 This journal is

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Section: Methodsmentioning

confidence: 99%

Porous organic polymers derived from tetrahedral silicon-centered monomers and a stereocontorted spirobifluorene-based precursor: synthesis, porosity and carbon dioxide sorption

Yang

2015

RSC Adv.

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“…The α-duryl-β-diketone ancillary ligand was synthesized using a modified procedure reported by Ramirez and coworkers (Scheme 1). 23 Lithiation of 3-bromo-1,2,4,5-tetra-methylbenzene 24 followed by quenching the aryllithium using anhydrous DMF produced 2,3,5,6-tetramethylbenzaldehyde (1), which after reacting with neat 2,2,2-trimethoxy-4,5-dimethyl-1,3-dioxaphospholene under heating produced a diketone, 4-hydroxy-3-(2,3,5,6-tetramethylphenyl)pent-3-en-2-one (2), in a moderate yield. The aryl functionalized imidazolium salts and 1,2,4-triazolium salts were prepared according to the procedures shown in Scheme 1.…”

Section: Synthesesmentioning

confidence: 99%

“…Tetrahydrofuran (THF) was distilled using sodium and benzophenone as an indicator under nitrogen prior to use. The starting materials, 1-phenyl-1H-imidazole (3), 25 1-phenyl-1-H-1,2,4-triazole (4), 25 (4-bromophenyl)trimethylsilane, 24 1-(4-(tri-methylsilyl)phenyl)-1H-imidazole (5), 24 3-methyl-1-phenyl-1H-imidazol-3-ium iodide (7), 20 4-methyl-1-phenyl-1H-1,2,4-triazol-4-ium iodide (8), 19b and [Pt-Me 2 (SMe 2 )] 2 (bis[dimethyl(μ-dimethylsulfide)platinum(II)]), 27 were synthesized according to literature procedures. Deuterated solvents CDCl 3 and DMSO were purchased from Cambridge Isotopes and used as acquired without further purification.…”

Section: General Informationmentioning

confidence: 99%

Blue phosphorescent N-heterocyclic carbene chelated Pt(ii) complexes with an α-duryl-β-diketonato ancillary ligand

Park

Gong

et al. 2015

Dalton Trans.

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C^C* chelated Pt(II) compounds that contain an N-heterocyclic carbene (NHC) donor have recently attracted great interest as blue or white phosphorescent emitters for organic light-emitting devices (OLEDs). To overcome the tendency for excimer formation in Pt(II) compounds, an α-duryl-β-diketonato ligand was selected as the ancillary ligand for blue phosphorescent C^C* chelated Pt(II) compounds. Using this approach, a series of NHC-based C^C* chelated Pt(II) compounds has been designed and synthesized. The chelate ligands used in the new C^C* chelated Pt(II) compounds include 1-phenylimidazol-2-ylidene in Pt1, 1-phenyl-1,2,4-triazol-5-ylidene in Pt2, p-TMS-1-phenylimidazol-2-ylidene in Pt3, and p-TMS-1-phenyl-1,2,4-triazol-5-ylidene in Pt4. A single-crystal X-ray diffraction analysis revealed that the presence of the α-duryl-β-diketonato ligand in the Pt(II) compounds effectively suppresses the dimer formation in the crystal lattice. Pt1, Pt2, Pt3, and Pt4 display blue phosphorescence at room temperature. The p-TMS substituted complex Pt3 was found to display the most efficient blue phosphorescence at λ(em) = 468 nm with a Φ(PL) of 0.68. Spectroscopic and computational studies established that the blue phosphorescence in the phenyl-imidazolylidene chelated complexes originates mainly from a (3)MLCT state while that in the phenyl-triazolylidene chelated compounds arises from a (3)ILCT state. Electroluminescent devices using Pt1 and Pt3 as the dopant were fabricated which display both monomer and exciplex emission, leading to pure white light electroluminescence with CIE coordinates of (0.32, 0.31).

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“…DMF was dehydrated with CaH 2 at 80 °C for 12 h, distilled under vacuum, and stored with 4 Ǻ molecule sieves prior to use. 1,1′-Divinylferrocene, tetrakis(4-bromophenyl)silane, and tetrakis(4-bromobiphenyl)silane were prepared based on the methods in previous reports [ 37 , 38 , 39 ].…”

Section: Methodsmentioning

confidence: 99%

Porous Organic Polymers Derived from Ferrocene and Tetrahedral Silicon-Centered Monomers for Carbon Dioxide Sorption

Zhao

et al. 2022

Polymers

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Herein, we present two novel ferrocene-containing porous organic polymers, FPOP-1 and FPOP-2, by the Heck reactions of 1,1’-divinylferrocene with two tetrahedral silicon-centered units, i.e., tetrakis(4-bromophenyl)silane and tetrakis(4’-bromo-[1,1’-biphenyl]-4-yl)silane. The resulting materials possess high thermal stability and moderate porosity with the Brunauer–Emmer–Teller (BET) surface areas of 499 m2 g−1 (FPOP-1) and 354 m2 g−1 (FPOP-2) and total pore volumes of 0.43 cm3 g−1 (FPOP-1) and 0.49 cm3 g−1 (FPOP-2). The porosity is comparable to previously reported ferrocene-containing porous polymers. These materials possess comparable CO2 capacities of 1.16 mmol g−1 (5.10 wt%) at 273 K and 1.0 bar, and 0.54 mmol g−1 (2.38 wt%) at 298 K and 1.0 bar (FPOP-1). The found capacities are comparable to, or higher than many porous polymers having similar or higher surface areas. They have high isosteric heats of up to 32.9 kJ mol−1, proving that the affinity between the polymer network and CO2 is high, which can be explained by the presence of ferrocene units in the porous networks. These results indicate that these materials can be promisingly utilized as candidates for the storage or capture of CO2. More ferrocene-containing porous polymers can be designed and synthesized by combining ferrocene units with various aromatic monomers under this strategy and their applications could be explored.

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Tetrahedral silicon-centered imidazolyl derivatives: Promising candidates for OLEDs and fluorescence response of Ag (I) ion

Cited by 30 publications

References 47 publications

Porous organic polymers derived from tetrahedral silicon-centered monomers and a stereocontorted spirobifluorene-based precursor: synthesis, porosity and carbon dioxide sorption

Porous organic polymers derived from tetrahedral silicon-centered monomers and a stereocontorted spirobifluorene-based precursor: synthesis, porosity and carbon dioxide sorption

Blue phosphorescent N-heterocyclic carbene chelated Pt(ii) complexes with an α-duryl-β-diketonato ancillary ligand

Porous Organic Polymers Derived from Ferrocene and Tetrahedral Silicon-Centered Monomers for Carbon Dioxide Sorption

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