479-33-4Relevant articles and documents
1,1-Cycloaddition of oxalyl dichloride with dialkenylmetal compounds: Formation of cyclopentadienone derivatives by the reaction of 1,4,-dilithio-1,3-dienes or zirconacyclopentadienes with oxalyl chloride in the presence of CuCl
Chen, Chao,Xi, Chanjuan,Jiang, Yanfeng,Hong, Xiaoyin
, p. 8024 - 8025 (2005)
1,4-Dilithio-1,3-dienes or zirconacyclopentadienes reacted with oxalyl chloride in the presence of CuCl in a 1,1-cycloaddition manner to give cyclopentadienone derivatives in high yields along with the elimination of CO. Copyright
Hexaphenylbenzene based push-pull fluorophores displaying intriguing polarity-dependent fluorescence behavior, AIE(E) characteristics and mega-large Stokes shifts
Cao, Xiaohui,Li, Si,Li, Yan,Xu, Bo,Yang, Qiusheng,Yin, Guohui,Zhang, Yuecheng,Zhao, Jiquan
, (2021/12/10)
In general, most donor-acceptor type fluorophores are known to exhibit solvatochromic behavior and obey the energy gap law simultaneously, showing decreased emission with increasing solvent polarity. In this work, four push-pull hexaphenylbenzene (HPB) derivatives 1–4 have been designed and synthesized by introducing methoxy and dicyanovinyl groups at the tip of aromatic blades, which behave exceptionally polarity-dependent emission properties. In the low to medium solvent polarity region, the four dipole fluorophores display gradually enhanced fluorescence, whereas a reverse trend is observed with the further increase of solvent polarity. Meanwhile, 1–4 are found to exhibit the strongest emission at the same wavelength remarkably, which appears to be somewhat relevant to the intrinsic characteristics of dicyanovinyl-phenyl acceptor. A mechanistic scheme containing a conical intersection (CI) has been proposed to explain the up-down emission of 1–4 with increasing solvent polarity. Large Stokes shifts (up to 254 nm) and AIE(E) characteristics have also been achieved in these four HPB fluorophores. Besides, fluorophores 1–4 exhibit obvious freezing-solution induced chromism (FSIC), demonstrating an enhancement of the local matrix polarity upon freezing solutions.
Tetraaryl Cyclopentadienones: Experimental and Theoretical Insights into Negative Solvatochromism and Electrochemistry
Meitinger, Nicolas,Mengele, Alexander K.,Witas, Kamil,Kupfer, Stephan,Rau, Sven,Nauroozi, Djawed
, p. 6555 - 6562 (2020/10/02)
The synthesis of a series of tetraaryl cyclopentadienones comprising different substitution patterns is reported. Their photophysical and electrochemical properties are investigated by UV/Vis spectroscopy and cyclic voltammetry as well as by supporting quantum chemical simulations and reveal a distinct effect of substituents on the redox behavior of the molecules as well as the absorption properties of this class of compounds. While electrochemical data display a shift in reduction potential of up to 200 mV between the differently substituted cyclopentadienones, their photophysical investigations in differently polar solvents suggest a negative solvatochromic effect, although protic solvents induce a bathochromic shift. Crystal structure analyses of some derivatives confirm similarity with related cyclopentadienones while providing insight into intermolecular C–H···O and C–H···π interactions in the solid state.
A silicon-cored tetraphenyl benzene derivative with aggregation-induced emission enhancement as a fluorescent probe for nitroaromatic compounds detection
Liang, Yan
, p. 395 - 403 (2019/03/27)
Two benzene with multiple contiguous phenyl substituent derivatives, namely, 1, 2, 3, 4-tetraphenyl benzene (TPB) and bis(1,2,3,4-tetraphenylbenzene-yl) diphenylsilane (TPB-Si), were synthesized by the Knoevenagel/Diels–Alder method. TPB and TPB-Si both showed aggregation-induced emission enhancement (AIEE) properties in tetrahydrofuran/water mixtures. The fluorescence-quenching behaviors of the two compounds with different nitroaromatic compounds were also investigated. TPB and TPB-Si both showed low detection limit, high sensitivity, and high quenching efficiency in detecting nitroaromatic compounds. Furthermore, the two compounds in aggregate state exhibited much better detection abilities than in THF solution. And TPB-Si exhibited better detection ability than TPB in both solution and aggregate state. The reason could be attributed to the special tetrahedral molecular structure of TPB-Si, which was demonstrated by theoretical calculations and crystal structures. Moreover, TPB-Si in solid film also exhibited excellent detection performance to nitroaromatic explosive vapor. This work may serve as a basis for designing new organic materials with great efficiency and sensitivity in fluorescence detection.
Highly Stable, Low Gas Crossover, Proton-Conducting Phenylated Polyphenylenes
Adamski, Michael,Skalski, Thomas J. G.,Britton, Benjamin,Peckham, Timothy J.,Metzler, Lukas,Holdcroft, Steven
supporting information, p. 9058 - 9061 (2017/07/24)
Two classes of novel sulfonated phenylated polyphenylene ionomers are investigated as polyaromatic-based proton exchange membranes. Both types of ionomer possess high ion exchange capacities yet are insoluble in water at elevated temperatures. They exhibit high proton conductivity under both fully hydrated conditions and reduced relative humidity, and are markedly resilient to free radical attack. Fuel cells constructed with membrane-electrode assemblies containing each ionomer membrane yield high in situ proton conductivity and peak power densities that are greater than obtained using Nafion reference membranes. In situ chemical stability accelerated stress tests reveal that this class of the polyaromatic membranes allow significantly lower gas crossover and lower rates of degradation than Nafion benchmark systems. These results point to a promising future for molecularly designed sulfonated phenylated polyphenylenes as proton-conducting media in electrochemical technologies.
A soluble conjugated porous organic polymer: efficient white light emission in solution, nanoparticles, gel and transparent thin film
Pallavi, Pragyan,Bandyopadhyay, Sujoy,Louis, Jesna,Deshmukh, Arundhati,Patra, Abhijit
supporting information, p. 1257 - 1260 (2017/02/05)
A tetraphenylcyclopentadiene based multifunctional, solution processable, fluorescent, ultramicroporous polymer exhibiting high hydrogen uptake was employed for encapsulation of dyes to obtain enhanced white light emission in solution, nanoparticles, gel and transparent thin film. Hybrid nanoparticles showed a quantum yield of 35% with a high color rendering index.
Structurally-Defined, Sulfo-Phenylated, Oligophenylenes and Polyphenylenes
Skalski, Thomas J. G.,Britton, Benjamin,Peckham, Timothy J.,Holdcroft, Steven
supporting information, p. 12223 - 12226 (2015/10/12)
We report the synthesis and molecular characterization of structurally defined, sulfo-phenylated, oligo- and polyphenylenes that incorporate a novel tetra-sulfonic acid bistetracyclone monomer. The utility of this monomer in the [4 + 2] Diels-Alder cycloaddition to produce well-defined, sulfonated oligophenylenes and pre-functionalized polyphenylene homopolymers is demonstrated. Characterization of the oligophenylenes indicates formation of the meta-meta and para-para adducts in a ～ 1:1 ratio. These functionalized monomers and their subsequent coupling provide a route to prepare novel, sterically encumbered, sulfonated polyphenylenes possessing unprecedented structural control.
New pyrimidine derivative and organic light-emitting devices including the same
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Paragraph 0091-0093; 0112-0114, (2020/03/31)
The present invention relates to a novel pyrimidine derivative and an organic light-emitting device including the same on a light-emitting layer. The organic light-emitting device according to the present invention improves light-emitting properties and reduces power consumption by inducing an increase in power efficiency by enhancing driving voltage.
Covalent attachment and release of small molecules from functional polyphenylene dendrimers
Hammer, Brenton A. G.,Baumgarten, Martin,Muellen, Klaus
supporting information, p. 2034 - 2036 (2014/03/21)
Herein, we report the synthesis of 2nd generation PPDs functionalized with free thiol moieties within the scaffold, which were used as anchor points for the covalent attachment of guest species (p-nitrophenol derivatives) through the oxidative formation of disulfide linkages. The disulfide bonds were then cleaved under reductive conditions using dithiothreitol to discharge the molecules.
Emission enhancement and color adjustment of silicon-cored structure in tetraphenyl benzene with aggregation-enhanced emission
Wang, Hua,Liang, Yan,Xie, Huanling,Feng, Linglong,Lu, Haifeng,Feng, Shengyu
supporting information, p. 5601 - 5606 (2014/07/08)
In this paper, we report the synthesis and optical behavior of tetraphenyl benzene and its two derivatives. All the three compounds exhibited aggregation-enhanced emission (AEE) properties at a low concentration. The AEE mechanism was investigated and is due to restricted intramolecular rotation and unique packing structure. Furthermore, this kind of dendritic benzene derivatives exhibited interesting optical properties with increased concentration. Furthermore, we found a new phenomenon that the silicon-cored structure could efficiently enhance emission intensity and adjust the emission colors of dendritic benzene. The phenomenon was called "silicon-cored effect." This effect may give some guidance to the design of new luminescent materials with AIE and AEE properties. This journal is the Partner Organisations 2014.
