- Crystal and molecular structure of benzophenone azine: evidence for an Fe(II) carbene intermediate
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Benzophenone azine crystallizes in the monoclinic space group A2/a (No. 15) with a=16.303(3) Angstroem, b=5.4864(2) Angstroem, c=21.973(5) Angstroem, β=85.52(2)deg, V=1959.4(8) Angstroem3, and Dcalc=1.22 g cm-3 for Z=4.The structure was solved by direct methods and refined against F to a final R value of 0.047.The unit cell contains four molecules of the title compound; the asymmetric unit consists of half a molecule.Despite the high crystallographic symmetry, the two halves of the molecule are not related by a center of symmetry; instead, the molecule adopts C2 symmetry; the molecular C2 axis is coincident with the crystallographic twofold axis.The formation of benzophenone azine from the reaction of the iron-containing Lewis acid complex 5-C5H5)Fe(CO)2(THF)>+ - and diphenyldiazomethane provides strong evidence for an Fe(II) carbene intermediate.KEY WORDS: Azine; azitine; iron(II) carbene; catalyst.
- Saha, Anjan K.,Hossain, M. Mahmun,Grubisha, Desiree S.,Bennett, Dennis W.
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- Coupling of geminal dihalides with disodium tetracarbonyl ferrate: A novel reactivity pattern for Collman's reagent
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The reaction of gem-dihalides with Na2Fe(CO)4 results in the formation of alkenes instead of the iron(O) carbene complexes.
- Warner, Kirstin F.,Rehman, Atiq-Ur,Jha, Salil K.,Schnatter, Wayne F. K.
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- Radical ions of crownophanes derived from tetraphenylethene. Solution structures and ion-pairing phenomena
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Radical anions and radical cations of parent tetraphenylethene (1) and its cyclophane derivatives 2-8 were generated by chemical methods. These paramagnetic species were characterized by their ESR and simultaneously recorded optical spectra. The hyperfine coupling constants were substantiated by ENDOR and their signs by general TRIPLE spectroscopy. The structures of the radical ions were established with the help of quantum chemical calculations. The electron distribution in the phane radical ions is closely related to that found for 1.-/1.+. In the radical anions no specific complexation of alkali-metal counterions, K+ and Li+, by the crown-ether moieties could be observed. When the radical cations were generated by oxidation with Tl(III) trifluoroacetate in 1,1,1,3,3,3-hexafluoropropanol, distinctly different ESR spectra were recorded as with the use of other oxidants. This observation is rationalized by the characteristic solvation properties of 1,1,1,3,3,3-hexafluoropropanol.
- Barbosa, Frederique,Peron, Vincent,Gescheidt, Georg,Fuerstner, Alois
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- Synthesis of wholly aromatic polymers possessing tetra-aryl-substituted vinylene units by palladium-catalyzed three-component coupling polymerization
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The synthesis of novel wholly aromatic poly(arylenevinylene)s containing tetra-aryl-substituted olefin units in the main chain by the three-component coupling polymerization of aryl dihalides, aryl diboronic acids, and acetylene derivatives is described. For instance, a polymer (Mn = 2600, M w/Mn = 1.6) was obtained in a 76% yield by the polymerization of 1,4-diiodobenzene, diphenylacetylene, and 1,4- phenylenediboronic acid in DMF/H2O at 100°C for 24 h in the presence of PdCl2(PhCN)2 (1 mol %) and KHCO3. The obtained polymer is soluble in organic solvents such as CHCl3, THF, and toluene, although it does not have any soft lateral segments. Copyright
- Nakagawa, Kojiro,Tomita, Ikuyoshi
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- Synthesis of highly substituted 1,3-butadienes by palladium-catalyzed arylation of internal alkynes
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Four molecules are coupled together by the single treatment of aryl boronic acids with alkynes in the absence or presence of iodobenzene under palladium catalysis to afford 1,4-diaryl-1,3-butadienes as the major product. Addition of a silver salt as oxidant and/or base effectively enables the selective catalytic production of the π-conjugated compounds.
- Satoh, Tetsuya,Ogino, Shinji,Miura, Masahiro,Nomura, Masakatsu
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- Meso/microporous carbons from conjugated hyper-crosslinked polymers based on tetraphenylethene for high-performance co2 capture and supercapacitor
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In this study, we successfully synthesized two types of meso/microporous carbon materials through the carbonization and potassium hydroxide (KOH) activation for two different kinds of hyper-crosslinked polymers of TPE-CPOP1 and TPE-CPOP2, which were synthesized by using Friedel–Crafts reaction of tetraphenylethene (TPE) monomer with or without cyanuric chloride in the presence of AlCl3 as a catalyst. The resultant porous carbon materials exhibited the high specific area (up to 1100 m2 g?1 ), total pore volume, good thermal stability, and amorphous character based on thermogravimetric (TGA), N2 adsoprtion/desorption, and powder X-ray diffraction (PXRD) analyses. The as-prepared TPE-CPOP1 after thermal treatment at 800?C (TPE-CPOP1-800) displayed excellent CO2 uptake performance (1.74 mmol g?1 at 298 K and 3.19 mmol g?1 at 273 K). Furthermore, this material possesses a high specific capacitance of 453 F g?1 at 5 mV s?1 comparable to others porous carbon materials with excellent columbic efficiencies for 10,000 cycle at 20 A g?1 .
- Ahmed, Mahmoud M. M.,Du, Wei-Ting,Kuo, Shiao-Wei,Mohamed, Mohamed Gamal
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- Synthesis, aggregation-induced emission (AIE) and electroluminescence of carbazole-benzoyl substituted tetraphenylethylene derivatives
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Aggregation-induced emission (AIE) materials offer a solution to obtain high fluorescence efficiencies in solid state which is desirable for optoelectronic devices and display. Here in this work, three new types of D-π-A-π-D AIE luminogens based on carbazole-benzoyl substituted tetraphenylethylene (TPE) derivatives were designed and successfully synthesized. Meanwhile, their photophysical properties as well as electroluminescence (EL) characteristics were studied. These luminogens show good AIE property with high solid-state fluorescence quantum yields. Furthermore, the emission wavelengths for these three luminogens, both in solutions and in solid state, exhibit negligible variation by increasing the number of donor group. All three luminogens show solvatochromism and negative solvatokinetic effect in different solvents. More interesting is that on increasing number of donor groups, their thermal and morphological stability present regular change by increasing the number of carbazole-benzoyl group. The performance of non-doped OLED device based on TPE-3BZ-Cz is superior than the other two luminogens, which has been proved by further electroluminescence evaluation.
- Zhan, Yingying,Yang, Zhiwen,Tan, Jihua,Qiu, Zhipeng,Mao, Yuanyou,He, Jia,Yang, Qingdan,Ji, Shaomin,Cai, Ning,Huo, Yanping
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- Pyrene-containing conjugated organic microporous polymers for photocatalytic hydrogen evolution from water
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Photoactive conjugated microporous polymers (CMPs) are emerging as porous materials capable of mediating the photocatalytic evolution of H2from water. In this study, we synthesized three pyrene-based CMPs (Py-F-CMP, Py-TPA-CMP, Py-TPE-CMP) through Sonogashira-Hagihara cross-couplings of 1,3,6,8-tetraethynylpyrene (Py-T, as a common monomer building block) with 2,7-dibromo-9H-fluorene (F-Br2), tris(4-bromophenyl)amine (TPA-Br3), and 1,1,2,2-tetrakis(4-bromophenyl)ethene (TPE-Br4), respectively, in the presence of Pd(PPh3)4in DMF/Et3N. We then characterized the chemical structures, crystallinities, thermal stabilities, surface morphologies, and porosities of these three new CMPs. Brunauer-Emmett-Teller (BET) analyses and tests of photocatalytic H2production revealed that Py-TPA-CMP displayed the highest BET surface area (454 m2g?1), highest total pore volume (0.28 cm3g?1), highest H2evolution rate (19?200 μmol h?1g?1), and highest apparent quantum yield (15.3%) when compared with those of Py-F-CMP, Py-TPE-CMP, and other organic porous materials.
- Mohamed, Mohamed Gamal,Elsayed, Mohamed Hammad,Elewa, Ahmed M.,EL-Mahdy, Ahmed F. M.,Yang, Cheng-Han,Mohammed, Ahmed A. K.,Chou, Ho-Hsiu,Kuo, Shiao-Wei
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p. 2229 - 2241
(2021/04/09)
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- A Tetradentate Phosphonate Ligand-based Ni-MOF as a Support for Designing High-performance Proton-conducting Materials
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Developing a robust metal-organic framework (MOF) which facilitates proton hopping along the pore channels is very demanding in the context of fabricating an efficient proton-conducting membrane for fuel cells. Herein, we report the synthesis of a novel tetradentate aromatic phosphonate ligand H8L (L=tetraphenylethylene tetraphosphonic acid) based Ni-MOF, whose crystal structure has been solved from single-crystal X-ray diffraction. Ni-MOF [Ni2(H4L)(H2O)9(C2H7SO)(C2H7NCO)] displays a monoclinic crystal structure with a space group of P 21/c, a=11.887 ?, b=34.148 ?, c=11.131 ?, α=γ=90°, β=103.374°, where a nickel-hexahydrate moiety located inside the void space of the framework through several H-bonding interactions. Upon treatment of the Ni-MOF in different pH media as well as solvents, the framework remained unaltered, suggesting the presence of strong H-bonding interactions in the framework. High framework stability of Ni-MOF bearing H-bonding interactions motivated us to explore this metal-organic framework material as proton-conducting medium after external proton doping. Due to the presence of a large number of H-bonding interactions and the presence of water molecules in the framework we have carried out the doping of organic p-toluenesulfonic acid (PTSA) and inorganic sulphuric acid (SA) in this Ni-MOF and observed high proton conductivity of 5.28×10?2 S cm?1 at 90 °C and 98% relative humidity for the SA-doped material. Enhancement of proton conductivity by proton doping under humid conditions suggested a very promising feature of this Ni-MOF.
- Chakraborty, Debabrata,Ghorai, Arijit,Chowdhury, Avik,Banerjee, Susanta,Bhaumik, Asim
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supporting information
p. 1562 - 1569
(2021/05/13)
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- A novel crystalline nanoporous iron phosphonate based metal-organic framework as an efficient anode material for lithium ion batteries
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Metal-organic framework (MOF) materials show extraordinary performances in several frontier applications of energy research due to their well-defined crystalline porous architecture, high specific surface area and the periodicity of the functional groups in their structures. Here, we report a new self-assembled nanoporous iron phosphonate material (H8L-Fe-MOF) with a crystalline architecture. Hydrothermal synthesis was performed by using a novel (ethene-1,1,2,2-tetrayltetrakis(benzene-4,1-diyl))tetraphosphonic acid (TPE-acid, designated as H8L) as the organic linker and the ferric (Fe3+) ion precursor as a metal node. Several instrumental techniques were used for the characterization of this crystalline porous MOF. N2adsorption-desorption analysis revealed the presence of a broad range of pores in nanoscale dimensions, together with a high BET surface area. The MOF crystal structure was resolved through Rietveld refinement from the powder XRD patterns using EXPO2014 and VESTA 3D. The computed unit cell parameters for this monoclinic phase area= 28.211 ?,b= 12.265 ?,c= 10.533 ?,α= 90°,β= 99.295°, andγ= 90° together with a unit cell volume of 3597.33 ?3. FE-SEM image analysis revealed that tiny spherical nanocrystals with dimensions ofca.3-4 nm self-assembled into H8L-Fe-MOF. Elemental mapping and FT-IR spectroscopic data confirmed uniform distribution of iron over the organic tetraphosphonic acid ligand. TG-DTA suggested high thermal stability of H8L-Fe-MOF. In lithium-ion batteries (LIBs), this organic-inorganic hybrid MOF can be used as an anode material. Here the counter cation plays a crucial role in stabilizing the material. Conceptually the robust nature and ordered crystalline framework of this MOF should open a new alternative to existing graphite-based anodes presently used in LIBs. Considering the progressive change in LIBs, which now incorporate solid electrolytes instead of organic carbonate-based liquid electrolytes, for improved safety in this present investigation we used a gel polymer electrolyte membrane to fabricate and characterize the device. This approach provides a better understanding of how the MOF will behave in an actual application. The device performs fairly well in terms of stability in the recycling process and shows a high specific capacity with excellent retention capacity.
- Bhaumik, Asim,Chakraborty, Debabrata,Chandra, Bijan Krishna,Dam, Tapabrata,Ghosh, Aswini,Majee, Adinath,Modak, Arindam,Pant, Kamal K.
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p. 15458 - 15468
(2021/09/07)
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- Stimuli-responsive transmembrane anion transport by AIE-active fluorescent probes
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Anticancer drug resistance implicates multifunctional mechanisms, and hypoxia is one of the key factors in therapeutic resistance. Hypoxia-specific therapy is considered an extremely effective strategy to fight against cancer. The development of small molecule-based synthetic anion transporters has also recently drawn attention for their potential therapeutic applications against several ion-transport-associated diseases, such as cancer and others. Herein, we describe the development of a hypoxia-responsive proanionophore to trigger controlled transport of anions across membranes under pathogenic conditions. Herein, we report the development of tetraphenylethene (TPE)-based anion transporters. The sulfonium-linkedp-nitrobenzyl containing TPE-based proanionophore could be converted into a lipophilic fluorescent Cl?ion carrier in a hypoxic or reductive environment. Stimuli such as nitroreductase (NTR) and glutathione (GSH) mediated regeneration of the TPE-based active Cl?ion transporter also showed aggregation-induced emission (AIE) properties. We hypothesize that such hypoxia and reductive stimuli activatable proanionophores have tremendous potential to fight against channelopathies, including cancer.
- Akhtar, Nasim,Biswas, Oindrila,Manna, Debasis
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supporting information
p. 7446 - 7459
(2021/09/08)
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- Anionic fluorescent probe, preparation method and application thereof
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The invention discloses an anionic fluorescent probe, and a preparation method and an application thereof. The anionic fluorescent probe is prepared by mixing 1-(4-amino) phenyl-1, 2, 2-triphenylethylene with a phenyl isothiocyanate derivative and carrying out a condensation reaction. The fluorescent probe has selectivity on anions and can be used for quantitatively analyzing the recognized anions.
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Paragraph 0032; 0037-0038
(2021/05/01)
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- Method for synthesizing alkyl olefin through coupling of double-bond carbon-hydrogen bond and saturated carbon-hydrogen bond
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The invention discloses a method for synthesizing alkyl olefin through coupling of a double-bond carbon-hydrogen bond and a saturated carbon-hydrogen bond. According to to the method, one-pot reactionis implemented on olefin and sulfoxide in the presence of ferric salt and hydrogen peroxide to generate alkyl olefin; in the method, sulfoxide is simultaneously used as a hydrocarbylation reagent anda solvent of olefin, and a reaction product is alkyl olefin from sulfoxide alkyl coupled with olefin carbon atoms, so that an olefin carbon chain is increased; the reaction conditions are mild, the selectivity is good, the yield is high, and industrial production is facilitated.
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Paragraph 0070-0073; 0098
(2021/02/10)
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- Dibrominated addition and substitution of alkenes catalyzed by Mn2(CO)10
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A practical method for the dibromination of alkenes without using molecular bromine is consistently appealing in organic synthesis. Herein, we report Mn-catalyzed dibrominated addition and substitution of alkenes only with N-bromosuccinimide, producing a variety of synthetically valuable dibrominated compounds in moderate to high yields. This journal is
- Chan, Albert S. C.,Jiang, Yi,Meng, Shanshui,Song, Xianheng,Zhang, Hong,Zou, Yong
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supporting information
p. 13385 - 13388
(2021/12/17)
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- Method for hydrocarbylation synthesis of trisubstituted and tetrasubstituted olefins from non-terminal olefins
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The invention discloses a method for hydrocarbylation synthesis of trisubstituted and tetrasubstituted olefins from non-terminal olefins, wherein the method comprises the steps: carrying out hydrocarbylation reaction on the non-terminal olefins and sulfoxide in the presence of ferric salt and hydrogen peroxide, carrying out one-pot reaction on disubstituted non-terminal olefins to generate the trisubstituted olefins, and carrying out one-pot reaction on the trisubstituted non-terminal olefins to generate the tetrasubstituted olefins. In the method, sulfoxide is simultaneously used as a hydrocarbylation reagent and a solvent of olefins, and one more hydrocarbyl substituent is added to a reaction product compared with a double-bond carbon atom of a reactant, so that an olefin carbon chain isincreased; the reaction conditions are mild, the selectivity is good, the yield is high, and industrial production is facilitated.
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Paragraph 0054-0063; 0088-0090
(2021/02/06)
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- Metathesis of P=C Bonds Catalyzed by N-Heterocyclic Carbenes
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The catalytic metathesis of C=C bonds is a textbook reaction that has no parallel in the widely studied area of multiple bonds involving heavier p-block elements. A high-yielding P=C bond metathesis of phosphaalkenes (ArP=CPh2, Ar=Mes, o-Tol, Ph) has been discovered that is catalyzed by N-heterocyclic carbenes (NHC=Me2IMe, Me2IiPr). The products are cyclic oligomers formally derived from ArP=PAr [i. e. cyclo-(ArP)n; n=3, 4, 5, 6] and Ph2C=CPh2. Preliminary mechanistic studies of this remarkable transformation have established NHC=PAr (Ar=Mes, o-Tol, Ph) as key phosphinidene transfer agents. In addition, novel cyclic intermediates, such as, cyclo-(ArP)2CPh2 and cyclo-(ArP)4CPh2 have also been observed. This work represents a rare application of non-metal-based catalysts for transformations involving main-group elements.
- Han, Zeyu,Gates, Derek P.
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supporting information
p. 14594 - 14599
(2021/09/25)
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- Dissipative aggregation-induced emission behaviour of an amino-functionalized tetraphenylethene using a pH oscillator
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A dissipative aggregation-induced emission (DAIE) system is successfully fabricated by coupling a stimuli-responsive AIE luminogens (AIEgens) with a pH oscillator. The novel DAIE system exhibits reversible, autonomous and sustainable AIE behaviour. Moreover, the DAIE behaviour can be regulated with the system temperature. The novel strategy will boost the development of bioinspired intelligent systems for real-world applications. This journal is
- Liang, Enxiang,Su, Fang,Liang, Yan,Wang, Guoxiang,Xu, Wenyuan,Li, Shan,Yang, Caixia,Tang, Jianxin,Zhou, Ningbo
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supporting information
p. 15169 - 15172
(2020/12/21)
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- METHOD OF DETECTING HUMAN SERUM ALBUMIN IN BIOLOGICAL FLUIDS
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A method for human serum albumin (HSA) detection in a biological fluid using small molecule, fluorescent compounds having aggregation-induced emission (AIE) characteristics includes contacting the biological fluid with a fluorescent compound to provide a mixture, irradiating the mixture with ultraviolet light, and determining a presence of human serum albumin when an observable emission is detected. The fluorescent compound binds with human serum albumin in the biological fluid and the binding of the compound with the human serum albumin produces the emission. The biological fluid can be urine. The compounds can be water soluble and can include tetrazole-tagged AIEgens. The present methods can be performed using conventional fluorescent spectrometers, normally present in hospitals, or using an HSA detection device. The HSA detection device is portable and can be used by a patient at home.
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Page/Page column 16
(2020/03/23)
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- Efficient bipolar AIE emitters for high-performance nondoped OLEDs
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Three luminogens were designed and synthesized by integratingTPEwith hole-transporting carbazole (Cz) and/or electron-transporting 1,2-diphenyl-1H-benzimidazole (PBi), and bare tetraphenylethene and another donor-acceptor (D-A) compound with aggregation-caused quenching (ACQ) were also prepared for comparison. In nondoped OLEDs, the best one with both aggregation-induced emission (AIE) properties and donor-acceptor (D-A) structures showed excellent performances withLmax, CEmax, PEmax, and EQEmaxof 24 308 cd m?2, and 15.10 cd A?1, 14.82 lm W?1, and 5.34%, respectively, which reached the theoretical limit of fluorescent OLEDs.
- Bai, Yongqi,Cao, Liang,Ge, Ziyi,Wang, Tao,Wei, Qiang,Zhang, Jiasen
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supporting information
p. 11771 - 11777
(2020/09/16)
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- Nickel-catalyzed deoxygenation of oxiranes: Conversion of epoxides to alkenes
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Deoxygenation of epoxides takes place under the catalysis of nickel in the presence of diethylzinc as a deoxygenation agent to yield alkenes. Epoxides with a wide variety of substitution patterns are deoxygenated in this catalytic system to give terminal, 1,1-disubstituted, 1,2-disubstituted, trisubstituted, and tetrasubstituted alkenes in high yields. Reactions of 1,2-disubstituted epoxides we examined proceeded in an E-stereoselective manner. High compatibility with other functional groups through this transformation was also observed.
- Mori, Takamichi,Takeuchi, Yoshihito,Hojo, Makoto
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supporting information
(2020/01/24)
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- Efficient hydroarylation of terminal alkynes with sodium tetraphenylborate performed in water under mild conditions
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The hydroarylation of terminal alkynes with sodium tetraphenylborate was performed in high yield within 3 h at room temperature in water, using palladium(II) complexes with imidazole ligands as catalysts. Under these conditions, differently substituted phenylacetylene substrates were converted to arylalkenes and aryl-substituted dienes. High conversion and excellent selectivity were achieved in the hydroarylation of alkynols with sodium tetraphenylborate. Only one product, arylalkene with an OH group, was formed in these reactions with the yield dependent on the kind of alkynol used. A plausible hydroarylation reaction mechanism was proposed on the basis of the palladium species identified in the reaction mixture and H/D exchange studies. The contribution of water as the hydride source was evidenced.
- Koci?cka,Trzeciak
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- Synthesis of Tetraarylethene Luminogens by C?H Vinylation of Aromatic Compounds with Triazenes
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Tetraarylethenes are obtained by acid-induced coupling of vinyl triazenes with aromatic compounds. This new C?H activation route for the synthesis of aggregation-induced emission luminogens is simple, fast, and versatile. It allows the direct grafting of triarylethenyl groups onto a variety of aromatic compounds, including heterocycles, supramolecular hosts, biologically relevant molecules, and commercial polymers.
- Doll, Martin,Fadaei-Tirani, Farzaneh,Ruggi, Albert,Scopelliti, Rosario,Severin, Kay,Suleymanov, Abdusalom A.
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supporting information
p. 9957 - 9961
(2019/11/03)
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- Divergent and Stereoselective Synthesis of Tetraarylethylenes from Vinylboronates
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The synthesis of a new tetraborylethylene (TBE) is reported, and its application in the preparation of [4+0]-tetraarylethenes (TAEs) is elucidated. TAEs have widespread applications in material science and supramolecular chemistry due to their aggregation-induced emission (AIE) properties. The divergent and stereoselective synthesis of [3+1]-, [2+2]-, and [2+1+1]-TAEs via multiple couplings of vinylboronates with aryl bromides is demonstrated. These couplings feature a broad substrate scope and excellent functional group compatibility due to mild reaction conditions. Facile access to various tetraarylethenes is provided. This strategy represents an important complement to the conventional methods employed for the synthesis of TAEs, and would be a valuable tool for synthesizing TAE-based molecules useful in functional materials, biological imaging and chemical sensing.
- Stang, Peter J.,Yao, Yisen,Zhang, Minghao,Zhao, Wanxiang
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supporting information
p. 20090 - 20098
(2020/09/02)
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- Microwave-assisted periselective annulation of triarylphosphenes with aldehydes and ketones
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The reaction of diazo(aryl)methyl(diaryl)phosphine oxides with aldehydes and ketones generates benzo-δ-phosphinolactones in low to good yields with 1,1-diarylalk-1-enes as byproducts under microwave irradiation. Diazo(aryl)methyl(diaryl)phosphine oxides first undergo a Wolff rearrangement to form diaryl(aryl)phosphenes, which further react with aldehydes and ketones to afford benzo-δ-phosphinolactones and β-phosphinolactones. The latter are unstable under heating and fragment into the corresponding 1,1-diarylalk-1-enes and arylphosphine dioxides under reaction conditions. The arylphosphine dioxides become arylphosphonic acids during workup. The periselectivity in the annulation shows that the reaction of diaryl(aryl)phosphenes with most aldehydes and ketones favors phosphene phenyl participation in (4 + 2) annulation(2 + 2) annulation. This journal is
- Du, Changle,Fu, Xingyang,Fu, Zhicheng,Luo, Yun,Xu, Jiaxi
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p. 9526 - 9537
(2020/12/15)
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- Tetraphenylethylene-benzophenone-carbazole derivative, crystal and preparation method and application thereof
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The invention discloses a tetraphenylethylene-benzophenone-carbazole derivative, a crystal and a preparation method and application thereof. The tetraphenylethylene-benzophenone-carbazole derivative is named (4-(9H-carbazole-9-yl)phenyl)(4-(1,2,2-triphenylvinyl)phenyl)ketone, and a structural formula is as shown in the specification. The crystal prepared from the tetraphenylethylene-benzophenone-carbazole derivative has unique AIE effect, high luminous intensity, high thermal stability and high solubility, can be used as a novel soluble luminous molecule which is excellent in performance, lowin cost and high in space structural distortion, and has a remarkable economic value in application to preparation of luminous materials, light-emitting devices or intelligent materials. In addition,controllable preparation of the crystal containing the tetraphenylethylene-benzophenone-carbazole derivative is realized.
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Paragraph 0057; 0059; 0060; 0061; 0062; 0063; 0065
(2019/03/25)
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- FLUORESCENT PROBES FOR SILVER ION DETECTION
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Fluorescent probes for silver ion detection include organic, water-soluble compounds having aggregation-induced emission (AIE) characteristics. The probes can sense or detect silver ions through aggregation or a precipitation reaction between the silver ions and the organic compounds which induces fluorescence. The compounds are acidic, soluble in aqueous phase, and provide low background fluorescence in aqueous solutions.
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Page/Page column 25
(2019/05/30)
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- Metal-Organic Framework with Rich Accessible Nitrogen Sites for Highly Efficient CO2 Capture and Separation
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A novel microporous metal-organic framework (FJU-44), with abundant accessible nitrogen sites on its internal surface, was constructed from the tetrapodal tetrazole ligand tetrakis(4-tetrazolylphenyl)ethylene (H4TTPE) and copper chloride. Notably, the CO2 uptake capacity (83.4 cm3/g, at 273 K and 1 bar) in the activated FJU-44a is higher than most of tetrazolate-containing MOF materials. Particularly, FJU-44a exhibits superior adsorption selectivity of CO2/N2 (278-128) and CO2/CH4 (44-16), which is comparable to some well-known CO2 capture materials. Furthermore, the fixed-bed breakthrough experiment indicates that the postcombustion flue gas flow over a packed column with FJU-44a adsorbents can be effectively separated.
- Ye, Yingxiang,Zhang, Heng,Chen, Liangji,Chen, Shimin,Lin, Quanjie,Wei, Fangfang,Zhang, Zhangjing,Xiang, Shengchang
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supporting information
p. 7754 - 7759
(2019/06/17)
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- Halogenated tetraphenylethene with enhanced aggregation-induced emission: An anomalous anti-heavy-atom effect and self-reversible mechanochromism
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Halogenated tetraphenylethene derivatives show a unique anti-heavy-atom effect where introducing heavy halogens like bromine greatly improves the fluorescence quantum yield upon aggregation, contrary to the classic heavy-atom effect. The unique self-reversible mechanochromism of brominated TPE is attributed to re-generation of halogen-halogen bonding after its breakage.
- Xu, Pengfei,Qiu, Qianqian,Ye, Xinru,Wei, Mengru,Xi, Wenbin,Feng, Hui,Qian, Zhaosheng
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supporting information
p. 14938 - 14941
(2019/12/24)
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- Toward a Porphyrin-Style NHC: A 16-Atom Ringed Dianionic Tetra-NHC Macrocycle and Its Fe(II) and Fe(III) Complexes
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N-heterocyclic carbenes (NHCs), and macrocyclic NHCs in particular, have been applied successfully to the stabilization of high oxidation states on transition metal complexes. This access to high oxidation states has enabled their application in oxidative catalysis including aziridination and epoxidation. However, the number of macrocyclic tetra-NHC ligands is still limited, especially those featuring anionic charge, which is beneficial in this regard. In this manuscript, we report a facile and high yielding synthesis for only the second example of such a dianionic, macrocyclic tetra-NHC ligand. This 16-atom macrocycle has the ring size and charge of a porphyrin but with the increased electron donation of NHCs. Its Fe(II) and Fe(III) complexes are reported, and their reactivities for ligand addition and oxidation were tested. Multiple oxidation catalysis reactions were tested with both the Fe(II) and Fe(III) complexes with reagents such as trimethylamine-N-oxide, oxygen (from air), diazodiphenylmethane, and P-tert-butyl-dibenzo-73phosphanorbornadiene (tBuPA) to explore the possibilities for single site oxidation reactions.
- Anneser, Markus R.,Elpitiya, Gaya R.,Powers, Xian B.,Jenkins, David M.
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p. 981 - 987
(2019/02/26)
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- Cu-Catalyzed Desulfonylative Amination of Benzhydryl Sulfones
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A new method for the synthesis of benzhydryl amines from the reaction of readily available sulfone derivatives with amines is described. The Cu-catalyzed desulfonylative amination not only provides structurally diverse benzhydryl amines in good yields, but is also applicable to iterative and intramolecular aminations. Control experiments suggested that the formation of a Cu-carbene intermediate generated from the sulfone substrate, which represents a new route for desulfonylative transformations.
- Nambo, Masakazu,Tahara, Yasuyo,Yim, Jacky C.-H.,Crudden, Cathleen M.
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supporting information
p. 1923 - 1926
(2019/01/24)
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- 3-Acetoxyquinuclidine as Catalyst in Electron Donor-Acceptor Complex-Mediated Reactions Triggered by Visible Light
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3-Acetoxyquinuclidine was found to act as a catalytic electron donor species in a variety of electron donor-acceptor complex-mediated reactions. Only substoichiometric amounts (10-25 mol %) were needed to trigger the desired reaction. The outcome could be tuned by selecting the nature of the formed radical to perform amino- and hydro-decarboxylation, dimerization, and cyclization reactions. Importantly, no external additives were needed in this reaction.
- Bosque, Irene,Bach, Thorsten
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p. 9103 - 9109
(2019/10/16)
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- N, C-Disubstituted Biarylpalladacycles as Precatalysts for ppm Pd-Catalyzed Cross Couplings in Water under Mild Conditions
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Various monosubstitution and disubstitution patterns on the parent biarylamine skeleton characteristic of palladacycles, as well as the counterion effect, have been studied while looking for ways to increase the effectiveness of the catalyst formed under micellar catalysis conditions in water, with the goal of reducing the amount of Pd needed for coupling reactions. Several substituted palladacycles containing readily accessible ligands were chosen for evaluation. The results indicate that (1) preactivation of Pd(II) salts as precursors for Suzuki-Miyaura (SM) couplings via treatment with a reducing agent is not required; (2) reactions could be performed with approximately half the loading of Pd, relative to that previously required based on a combination of a Pd(II) salt and ligand; and (3) the most effective palladacycle precatalyst has been identified as that containing an isopropyl group on both an aryl ring and on nitrogen, together with the ligand EvanPhos and triflate as the counterion (P13). This precatalyst is also effective in other C-C bond-forming reactions, such as Heck and Sonogashira couplings. No organic solvents were needed for these processes, while the aqueous reaction medium could be recycled several times. A one-pot, four-step sequence involving Suzuki-Miyaura, reduction, alkylation, and acylation reactions highlights the potential for this precatalyst to maximize synthetic gain while minimizing costs and waste generation.
- Thakore, Ruchita R.,Takale, Balaram S.,Gallou, Fabrice,Reilly, John,Lipshutz, Bruce H.
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p. 11647 - 11657
(2019/11/29)
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- Azo-linked porous organic polymers: Robust and time-efficient synthesis: Via NaBH4-mediated reductive homocoupling on polynitro monomers and adsorption capacity towards aniline in water
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Time-efficient synthetic methods of porous organic polymers are searched in order to extend the applications of these materials. In this work, we show a robust and time-efficient synthetic method of azo-linked porous organic polymers named Azo-POPs based on a NaBH4-mediated reductive coupling polymerization on well-known polynitro monomers. Azo-POPs were found to have a high Brunauer-Emmett-Teller (BET) surface area and potential for aniline adsorption. Interestingly, Azo-POP-1 showed adsorption capacity towards aniline as high as 1059.68 mg g-1 at 293 K, which surpassed that of adsorbent materials reported in the literature.
- Zhou, Jin-Xiu,Luo, Xian-Sheng,Liu, Xiangxiang,Qiao, Yan,Wang, Pengfei,Mecerreyes, David,Bogliotti, Nicolas,Chen, Shi-Lu,Huang, Mu-Hua
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supporting information
p. 5608 - 5612
(2018/04/12)
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- A new aggregation-induced emission fluorescent probe for rapid detection of nitroreductase and its application in living cells
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The biological activity of nitroreductase (NTR) is closely related to biological hypoxia status in organisms. The development of effective methods for monitoring the activity of NTR is of great significance for medical diagnosis and tumor research. Toward this goal, we have developed a new aggregation-induced emission (AIE) fluorescence NTR probe TPE-HY used the tetraphenylethene as the fluorophore, and used the nitro group as the NTR recognition site. The probe TPE-HY has many excellent properties, including rapid response, AIE characteristics, high sensitivity and selectivity, and low cytotoxicity. Importantly, the probe TPE-HY is successfully applied to monitor endogenous NTR in living HeLa cells.
- Xu, Gaoping,Tang, Yonghe,Ma, Yanyan,Xu, An,Lin, Weiying
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p. 197 - 201
(2017/07/17)
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- Composition and synthesis of aggregation-induced emission materials
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The present subject matter relates to compositions containing and synthesis of fluorescent materials e made from tetraphenylethylene (TPE) derivative compounds exhibiting aggregation induced emission (AIE) properties. Further contemplated herein are applications for TPE derivative compounds such as electroluminescent devices since they have a high efficiency, low turn on voltage, and excellent brightness. Additionally, application of TPE derivatives exhibiting AIE properties in various fields such as OLEDs, fingerprinting and forensic technology, and various other biological and industrial sectors are discussed.
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Page/Page column 34; 35-36
(2018/04/20)
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- Shape-Controllable and Fluorescent Supramolecular Organic Frameworks Through Aqueous Host–Guest Complexation
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Two kinds of shape-controllable and fluorescent supramolecular organic frameworks (cuboid or spheroid) are constructed hierarchically from CB[8] and tetraphenylethylene derivatives through host–guest interaction in water. These two fluorescent SOFs exhibit intriguing and varied photophysical properties, including large red-shifts (up to 82 nm) and stimuli-responsive behavior to competitive guest by binding with CB[8], the turn-on fluorescence of which is applied in cellular imaging.
- Li, Yawen,Dong, Yunhong,Miao, Xiaran,Ren, Yulin,Zhang, Beilin,Wang, Pinpin,Yu, Yang,Li, Bin,Isaacs, Lyle,Cao, Liping
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supporting information
p. 729 - 733
(2017/12/26)
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- Fluorogenic Ag+–Tetrazolate Aggregation Enables Efficient Fluorescent Biological Silver Staining
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Silver staining, which exploits the special bioaffinity and the chromogenic reduction of silver ions, is an indispensable visualization method in biology. It is a most popular method for in-gel protein detection. However, it is limited by run-to-run variability, background staining, inability for protein quantification, and limited compatibility with mass spectroscopic (MS) analysis; limitations that are largely attributed to the tricky chromogenic visualization. Herein, we reported a novel water-soluble fluorogenic Ag+ probe, the sensing mechanism of which is based on an aggregation-induced emission (AIE) process driven by tetrazolate-Ag+ interactions. The fluorogenic sensing can substitute the chromogenic reaction, leading to a new fluorescence silver staining method. This new staining method offers sensitive detection of total proteins in polyacrylamide gels with a broad linear dynamic range and robust operations that rival the silver nitrate stain and the best fluorescent stains.
- Xie, Sheng,Wong, Alex Y. H.,Kwok, Ryan T. K.,Li, Ying,Su, Huifang,Lam, Jacky W. Y.,Chen, Sijie,Tang, Ben Zhong
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supporting information
p. 5750 - 5753
(2018/04/19)
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- Anhydrous proton conduction in porous organic networks
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Solid electrolyte separators within fuel cells enable efficient charge transport and prevent a mass bypass between the two half cells. Hydrated systems, like Nafion, reach unprecedented proton conductivities at ambient temperatures, but the demanding humidity management prevents their use beyond 80 °C, hence limiting the efficiency of current polymer-based systems. As such, water free and chemically inert, solid materials with excellent conductivities between 100 °C and 200 °C, are of high interest. A promising approach is the incorporation of heavier amphoteric molecules into micro- and mesoporous frameworks. Stronger host-guest interactions allow for higher temperatures, while still maintaining sufficient mobility and efficient transport pathways. Here, we present a systematic study investigating the influence of porosity, framework topology and dimensionality as well as framework functionality and charge carrier uptake on the proton conductivity for six porous organic networks (PONs) loaded with imidazole via gas phase adsorption. The resulting materials were thoroughly characterized by multinuclear NMR and IR spectroscopy and physisorption as well as powder X-ray diffraction and DSC experiments, revealing homogeneous distribution of the amphoteric guests within the pore structure. Electrochemical impedance spectroscopy up to 130 °C revealed remarkable conductivities of up to 10?3 S cm?1 under anhydrous conditions. We found 3D networks to favour high imidazole loading leading to high proton conductivities based on the Grotthuss mechanism. In contrast, 2D networks showed a lower guest molecule uptake and thus lower proton conductivities, which were governed by vehicle transport. Additional acid/base functionalities within the frameworks seem to have a negative effect on the proton conduction.
- Klumpen,Winterstein,Papastavrou,Senker
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supporting information
p. 21542 - 21549
(2018/11/20)
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- Synthesis of tetraphenylethylene-based conjugated microporous polymers for detection of nitroaromatic explosive compounds
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Conjugated microporous polymers (CMPs) containing tetraphenylethylene (TPE) were synthesized via the Suzuki coupling polymerization. The tetrafunctional TPE moiety in the polymer backbone was linked with the difunctional phenylene group to exhibit a porous structure with high fluorescence in the solid state because of aggregation-induced emissive TPE. The porous polymer with a fluorescent TPE group successfully detected nitroaromatic explosive compounds that exhibited fluorescence quenching, in which the polymer shows high quenching efficiency to picric acid among nitroaromatic explosive compounds. The interaction between the electron-rich TPE group and the electron-deficient nitroaromatic compounds played a decisive role in fluorescence quenching via a photoinduced electron transfer (PET). Compared with a linear polymer containing TPE, the porous, crosslinked polymer showed better sensing performance toward nitroaromatic compounds, presumably because of the more efficient interaction between TPE and nitroaromatic compounds in the pores of TPE-based CMP (TPE-CMP).
- Namgung, Ho,Lee, Jeong Jun,Gwon, Young Jin,Lee, Taek Seung
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p. 34291 - 34296
(2018/10/24)
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- Method for synthesizing tetraaryl ethylene compound
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The invention relates to a method for synthesizing a tetraaryl ethylene compound. The method comprises the steps: using arylethylene as a raw material, a diaryl iodide salt as an arylating agent and acopper salt or a cuprous salt as a catalyst, and performing a reaction in an aprotic polar organic solvent at 80-150 DEG C for at least 10 hours so as to obtain the target product. The method has thecharacteristics of simple synthesis steps, mild synthesis conditions, high product yield and the like, and is a commercially valuable method for synthesizing the tetraaryl ethylene compound.
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Paragraph 0119-0123
(2019/01/06)
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- An Elastic Hydrogen-Bonded Cross-Linked Organic Framework for Effective Iodine Capture in Water
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A crystalline microporous hydrogen-bonded cross-linked organic framework has been developed through covalent photo-cross-linking of molecular monomers that are assembled in a crystalline state. The elastic framework expands its void space to adsorb iodine rapidly with a high uptake capacity in an aqueous environment as well as recovering its crystalline form after the release of iodine.
- Lin, Yunxiao,Jiang, Xuanfeng,Kim, Samuel T.,Alahakoon, Sampath B.,Hou, Xisen,Zhang, Zhiyun,Thompson, Christina M.,Smaldone, Ronald A.,Ke, Chenfeng
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supporting information
p. 7172 - 7175
(2017/06/05)
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- Two-Dimensional Metal-Organic Layers as a Bright and Processable Phosphor for Fast White-Light Communication
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A metal–organic layer (MOL) is a new type of 2D material that is derived from metal–organic frameworks (MOFs) by reducing one dimension to a single layer or a few layers. Tetraphenylethylene-based tetracarboxylate ligands (TCBPE), with aggregation-induced emission properties, were assembled into the first luminescent MOL by linking with Zr6O4(OH)6(H2O)2(HCO2)6 clusters. The emissive MOL can replace the lanthanide phosphors in white light emitting diodes (WLEDs) with remarkable processability, color rendering, and brightness. Importantly, the MOL-WLED exhibited a physical switching speed three times that of commercial WLEDs, which is crucial for visible-light communication (VLC), an alternative wireless communication technology to Wi-Fi and Bluetooth, by using room lighting to carry transmitted signals. The short fluorescence lifetime (2.6 ns) together with high quantum yield (50 %) of the MOL affords fast switching of the assembled WLEDs for efficient information encoding and transmission.
- Hu, Xuefu,Wang, Zi,Lin, Bangjiang,Zhang, Cankun,Cao, Lingyun,Wang, Tingting,Zhang, Jingzheng,Wang, Cheng,Lin, Wenbin
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supporting information
p. 8390 - 8394
(2017/06/28)
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- Fluorescence probe for detecting nitroreductase
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The invention discloses aggregation-induced emission (AIE) type fluorescence probe for detecting nitroreductase. The fluorescence probe is named as [2-(4-nitrophenyl)-1,1,2-triphenyl]ethylene, TPE-NO2 for short. The chemical structural formula of the fluorescence probe is represented by formula (I) (shown in the description). The fluorescence probe provided by the invention has response to nitroreductase in cells and can be used for detecting nitroreductase at an anoxic state of tumor cells by virtue of fluorescence imaging.
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Paragraph 0010
(2017/09/02)
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- Tetrakis(trialkylsilylethynylphenyl)ethenes: Mechanofluorochromism arising from steric considerations with an unusual crystal structure
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Mechanofluorochromism (MFC) arising from extended partial planarization of a conjugated molecular framework through the transfer of mechanical stress by terminal bulky groups is demonstrated. Thus the tetrakis(triisopropylsilyl-4-ethynylphenyl)ethene [TPE-(TIPS)4] luminophore, synthesized for the first time, is shown to exhibit MFC when the threshold pressure exceeds about 1.3 MPa. An analogous luminophore, tetra(trimethylsilyl-4-ethynylphenyl)ethene [TPE-(TMS)4], with smaller bulky groups at the periphery of TPE, synthesized for comparative studies, was also observed to exhibit MFC. MFC is observed under visible and UV light excitation. The color change is reversed upon annealing or under solvent fumigation conditions. The luminophores show high quantum yields in the solid state ranging from 60 to 74%. Very interestingly, TPE-(TMS)4 exhibited quite an unusual crystal structure, where no intermolecular interactions attributed to mechanofluorochromism are observed. The solid state optical absorption and CP-MAS 13C NMR measurements strongly suggested that the mechanism of MFC could have originated from partial planarization of the molecule upon grinding/shearing, facilitated by the bulky peripheral/terminal groups. These high solid state emitting luminophores with MFC properties could find applications in the areas of solid state lighting and sensors. The synthetic design, in principle, should enable MFC as a function of pressure (through variation in steric handle) and temperature (through electronic and conformational handles). The novel and rational synthetic design, in principle, should enable MFC in a family of organic molecules as a function of pressure and temperature.
- Ramachandran, Elumalai,Dhamodharan, Raghavachari
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supporting information
p. 10469 - 10476
(2017/10/27)
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- Synthesis and application of fluorescent reagent for selectively detecting cysteine based on aggregation-induced emission principle
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The invention discloses a fluorescent reagent for selectively detecting cysteine based on an aggregation-induced emission principle, a synthesis method and application thereof. Benzophenone is used as an initial raw material for synthesizing a target compound TPENNO2. The detection research of the target compound TPENNO2 to sulfydryl-contained amino acids (such as the cysteine, homocysteine and glutathione) is developed, and the target compound TPENNO2 is discovered to have the good sensitivity and the high selectivity to the cysteine, and the interference to the homocysteine and the glutathione is small. Compared with the prior art, the fluorescent reagent has the advantages of simple synthesis, easily obtained raw materials, high target compound fluorescence quantum yield, and strong photobleaching resistant capacity. The defect of traditional fluorochrome that cannot be detected in the high concentration is avoided, and the target compound TPENNO2 is successfully used for the fluorescence imaging of a sulfhydryl compound in cells. The target compound TPENNO2 has the large application prospect in the aspects of selectively detecting the cysteine and detecting the content of the sulfhydryl compound in the cells.
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Paragraph 0026
(2017/07/20)
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- A novel application of 2-silylated 1,3-dithiolanes for the synthesis of aryl/hetaryl-substituted ethenes and dibenzofulvenes
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Trimethylsilyldiazomethane (TMS-CHN2) reacts readily with hetaryl thioketones to give sterically crowded 2-trimethylsilyl- 4,4,5,5-tetrahetaryl-1,3-dithiolanes with complete regioselectivity at -75 °C as well as at rt. Thiofluorenone, a relatively stable and highly reactive aryl thioketone, yields upon treatment with TMS-CHN2at -60 °C the corresponding 1,3,4-thiadiazoline. This unstable cycloadduct undergoes decomposition at ca. -45 °C and the silylated thiocarbonyl S-methanide generated thereby is trapped with complete regioselectivity by aryl or hetaryl thioketones forming also sterically crowded 2-trimethylsilyl-1,3- dithiolanes. The obtained 1,3-dithiolanes, by treatment with an equimolar amount of TBAF in a one-pot procedure, are converted in high yields into hetaryl/aryl-substituted ethenes or dibenzofulvenes, respectively, via a cycloreversion reaction of the intermediate 1,3-dithiolane carbanion. The presented protocol offers a new, highly efficient approach to tetrasubstituted ethenes and dibenzofulvenes bearing aryl and/or hetaryl substituents.
- Mloston, Grzegorz,Pipiak, Paulina,Hamera-Fa?dyga, Róza,Heimgartner, Heinz
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p. 1900 - 1906
(2017/09/27)
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- For cell fluorescent color rendering of the water-soluble fluorescent dye (by machine translation)
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The present invention discloses a structure of the formula (I) compounds, its four styrene as mother nucleus, by Suzuki, Heck other simple coupling reaction, and Sn2 substitution reaction of the introduction of the water-soluble group design is obtained by the synthesis. This compound has excellent light-emitting performance, while at the same time also has a water-soluble, and short synthetic route, the method is simple, it has very strong practical value. (by machine translation)
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Paragraph 0013
(2017/10/27)
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- Ultrasonic activation of the arylation reaction of styrene catalyzed by transition metals
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The arylation reaction of styrene was tested in the presence of different transition metal-based catalysts, mainly iron-based, given its low cost and its nonpolluting and nontoxic characteristics. The study of the effect of sonochemical activation on the evolution of the selectivity of the reaction is also proposed. Higher efficiency was observed for a very short period of time of just a few minutes. Furthermore, an improvement of the selectivity of the arylation of the external carbon of styrene was observed.
- Atoui, Dhiab,Sa?d, Khemais,Ben Salem, Ridha
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p. 587 - 600
(2017/09/18)
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- Molecular Face-Rotating Cube with Emergent Chiral and Fluorescence Properties
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Chiral cage compounds are mainly constructed from chiral precursors or based on the symmetry breaking during coordination-driven self-assembly. Herein, we present a strategy to construct chiral organic cages by restricting the P or M rotational configuration of tetraphenylethylene (TPE) faces through dynamic covalent chemistry. The combination of graph theory, experimental characterizations and theoretical calculations suggests emergent chirality of cages is originated from complex arrangements of TPE faces with different orientational and rotational configurations. Accompanied by the generation of chirality, strong fluorescence also emerged during cage formation, even in dilute solutions with various solvents. In addition, the circularly polarized luminescence of the cages is realized as a synergy of their dual chiral and fluorescence properties. Chirality and fluorescence of cages are remarkably stable, because intramolecular flipping of phenyl rings in TPE faces is restricted, as indicated by calculations. This study provides insight into construct chiral cages by the rational design through graph theory, and might facilitate further design of cages and other supramolecular assemblies from aggregation-induced emission active building blocks.
- Qu, Hang,Wang, Yu,Li, Zhihao,Wang, Xinchang,Fang, Hongxun,Tian, Zhongqun,Cao, Xiaoyu
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supporting information
p. 18142 - 18145
(2017/12/27)
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- Exploring highly efficient light conversion agents for agricultural film based on aggregation induced emission effects
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Aggregation-induced emission (AIE) is a unique photo-physical phenomenon that has become an emerging and hot research area. It has a wide range of applications due to its excellent luminous properties. In this paper, five compounds and their corresponding light conversion films were prepared based on AIE effects and the thermally activated delayed fluorescence (TADF) phenomenon. Furthermore, ultraviolet conversion, dispersion and photo-physical properties such as UV-vis spectra, fluorescence spectra, and photo stability as well as the mechanical properties of the light conversion films were investigated in detail. The results reveal that triphenylacrylonitrile (TPA) exhibits excellent photo stability and ultraviolet light conversion properties. In addition, the fluorescence emission spectrum of TPA corresponds well with the absorption spectrum of plants in the blue-violet region. In particular, the light conversion film with added TPA also shows enhanced mechanical properties and slightly lower visible light transmittance (3.79%) compared to PVC blank film. Based on the photo stabilities of the five compounds, it can be concluded that the electron-withdrawing cyano group can increase the photo stability of TPA, while carbazole substituents are proved to have an uncertain effect on the rate of photo oxidation, which is attributed to the electron-donating properties of carbazole and increased molecular distortion or rigidity. Finally, it is worth mentioning that this is the first report utilizing AIE-active luminogens (AIEgens) in agricultural light conversion film.
- Qi, Yunpeng,Wang, Yongtao,Yu, Yongjiang,Liu, Zhiyong,Zhang, Yan,Qi,Zhou, Changtong
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p. 11291 - 11297
(2016/12/09)
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- Synthesis and property of new propeller shaped emitting materials for organic light-emitting devices
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New propeller type emitting compound, namely 3,6-di-anthracen-9-yl-9,10-bis-(4-anthracen- 9-yl-phenyl)-phenanthrene[TAnDAP] and 3,6-bis-(10-phenyl-anthracen-9-yl)-9,10-bis-[4-(10-phenylanthracen- 9-yl)-phenyl]-phenanthrene [TAnPDAP] were synthesized through Suzuki and McMurry reactions. We investigated their physical properties such as optical, electrochemical, and electroluminescent properties. The two compounds were used as an emitting layer in OLED devices: ITO/2-TNATA (60 nm)/NPB (15 nm)/non-doped: TAnDAP or TAnPDAP (35 nm)/Alq3 (20 nm)/LiF (1 nm)/Al (200 nm). The TAnDAP OLED device showed C.I.E. value of (0.28, 0.41) and luminance efficiency of 3.81 cd/A at 10 mA/cm2. The TAnPDAP device showed C.I.E. value of (0.20, 0.27) and high luminance efficiency of 5.40 cd/A at 10 mA/cm2. TAnPDAP was found to show better luminance efficiency and C.I.E. value than TAnDAP because it has a bulky 9-phenylanthracene.
- Kang, Seokwoo,Lee, Hayoon,Kim, Beomjin,Park, Youngil,Park, Jongwook
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p. 3102 - 3105
(2016/03/19)
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- Tetraarylethylenes from Diarylmethanones and Hexachlorodisilane: The “Sila-McMurry” Reaction
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Hexachlorodisilane reacts with diarylmethanones (aryl=C6H5, 4-MeC6H4, 4-tBuC6H4, 4-ClC6H4, 4-BrC6H4) to furnish the corresponding tetraarylethylenes in good yields. The reductive conversion requires temperatures of about 160 °C and reaction times of 60–72 h. In the initial step, the Lewis-basic carbonyl groups likely generate low-valent [SiCl2] as an analogue of [TiCl2] in the classical McMurry reaction. The coupling sequence further proceeds via benzopinacolones, which have been isolated as key intermediates.
- Moxter, Maximilian,Tillmann, Jan,Füser, Matthias,Bolte, Michael,Lerner, Hans-Wolfram,Wagner, Matthias
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supporting information
p. 16028 - 16031
(2016/10/26)
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- Full-color tunable mechanofluorochromism and excitation-dependent emissions of single-arm extended tetraphenylethylenes
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We propose a new single-arm extension strategy on traditional tetraphenylethylene and successfully develop a new series of full-color (from ~450 nm to ~740 nm) tunable mechanofluorochromic materials. These materials exhibit efficient solid-state emission (quantum yield Φf > 10%) and high mechanofluorochromic contrast (wavelength shift from ~50 nm to ~100 nm). More importantly, we discover an unexpected excitation-dependent emission phenomenon of mechanofluorochromic materials and propose to utilize this new excitation-dependent emission behavior of materials to evaluate their mechanical-responsive performances more comprehensively. Finally, the unique feature of abundant emissions of mechanofluorochromic materials by changing the excitation light has shown application potential in dual channel anti-counterfeiting.
- Wang, Yi,Zhang, Ivan,Yu, Binhong,Fang, Xiaofeng,Su, Xing,Zhang, Yu-Mo,Zhang, Ting,Yang, Bing,Li, Minjie,Zhang, Sean Xiao-An
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supporting information
p. 12328 - 12334
(2015/12/08)
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- SnCl4-Zn: A novel reductive system for deoxygenative coupling of aliphatic, aromatic, chalcone epoxide, and indanone carbonyl compounds to olefins
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SnCl4-Zn complex provided a novel reductive system in the deoxygenative cross-coupling of aliphatic, aromatic, chalcone epoxide and indanone carbonyl compounds to olefins in high yield (55-86%) at reflux temperature in THF. The advantage of this reagent is inexpensive, short reaction time, and high yield compared to the reagents used in the McMurry cross-coupling reaction.
- Pathe, Gulab Khushalrao,Ahmed, Naseem
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supporting information
p. 1555 - 1561
(2015/03/14)
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- A heterobimetallic complex featuring a Ti-Co multiple bond and its application to the reductive coupling of ketones to alkenes
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To explore metal-metal multiple bonds between first row transition metals, Ti/Co complexes supported by two phosphinoamide ligands have been synthesized and characterized. The Ti metalloligand Cl2Ti(XylNPiPr2)2 (1) was treated with CoI2 under reducing conditions, permitting isolation of the Ti/Co complex [(μ-Cl)Ti(XylNPiPr2)2CoI]2 (2). One electron reduction of complex 2 affords ClTi(XylNPiPr2)2CoPMe3 (3), which features a metal-metal triple bond and an unprecedentedly short Ti-Co distance of 2.0236(9) ?. This complex is shown to promote the McMurry coupling reaction of aryl ketones into alkenes, with concomitant formation of the tetranuclear complex [Ti(μ3-O)(NXylPiPr2)2CoI]2 (4). A cooperative mechanism involving bimetallic C=O bond activation and a cobalt carbene intermediate is proposed.
- Wu, Bing,Bezpalko, Mark W.,Foxman, Bruce M.,Thomas, Christine M.
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p. 2044 - 2049
(2015/03/04)
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