- Self-assembly of homochiral porous supramolecular organic frameworks with significant CO2 capture and CO2/N2 selectivity
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A pair of homochiral porous supramolecular organic frameworks (JLU-SOF1-R and JLU-SOF1-S) has been assembled from brand-new enantiopure blocks via hydrogen bonding and π-π interactions. The frameworks not only maintain crystallinity well until 250 °C but
- Zhou, Yue,Liu, Bing,Sun, Xiaodong,Li, Jiantang,Li, Guanghua,Huo, Qisheng,Liu, Yunling
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- Excited State Luminescence of Multi-(5-phenyl-1, 3, 4-oxadiazo-2-yl) benzenes in an Electron-Donating Matrix: Exciplex or Electroplex?
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Multi-(5-phenyl-1, 3, 4-oxadiazo-2-yl)benzenes show emission in organic solvents from ultraviolet to blue (339-447 nm). The reduction potentials E 1/2red cover a large range of -2.11 V for 2, 5-diphenyl-1, 3, 4-oxadiazole to -0.76 V for 1, 2, 3, 4, 5, 6-hexa(5-phenyl-1, 3, 4-oxadiazo-2-yl)benzene. An unexpectedly wide spectral range of the oxadiazole (OXD) exciplex emissions in PVK is observed, ranging from 406 to 603 nm. The OXDs also exhibit similar electroluminescence (EL) when blended into polyvinylcarbazole (PVK). A linear correlation between the λ max of the electroluminescence and photoluminescence is observed, implying that the emission mechanisms in both processes are similar. In addition, the linear correlation between the E1/2red versus λmax of EL (eV) reflected that the term of the charge-transfer configuration of the contact electron-hole pair plays a major role in the exciplex emission. The exciplex EL of 1, 2, 5-tri(5-phenyl-1, 3, 4-oxadiazo-2-yl)benzene (5) could be as high as 1.0 cd/A. Since the exciplex emission usually has a large Stokes shift, this provides a window for us to generate duo emissions for near white light EL with high efficiency. Among the devices we tried, the device of PVK/2-tert-butylphenyl-5-biphenyl-1, 3, 4-oxadiazole/5/2, 5, 8, 11-tetra-tert-butylperylene (100:40:40:4) gave EL with good current efficiency of 1.63 cd/A.
- Yang, Chih-Chiang,Hsu, Chia-Jung,Chou, Pi-Tai,Cheng, Hsu Chun,Su, Yuhlong Oliver,Leung, Man-Kit
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- Robust Ordered Bundles of Porous Helical Nanotubes Assembled from Fully Rigid Ionic Benzene-1,3,5-tricarboxamides
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Size-controlled and ordered assemblies of artificial nanotubes are promising for practical applications; however, the supramolecular assembly of such systems remains challenging. A novel strategy is proposed that can be used to reinforce intermolecular no
- Wu, Xibo,Wang, Daoliang,Chen, Mingming,Wei, Chengsha,Wei, Shenghui,Huang, Ningdong,Li, Liangbin,Zhang, Guobing
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- Synthesis of sulfido- and thiolato-bridged Ir3 cluster and its reactions with alkyne and isocyanide including highly regioselective cyclotrimerization of methyl propiolate
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Reactions of a sulfido- and thiolato-bridged diiridium complex [(Cp*Ir)2(μ-S)(μ-SCH2CH2CN)2] (Cp* = η5-C5Me5) with [(Cp*MCl)2(μ-Cl)su
- Saito, Akihiro,Seino, Hidetake,Kajitani, Hidenobu,Takagi, Fusao,Yashiro, Akihito,Ohnishi, Takeshi,Mizobe, Yasushi
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- An acylhydrazone-based AIE organogel for the selective sensing of submicromolar level Al3+and Al(iii)-based metallogel formation to detect oxalic acid
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A tripodal acylhydrazone derivative (L) was designed, synthesized, and fully characterized. Through the investigation, it had a typical bluish-green aggregation-induced emission (AIE) effect. Notably, the gelator was reported to accurately detect Al3
- Wang, Bin,Li, Juan,Shui, Shipeng,Xu, Jie
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- Lyotropic supramolecular helical columnar phases formed by C 3-symmetric and unsymmetric rigid molecules
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Unlike thermotropic liquid-crystalline C3-symmetric molecules with flexible chains, the herein-designed fully rigid three-armed molecules (C3-symmetric and unsymmetric) create a fancy architecture for the formation of lyotropic liqui
- Wang, Daoliang,Huang, Youju,Li, Junjun,Xu, Lu,Chen, Mingming,Tao, Jiaojiao,Li, Liangbin
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- Redox-Active Two-Dimensional Covalent Organic Frameworks (COFs) for Selective Reductive Separation of Valence-Variable, Redox-Sensitive and Long-Lived Radionuclides
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We report the first example of 2D covalent organic framework nanosheets (Redox-COF1) for the selective reduction and in situ loading of valence-variable, redox-sensitive and long-lived radionuclides (abbreviated as VRL nuclides). Compared with sorbents ba
- Deng, Yun,Guo, Xinghua,Jia, Zhimin,Li, Shoujian,Li, Xiaofeng,Li, Yang,Ma, Lijian,Tian, Yin,Zhang, Meicheng
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- Synthesis and characterization of linear and cyclic endothelin peptides on PEGylated poly(O-benzyl ether) dendrimeric supports
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Synthesis and evaluation of poly(ethylene glycol) grafted poly(O-benzyl ether) dendrimers for polymer assisted organic reaction is presented here. Initially a cross-linked polymer Polystyrene-Poly(ethyleneglycol)dimethacrylate-Vinylbenzylchloride (PS-PEGDMA-VBC) was synthesized by radical suspension polymerization. 1,3,5-tris(hydroxymethyl)benzene dendron was prepared by the reduction of trimesic acid using LiAlH4. Dendrimers were generated on 2 mol% cross-linked resin by repetitive Williamson etherification and thionyl chloride reactions. The dendrimer was cleanly and efficiently prepared up to third generations (G3) and each stage of reaction was quantitatively and qualitatively analyzed. Poly(ethylene glycol) having different chain lengths (400 Da and 1500 Da) were grafted to G3 generation and tested for various physico-chemical properties. The utility of supports were checked by synthesizing linear as well as disulfide bonded endothelin peptides in high yield and purity by standard Fmoc method.
- Siyad,Kumar, G.S. Vinod
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- Hierarchical Co-Assembly Enhanced Direct Ink Writing
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Integrating intelligent molecular systems into 3D printing materials and transforming their molecular functions to the macroscale with controlled superstructures will unleash great potential for the development of smart materials. Compared to macromolecul
- Li, Longyu,Zhang, Pengfei,Zhang, Zhiyun,Lin, Qianming,Wu, Yuyang,Cheng, Alexander,Lin, Yunxiao,Thompson, Christina M.,Smaldone, Ronald A.,Ke, Chenfeng
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- Readily useable bulk phenoxazine-based covalent organic framework cathode materials with superior kinetics and high redox potentials
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Redox-active covalent organic frameworks (COFs) with dense redox sites are promising electrical energy storage materials with robust architectures, high surface areas, insolubility in electrolytes, and open pores for electrolyte transportation. However, low redox potentials and poor electrical conductivity of pristine COFs often result in low accessibilities of redox-active sites and slow redox kinetics, greatly limiting their practical applications. Herein, we report the design and synthesis of two novel p-type phenoxazine-based COFs (DAPO-COFs) with high redox potentials (~3.6 V vs. Li/Li+) and excellent electrical conductivities. Simply blended with conductive additives (CAs) and binders, pristine bulk DAPO-COFs without pre-composition with CAs or extra exfoliation are readily useable as cathode materials for lithium-ion batteries. Both as-synthesized DAPO-COF powders displayed superior active-site accessibility, ultrafast redox kinetics, and remarkable cycling stability. This work provides new perspectives on the development of readily useable COF-based cathode materials, and contributes to the advancement of eco-friendly and sustainable organic-based energy storage devices. This journal is
- Meng, Zhiying,Zhang, Ying,Dong, Mengqing,Zhang, Yue,Cui, Fengmin,Loh, Teck-Peng,Jin, Yinghua,Zhang, Wei,Yang, Haishen,Du, Ya
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- Selective Synthesis of the Aminobutadiene Intermediate and Mechanistic Analysis of 1,4-Dihydropyridine Formation Reaction in Water
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We previously isolated an aminobutadiene derivative as a by-product in the synthesis of a 1,4-dihydro-pyridine (1,4-DHP) derivative by the reaction of methyl propiolate with excess ammonium acetate in water, and we proposed that it is an intermediate in the formation of 1,4-DHP. Here, to test this idea and to investigate the reaction mechanism, we selectively synthesized the aminobutadiene derivative in EtOH and examined its reactivity. The yield of the aminobutadiene derivative was increased in the presence of excess ammonium salt. X-Ray crystal structure analysis indicated the presence of an intramolecular hydrogen bond between the terminal amine and ester carbonyl oxygen, together with a short C–N bond length consistent with enamine-imine equilibrium. Direct cyclization of the aminobutadiene derivative with methyl propiolate to afford the 1,4-DHP derivative did not proceed well, but the yield was increased in the presence of morpholine salt as an additive. These results suggest that the predominant reaction pathway from the intermediate to 1,4-DHP in water involves Michael addition of a second amine molecule and reaction with methyl propiolate, followed by intramolecular cyclization and elimination of amine.
- Azumaya, Isao,Isomura, Shigeki,Okayasu, Misaki,Okuno, Yoshinori,Sato, Yasuo,Suzuki, Ayano,Watanabe, Miyu
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p. 240 - 243
(2022/03/16)
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- Benzene tricarboxamide derivatives with lipid and ethylene glycol chains self-assemble into distinct nanostructures driven by molecular packing
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The self-assembly in aqueous solution of benzene-1,3,5-tricarboxamide (BTA) bearing one alkyl chain and two PEG (polyethylene glycol) chains or two alkyl chains and one PEG chain yields completely distinct nanostructures. Two series of derivatives were sy
- Aljuaid, Nada,Hamley, Ian W.,Ruokolainen, Janne,Seitsonen, Jani,Tully, Mark
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supporting information
p. 8360 - 8363
(2021/08/25)
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- H-BPin/KOtBu Promoted Activation of Cobalt Salt to a Heterotopic Catalyst for Highly Selective Cyclotrimerization of Alkynes
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A mixture of HBPin with KOtBu was found to activate cobalt salt to form a heterotopic cobalt species that is highly active for catalytic intermolecular trimerization of alkynes. This protocol affords 1,2,4-regioisomers in good yields with high regioselectivities under mild conditions. These salient features, together with the operational simplicity and high efficiency, as well as obviating the use of any costly and/or air sensitive ligands, renders the protocol promising for practical applications.
- Song, Shuo,Li, Chuhan,Liu, Tianfen,Zhang, Panke,Wang, Xiaoming
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supporting information
p. 6925 - 6930
(2021/09/14)
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- Case Study of N-iPr versus N-Mes Substituted NHC Ligands in Nickel Chemistry: The Coordination and Cyclotrimerization of Alkynes at [Ni(NHC)2]
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A case study on the effect of the employment of two different NHC ligands in complexes [Ni(NHC)2] (NHC=iPr2ImMe 1Me, Mes2Im 2) and their behavior towards alkynes is reported. The reaction of a mixture of [Ni2(iPr2ImMe)4(μ-(η2 : η2)-COD)] B/ [Ni(iPr2ImMe)2(η4-COD)] B’ or [Ni(Mes2Im)2] 2, respectively, with alkynes afforded complexes [Ni(NHC)2(η2-alkyne)] (NHC=iPr2ImMe: alkyne=MeC≡CMe 3, H7C3C≡CC3H7 4, PhC≡CPh 5, MeOOCC≡CCOOMe 6, Me3SiC≡CSiMe3 7, PhC≡CMe 8, HC≡CC3H7 9, HC≡CPh 10, HC≡C(p-Tol) 11, HC≡C(4-tBu-C6H4) 12, HC≡CCOOMe 13; NHC=Mes2Im: alkyne=MeC≡CMe 14, MeOOCC≡CCOOMe 15, PhC≡CMe 16, HC≡C(4-tBu-C6H4) 17, HC≡CCOOMe 18). Unusual rearrangement products 11 a and 12 a were identified for the complexes of the terminal alkynes HC≡C(p-Tol) and HC≡C(4-tBu-C6H4), 11 and 12, which were formed by addition of a C?H bond of one of the NHC N-iPr methyl groups to the C≡C triple bond of the coordinated alkyne. Complex 2 catalyzes the cyclotrimerization of 2-butyne, 4-octyne, diphenylacetylene, dimethyl acetylendicarboxylate, 1-pentyne, phenylacetylene and methyl propiolate at ambient conditions, whereas 1Me is not a good catalyst. The reaction of 2 with 2-butyne was monitored in some detail, which led to a mechanistic proposal for the cyclotrimerization at [Ni(NHC)2]. DFT calculations reveal that the differences between 1Me and 2 for alkyne cyclotrimerization lie in the energy profile of the initiation steps, which is very shallow for 2, and each step is associated with only a moderate energy change. The higher stability of 3 compared to 14 is attributed to a better electron transfer from the NHC to the metal to the alkyne ligand for the N-alkyl substituted NHC, to enhanced Ni-alkyne backbonding due to a smaller CNHC?Ni?CNHC bite angle, and to less steric repulsion of the smaller NHC iPr2ImMe.
- Tendera, Lukas,Helm, Moritz,Krahfuss, Mirjam J.,Kuntze-Fechner, Maximilian W.,Radius, Udo
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supporting information
p. 17849 - 17861
(2021/11/17)
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- Functional Porphyrinic Metal–Organic Framework as a New Class of Heterogeneous Halogen-Bond-Donor Catalyst
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Biomimetic metal-organic frameworks have attracted great attention as they can be used as bio-inspired models, allowing us to gain important insights into how large biological molecules function as catalysts. In this work, we report the synthesis and utilization of such a metal-metalloporphyrin framework (MMPF) that is constructed from a custom-designed ligand as an efficient halogen bond donor catalyst for Diels–Alder reactions under ambient conditions. The implementation of fabricated halogen bonding capsule as binding pocket with high-density C?Br bonds enabled the use of halogen bonding to facilitate organic transformations in their three-dimensional cavities. Through combined experimental and computational studies, we showed that the substrate molecules diffuse through the pores of the MMPF, establishing a host-guest system via the C?Br???π interaction. The formation of halogen bonds is a plausible explanation for the observed boosted catalytic efficiency in Diels–Alder reactions. Moreover, the unique capability of MMPF highlights new opportunities in using artificial non-covalent binding pockets as highly tunable and selective catalytic materials.
- Chen, Yu-Sheng,Cheng, Qigan,Ma, Shengqian,Nafady, Ayman,Shan, Chuan,Wojtas, Lukasz,Zhang, Weijie,Zhang, X. Peter
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supporting information
p. 24312 - 24317
(2021/10/04)
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- Br?nsted acid-catalyzed chlorination of aromatic carboxylic acids
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The chlorination of aromatic carboxylic acids with SOCl2 has been effectively performed by reacting with a Br?nsted acid as the catalyst. Based on this discovery, an efficient catalytic method that is cheaper than traditional catalytic methods was developed. 20 substrates were chlorinated offering excellent yields in a short reaction time. And the SOCl2/Br?nsted acid system has been used in a larger scale preparative reaction. A dual activation mechanism was proposed to prove the irreplaceable system of SOCl2/Br?nsted acid.
- Yu, Zhiqun,Yao, Hongmiao,Xu, Qilin,Liu, Jiming,Le, Xingmao,Ren, Minna
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supporting information
p. 685 - 689
(2021/04/09)
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- A porous fluorinated organic [4+4] imine cage showing CO2and H2adsorption
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We present the synthesis of a porous, organic [4+4] imine cage containing perfluorinated aromatic panels. Gas adsorption experiments show an uptake of 19.0 wt% CO2(4.2 mmol g-1, 273 K and at 1 bar) and 1.5 wt% H2(7.5 mmol g-1, 77 K and at 1 bar) for the specific surface area of 536 m2g-1of the crystalline material obtained directly from the reaction mixture, combined with an outstanding thermal stability, making it a very interesting porous material suitable for gas adsorption.
- Kunde, Tom,Nieland, Esther,Schr?der, Hendrik V.,Schalley, Christoph A.,Schmidt, Bernd M.
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supporting information
p. 4761 - 4764
(2020/05/13)
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- Polythiophene Doping of the Cu-Based Metal-Organic Framework (MOF) HKUST-1 Using Innate MOF-Initiated Oxidative Polymerization
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The copper-based metal-organic framework (MOF) HKUST-1 adsorbs organic molecules into its pores. When loaded with electron-rich oligothiophenes, the resulting system reacts under heat to initiate oxidative polymerization without the use of any other oxidant or catalyst. This reaction is not observed in the non-redox-active MOF MIL-100(Al). We have characterized the composites by optical and nanoscale microscopy, vibrational and UV-vis spectroscopy, X-ray photoelectron spectroscopy, N2 sorption analysis, and thermogravimetric analysis/residual gas analysis. Unsubstituted oligothiophenes polymerize within MOF pores, while 3,4-ethylenedioxythiophene forms a coating on the MOF surface. MOF composites with conjugated polymer dopants trapped inside their pores undergo profound shifts in the composite electronic structure. Reasoning from time-dependent density functional theory calculations of an HKUST-1 model system bound to monomers, we rationalize the observed reactivity and propose an initiation mechanism based on a ligand-to-metal charge-transfer state.
- Marshall, Nicholas,James, William,Fulmer, Jeremy,Crittenden, Scott,Thompson, Anthony B.,Ward, Patrick A.,Rowe, Gerard T.
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supporting information
p. 5561 - 5575
(2019/04/25)
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- Enhanced Catalytic Activity of Nickel Complexes of an Adaptive Diphosphine-Benzophenone Ligand in Alkyne Cyclotrimerization
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Adaptive ligands, which can adapt their coordination mode to the electronic structure of various catalytic intermediates, offer the potential to develop improved homogeneous catalysts in terms of activity and selectivity. 2,2′-Diphosphinobenzophenones have previously been shown to act as adaptive ligands, the central ketone moiety preferentially coordinating reduced metal centers. Herein, the utility of this scaffold in nickel-catalyzed alkyne cyclotrimerization is investigated. The complex [(p-tolL1)Ni(BPI)] (p-tolL1 = 2,2′-bis(di(para-tolyl)phosphino)-benzophenone; BPI = benzophenone imine) is an active catalyst in the [2 + 2 + 2] cyclotrimerization of terminal alkynes, selectively affording 1,2,4-substituted benzenes from terminal alkynes. In particular, this catalyst outperforms closely related bi- and tridentate phosphine-based Ni catalysts. This suggests a reaction pathway involving a hemilabile interaction of the C-O unit with the nickel center. This is further borne out by a comparative study of the observed resting states and DFT calculations.
- Orsino, Alessio F.,Gutiérrez Del Campo, Manuel,Lutz, Martin,Moret, Marc-Etienne
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p. 2458 - 2481
(2019/03/08)
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- Synthesis method and application for trimethyl 1,3,5-benzene tricarboxylate
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The invention discloses a synthesis method for trimethyl 1,3,5-benzene tricarboxylate. Methyl 3-methoxyacrylate or methyl 3,3-dimethoxypropionate is taken as a raw material, and the raw material is subjected to self molecular condensation and cyclization
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Paragraph 0022
(2019/02/21)
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- METHOD FOR PRODUCING BENZENE COMPOUND AND CATALYST FOR PRODUCING BENZENE COMPOUND
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PROBLEM TO BE SOLVED: To provide a method for producing a benzene compound capable of performing production of various benzene compounds with low environmental load without generating waste as in the case of using benzene as a starting raw material and to provide a catalyst used for the production method. SOLUTION: There are provided: a method for producing a benzene compound from alkynes in the presence of a catalyst, wherein the catalyst is a PdAu supported catalyst obtained by supporting Pd and Au in a molar ratio of 1:1 to 1:10 on a carrier; and a catalyst used for the production method. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT
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Paragraph 0028
(2019/03/02)
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- A water-stable lanthanide coordination polymer as a multiresponsive luminescent sensor for Fe3+, Cr(vi) and 4-nitrophenol
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Constructing water stable lanthanide coordination polymers (Ln-CPs) is of great importance for practical applications in biological and environmental areas and necessary for systematic research on the relationship between the properties of Ln-CPs and stru
- Liu, Yan,Ma, Jingjing,Xu, Cong,Yang, Yang,Xia, Minfang,Jiang, Huie,Liu, Weisheng
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supporting information
p. 13543 - 13549
(2018/10/15)
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- A Degradable and Recyclable Photothermal Conversion Polymer
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Decomposition and repolymerization of conjugated polymers offer great promise for developing recyclable photothermal conversion materials, which yet remain challenging. Herein, a crosslinked conjugated polymer based on a dynamic covalent bond of Schiff base is developed. This polymer possesses photothermal conversion efficiency as high as 90.4 %. Decomposition of the polymer under specialized conditions is corroborated by various characterizations. The kinetics study is also investigated to understand this degradation process. Furthermore, those decomposed species can be repolymerized back to conjugated polymers which possess the same photothermal conversion efficiency as the pristine polymer. Such a degradable and recyclable photothermal polymer is successfully used as a heat source for photothermal-electrical conversion to generate Seebeck voltage under either near infrared (NIR) irradiation or solar illumination.
- Xu, Xiao-Qi,Wang, Zhen,Li, Ruiting,He, Yonglin,Wang, Yapei
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supporting information
p. 9769 - 9772
(2018/07/25)
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- Cyclotrimerization of phenylacetylene catalyzed by a cobalt half-sandwich complex embedded in an engineered variant of transmembrane protein FhuA
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An (η5-cyclopentadienyl)cobalt(i) complex was covalently incorporated into an engineered variant of the transmembrane protein ferric hydroxamate uptake protein component: A, FhuA ΔCVFtev, using a thiol-ene reaction. A CD spectrum shows the structural integrity of the biohybrid catalyst. MALDI-TOF of the segment containing the anchoring site for the cobalt complex Cys545 confirmed successful conjugation. This biohybrid catalyst catalyzed the cyclotrimerization of phenylacetylene to give a mixture of regioisomeric 1,2,4- and 1,3,5-triphenylbenzene in aqueous medium.
- Thiel,Sauer,Mertens,Polen,Chen,Schwaneberg,Okuda
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supporting information
p. 5452 - 5456
(2018/08/12)
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- Pseudo-tetrahedral Rhodium and Iridium Complexes: Catalytic Synthesis of E-Enynes
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The reactions of the rhodium(I) and iridium(I) complexes [M(PhBP3)(C2H4)(NCMe)] (PhBP3=PhB(CH2PPh2)3?) with alkynes have resulted in the synthesis of a new family of p
- Geer, Ana M.,Julián, Alejandro,López, José A.,Ciriano, Miguel A.,Tejel, Cristina
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p. 17545 - 17556
(2018/11/23)
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- Concerted Catalysis by Adjacent Palladium and Gold in Alloy Nanoparticles for the Versatile and Practical [2+2+2] Cycloaddition of Alkynes
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A Pd-Au alloy efficiently catalyzed the [2+2+2] cycloaddition of substituted alkynes. Whereas monometallic Pd and Au catalysts were totally ineffective, Pd-Au alloy nanoparticle catalysts with a low Pd/Au molar ratio showed high activity to give the corresponding polysubstituted arenes in high yields. A variety of substituted alkynes participated in various modes of cycloaddition under Pd-Au alloy catalysis. The Pd-Au alloy catalysts exhibited high air tolerance and reusability.
- Miura, Hiroki,Tanaka, Yumi,Nakahara, Karin,Hachiya, Yuka,Endo, Keisuke,Shishido, Tetsuya
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supporting information
p. 6136 - 6140
(2018/05/03)
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- Tri-Orthogonal Scaffolds for the Solid-Phase Synthesis of Peptides
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Multi-orthogonal scaffolds can be useful for the attachment of several different compounds to the same central skeleton. Such compounds can find applications in the development of protein mimics because of their potential to mimic several distant epitopes
- Pícha, Jan,Fabre, Benjamin,Budě?ínsky, Milo?,Hajduch, Jan,Abdellaoui, Mehdi,Jirá?ek, Ji?í
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p. 5180 - 5192
(2018/08/01)
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- Radiolabeled Dibenzodiazepinone-Type Antagonists Give Evidence of Dualsteric Binding at the M2 Muscarinic Acetylcholine Receptor
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The dualsteric ligand approach, aiming at ligands with improved subtype selectivity, has been increasingly applied to muscarinic receptors (MRs). In this article, we present the synthesis and characterization of a M2R subtype-preferring radiola
- Pegoli, Andrea,She, Xueke,Wifling, David,Hübner, Harald,Bernhardt, Günther,Gmeiner, Peter,Keller, Max
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supporting information
p. 3314 - 3334
(2017/05/05)
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- Method for synthetizing 1,3,5-benzenetricarboxaldehyde from trimesic acid
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The invention provides an experiment method for synthetizing 1,3,5-benzenetricarboxaldehyde by using trimesic acid as raw materials. The experiment conditions are improved; the purification process of the 1,3,5-benzenetricarboxaldehyde is optimized; a 1,3,5-benzenetricarboxaldehyde synthetizing method with mild reaction conditions, low production cost and high product yield is obtained.
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Paragraph 0018
(2018/01/17)
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- Metal-induced supramolecular chirality inversion of small self-assembled molecules in solution
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A non-covalent self-assembled chiral alanyl aminopyridine ligand exhibits supramolecular chirality in solution, independent of the organic solvent used. The supramolecular chirality of the assemblies is completely inverted by complexation to zinc ions. To date, such a supramolecular metal-ligand system has not been reported in the literature.
- Kokan, Zoran,Peri?, Berislav,Vazdar, Mario,Marini?, ?eljko,Viki?-Topi?, Dra?en,Me?trovi?, Ernest,Kirin, Sre?ko I.
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supporting information
p. 1945 - 1948
(2017/02/15)
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- Adsorbed film type imidazoline corrosion inhibitor and preparing method thereof
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The invention discloses an adsorbed type imidazoline corrosion inhibitor and a preparing method thereof. The structural formula of the imidazoline corrosion inhibitor is shown in the description, wherein R is linear-chain or branched-chain hydrocarbon or
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Paragraph 0027; 0028; 0029; 0035-0037; 0043-0045; 0051-0053
(2017/04/29)
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- A pharmaceutical hydrogen-bonded covalent organic polymer for enrichment of volatile iodine
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Porous organic polymers (POPs) are emerging porous materials for various applications. So far, POPs are currently synthesised by a few limited synthetic chemical reactions, leading to a lack of new structures and properties. Thus, expanding structural div
- Lin, Lin,Guan, Heda,Zou, Donglei,Dong, Zhaojun,Liu, Zhi,Xu, Feifan,Xie, Zhigang,Li, Yangxue
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p. 54407 - 54415
(2017/12/12)
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- Pd and Ni complexes of a novel vinylidene β-diketimine ligand: Their application as catalysts in Heck coupling and alkyne trimerization
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A β-diketimine ligand with vinylidene substitution at γ-carbon, CH2C(CH3CNAr)2 (Ar?=?2,6-diisopropylphenyl) (L2), was synthesized by treating β-diketimine H2C(CH3CNAr)2 with n-BuLi followed by paraformaldehyde. L2 formed the homobimetallic ether-bridged β-diketiminate complex [O{(CH2-β-diketiminate)Pd(OAc)}2] (1) with (PdOAc)2. It also gave complexes [L2PdCl2] (2) and [L2NiBr2] (3) when treated with PdCl2(CH3CN)2 and NiBr2(dimethoxyethane), respectively. All the compounds were characterized using 1H/13C NMR spectroscopy and single-crystal X-ray diffraction studies. The catalytic activity of Pd and Ni complexes 1, 2 and 3 was explored in Heck coupling and alkyne trimerization reactions and it was found that they are very good catalysts. The results are reported in detail.
- Beesam, Raghavendra,Nareddula, Dastagiri Reddy
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- POTENT AND SELECTIVE INHIBITORS OF NAV1.7
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Disclosed is a composition of matter comprising an isolated polypeptide, which is a peripherally-restricted NaV1.7 inhibitor. In some disclosed embodiments, the isolated polypeptide is an inhibitor of NaV1.7. Other embodiments are co
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Paragraph 1042
(2016/02/18)
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- Hybrid materials based on novel 2D lanthanide coordination polymers covalently bonded to amine-modified SBA-15 and MCM-41: assembly, characterization, structural features, thermal and luminescence properties
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Three novel 2D coordination polymers [Tb2(μ4-L)2(μ-HL)(μ-HCOO)(DEF)]n (Tb-L), [Eu(μ4-L)(L)(H2O)2]n (Eu-L), and [Nd(μ4-L)(L)(H2O)2]sub
- Wang, Jun,Dou, Wei,Kirillov, Alexander M.,Liu, Weisheng,Xu, Cailing,Fang, Ran,Yang, Lizi
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supporting information
p. 18610 - 18621
(2016/12/03)
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- Synthesis of C3-symmetric tri(alkylamino) guests and their interaction with cyclodextrins
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The synthesis of a series of star-shaped C3-symmetric amines and their inclusion complexation properties toward α-, β-, γ-cyclodextrins and their permethylated derivatives has been described. The star molecules comprise of 1, 3, 5-trisubstited benzene core and the points formed by (alkylamino)methyl or 4-((alkylamino)methyl)phenyl groups. The modes of host-guest interaction were studied by UV-Vis spectroscopy, ITC, 1H NMR and 2D-NMR (NOESY). It was found that star molecules containing (tert-butylamino)methyl, (adamantan-1-ylamino)methyl, 4-((isopropylamino)methyl) phenyl, 4-((tert-butylamino)methyl)phenyl and protonated 4-((adamantan-1-ylamino)methyl)phenyl points form strong host-guest complexes with β-cyclodextrin. It was also proved that the largest C3-symmetric guest can form complexes with bcyclodextrin with stoichiometry 3 which is required for construction of dendrimer supramolecular structures. None of the investigated amines forms a strong complex with permethylated cyclodextrins.
- Bedna?íková, Tereza,Tosňer, Zdeněk,Horsky, Ji?í,Jind?ich, Jind?ich
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p. 141 - 152
(2015/04/22)
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- A facile synthesis of microporous organic polymers for efficient gas storage and separation
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A series of porous hyper-cross-linked polymers with excellent physiochemical stability have been designed and prepared facilely through template-free Friedel-Crafts alkylation reactions between benzene/biphenyl/1,3,5-triphenylbenzene as co-condensing rigid aromatic building blocks and 1,3,5-tris(bromomethyl)benzene or 1,3,5-tris(bromomethyl)-2,4,6-trimethylbenzene as cross-linkers under the catalysis of anhydrous AlCl3 or FeCl3. The systematic study of gas uptake ability shows that anhydrous AlCl3 is a much more effective catalyst than anhydrous FeCl3. The synthesized polymers are thermally stable and are predominantly microporous with high surface areas up to 1783 m2 g-1. In addition, they exhibit high H2 and CO2 uptake capacity/selectivity. Among these materials, C1M3-Al has the highest H2 uptake capacity at 77 K and 1 bar (19.1 mg g-1) and CO2 uptake capacity at 273 K and 1 bar (181 mg g-1); the best CO2/N2 (15/85) selectivity calculated by IAST at 273 K and 1 bar belongs to C1M2-Al (32.3). Moreover, the synthesis route exhibits cost-effective advantages, which are essential for scale-up preparation, thus showing great potential for clean energy applications.
- Liu, Guoliang,Wang, Yangxin,Shen, Chaojun,Ju, Zhanfeng,Yuan, Daqiang
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supporting information
p. 3051 - 3058
(2015/02/19)
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- Peptide dendrimers with designer core for directed self-assembly
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A series of designer peptide dendrimers with urea and urea-triazole cores were synthesized. Urea cored dendrimers assembled into fibrillar morphology, while dendrimers with urea-triazole core assembled into vesicular morphology. The core-dependent self-as
- Verma, Ram P.,Shandilya, Ashutosh,Haridas
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supporting information
p. 8758 - 8765
(2015/10/20)
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- Functionalized defects through solvent-assisted linker exchange: Synthesis, characterization, and partial postsynthesis elaboration of a metal-organic framework containing free carboxylic acid moieties
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Intentional incorporation of defect sites functionalized with free carboxylic acid groups was achieved in a paddlewheel-based metal-organic framework (MOF) of rht topology, NU-125. Solvent-assisted linker exchange (SALE) performed on a mixed-linker deriva
- Karagiaridi, Olga,Vermeulen, Nicolaas A.,Klet, Rachel C.,Wang, Timothy C.,Moghadam, Peyman Z.,Al-Juaid, Salih S.,Stoddart, J. Fraser.,Hupp, Joseph T.,Farha, Omar K.
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supporting information
p. 1785 - 1790
(2015/06/16)
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- Homochiral metal-organic frameworks with enantiopure proline units for the catalytic synthesis of -lactams
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Two enantiopure organic ligands integrating flexible proline units and rigid isophthalate units have been rationally designed and employed for the construction of four homochiral porous metal-organic frameworks (MOFs), respectively. One pair of these MOFs
- Xu, Zhong-Xuan,Tan, Yan-Xi,Fu, Hong-Ru,Liu, Juan,Zhang, Jian
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p. 12199 - 12204
(2015/01/09)
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- Metallaboranes from metal carbonyl compounds and their utilization as catalysts for alkyne cyclotrimerization
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The photolysis of [M2(CO)10] (M=Re or Mn) with BH3·thf at room temperature yields arachno-1 and 2, [(CO) 8M2B2H6] (1: M=Re, 2: M=Mn). Both the compounds show a butterfly structure with seven skeletal electron pairs and 42 valence electrons. This result presents a new method for general access to low-boron-content metal-boron compounds without the cyclopentadienyl ligand at the metal centers. This new synthetic route is superior to the existing procedures because it avoids the use of [LiBH4] and metal polychlorides, for which the synthesis is very tedious. Compound 1 catalyzes the cyclotrimerization of a series of internal and terminal alkynes to yield mixtures of 1,3,5- and 1,2,4-substituted benzenes. The reactivity of 1 with alkynes demonstrates for the first time that the introduction of the [B 2H6] moiety into the [Re2(CO)10] framework significantly enhances the catalytic activity. Note that [Re 2(CO)10] catalyzes the same set of alkynes under harsh conditions over a prolonged period of time. Quantum-chemical calculations using DFT methods are applied to afford further insight into the electronic structure, stability, and bonding of 1 and 2. All the compounds are characterized by IR and 1H, 11B, and 13C NMR spectroscopy, and the geometry of 1 is established unambiguously through crystallographic analysis. Arachno compounds: Room-temperature UV photolysis of [Re2(CO) 10] with BH3·thf yielded arachno-[(CO) 8Re2B2H6], which catalyzed the cyclotrimerization of various internal and terminal alkynes to yield mixtures of 1,3,5- and 1,2,4-substituted benzenes (see figure). Copyright
- Anju,Barik, Subrat Kumar,Mondal, Bijnaneswar,Ramkumar,Ghosh, Sundargopal
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p. 546 - 551
(2014/05/06)
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- Metal-free synthesis of 1,3,5-trisubstituted benzenes by the cyclotrimerization of enaminones or alkynes in water
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The cyclotrimerization reactions of enaminones and electron deficient terminal alkynes have been efficiently performed in water in the presence of only a small amount of lactic acid. The reactions led to the green synthesis of a variety of 1,3,5-triacylbenzenes without using any metal as catalyst. Brief investigation on different elaboration of the triacylbenzene product demonstrated the versatile synthetic application of these 1,3,5-triacylbenzenes. This journal is the Partner Organisations 2014.
- Wan, Jie-Ping,Lin, Yunfang,Hu, Kaikai,Liu, Yunyun
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p. 20499 - 20505
(2014/06/09)
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- Novel analogues of resveratrol: Metabolism and inhibition of colon cancer cell proliferation
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Resveratrol is a phytochemical present in the skin of red grapes, and hence red wine as well as a variety of berries and nuts. It is an anti-oxidant, which has shown cancer chemopreventive properties in preclinical rodent models of carcinogenesis. The bioavailability of resveratrol is low, as it is rapidly metabolised to glucuronides and sulfates. The pharmacological activities of conjugate metabolites of phenols are often much lower than those of their metabolic progenitors. Therefore chemical synthetic manipulations aimed at slowing the rate of metabolic conjugation of phenols may generate analogues with increased bioavailability and efficacy. Here we describe the synthesis using the Wittig-Horner-Emmons reaction of a new series of resveratrol analogues in which the phenol moieties were systematically replaced by hydroxymethyl and/or methoxy groups. Incubation of analogues, which lack phenol groups with phase II metabolising enzyme preparations generated hardly any, or only small amounts of, conjugates. Four of the new analogue inhibited the growth of human-derived HCA-7 colon cancer cells, but with much less potency than resveratrol.
- Simon, Charles,Britton, Robert G.,Cai, Hong,Gescher, Andreas J.,Brown, Karen,Jenkins, Paul R.
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p. 6203 - 6212
(2013/07/19)
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- Transition-metal variation as a probe into the catalytic activity of metallaboranes
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The reactivity of two isoelectronic and isostructural metallaboranes, nido-[(Cp*Rh)2B6H10], 1 and nido-[(Cp*Ru)2B6H12], 2 with alkynes demonstrates that a change in metal from group 9 to group 8 creates difference in the reactivity pattern. Compound 1 catalyzes the cyclotrimerization of a variety of internal and terminal alkynes to yield 1,3,5- and 1,2,4-substituted benzene. In contrast, compound 2 shows no reactivity toward alkynes. A set of alkynes have been verified with nido-1 that yielded several benzene derivatives in satisfactory yields.
- Anju,Roy, Dipak Kumar,Anju,Ghosh, Sundargopal
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- Reactivity of the 16-electron CpCo half-sandwich complex containing a B(3,6)-disubstituted o-carborane-1,2-dithiolate ligand
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The 16-electron (16e) half-sandwich complex CpCo(S2C 2B10H8)(CHCHCO2Me)2 (1; Cp = cyclopentadienyl) was considered as inert owing to hindered di-substitution at B sites. However in methanol complex 1 reacts with ethynylferrocene (FcCCH) and dimethyl acetylenedicarboxylate (DMAD, MeO2CCCCO2Me) to lead to two-fold alkyne insertion at Co-S bond to give rise to unusual stable 18e adduct CpCo(S2C2B10H8) (CHCHCO2Me)2(HCCFc)(MeO2CCCCO2Me) (2) containing mixed alkynes. Also in methanol complex 1 undergoes intramolecular hydrogen transfer of one CHCHCO2Me unit to adjacent carbon to form a CH2CCO2Me unit, thus producing the 18e complex CpCo(S2C2B10H8)[CH 2CCO2Me][CHCHCO2Me] (3). Further investigation indicates that complex 1 can catalyze [2 + 2 + 2] cycloaddition of alkynes. The catalytic efficiency is determined by temperature and nature of alkynes. In THF in the presence of [N(n-Bu)4]Br complex 1 is transformed to ionic complex [N(n-Bu)4]+[Co(S2C2B 10H8)2(CHCHCO2Me)4] - (4), in which metal-dithiolene is planar. Analogous [N(n-Bu) 4]+[Co(S2C2B10H 9)2(CHCHCO2Me)2]- (5) was also synthesized from mono-substituted precursor CpCo(S2C 2B10H9)(CHCHCO2Me) (1′). The electrochemical properties of both 4 and 5 show significant positive shift of redox peaks versus the analogous bis(1,2-benzenedithiolato)cobaltate (III) (Co(bdt)2). Reactivity of both neutral 16e CpCo complexes and ionic metal-dithiolene derivatives declines with the increase of substituents on carborane cage. All the new compounds have been characterized by NMR, IR, mass spectrometry, elemental analysis, and 2, 3, and 4 have been structurally characterized by X-ray diffraction.
- Tang, Xiao,Wang, Zhaojin,Li, Yizhi,Yan, Hong
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supporting information
p. 90 - 97
(2013/11/19)
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- Selective oxidation of alcohols to esters using heterogeneous Co 3O4-N@C catalysts under mild conditions
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Novel cobalt-based heterogeneous catalysts have been developed for the direct oxidative esterification of alcohols using molecular oxygen as benign oxidant. Pyrolysis of nitrogen-ligated cobalt(II) acetate supported on commercial carbon transforms typical homogeneous complexes to highly active and selective heterogeneous Co3O4-N@C materials. By applying these catalysts in the presence of oxygen, the cross and self-esterification of alcohols to esters proceeds in good to excellent yields.
- Jagadeesh, Rajenahally V.,Junge, Henrik,Pohl, Marga-Martina,Radnik, Joerg,Brueckner, Angelika,Beller, Matthias
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supporting information
p. 10776 - 10782
(2013/08/23)
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- Poly(ethylene glycol) grafted polystyrene dendrimer resins: Novel class of supports for solid phase peptide synthesis
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Poly(propyleneglycol)dimethacrylate cross-linked support using monomers Styrene and 4-chloromethyl styrene (PS-PPGDMA-VBC resin) was prepared by suspension polymerization method. Dendritic templates were synthesized from Schiff base and trimesic acid molecules and assembled independently on PS-PPGDMA-VBC support to the second generation. N,N-bischloro ethyl amine dendrimer was generated from Schiff base units and introduced to the chloromethyl groups uniquely through secondary amine. It was followed by acidolytic cleavage, diazotization and thionyl chloride reactions leading to first generation dendrimer. O-benzyl ether dendrimer was created using 1,3,5-tris(hydroxyl methyl)benzene unit which was produced by the LiAlH 4 reduction of carbonyl groups of trimesic acid molecule. The hydroxyl methyl groups formed were converted to chloro methyl groups by adding thionyl chloride that leads to first generation dendrimer. Similar synthetic routes were followed to produce second generation dendrimers too. Poly(ethylene glycol), Mn ≈ 1500) has been grafted to chlorine termini of both dendrimers and used to check various physical and chemical properties of different peptide synthetic conditions. Reactions were qualitatively analyzed by FTIR, 13C NMR, SEM and quantitatively analyzed by UV measurements and CHN analysis. Classically difficult ACP sequence was synthesized on both PEGylated dendrimer supports and compared to Tenta Gel. Biologically significant disulfide bonded endothelin class of peptides were also synthesized using novel supports using various literature reported methods.
- Siyad,Kumar, G.S. Vinod
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p. 4076 - 4090
(2012/11/13)
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- Crystal engineering of a microporous, catalytically active fcu topology MOF using a custom-designed metalloporphyrin linker
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A 12-connected fcu metal-organic framework (MOF), MMPF-3, has been prepared using a CoII metalloporphyrin. MMPF-3 is comprised of the same polyhedral supermolecular building blocks as the prototypal fcu-MOF, fcu-MOF-1, and its nanoscale cavities feature 18 catalytically active cobalt centers. The high density (ca. 5 cobalt sites/nm3) affords MMPF-3 superior performance in catalytic epoxidation of trans-stilbene compared to other MOFs. Copyright
- Meng, Le,Cheng, Qigan,Kim, Chungsik,Gao, Wen-Yang,Wojtas, Lukasz,Zaworotko, Michael J.,Zhang, X. Peter,Ma, Shengqian,Chen, Yu-Sheng
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supporting information
p. 10082 - 10085,4
(2020/09/09)
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- Exploiting guanidine as a ligand in cobalt-catalyzed alkyne cyclotrimerizations
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The synthesis of polysubstituted arenes is accomplished via the regioselective cyclotrimerization of alkynes utilizing a guanidine-ligated cobalt catalyst. Georg Thieme Verlag Stuttgart - New York.
- Eichman, Chad C.,Bragdon, Jason P.,Stambuli, James P.
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supporting information; experimental part
p. 1109 - 1112
(2011/06/20)
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- Palladium nanoparticles-decorated graphene nanosheets as highly regioselective catalyst for cyclotrimerization reaction
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Novel palladium nanoparticles/graphene-based composites were prepared by a method involving palladium nanoparticles in situ growth on chitosan- functionalized graphene. The resulted composites showed uniform palladium nanoparticles distribution, which were characterized by Fourier transform infrared spectrometry (FTIR), transmission electron microscopy (TEM), scanning electron microscopy (SEM), Raman spectroscopy, atomic force microscopy (AFM), X-ray diffraction spectroscopy (XRD) and electron diffraction pattern (ED), etc. Moreover, such graphene-based nanocomposites were successfully applied to catalyze the cyclotrimerization of acetylene with high regioselectivity (=99.5%) and superior recycling performance without the assistance of any ligands. Copyright
- Cheng, Jinsheng,Tang, Longhua,Li, Jinghong
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experimental part
p. 5159 - 5168
(2012/07/28)
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- Cyclotrimerization of alkynes catalyzed by the naphthalene ruthenium complex [CpRu(10H8)] +
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The naphthalene ruthenium complex [CpRu(10H8)] + (in the presence of Cl- ions) catalyzes the cyclotrimerization of 2,2-dimethyl-5,5-dipropargyl-1,3-dioxane-4,6-dione with alkynes (acetylene, hex-1-yne, hex-3-yne, oct-1-yne, phenylacetylene, trimetylsilylacetylene, octa-1,7-diyne, pent-1-yn-5-ol, methyl propargyl ether, and propargyl acetate) giving tricyclic aromatic compounds in 55-85% yields.
- Perekalin,Trifonova,Petrovskii,Kudinov
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experimental part
p. 2110 - 2113
(2012/09/22)
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