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Ruthenium(Ⅱ) Containing Supramolecular Polymers for Photovoltaic Applications

Ruthenium(Ⅱ) Containing Supramolecular Polymers for Photovo...

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中国化学会第八届有机化学学术会议暨首届重庆有机化学国际研讨会

作者： Feng,Kui Shen,Xiaoyan Li,Ying Peng,Qiang College of Chemistry Sichuan University

Considerable attention has been paid to polymer solar cells(PSCs)due to their unique advantages of low cost,flexibility,easy fabrication,light-weight nature and solution processability for large-area ***,it is imperative for exploration and development of new polymer systems with novel concepts maintaining the low cost objective of *** chemistry is a relatively new field of chemistry and materials,which focuses quite literally on going"beyond"molecular *** combination of supramolecular chemistry and polymer science has led to the appearance of supramolecular polymers,which are made up of repeating blocks held together with directional and reversible non-covalent ***,the defined properties of small molecules and the processing advantages of polymers can be merged at the same *** this paper,we describe the synthesis,characterization and photovoltaic properties of two novel Ru(Ⅱ)containing supramolecular polymers with D-A-D bis-terpyridyl ligands(PHBTRU and PFBTRU).By incorporation of the cyclopenta[2,1-b:3,4-b’]dithiophene,thiophene donor units with benzodiazole and fluorinated benzodiazole acceptor units at the cores of bis-terpyridyl ligands in the prepared Ru(Ⅱ)containing polymers,excellent thermal stabilities,good absorptions and ideal energy levels were *** photovoltaic properties were also examined in detail with an optimized PCE of 2.66%,which is the best efficiency of the reported supramolecular polymer-based PSCs so far.

关键词： supramolecular polymers ruthenium complex cyclopentadithiophene benzothiazole polymer solar cell

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One-Pot Synthesis and Biological Evaluation of Spiroisoxazolines against PTP1B

One-Pot Synthesis and Biological Evaluation of Spiroisoxazol...

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中国化学会第八届有机化学学术会议暨首届重庆有机化学国际研讨会

作者： Wang,Wen-Long Chen,Xia Gao,Li-Xing Li,Jia Feng,Bainian School of Pharmaceutical Science Jiangnan University State key Laboratory of Drug Research Shanghai Institute of Materia MedicaChinese Academy of Sciences

Protein tyrosine phosphatase 1B(PTP1B),an intracellular nonreceptor PTPase,has received much attention due to its pivotal role in type Ⅱ diabetes and obesity as a negative regulator of the insulin signaling pathway by dephosphorylating the activated insulin receptor[1],therefore been viewed as a potential target for the treatment of type 2diabetes.A variety of PTP1B inhibitors have been disclosed among academic and industrial laboratories[2].However,there are two significant challenges to develop orally bioavailable,small molecular PTP1B inhibitors[3]:(1)it difficult to design inhibitors that are specific for PTP1B due to the close homology with other PTPs,and(2)many small molecules that bind with high affinity in active site are hydrophilic,and as a result they have poor cell ***,imminent development of potent and PTP1B specific inhibitor remains *** have been found extensive usage as pharmacophores with a wide array of bioactivities[4].In searching for novel PTP1B inhibitors,we synthesized a small library containing 20 spiroisoxazoline derivatives with the one-pot *** compounds showed moderate PTP1B inhibitory *** results provided novel lead compounds for the design of inhibitors of PTP1B as well as other PTPs.

关键词： spiroisoxazolines one-pot synthesis PTP1B inhibitors selectivity

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Pd（PPh3）4-catalyzed direct ortho-fluorination of 2-arylbenzothiazoles with an electrophilic fluoride N-fluorobenzenesulfonimide（NFSI）

Pd（PPh3）4-catalyzed direct ortho-fluorination of 2-arylben...

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中国化学会第八届有机化学学术会议暨首届重庆有机化学国际研讨会

作者： Ding,Qiuping Ye,Changqing Pu,Shouzhi Jiangxi Key Laboratory of Organic Chemistry Jiangxi Science & Technology Normal University Key Laboratory of Functional Small Organic Molecules Ministry of Education and College of Chemistry & Chemical EngineeringJiangxi Normal University

2-Arylbenzothiazoles as privileged motifs are present in many natural products and pharmaceuticals that exhibit remarkable biological and therapeutic activities, such as antitumor, antiviral, and antimicrobial activities. The substitution of hydrogen with fluorine can dramatically improve the physical, chemical, and biological activity of organic molecules. Recently, there are more than 20% newly registered pharmaceuticals and 40% agrochemicals containing one or more fluorine atoms. In particular, fluoro-substituted-1,3-benzothiazoles are versatile building blocks found in a broad range of pharmaceutically active molecules. In addition, fluoro-substituted-1,3-benzothiazoles have been used as phosphorescent material. Although much remarkable achievements have been made in C–F bond formation in the last few years, development of more efficient methods via ligand-directed C–H bond activation/fluorination for the synthesis of fluorine containing arenes is still full of challenge[1-3]. Herein, we reported the simple Pd(0)-catalyzed direct C–H bond fluorination to synthesize fluoro-substituted-1,3-benzothiazoles 2 and 3 using an electrophilic fluoride(NFSI) promoted by L-proline. The reaction tolerated a range of different substrates with a variety of functional groups. The present protocol offered an efficient route to synthesize valuable fluorinated products, which are of potential importance in the pharmaceutical and agrochemical industries.

关键词： 2-arylbenzothiazoles fluorine atoms L-proline

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Exploration of New Reactivities Mediated by Hypervalent Iodine Reagents

Exploration of New Reactivities Mediated by Hypervalent Iodi...

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中国化学会第八届有机化学学术会议暨首届重庆有机化学国际研讨会

作者： Zhang,Chi 南开大学元素有机化学国家重点实验室天津化学化工协同创新中心

As a kind of efficient, high selective and environment-friendly oxidative reagents, hypervalent iodine compounds have received much attention recently. Along with their relative simple preparation and mild reaction condition, more importantly, they have shown versatile reactivity, realized various transformations, and been applied widely in the total syntheses of natural products and new functional materials. In the last several years, Zhang and coworkers devoted to the new reaction exploration of hypervalent iodine compounds, design and synthesis of novel hypervalent iodine reagents, and the research of reactions mediated by chiral hypervalent iodine reagents. Alcohols are ubiquitous in nature. The oxidation of alcohol is one of most valuable conversions in organic chemistry. Zhang and coworkers developed the methods for the synthesis of carbamoyl azides from the primary alcohol by using the combination of Ph ICl2/Na N3 and ureas by the use of Ph I(OAc)2/Na N3 system. These protocols introduced four or two nitrogen atoms into primary alcohols in one-pot procedure, which showed high step-economy[1-3]. Intermolecular C-O and C?N bond formation are the significant reaction in synthetic chemistry, especially for the metal-free process. Zhang and coworkers developed the method for effective introduction of various oxygen-containing functionalities to β-dicarbonyl compounds with p-iodotoluene difluoride(Tol IF2), and reported the direct α-amination of β-dicarbonyl compounds using iodosobenzene(Ph IO). These methods enriched the present transformation mediated by hypervalent iodine reagent[2-5]. IBX is a commonly used oxidant in organic synthesis. The insolubility of IBX in common organic solvents is a major drawback to restrict its practical application. Zhang and coworkers prepared two water-soluble and stable organo-pentavalent iodine reagents, which showed specific reactivity that was different with IBX. Besides, exploration of other novel reaction with these oxidants

关键词： hypervalent iodine reagents new reactivities oxidation peptide coupling reagents

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Construction of Multi-porphyrin Arrays through Suzuki-Miyaura Reaction

Construction of Multi-porphyrin Arrays through Suzuki-Miyaur...

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中国化学会第八届有机化学学术会议暨首届重庆有机化学国际研讨会

作者： Song Jianxin College of Chemistry and Chemical Engineering Hunan Normal University

Porphyrins are widely seen in nature, such as heme and cholophyll. Highly conjugated multi-porphyrin arrays have received much attention in light of their potential applications in optoelectronic devices, sensors, photovoltaic devices, non-linear optical(NLO) materials, photodynamic therapy(PDT) pigments, and light-harvesting models. The manipulation of interporphyrinic interaction is often essential to achieve desirable electronic and photophysical properties. In order to prepare multi-porphyrin arrays, many strategies have been used. Ten years before, Osuka group has developed a transition metal-catalyzed coupling reaction that has proven to be very useful to construct multiporphyrinic systems, but it is difficult to ask the reaction to stop at the needed step. And then they also developed a palladium catalyzed cross coupling of borylated porphyrins and aryl halides, it is used to synthesize some porphyrin arrays which could not be obtained in other *** have successfully synthesized 2,5-thienylene bridged β-to-β porphyrin nanorings, 2,6-pyridylene-bridged β-to-β porphyrin nanorings, directly Pd(II)-bridged porphyrin belts, porphyrin barrel, and meso,meso-porphyrinic bridged β-to-β porphyrin nanorings by this way. The photophysical study revealed that these porphyrin arrays exhibit either longer fluorescent lifetime or larger two photon absorption values. Although the borylated porphyrins are almost able to react with any aryl halides bought from market, it is still difficult to synthesis any porphyrin arrays as you need. Motivated by fascinating structure and properties of multi-porphyrin arrays, some new porphyrin arrays recently have been synthesized through Pd-catalyzed cross-coupling reactions in our lab with suitable precusor(Chart 1).

关键词： multi-porphyrin arrays cross-coupling reaction palladium-catalyzed

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Selective Reductive Cleavage of Inert Aryl C-O Bonds Catalyzed by an Iron Catalyst

Selective Reductive Cleavage of Inert Aryl C-O Bonds Catalyz...

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中国化学会第八届有机化学学术会议暨首届重庆有机化学国际研讨会

作者：王乾任运来商欢涛田明田欣哲河南科技大学化工与制药学院

Transition-metal catalyzed activation of aryl carbon-oxygen bonds is a challenging task for organic chemists due to their relatively high bond energy[1]. Although various effective Ni catalysts have been developed for activating the aryl C-O bonds to form carbon-carbon and carbon-heteroatom bonds[2], it is desirable to develop a nontoxic and low-cost iron catalyst from the environmental and economic perspectives[3]. In this paper, a catalytic system initiated from a solution containing ferric acetylacetonate was demonstrated to catalyze the reductive cleavage of inert aryl C-O bonds without saturating the aromatic rings(see the following Scheme). Preliminary mechanistic investigation suggests that heterogeneous species served as the active catalyst. Unlike the previously reported Ni catalyst systems[4,5], the present iron catalyst is low-cost and unique in its high effectiveness for the cleavage of typical aryl C-O bonds in phenyl methyl *** diphenyl ethers were employed as the substrates, only phenyl C-O bonds were cleaved, and hydrogenation of the π-bonds in phenyl rings hardly occurred. This complete selectivity for the cleavage of the C-O bonds over the hydrogenation of phenyl π-bonds is in a clear contrast to the hydrogenation of aryl ethers on heterogeneous catalysts[5], which typically leads to a mixture of arenes, cycloalkanes, phenols and cycloalkanols. In the coexistence of aryl C-O and alkyl C-O bonds, the reductive cleavage selectively occurred at the aryl C-O bonds, and only trace amounts of alkyl C-O bond-cleavage products were observed. Phenyl methyl ether without substitute group showed poor reactivity, while the introduction of methoxy or phenyl group to the phenyl rings increased the reactivity of phenyl methyl ether.

关键词： aryl C-O bonds reductive cleavage iron

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N-Oxide as a Traceless Oxidizing Directing Group:Mild Rhodium(Ⅲ)-Catalyzed C–H Olefination for the Synthesis of ortho-Alkenylated Tertiary Anilines

N-Oxide as a Traceless Oxidizing Directing Group:Mild Rhodiu...

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中国化学会第八届有机化学学术会议暨首届重庆有机化学国际研讨会

作者： Huang,Xiaolei Song,Feijie Lan,Jingbo Gao,Ge You,Jingsong College of Chemistry Sichuan University

Tertiary anilines are important structural motifs and their functionalization has been attracting great interest in the synthetic organic chemistry *** electron-donor characteristics and the steric hindrance of tertiary amino groups commonly lead to the preferential para-functionalization of anilines through the Friedel-Crafts *** is reasoned that the transition metal-catalyzed chelation-assisted aromatic C–H functionalization through a cyclometalation should be an ideal strategy to meet these substantial challenges[1].However,the direct use of the amino group of tertiary anilines as the directing group is challenging because the the four-membered cyclometalated intermediate is usually uneasily ***,the use of oxidizing directing groups as both an internal oxidant and a directing group is starting to attract interest in C–H activation[2].Considering that easily available N-oxides are not only prototypical oxidants[3],but also easily coordinate with metal centers[4],we envisioned that the two properties could be combined to develop a traceless oxidizing directing strategy to achieve ortho-selective aromatic C–H functionalization of tertiary *** this work,we have addressed for the first time a traceless internal oxidant/directing strategy to achieve ortho-C–H functionalization of tertiary *** novel tactics has demonstrated a highly selective ortho-C–Holefination of easily available tertiary aniline N-oxides to prepare 2-alkenylated tertiary *** rhodium-catalyzed external-oxidant-free synthesis presents a series of advantages,such as very mild condition(room temperature),avoidance of bisolefinated anilines,complete ortho-selectivity,and relatively broader functional group *** five-membered cyclometalated Rh(Ⅲ)complex is proposed as a plausible intermediate and testified by X-ray crystallographic analysis.

关键词： oxidizing directing group tertiary anilines ortho-C–H activation olefination

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