Chinese Journal of Chemistry

Cover image for Vol. 31 Issue 6

June, 2013

Volume 31, Issue 6

Pages 705–860

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Communication
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    6. Note
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      Cover Picture: Molecular Switches and Multiple Logic Gates Based on 4-(2-Pyridylazo)resorcinol (Chin. J. Chem. 6/2013) (page 705)

      Zhanhui Tao, Yinan Qin, Yaqing Liu, Lei Xu and Erkang Wang

      Article first published online: 14 JUN 2013 | DOI: 10.1002/cjoc.201390014

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      The cover picture shows A simple-structured 4-(2-pyridylazo)resorcinol (PAR) system whichpresents interesting properties with dual fluorescent outputs. Modulated by solution pH two kinds of reversible switch behaviors, "ON-OFF" and "OFF-ON", were realized with the PAR system. Stimulated by different combination of external stimulus, such as metal ions, UV irradiation and solution pH, the PAR system could perform multiple logic functions including three inputs AND, two inputs INHIBIT and combinatorial "NOR/AND" in parallel. The operation of the designed system is very simple and detected with a high sensitive fluorescent signal.

  2. Contents

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Communication
    5. Full Papers
    6. Note
    1. Contents: Chin. J. Chem. 6/2013 (pages 707–717)

      Article first published online: 14 JUN 2013 | DOI: 10.1002/cjoc.201390015

  3. Communication

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    4. Communication
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    6. Note
    1. Drug Target Identification Using Affinity Core-Shell Magnetic Nanoparticles and Mass Spectrometry (pages 715–720)

      Yunhuan Wei, Tongdan Wang, Chao Liu, Qianqian Zhang, Lishun Wang, Gongli Tang and Jingwu Kang

      Article first published online: 29 APR 2013 | DOI: 10.1002/cjoc.201300145

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  4. Full Papers

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Communication
    5. Full Papers
    6. Note
    1. Molecular Switches and Multiple Logic Gates Based on 4-(2-Pyridylazo)resorcinol (pages 721–725)

      Zhanhui Tao, Yinan Qin, Yaqing Liu, Lei Xu and Erkang Wang

      Article first published online: 29 APR 2013 | DOI: 10.1002/cjoc.201300109

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      Stimulated by different combination of external stimulus, including metal ions, UV irridiation and solution pH, the PAR system could perform multiple logic functions, presenting great potential for the construction of molecular devices.

    2. Enantioselective Organocatalytic Aza-Michael Additions of Phthalimide Derivatives to α,β-Unsaturated Aldehydes (pages 726–730)

      Shijun Ma, Ming Liu, Yaodong Huang and Yongmei Wang

      Article first published online: 21 MAY 2013 | DOI: 10.1002/cjoc.201300175

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      Phthalimide derivatives as nitrogen nucleophiles with α,β-unsaturated aldehydes for asymmetric aza-Michael additions have been reported. The reactions proceed smoothly to afford corresponding Michael adducts in good yields (up to 98%) and enantioselectivities (up to 95% ee).

    3. Morphology and Performance of Poly(2-methoxy-5-(20-ethyl-hexyloxy)-p-phenylenevinylene) (MEH-PPV):(6,6)-phenyl-C61-butyric Acid Methyl Ester (PCBM) Based Polymer Solar Cells (pages 731–736)

      Leijing Liu, Svetlana van Bavel, Shanpeng Wen, Xiaoniu Yang and Joachim Loos

      Article first published online: 21 MAY 2013 | DOI: 10.1002/cjoc.201300135

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      Some voids were found in the MEH-PPV:PCBM composite films, and the number of the voids decreases with the solvent. We found the voids are located at the bottom of the films through the electron tomography technique by transmission electron microscopy and film bottom-side morphology study by atomic force microscopy. The voids are disadvantageous to the device performance.

    4. Multicomponent Domino [4+1+1] Carbocyclization Providing an Efficient and Regioselective Strategy to Fluoren-9-ones (pages 737–744)

      Ying Li, Haiwei Xu, Liping Fu, Qingqing Shi, Bo Jiang and Shujiang Tu

      Article first published online: 29 MAY 2013 | DOI: 10.1002/cjoc.201201218

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      Concise and efficient three-component domino [4+1+1] carbocyclization to highly substituted fluoren-9-one derivatives promoted by K2CO3 has been developed under microwave irradiation conditions.

    5. Morphology Control of Bi2S3 Nanostructures and the Formation Mechanism (pages 752–756)

      HeeJin Kim, Ji-eun Park, Kyung Kim, Mi-Kyung Han, Sung-Jin Kim and Wooyoung Lee

      Article first published online: 29 APR 2013 | DOI: 10.1002/cjoc.201300006

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      Bismuthinite (Bi2S3) nanostructures were prepared by a hydrothermal method with sodium ethylenediaminetetraacetate (EDTA-Na2). The successful synthesis of various morphologies of nanostructured Bi2S3 may open up new possibilities for thermoelectric, electronic and optoelectronic uses of nanodevices based on Bi2S3 nanostructure.

    6. Highly Efficient Low Melting Mixture Catalyzed Synthesis of 1,8-Dioxo-dodecahydroxanthene Derivatives (pages 757–763)

      Peihe Li, Feiping Ma, Ping Wang and Zhanhui Zhang

      Article first published online: 21 MAY 2013 | DOI: 10.1002/cjoc.201300152

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      Low melting citric acid-urea mixture was found to be a new and effective promoting medium for the environmentally friendly synthesis of 1,8-dioxo-dodecahydroxanthene derivatives by condensation of aromatic aldehydes and cyclic 1,3-dicarbobonyl compounds. This deep eutectic solvent acts as both the reaction medium and catalyst, furnishing xanthenediones in high to excellent yield.

    7. Efficient Synthesis of Unsymmetrical Heteroaryl Ethers by a Transition Metal-Free C[BOND]O Cross-Coupling Reaction of Activated and Unactivated Heteroaryl Chlorides with Alcohols and Phenols (pages 764–772)

      Quan Liu, Zhongxiang Lu, Wenfei Ren, Kaibo Shen, Yu Wang and Qing Xu

      Article first published online: 29 APR 2013 | DOI: 10.1002/cjoc.201300120

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      By optimizing the reaction conditions via a careful screening of the bases and solvents, we developed an efficient transition metal-free method for C[BOND]O cross-coupling of activated and unactivated heteroaryl chlorides with primary and secondary alcohols and phenols, providing a simple, efficient, and practical method for synthesis of the useful unsymmetrical heteroaryl alkyl and heteroaryl aryl ethers.

    8. Carboalumination-Epoxide Ring Opening for the Formation of 1,4-Disubstituted (Z)-3,6-Alkadienols (pages 773–778)

      Quan Zhang, Yuhuan Jing, David C. Myles, Yong Li and Yue Chen

      Article first published online: 29 MAY 2013 | DOI: 10.1002/cjoc.201300235

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      Allylalumination of alkynes (i.e. forming Negishi's (Z)-alkenyl dialkylalane) followed by alkenylation of epoxides provides 1,4-disubstituted (Z)-3,6-alkadienols. The alkenylation can be facilitated by the presence of a neighbouring coordinating group in the epoxides. This "one-pot" approach has been successfully applied in the large-scale production of C10–C15 fragment of 9,10-didehydroepothilone D (a synthetic epothilone analog as an anti-cancer agent in phase 2 clinical trials).

    9. Synthesis, Structure and Photophysical Properties of Silole-Oxadiazole Copolymers (pages 779–786)

      Tingting Zhang, Chaoqiang Zhu, Yuwen Ma, Chengyun Wang and Yongjia Shen

      Article first published online: 29 MAY 2013 | DOI: 10.1002/cjoc.201300121

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      Conjugated polymers PTST-DyOXD and PTST-OXD were synthesized by Pd(0)-catallyzed Sonogashira or Suzuki coupling reaction.

    10. Continuous Detection of pH-responsive Drug Delivery System in Cells in situ by Confocal Laser Scanning Microscopy (pages 787–793)

      Yang Sun, Zhipeng Ran, Hongyan Tang, Yong Li, Wenshuang Song, Qingguang Ren, Wuli Yang and Jilie Kong

      Article first published online: 21 MAY 2013 | DOI: 10.1002/cjoc.201300113

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      A continuous detection of pH-responsive drug delivery system in cells in situ, utilizing MSN/CS-PMAA composite microspheres, was proposed. The continuous fluorescent observation in situ could be widely used in the pH-responsive releasing process of drug delivery system in the cells.

    11. Transition-Metal-Free TEMPO Catalyzed Aerobic Oxidation of Alcohols to Carbonyls Using an Efficient Br2 Equivalent under Mild Conditions (pages 794–798)

      Jie Zhang, Zengqiang Jiang, Dan Zhao, Guozhen He, Shuangli Zhou and Shiqing Han

      Article first published online: 21 MAY 2013 | DOI: 10.1002/cjoc.201300052

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      An effective transition-metal-free catalytic system is developed for aerobic oxidations of alcohols. Using catalytic amount of bromide-bromate coupling, H2SO4, and NaNO2, together with 2,2,6,6-tetramethylpiperidine N-oxyl radical (TEMPO) in the presence of air, various alcohols could be converted into the corresponding aldehydes or ketones in good to excellent isolated yields under mild conditions.

    12. CuI-Catalyzed Multicomponent Synthesis of Aminoindolizines from Aldehydes, Amines, and Alkynes under Solvent-Free Conditions (pages 799–804)

      Changming Pan, Jianping Zou and Runsheng Zeng

      Article first published online: 21 MAY 2013 | DOI: 10.1002/cjoc.201201211

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      A direct and efficient approach to 1-aminoindolizines through three-component one-pot reaction of heteroaryl aldehydes, secondary amines and terminal alkynes catalyzed by CuI under solvent-free conditions has been developed. This methodology provides a rapid access to substituted aminoindolizines with good yields (up to 97%).

    13. Synthesis and Antitumor Activity Evaluation of γ-Monofluorinated and γ,γ-Difluorinated Goniothalamin Analogues (pages 805–812)

      Yi Yang, Zhenjun Yang, Chunru Cheng and Fengling Qing

      Article first published online: 21 MAY 2013 | DOI: 10.1002/cjoc.201300227

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      A series of novel γ,γ-difluorinated Goniothalamin analogues 4a4i and 6a6i were synthesized by way of lipase AK catalyzed kinetic resolution, Stille coupling and 1,5-oxidative cyclization. These difluorinated analogues and several monofluorinated analogues were biologically evaluated together against four different cancer cell lines. From the analysis of bioassay data, it was found that adding one fluorine at the γ position of Goniothalamin was a better modification than introducing two fluorine atoms.

    14. Theoretical Study on the Cyclization Mechanism of Dipeptides (pages 813–818)

      Ping Xia, Chen Wang and Chenze Qi

      Article first published online: 21 MAY 2013 | DOI: 10.1002/cjoc.201300035

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      Theoretical calculations were carried out to investigate the mechanism of the cyclization of dipeptides. The "proton shuttle"-catalyzed stepwise mechanism is most favored and the attack of the N-terminal amino nitrogen at the C-terminal carbonyl carbon along with the proton transfer is the rate-limiting step. The solvation effect, electronic effect and steric effect were found to contribute to the cyclization.

    15. Sol-gel Synthesis and Electrochemical Performance of Li4−xMgxTi5−xZrxO12 Anode Material for Lithium-ion Batteries (pages 819–825)

      Caixia Qiu, Zhongzhi Yuan, Ling Liu, Sijie Cheng and Jincheng Liu

      Article first published online: 29 MAY 2013 | DOI: 10.1002/cjoc.201201111

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      The anode materials Li4−xMgxTi5−xZrxO12 (x=0, 0.05, 0.1) were successfully synthesized by sol-gel method. The crystalline structure, morphology and electrochemical properties of the as-prepared materials were characterized by XRD, SEM, electrochemical impedance spectroscopy (EIS) and charge-discharge cycling tests. The as-prepared material Li3.95Mg0.05Ti4.95Zr0.05O12 represented a relatively good rate capability and cycling stability.

    16. Promotion of Mn Doped Co/CNTs Catalysts for CO Hydrogenation to Light Olefins (pages 826–830)

      Liping Tang, Chengli Song, Xiaolong Yang, Mengli Li and Bin Hu

      Article first published online: 29 MAY 2013 | DOI: 10.1002/cjoc.201300248

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      A series of Mn doped Co/CNTs catalysts was prepared and used for CO hydrogenation to light olefins. The results indicate that the addition of a small amount of Mn (0.3 wt%) to CNTs-supported Co catalyst significantly increased the selectivity of C2–C4 olefins and decreased the selectivity of CH4. However, with further addition of Mn to the cobalt catalysts, the CH4 selectivity decreased obviously along with the increase of the C5+ selectivity. Compared with the unpromoted catalysts, the Mn-promoted cobalt catalysts increased the C2[DOUBLE BOND]–C4[DOUBLE BOND]/C20–C40 molar ratio.

    17. Synthesis, Structure and H+/K+-ATPase Inhibitory Activity of Novel Triazolyl Substituted Tetrahydrobenzofuran Derivatives via One-pot Three-component Click Reaction (pages 831–836)

      Hubiao Fang, Lei Jin, Nianyu Huang, Junzhi Wang, Kun Zou and Zaigang Luo

      Article first published online: 29 APR 2013 | DOI: 10.1002/cjoc.201300119

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      Eleven triazolyl substituted tetrahydrobenzofuran derivatives were synthesized in high yields as novel H+/K+-ATPase inhibitor via one-pot CuI-catalyzed three-component click reaction under mild conditions in water, and most of them exhibited better H+/K+-ATPase inhibitory activity than commercial omeprazole with IC50 values less than 15 µmol·L−1.

    18. Ionic Bent Shape Ternary Facial Amphiphiles (pages 839–844)

      Chixian He, Qingye He, Sijing Zhang, Xiaoping Tan, Hongfei Gao and Xiaohong Cheng

      Article first published online: 29 MAY 2013 | DOI: 10.1002/cjoc.201201165

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      Synthesized bent shape tenary facial amphiphilic imidazolium salt can self-organize into a hexagonal columnar mesophase with core shell structure.

    19. (4-Ferrocenylethyne) phenylamine on Graphene as the Signal Amplificator to Determinate Dopamine and Acetaminophen Simultaneously (pages 845–854)

      Linping Wang, Meiling Liu, Yue Meng, Haitao Li, Youyu Zhang and Shouzhuo Yao

      Article first published online: 29 APR 2013 | DOI: 10.1002/cjoc.201201229

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      A dual signal amplification platform for simultaneous and sensitive determination of dopamine (DA) and acetaminophen (AC) is proposed by the synergistic effect of graphene (GR) and (4-ferrocenylethyne) phenylamine (FEPA). The synthesized FEPA serves as an electron mediator for amplification of the detection signals, and it can be strongly adsorbed on GR surface via the strong π-π stacking interaction between the conjugate chain of FEPA and GR. The proposed strategy provided a stable electronic mediator immobilization method on electrode surfaces for electrochemical analysis.

  5. Note

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Communication
    5. Full Papers
    6. Note
    1. Directly Regioselective Protection of Secondary Hydroxyl Group on Ribosides in Aqueous Solution (pages 855–860)

      Ruigang Xu, Fei Liu, Yingju Liu, Beiqing Chen and Feng-Wu Liu

      Article first published online: 3 APR 2013 | DOI: 10.1002/cjoc.201300045

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      Regioselective protection of secondary hydroxyl groups on ribosides and 2′-deoxyribosides was investigated. A most simple and efficient method for preparation of 2′,3′-di-O-benzoylribonucleosides was developed.

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