Chemistry – An Asian Journal

Cover image for Vol. 7 Issue 7

July 2012

Volume 7, Issue 7

Pages 1465–1723

  1. Cover Picture

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    4. Community Report
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      Cover Picture: Atropisomerism in a Belt-Persistent Nanohoop Molecule: Rotational Restriction Forced by Macrocyclic Ring Strain (Chem. Asian J. 7/2012) (page 1465)

      Shunpei Hitosugi, Dr. Waka Nakanishi and Prof. Hiroyuki Isobe

      Article first published online: 14 JUN 2012 | DOI: 10.1002/asia.201290025

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      Biaryl Atropisomerism has been an important notion in chemistry since its discovery in 1922 and the conceptual foundation in 1933, and introduction of steric constraints at the ortho-positions of aryl units has been regarded as a requisite condition for the emergence of the atropisomerism. Hiroyuki Isobe et al. disclose in their Communication on page 1550 ff., that this is not always the case. In their belt-persistent nanohoop molecules, atropisomerism arising from macrocyclic ring strain has been observed.

  2. Inside Cover

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      Inside Cover: Elucidation of π-Conjugation Modes in Diarene-Fused 1,2-Dihydro-1,2-diborin Dianions (Chem. Asian J. 7/2012) (page 1466)

      Takafumi Araki, Prof. Dr. Atsushi Wakamiya, Kenji Mori and Prof. Dr. Shigehiro Yamaguchi

      Article first published online: 14 JUN 2012 | DOI: 10.1002/asia.201290026

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      1,2-Dihydro-1,2-diborin is an intriguing building unit with a B[BOND]B bond. As described in their Full paper on page 1594 ff., Atsushi Wakamiya and Shigehiro Yamaguchi et al. present new π-electron systems consisting of dithiophene-fused 1,2-dihydro-1,2-diborins. Metal reduction produces their dianions, in which the orientation of thiophene rings determines the road of π conjugation. The 3,3′-bithiophene skeleton enhances a 6π-aromatic conjugation in the diborin moiety, while the 2,2′-bithiophene skeleton favors a peripheral conjugation extended over the tricyclic framework.

  3. Community Report

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      JSPS Asian Core Program: Cutting-Edge Organic Chemistry in Asia (Phase II), 14th Asian Chemical Congress, and IUPAC Joint Workshop: Strategic Planning for a New East and Southeast Asian Network for Organic Chemistry (pages 1468–1471)

      Minoru Isobe, Henry N. C. Wong, Tony K. M. Shing, Pei-Qiang Huang, Somdej Kanokmedhakul, Supa Hannongbua, Montakarn Chittchang and Atsushi Nishida

      Article first published online: 12 APR 2012 | DOI: 10.1002/asia.201200193

  4. Graphical Abstract

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    1. Graphical Abstract: Chem. Asian J. 7/2012 (pages 1473–1483)

      Article first published online: 14 JUN 2012 | DOI: 10.1002/asia.201290027

  5. News

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  6. Focus Reviews

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    1. C[BOND]C Coupling Reactions

      Advances in Copper-Catalyzed C[BOND]C Coupling Reactions and Related Domino Reactions Based on Active Methylene Compounds (pages 1488–1501)

      Dr. Yunyun Liu and Dr. Jie-Ping Wan

      Article first published online: 29 MAR 2012 | DOI: 10.1002/asia.201101063

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      A bent copper: Copper catalysis is rapidly becoming a highly efficient and useful economical option in Ullmann coupling reactions and, in particular, the activated-methylene-based C[BOND]C coupling reaction is gaining increasing attention. This review considers the recent advances in the copper-catalyzed intermolecular- and intramolecular C[BOND]C coupling reactions of active methylene and the tandem reactions involving this coupling reaction.

    2. C[BOND]H Activation

      Amide-Directed Tandem C[BOND]C/C[BOND]N Bond Formation through C[BOND]H Activation (pages 1502–1514)

      Dr. Chen Zhu, Dr. Rui Wang and Prof. Dr. John R. Falck

      Article first published online: 11 APR 2012 | DOI: 10.1002/asia.201200035

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      Best director: C[BOND]H activation reactions have received widespread interest over the past decade. This Focus Review addresses the recent developments in the amide-directed tandem process of C[BOND]C/C[BOND]N bond formation through C[BOND]H activation.

  7. Communications

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    1. Domino Reactions

      A Convenient Access to γ-Lactones from O-Allyl-α-Bromoesters using a One-Pot Ionic–Radical–Ionic Sequence (pages 1516–1520)

      Romain Bénéteau, Prof. Jacques Lebreton and Dr. Fabrice Dénès

      Article first published online: 3 MAY 2012 | DOI: 10.1002/asia.201200212

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      Cognac in the jar! An efficient one-pot sequence for the preparation of γ-lactones is described. Following reduction of α-bromo ester precursors with DIBAL-H and radical cyclization of the resulting O-aluminum acetals, a preparative in-situ Oppenauer-type oxidation of the cyclic O-aluminum acetal using simple aldehydes or ketones gives access to γ-lactones in high yields.

    2. Intramolecular Cyclization

      Ruthenium-Catalyzed Intramolecular [2+2+2] Cyclization of Allene–Yne–Enes: Construction of Fused-Tricyclic Skeletons (pages 1521–1523)

      Dr. Nozomi Saito, Taisuke Ichimaru and Prof. Dr. Yoshihiro Sato

      Article first published online: 23 APR 2012 | DOI: 10.1002/asia.201200201

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      Three′s not a crowd: An intramolecular [2+2+2] cyclization between three different components, allene, alkyne, and alkene, has been realized using a catalytic amount of [Cp*RuCl(cod)] complex (cod=1,5-cyclooctadiene), and afforded fused-tricyclic compounds in a highly stereoselective manner.

    3. Sialylation

      N-Acetyl-5-N,4-O-oxazolidinone-Protected Sialyl Sulfoxide: An α-Selective Sialyl Donor with Tf2O/(Tol)2SO in Dichloromethane (pages 1524–1528)

      Zhen-yuan Gu, Dr. Jia-xin Zhang and Dr. Guo-wen Xing

      Article first published online: 4 APR 2012 | DOI: 10.1002/asia.201200172

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      Sweet as sugar: Sialyl sulfoxide protected by N-acetyl-5-N,4-O-oxazolidinone was readily prepared, and its coupling to various sugar acceptors was investigated. When the reaction was promoted by Tf2O/(Tol)2SO, efficient and highly α-selective sialylation yielded α(2,6), α(2,3), and α(2,4) glycosidic linkages between sialic acid and glucose/glacotose.

    4. Cyclophanes

      Tris(spiroborate)-Type Anionic Nanocycles (pages 1529–1532)

      Dr. Hiroshi Danjo, Natsuyo Mitani, Yusuke Muraki, Dr. Masatoshi Kawahata, Prof. Dr. Isao Azumaya, Prof. Dr. Kentaro Yamaguchi and Prof. Dr. Toshifumi Miyazawa

      Article first published online: 4 APR 2012 | DOI: 10.1002/asia.201200162

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      Full circle: New cyclic tris(spiroborate)s were prepared as molecular recognition modules for nanometer-sized cationic guests. These cyclophanes were simply prepared by treating corresponding bis(2,3-dihydroxynaphthalene)s with an equimolar amount of boric acid. The molecular recognition ability of these cyclic spiroborates was estimated in solution and crystal phases by the use of [Ir(tpy2)]3+ as a typical example of a cationic guest.

    5. Domino Reactions

      Phosphine-Catalyzed Domino Reaction for the Synthesis of Conjugated 2,3-Dihydrofurans from Allenoates and Nazarov Reagents (pages 1533–1537)

      Peizhong Xie, Wenqing Lai, Zhishuai Geng, Prof. Dr. You Huang and Prof. Dr. Ruyu Chen

      Article first published online: 18 APR 2012 | DOI: 10.1002/asia.201200140

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      A new domino reaction for Nazarov reagents: An efficient approach was developed for the construction of highly functionalized conjugated 2,3-dihydrofuran skeletons. Nazarov reagents were used for the first time in a phosphine-catalyzed domino reaction and successfully used to construct five-membered ring compounds using alcohol as the solvent. DFT calculations indicate that alcohol is essential for the catalysis of the [1,2]-proton transfer.

    6. Cycloaddition

      Lewis Acid-Catalyzed Intramolecular [3+2] Cycloaddition of Cyclopropane 1,1-Diesters with Alkynes for the Synthesis of Cyclopenta[c]chromene Skeletons (pages 1538–1541)

      Dr. Xiao-Feng Xia, Xian-Rong Song, Dr. Xue-Yuan Liu and Prof. Dr. Yong-Min Liang

      Article first published online: 5 APR 2012 | DOI: 10.1002/asia.201200104

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      An efficient method to construct cyclopenta[c]chromene skeletons by Lewis acid-catalyzed intramolecular [3+2] cycloaddition of cyclopropane 1,1-diesters with alkynes is presented. Two new fused cycles can be formed in one step in moderate to excellent yields (up to 94 %), and the products can be converted into bioactive barbituric acid derivatives (1) under simple reaction conditions.

    7. Amide Formation

      Aerobic Amide Bond Formation with N-hydroxysuccinimide (pages 1542–1545)

      Haoyi Yao and Prof. Dr. Kana Yamamoto

      Article first published online: 18 APR 2012 | DOI: 10.1002/asia.201200017

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      Breathe easy: Molecular oxygen is one of the most abundant, atom-efficient, and economical oxidants. An aerobic oxidative amide formation from aldehydes and amines is reported. The method uses a catalytic amount of Co(OAc)2 and N-hydroxysuccinimide as reaction promoters. It is applicable to chiral substrates without loss of their optical purity.

    8. Fluorescent Sensors

      Single-Step Turn-On Homogeneous Fluorescent Immunosensor for Rapid, Sensitive, and Selective Detection of Proteins (pages 1546–1549)

      Dan Wang, Xiaocui Zhu, Dongqin Zhao, Yingxiao Cai and Prof. Dr. Meiping Zhao

      Article first published online: 27 APR 2012 | DOI: 10.1002/asia.201200086

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      Quick & easy: A simple and positive-readout fluorescent immunosensor was developed based on a quencher composed of a 3 nm gold nanoparticle (GNP) covalently linked to a Fab fragment, which proved to be stable and specific. The method allows for direct and sensitive detection of target antigens in homogeneous solutions in one step without any separation steps. It has been successfully applied to rapidly quantify the amount of secretory immunoglobulin A (sIgA) in human saliva samples.

    9. Macrocycles

      Atropisomerism in a Belt-Persistent Nanohoop Molecule: Rotational Restriction Forced by Macrocyclic Ring Strain (pages 1550–1552)

      Shunpei Hitosugi, Dr. Waka Nakanishi and Prof. Hiroyuki Isobe

      Article first published online: 16 MAR 2012 | DOI: 10.1002/asia.201200187

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      Enough strain! Strain in a macrocyclic ring hinders the rotation of an arylene panel in a nanohoop molecule containing four chrysenylene units (see picture). Unlike conventional rotational restrictions in biaryl systems, the new atropisomerism does not require any steric hinderance from the substituents. The study of atropisomerism also provides the first experimental insights into the relative stability of nanohoop structures.

    10. Fluorescent Organic Dyes

      Red-Light-Emitting System Based on Aggregation of Donor–Acceptor Derivatives in Polar Aqueous Media (pages 1553–1557)

      Prof. Dr. Tsutomu Ishi-i, Kei Ikeda, Yuki Kichise and Michiaki Ogawa

      Article first published online: 3 MAY 2012 | DOI: 10.1002/asia.201200136

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      Glowing together: An efficient red-light-emitting system has been created in polar water media based on the aggregation of donor–acceptor molecules. In the THF/water mixture, the emission was quenched when a small volume of water was used, whereas it was recovered and enhanced upon aggregate formation with a large water volume.

    11. Cluster Compounds

      Stepwise Construction of a AgI9–CuII4 Heterometallic Cluster Incorporating Two Unusual Vertex-Shared Trigonal-Bipyramidal Silver Polyhedra (pages 1558–1561)

      Dr. Di Sun, Liangliang Zhang, Zhihao Yan and Prof. Daofeng Sun

      Article first published online: 5 APR 2012 | DOI: 10.1002/asia.201200181

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      One step at a time: A novel tridecanuclear AgI9–CuII4 heterometallic cluster comprising four [Cu(phen)2]2+ units on the periphery and one interior [Ag9(mna)8]7− cluster was synthesized in a stepwise manner and characterized. The interior [Ag9(mna)8]7− cluster contains two unusual vertex-shared trigonal-bipyramidal silver polyhedra.

    12. Fluorescent Probes

      A Diketopyrrolopyrrole-Based Colorimetric and Fluorescent Probe for Cyanide Detection (pages 1562–1566)

      Young-Hwan Jeong, Chi-Hwa Lee and Prof. Woo-Dong Jang

      Article first published online: 30 MAR 2012 | DOI: 10.1002/asia.201101038

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      Red means CN: A new type of diketopyrrolopyrrole-based chromophore has been synthesized as a colorimetric and fluorescent probe for the detection of cyanide using only two reaction steps. Through the addition of cyanide to the chromophore, the fluorescence emission and color were greatly changed in a highly sensitive and selective manner.

    13. Photoaffinity Labeling

      Active/Inactive Dual-Probe System for Selective Photoaffinity Labeling of Small Molecule-Binding Proteins (pages 1567–1571)

      Prof. Kaori Sakurai, Masaki Tawa, Ayumi Okada, Rika Yamada, Noriyuki Sato, Masahiro Inahara and Maia Inoue

      Article first published online: 19 APR 2012 | DOI: 10.1002/asia.201200085

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      Two are better than one: A new approach to selective photoaffinity labeling is described in which a bioactive probe is used in combination with its inactive analog as a scavenger of nonspecific proteins.

    14. Gas Sensors

      Synthesis of Tin Dioxide Nanooctahedra with Exposed High-Index {332} Facets and Enhanced Selective Gas Sensing Properties (pages 1572–1575)

      Dr. Xiguang Han, Prof. Liang Li and Chao Wang

      Article first published online: 4 APR 2012 | DOI: 10.1002/asia.201200116

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      High and mighty: Octahedral SnO2 particles bound by high-index {332} facets were synthesized by a simple hydrothermal route using SnCl2⋅5 H2O as the tin salt with the assistance of hydrochloric acid and poly(vinylpyrrolidone). These particles show excellent selective gas sensing performance because they have large numbers of dangling bonds on their surfaces.

  8. Full Papers

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    2. Cover Picture
    3. Inside Cover
    4. Community Report
    5. Graphical Abstract
    6. News
    7. Focus Reviews
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    1. Fluorescent Sensors

      An Ultrasensitive Fluorescent Sensing Nanofilm for Organic Amines Based on Cholesterol-Modified Perylene Bisimide (pages 1576–1582)

      Haonan Peng, Prof. Dr. Liping Ding, Taihong Liu, Xiangli Chen, Lan Li, Prof. Dr. Shiwei Yin and Prof. Dr. Yu Fang

      Article first published online: 5 APR 2012 | DOI: 10.1002/asia.201100958

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      Good cholesterol: A stable, ultrasensitive, and fully reversible fluorescent sensing film for organic amines has been fabricated by assembling cholesterol (Chol)-derived perylene bisimide on glass plate surface. The compound forms well-defined nanofibers, as evidenced by AFM measurement. The left-handed helical structure can be attributed to the circumrotating packing of the Chol moieties for spatial reasons.

    2. Fluorescent Polymers

      2,3,4,5-Tetraphenylsilole-Based Conjugated Polymers: Synthesis, Optical Properties, and as Sensors for Explosive Compounds (pages 1583–1593)

      Li-Hong Zhang, Tao Jiang, Dr. Lian-Bin Wu, Dr. Jun-Hua Wan, Dr. Chih-Hsien Chen, Dr. Yong-Bing Pei, Dr. Hua Lu, Yuan Deng, Gao-Feng Bian, Prof. Hua-Yu Qiu and Prof. Guo-Qiao Lai

      Article first published online: 23 APR 2012 | DOI: 10.1002/asia.201200070

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      Bang on: The bridging (vinylene or ethyne) group has a significant effect on the photophysical properties of polymers. 2,5-Tetraphenylsilole-ethyne-type polymers showed a pronounced aggregation-enhanced emission (AEE) effect but 2,5-tetraphenylsilole-vinylene-type polymers were AEE-inactive (Images in THF, left vials and in THF/water (1:9 v/v), right vials)

    3. Conjugation

      Elucidation of π-Conjugation Modes in Diarene-Fused 1,2-Dihydro-1,2-diborin Dianions (pages 1594–1603)

      Takafumi Araki, Prof. Dr. Atsushi Wakamiya, Kenji Mori and Prof. Dr. Shigehiro Yamaguchi

      Article first published online: 30 MAR 2012 | DOI: 10.1002/asia.201200055

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      A borin paper: The orientation of the thiophene rings in dithieno-fused 1,2-dihydro-1,2-diborins significantly altered the π-conjugation modes of their dianions. The countercations also influenced the absorption properties with drastic color changes.

    4. Radicals

      (Nitronyl Nitroxide)-Substituted Trioxytriphenylamine Radical Cation Tetrachlorogallate Salt: A 2p-Electron-Based Weak Ferromagnet Composed of a Triplet Diradical Cation (pages 1604–1609)

      Dr. Masato Kuratsu, Dr. Shuichi Suzuki, Dr. Masatoshi Kozaki, Dr. Daisuke Shiomi, Prof. Kazunobu Sato, Prof. Takeji Takui, Dr. Tsuneki Kanzawa, Prof. Yuko Hosokoshi, Dr. Xiao-Zheng Lan, Dr. Yuji Miyazaki, Prof. Akira Inaba and Prof. Keiji Okada

      Article first published online: 3 MAY 2012 | DOI: 10.1002/asia.201200084

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      A light magnet: An organic stable triplet diradical cation with a diamagnetic tetrachlorogallate anion (NNTOT+⋅GaCl4, see picture) was prepared and its magnetic properties were investigated by the measurements of magnetic susceptibilities and heat capacity. The compound exhibited a magnetic phase transition at TN=2.65 K from a short-range-ordered antiferromagnetic chain to a 3D weak ferromagnet.

    5. Nanocarriers

      Calcium Phosphate Nanocarriers Dual-Loaded with Bovine Serum Albumin and Ibuprofen: Facile Synthesis, Sequential Drug Loading and Sustained Drug Release (pages 1610–1615)

      Xin-Yu Zhao, Prof. Dr. Ying-Jie Zhu, Feng Chen and Dr. Jin Wu

      Article first published online: 13 APR 2012 | DOI: 10.1002/asia.201100954

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      Two to tango: When calcium phosphate nanoparticles are prepared in the presence of bovine serum albumin, protein-loaded nanocarriers are obtained. Further treatment with the hydrophobic drug ibuprofen gives a dual drug delivery system. This system has a high drug loading capacity and sustained drug release in simulated body fluid and thus is promising for the drug delivery applications.

    6. Protein Inhibitors

      Lamellarins as Inhibitors of P-Glycoprotein-Mediated Multidrug Resistance in a Human Colon Cancer Cell Line (pages 1616–1623)

      Fabien Plisson, Xiao-Cong Huang, Dr. Hua Zhang, Zeinab Khalil and Prof. Robert J. Capon

      Article first published online: 30 MAR 2012 | DOI: 10.1002/asia.201101049

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      New promise in fighting MDR: This study reports a selection of new (15, 14) and known (613, 1516) lamellarins from two southern Australian Didemnum sp. All structures were assigned by detailed spectroscopic analysis. This unique library of marine alkaloids, supported by semi-synthetic (17) and synthetic analogues (1926), was used to probe interactions with the ABC transporter efflux pump P-glycoprotein (P-gp), leading to the discovery an optimized P-gp inhibitor capable of reversing multidrug resistance (MDR) in a human cancer cell line.

    7. Dye-Sensitized Solar Cells

      Photocurrent Enhancement of Dye-Sensitized Solar Cells owing to Increased Dye-Adsorption onto Silicon-Nanoparticle-Coated Titanium-Dioxide Films (pages 1624–1629)

      Eun-Sung Ha, Beomjin Yoo, Dr. Hionsuck Baik, Dr. Yeonhee Lee and Prof. Kang-Jin Kim

      Article first published online: 29 MAR 2012 | DOI: 10.1002/asia.201101055

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      Dye another day: The preparation of Si nanoparticles (Nps) was improved by using sodium naphthalide. The Si Nps were functionalized with 4-vinylbenzoic acid and attached onto TiO2 films for application in dye-sensitized solar cells (DSSCs). The DSSCs that contained Si[BOND]COOH Nps exhibited 22 % and 27 % higher short-circuit photocurrent density and overall energy-conversion efficiency than the untreated DSSCs, respectively.

    8. Drug Delivery

      Self-Assembled Aptamer-Based Drug Carriers for Bispecific Cytotoxicity to Cancer Cells (pages 1630–1636)

      Guizhi Zhu, Dr. Ling Meng, Prof. Mao Ye, Dr. Liu Yang, Dr. Kwame Sefah, Dr. Meghan B. O'Donoghue, Dr. Yan Chen, Xiangling Xiong, Dr. Jin Huang, Prof. Erqun Song and Prof. Weihong Tan

      Article first published online: 11 APR 2012 | DOI: 10.1002/asia.201101060

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      Two is better than one! A self-assembled, bispecific drug carrier has been developed by engineering two DNA aptamers that recognize different types of cancer cells (see picture). The resultant drug carrier showed the bispecific abilities to recognize cancer cells, deliver an anticancer drug (Doxorubicin), and induce cytotoxicity, even in cell mixtures.

    9. Graphene

      Superior Electrochemical Performance of Sulfur/Graphene Nanocomposite Material for High-Capacity Lithium–Sulfur Batteries (pages 1637–1643)

      Bei Wang, Kefei Li, Dawei Su, Prof. Hyojun Ahn and Prof. Guoxiu Wang

      Article first published online: 27 MAR 2012 | DOI: 10.1002/asia.201200004

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      Charge of the Li brigade: Sandwich-like three-dimensional sulfur/graphene nanocomposites exhibit a super-high lithium-storage capacity and a satisfactory cycling performance in lithium–sulfur cells (see scheme). The enhancement of the reversible capacity and cycle life could be attributed to the flexible graphene nanosheet matrix, which acts as a conducting medium and a physical buffer.

    10. Cross-Coupling Reactions

      Palladium-Catalyzed Annulation of 1,2-Diborylalkenes and -Arenes with 1-Bromo-2-[(Z)-2-bromoethenyl]arenes: A Modular Approach to Multisubstituted Naphthalenes and Fused Phenanthrenes (pages 1644–1651)

      Prof. Dr. Masaki Shimizu, Yosuke Tomioka, Dr. Ikuhiro Nagao, Tsugumi Kadowaki and Prof. Dr. Tamejiro Hiyama

      Article first published online: 27 MAR 2012 | DOI: 10.1002/asia.201200132

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      A class apart: Bromo(bromoethenyl)arenes are a new class of electrophiles that successfully undergo palladium-catalyzed double-cross-coupling reactions with 1,2-diborylalkenes and -arenes. This straightforward, modular approach is suitable for the formation of multisubstituted polycyclic aromatic hydrocarbons, such as naphthalenes, anthracenes, and fused phenanthrenes.

    11. Fluorescent Probes

      Fluorescent Silver Nanoclusters as Effective Probes for Highly Selective Detection of Mercury(II) at Parts-per-Billion Levels (pages 1652–1656)

      Dr. Chuanxi Wang, Lin Xu, Yu Wang, Dan Zhang, Prof. Xiaodong Shi, Fengxia Dong, Prof. Kui Yu, Prof. Quan Lin and Prof. Bai Yang

      Article first published online: 12 APR 2012 | DOI: 10.1002/asia.201200033

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      Mighty small: Water-soluble and red-fluorescent silver nanoclusters (NCs; see picture) stabilized by glutathione (GSH) were prepared at room temperature. The resulting GSH-Ag NCs are highly sensitive and selective for detection of Hg2+ at concentrations as low as 10−10M.

    12. Energetic Materials

      High-Nitrogen-Based Pyrotechnics: Development of Perchlorate-Free Green-Light Illuminants for Military and Civilian Applications (pages 1657–1663)

      Dr. Jesse J. Sabatini, James M. Raab, Dr. Ronald K. Hann Jr., Dr. Reddy Damavarapu and Prof. Dr. Thomas M. Klapötke

      Article first published online: 4 APR 2012 | DOI: 10.1002/asia.201200036

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      It pays to be “green”: Perchlorate-free pyrotechnic formulations with green-light-emitting qualities (see picture) for both military use and civilian fireworks have been developed. The formulations, which are stable to impact, friction, electrostatic discharge, and thermal conditions, afforded excellent burn times and luminous intensity values.

    13. Antibacterial Agents

      Sodium 1-Naphthalenesulfonate-Functionalized Reduced Graphene Oxide Stabilizes Silver Nanoparticles with Lower Cytotoxicity and Long-Term Antibacterial Activity (pages 1664–1670)

      Dr. Xiang Cai, Prof. Shaozao Tan, Aili Yu, Jinglin Zhang, Jiahao Liu, Prof. Wenjie Mai and Prof. Zhenyou Jiang

      Article first published online: 27 MAR 2012 | DOI: 10.1002/asia.201200045

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      Tight-fisted GO: A hybrid material comprising silver nanoparticles deposited on reduced graphene oxide functionalized by sodium 1-naphthalenesulfonate (AgNP-NA-rGO) shows high antibacterial activity. The AgNPs on NA-rGO are more stable than those stabilized by poly(vinylpyrrolidone), resulting in long-term antibacterial effects. The hybrid also shows excellent water solubility and low cytotoxicity.

    14. Hybrid Peptides

      β-Turn Analogues in Model αβ-Hybrid Peptides: Structural Characterization of Peptides Containing β2,2Ac6c and β3,3Ac6c Residues (pages 1671–1678)

      Krishnayan Basuroy, Appavu Rajagopal, Dr. Srinivasarao Raghothama, Prof. Narayanaswamy Shamala and Prof. Padmanabhan Balaram

      Article first published online: 3 MAY 2012 | DOI: 10.1002/asia.201200052

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      Twists and turns: Backbone-expanded analogues of β turns have been structurally characterized in peptides containing stereochemically constrained β-amino acid residues. The αβ-hybrid sequences yield analogues of both type I/III (helical) and type II (non-helical) β-turn conformations (see picture).

    15. Extracting Agents

      Quadruple Click: A Facile Pathway leading to Tetrakis(4-(1,2,3-triazolyl)methyl)-ethylenediamine Derivatives as a New Class of Extracting Agents for Soft Metal Ions (pages 1679–1683)

      Wataru Watanabe, Tetsuya Maekawa, Dr. Yuji Miyazaki, Dr. Tatsuya Kida, Prof. Dr. Kenji Takeshita and Prof. Dr. Atsunori Mori

      Article first published online: 27 MAR 2012 | DOI: 10.1002/asia.201200089

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      Has it clicked yet? A quadruple click reaction of tetraalkynylethlenediamine with four equivalents of an azide gives tetrakistriazolylethlenediamine derivatives. The obtained compounds extract cadmium(II), a class of soft metal ions, efficiently in the presence of 2-bromooctanoic acid, whereas less soft europium(III) ions are hardly extracted. A poly(N-isopropylacrylamide) (NIPA) gel containing a tetrakistriazolylethlenediamine moiety as a cross-linker shows a temperature-dependent extraction performance.

    16. Privileged Structures

      Design and Synthesis of New Biprivileged Molecular Scaffolds: Indolo-Fused Benzodiazepinyl/quinoxalinyl benzimidazoles (pages 1684–1690)

      Indrajeet J. Barve, Chan-Yu Chen, Deepak B. Salunke, Prof. Wen-Sheng Chung and Prof. Chung-Ming Sun

      Article first published online: 18 APR 2012 | DOI: 10.1002/asia.201200121

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      Feeling privileged: Benzimidazole-linked tetracyclic indolo-benzodiazepines and indolo-quinoxalines were designed and synthesized as new bipriviliged molecular scaffolds. The key step in the synthesis is a Pictet–Spengler-type condensation. Analysis of single crystals of representative compounds showed that these molecular scaffolds have the potential to present various substituents with distinct three-dimensional orientations.

    17. Domino Reactions

      1-Bromo-2-(cyclopropylidenemethyl)benzene: A Useful Building Block in the Palladium-Catalyzed Reaction of 2-Alkynylbenzenamine (pages 1691–1696)

      Shaoyu Li, Yong Luo, Dr. Xiaocong Wang, Prof. Minjie Guo and Prof. Jie Wu

      Article first published online: 30 MAR 2012 | DOI: 10.1002/asia.201200122

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      This way or that: A novel palladium-catalyzed domino reaction of 1-bromo-2-(cyclopropylidenemethyl)benzene and 2-alkynylbenzenamine is reported, which generates 2-(naphthalen-2-yl)benzenamines and 5H-indeno[1,2-c]quinolines via 6-endo and 5-exo cyclization, respectively. The regioselectivity for the final outcome can be affected by phosphine and N-heterocyclic carbene ligands.

    18. Magnetic Dilution

      Zinc-Diluted Magnetic Metal Formate Perovskites: Synthesis, Structures, and Magnetism of [CH3NH3][MnxZn1−x(HCOO)3] (x=0–1) (pages 1697–1707)

      Ran Shang, Prof. Xuan Sun, Prof. Zhe-Ming Wang and Prof. Song Gao

      Article first published online: 23 APR 2012 | DOI: 10.1002/asia.201200139

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      Going, going, gone! The isostructural perovskite series of [CH3NH3][MnxZn1−x(HCOO)3] (x=0–1), adopting an anionic NaCl type metal-formate framework and CH3NH3+ cations in the framework cavities, show magnetic behaviors changing from weak ferromagnetism for x≥0.40 to paramagnetism for x≤0.30, with the estimated percolation limit xP=0.31(2).

    19. Radicals

      An Unusal Case of Facile Non-Degenerate P[BOND]C Bond Making and Breaking (pages 1708–1712)

      Dr. Vitaly Nesterov, Aysel Özbolat-Schön, Dr. Gregor Schnakenburg, Dr. Lili Shi, Asli Cangönül, Dr. Maurice van Gastel, Prof. Dr. Frank Neese and Prof. Dr. Rainer Streubel

      Article first published online: 5 APR 2012 | DOI: 10.1002/asia.201200161

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      Persistent meets short-lived: In situ reaction of the tris(p-methyl-phenyl)methyl radical 1 with P-fluoro organophosphanyl complex 2 at low temperature yielded several intermediates that converted easily into the final product, the complex 3. The latter complex showed a very long and weak P[BOND]C bond.

    20. Mesoporous Materials

      Synthesis of Continuous Mesoporous Alumina Films with Large-Sized Cage-Type Mesopores by Using Diblock Copolymers (pages 1713–1718)

      Xiangfen Jiang, Dr. Norihiro Suzuki, Dr. Bishnu Prasad Bastakoti, Dr. Kevin C.-W. Wu and Prof. Dr. Yusuke Yamauchi

      Article first published online: 3 MAY 2012 | DOI: 10.1002/asia.201200256

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      I′m fixing a hole: Mesoporous alumina films with large cage-type mesopores (see picture) were prepared by using commercially available diblock copolymer (PS-b-PEO) and economic inorganic salt (AlCl3) as aluminum source. Pore size and connectivity can be controlled by adjusting the solvent system and the amount of polymer used.

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      Preview: Chem. Asian J. 8/2012 (page 1723)

      Article first published online: 14 JUN 2012 | DOI: 10.1002/asia.201290029

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