Chemistry Letters

Highlight Review

Control of Molecular Arrangement and/or Orientation of D–π–A Fluorescent Dyes for Dye-sensitized Solar Cells

Yousuke Ooyama, Joji Ohshita, Yutaka Harima

2012 Volume 41 Issue 11 Pages 1384-1396
Published: November 05, 2012
Released on J-STAGE: November 03, 2012

DOIhttps://doi.org/10.1246/cl.2012.1384

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Dye-sensitized solar cells (DSSCs) based on organic dyes adsorbed on TiO₂ electrodes, which emerged as a new generation of sustainable photovoltaic devices, have received considerable attention because of high incident solar light-to-electricity conversion efficiency and low cost of production. The aim of this Highlight Review is to indicate the importance of creating effective D–π–A dye sensitizers capable of controlling not only photophysical and electrochemical properties of the dyes themselves but also molecular arrangement and/or orientation of the dyes on TiO₂ surface to provide a good electron communication between the dye and TiO₂ electrode, for developing high-performance DSSCs.

The aim of this Highlight Review is to indicate the importance of creating effective D–π–A organic dye sensitizers capable of controlling not only photophysical and electrochemical properties of the dyes themselves but also molecular arrangement and/or orientation of the dyes on TiO₂ surface to provide good electron communication between the dye and TiO₂ electrode, for developing high performance dye-sensitized solar cells (DSSCs). Fullsize Image

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CeO₂-catalyzed Transformations of Nitriles and Amides

Masazumi Tamura, Ken-ichi Shimizu, Atsushi Satsuma

2012 Volume 41 Issue 11 Pages 1397-1405
Published: November 05, 2012
Released on J-STAGE: November 03, 2012

DOIhttps://doi.org/10.1246/cl.2012.1397

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Recently, cerium oxides have been extensively used as heterogeneous catalysts for green organic reactions. This review describes recent progress in such reactions, with a focus on our studies on pure CeO₂-catalyzed reactions of nitriles and amides with nucleophiles (H₂O, alcohols, and amines). Hydration of nitriles to amides in water, one-pot ester synthesis from nitriles and alcohols, one-pot synthesis of N-alkylamides from nitriles with amines, and synthesis of N-alkylamides from amides and amines (transamidation) are selectively catalyzed by CeO₂ under aqueous or solvent-free conditions. Mechanistic studies suggest that a cooperation of Lewis acid site (Ce⁴⁺ cation) and acid–base (Ce–O) pair site plays essential roles in the catalytic reactions.

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Letter

Synthesis of a Novel Ruthenium Sensitizer Bearing an ortho-Dicarboxyphenyl Group as an Anchoring Unit for Dye-sensitized Solar Cells

Hironobu Ozawa, Shohei Oura, Ryosuke Shimizu, Hironori Arakawa

2012 Volume 41 Issue 11 Pages 1406-1408
Published: November 05, 2012
Released on J-STAGE: October 27, 2012

DOIhttps://doi.org/10.1246/cl.2012.1406

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A novel ruthenium sensitizer TUS-20, which is a structural analog of black dye, bearing an ortho-dicarboxyphenylterpyridine as an anchoring unit to TiO₂ surface has been synthesized. Adsorption rate of TUS-20 was much faster, and the maximum amount of dye adsorption was larger than that of black dye. The dye-sensitized solar cell with TUS-20 exhibited 7.3% conversion efficiency under AM 1.5 (100 mW cm⁻²) irradiation.

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Local Thermal Nonequilibrium on Solid and Liquid Interface Generated in a Microwave Magnetic Field

Dai Mochizuki, Masashi Shitara, Masato Maitani, Yuji Wada

2012 Volume 41 Issue 11 Pages 1409-1411
Published: November 05, 2012
Released on J-STAGE: October 27, 2012

DOIhttps://doi.org/10.1246/cl.2012.1409

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Dehalogenation of (2-haloethyl)benzene using Fe particles was carried out in the electric and magnetic fields in a microwave single mode cavity. Microwave irradiation in a magnetic field enhanced the conversion of (2-haloethyl)benzene compared with heating by a mantle heater and microwave in an electric field, while the ethylbenzene selectivities were comparable. Larger Fe particles generated sparks under microwave irradiation, resulting in the increase of ethylbenzene selectivities. These data suggested the reaction acceleration by a local thermal nonequilibrium in the solid–liquid system by the selective microwave heating of the solid.

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Absorption of Chlorinated Hydrocarbons Dissolved in Water with Pellets Made of p-tert-Butylcalix[4]arene and Silica Gel

Naoya Morohashi, Ozora Shibata, Tetsutaro Hattori

2012 Volume 41 Issue 11 Pages 1412-1413
Published: November 05, 2012
Released on J-STAGE: October 27, 2012

DOIhttps://doi.org/10.1246/cl.2012.1412

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Powdery crystals of p-tert-butylcalix[4]arene (1) pelletized using silica gel as a binder absorb chlorinated hydrocarbons from saturated aqueous solutions by forming inclusion complexes with compound 1.

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Fabrication of Large Porous ZSM-5 Bulk Bodies by a One-pot Hydrothermal Method

Eisaku Igi, Yoshikazu Kameshima, Shunsuke Nishimoto, Michihiro Miyake

2012 Volume 41 Issue 11 Pages 1414-1416
Published: November 05, 2012
Released on J-STAGE: October 27, 2012

DOIhttps://doi.org/10.1246/cl.2012.1414

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The fabrication of large ZSM-5 bulk bodies by a hydrothermal method was investigated. The results reveal that porous ZSM-5 bulk bodies with sizes of the order of centimeters could be prepared by the one-pot hydrothermal method using raw materials for synthesizing ZSM-5 powder. Machinability tests and mechanical strength measurements suggest that the bulk bodies obtained are promising as practical materials.

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Electrochemical and Photophysical Study in Solution and on Ruthenium(II) Polypyridyl Complexes Containing Thiophenylethynylphenanthrolines Self-assembled on Gold Surfaces

Michito Shiotsuka, Hiroshi Kondo, Tomohiko Inomata, Katsuya Sako, Hide ...

2012 Volume 41 Issue 11 Pages 1417-1419
Published: November 05, 2012
Released on J-STAGE: October 27, 2012

DOIhttps://doi.org/10.1246/cl.2012.1417

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Novel ruthenium(II) polypyridyl complexes with diethynylphenanthrolines containing acetylthiophenyl unit(s) have been prepared and characterized by photophysical measurements. These complexes showed the MLCT and the lowest energy π–π^* absorption bands, and also intensive broad emission bands assignable to a triplet MLCT transition were observed in the deaerated solution. The electrochemistry of these complexes in the solution and on self-assembled monolayers on the gold electrode clearly showed Ru(II)/R(III) redox waves.

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Gelation of Poly(L-lactic acid) Induced by Complex Crystallization with Solvents

Yasuhiro Matsuda, Akinobu Fukatsu, Shigeru Tasaka

2012 Volume 41 Issue 11 Pages 1420-1421
Published: November 05, 2012
Released on J-STAGE: October 27, 2012

DOIhttps://doi.org/10.1246/cl.2012.1420

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Gels of poly(L-lactic acid) (PLLA) in several solvents, including N,N-dimethylformamide (DMF) were formed by cooling solutions of PLLA. Polarizing optical micrographs showed the formation of spherulites of PLLA in the gels below 70 °C. The storage modulus of the gel decreased abruptly below 70 °C, which suggest that the crystalline structure of PLLA prevented the flow of DMF and induced the gelation. The X-ray diffraction (XRD) patterns of the gels were similar to those of the ε-crystals of PLLA which were induced by the formation of complex crystallization with DMF. The mechanism of the formation of the gel is discussed based on the experimental data.

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C–C Coupling Promoted by a NiCl₂/bpy/Mg System in DMF and Its Application to Dehalogenative Polycondensation

Takakazu Yamamoto

2012 Volume 41 Issue 11 Pages 1422-1424
Published: November 05, 2012
Released on J-STAGE: October 27, 2012

DOIhttps://doi.org/10.1246/cl.2012.1422

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A mixture of NiCl₂, 2,2′-bipyridine (bpy), and Mg in DMF promoted dehalogenative homocoupling of RX (e.g., bromobenzene and p-tolyl bromide) efficiently. This basic coupling reaction was applied for polycondensation of dihaloorganic compounds, X–R′–X, to give poly(9,9-dioctylfluorene-2,7-diyl), poly(9,10-dioctyl-9,10-dihydrophenanthrene-2,7-diyl), and poly(pyridine-2,5-diyl).

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Monte Carlo Simulation of Polymer–Nanoparticle Composites

Takamichi Terao

2012 Volume 41 Issue 11 Pages 1425-1427
Published: November 05, 2012
Released on J-STAGE: October 27, 2012

DOIhttps://doi.org/10.1246/cl.2012.1425

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The structural formation of polymer–nanoparticle composites (PNC), which are also called polymer spherical brushes, is investigated by Monte Carlo simulations. Based on an osmotic model, the solid–liquid transition of PNC systems due to the steric effect between PNCs is studied by employing the Lindemann criterion and the Hansen–Verlet criterion. The phase diagram of PNC systems is also clarified by the free-energy analysis of the system. These results indicate the existence of PNC crystals with sufficiently high density and the large number of polymer chains per each particle.

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Morphology Study of New Shaped Porous Nanotubes of LiFePO₄ by Electrospinning

Chung Soo Kang, Cheong Kim, Tae Jun Park, Jong Tae Son

2012 Volume 41 Issue 11 Pages 1428-1429
Published: November 05, 2012
Released on J-STAGE: October 27, 2012

DOIhttps://doi.org/10.1246/cl.2012.1428

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Porous nanotubes of lithium iron phosphate (LiFePO₄) were synthesized from a metal oxide precursor by the electrospinning method. After calcination of the above precursor nanotube at 800 °C, LiFePO₄ nanotubes with a diameter in the range of 150–500 nm, were obtained. Poly(vinylpyrrolidone) had an important role in the formation of hollow structure. The obtained nanotubes were characterized by X-ray diffraction (XRD), scanning electron microscopy (SEM), videoscopy, and transmission electron microscopy (TEM), respectively. The results showed that porous and hollow morphologies of nanotubes were successfully formed by electrospinning parameters and calcination temperature.

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Formation of Planar Bilayer Membranes on Solid Supports Using Peptide Gemini Surfactants

Katsunari Umezaki, Shunsuke Sakai, Shuhei Koeda, Yasushi Yamamoto, Mas ...

2012 Volume 41 Issue 11 Pages 1430-1432
Published: November 05, 2012
Released on J-STAGE: October 27, 2012

DOIhttps://doi.org/10.1246/cl.2012.1430

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Peptide-based gemini surfactants, called PG-surfactants, consisting of a tri- or tetra-Asp peptide core and acetylated dodecylamine-conjugated Cys residues at both the N- and C-terminal ends (D₃C₁₂ and D₄C₁₂), form a stable planar bilayer membrane on a solid support. From the DLS and TEM analyses, D₃C₁₂ and D₄C₁₂ have a tendency to form bilayer morphologies in a buffer solution, which reflects their tendency to form a stable planar bilayer membrane.

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Molecular Dynamics of Octyl Urea Crystals Analyzed by Solid-state NMR

Ryutaro Ohashi, Gou Wakabayashi, Motohiro Mizuno, Takahiro Soeta, Masa ...

2012 Volume 41 Issue 11 Pages 1433-1435
Published: November 05, 2012
Released on J-STAGE: October 27, 2012

DOIhttps://doi.org/10.1246/cl.2012.1433

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Octyl urea has one solid–solid phase transition at the temperature of 353.2 K. The solid–solid phase transition of octyl urea has a large entropy, that is comparable to its melting entropy. In this study, octyl urea was examined by solid-state NMR in order to investigate the sources of the large transition entropy. The NMR results indicate that conformational exchange and molecular motion in the octyl urea are the sources of the large entropy of the solid–solid transition.

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Editor’s Choice

Formation of Nanocrystals of a Zinc Pillared-layer Porous Coordination Polymer Using Microwave-assisted Coordination Modulation

Yoko Sakata, Shuhei Furukawa, Chiwon Kim, Susumu Kitagawa

2012 Volume 41 Issue 11 Pages 1436-1438
Published: November 05, 2012
Released on J-STAGE: October 27, 2012

DOIhttps://doi.org/10.1246/cl.2012.1436

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Nanocrystals of three-dimensional pillared-layer type porous coordination polymers, [Zn₂(ndc)₂(dabco)]_n, were fabricated by microwave-assisted coordination modulation, and its morphology was controlled by changing the modulator concentration. Adsorption measurement supported that the crystallinity and intrinsic porosity were maintained even for nanosized crystals, comparable to the corresponding micrometer-sized bulk powder crystals.

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Letter

Enantioselective Recognition of Tartaric Acid on Magnetoelectrodeposited Copper Film Electrodes

Iwao Mogi, Kazuo Watanabe

2012 Volume 41 Issue 11 Pages 1439-1441
Published: November 05, 2012
Released on J-STAGE: October 27, 2012

DOIhttps://doi.org/10.1246/cl.2012.1439

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Cu films were electrodeposited under a magnetic field of 5 T, and cyclic voltammograms (CVs) of the enantiomers of tartaric acid were investigated on the Cu film electrodes. The chiral behavior of the CVs was observed as the peak current difference between the enantiomers. The dependence of the chiral behavior on the potential sweep rate indicates that the enantioselective recognition is performed as the difference in the electron-transfer rate of the enantiomers at the chiral sites on the film surfaces.

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On–Off Switching of the Novel Thermochromic Chiroptical Behavior of Pseudoisocyanine Driven by Association/Dissociation

Takunori Harada, Mai Kurihara, Reiko Kuroda, Hiroshi Moriyama

2012 Volume 41 Issue 11 Pages 1442-1444
Published: November 05, 2012
Released on J-STAGE: November 03, 2012

DOIhttps://doi.org/10.1246/cl.2012.1442

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The compound 1,1′-diethyl-2,2′-cyanine iodide forms a chiral fluorescent self-aggregate in aqueous solution at high salt concentration. This compound shows reversible quenching and emitting behaviors and exhibits an interesting on–off switching of thermochromic circularly polarized luminescence behavior as a result of the association–dissociation process.

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Arylaminomaleimides as a New Class of Aggregation-induced Emission-active Molecules Obtained from Organoarsenic Compounds

Takuji Kato, Kensuke Naka

2012 Volume 41 Issue 11 Pages 1445-1447
Published: November 05, 2012
Released on J-STAGE: November 03, 2012

DOIhttps://doi.org/10.1246/cl.2012.1445

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Heating 1,4-dihydro-1,4-diarsininetetracarboxylic acid dianhydride with excess amounts of aniline and toluidine provided 3-anilino-N-phenylmaleimide and 3-p-toluidino-N-p-tolylmaleimide, respectively, which showed aggregation-induced emission (AIE) properties. Not only are the present aminomaleimide derivatives simple-structured AIE-active molecules, but they also exhibit pH responsive properties without introducing additional functional units.

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Chromatography Using Ternary Water–Acetonitrile–Ethyl Acetate Mixture as a Carrier Solution on a Microchip Incorporating Microchannels

Takafumi Matsuda, Naoya Jinno, Kenichi Yamashita, Hideaki Maeda, Akihi ...

2012 Volume 41 Issue 11 Pages 1448-1450
Published: November 05, 2012
Released on J-STAGE: November 03, 2012

DOIhttps://doi.org/10.1246/cl.2012.1448

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An open-tubular capillary chromatography system has been developed using a ternary mixed solvent solution, i.e., water–hydrophilic/hydrophobic organic solvent mixture as a carrier solution. The system is called “tube radial distribution chromatography (TRDC).” In this study, we tried to carry out the TRDC on a microchip incorporating microchannels. A model analyte solution of isoluminol isothiocyanate (ILITC) and ILITC-labeled bovine serum albumin (BSA) was injected to the double T-junction part (0.5 mm length, ca. 2 nL) on the microchip. The analyte solution was then delivered in the separation microchannel (40 µm in depth, 100 µm in width, and 22 cm in length) with a ternary water–acetonitrile–ethyl acetate mixture carrier solution (3:8:4, volume ratio). The model analytes, the ILITC and the labeled BSA were separated through the microchannel, where the carrier solvents were radially distributed in the separation channel generating inner and outer phases. This phenomenon of the solvents is called “tube radial distribution phenomenon (TRDP).” The outer phase functions as a pseudo-stationary phase under laminar flow conditions in the chromatography, i.e., TRDC. Finally, the ILITC and the labeled BSA were eluted in this order and detected with chemiluminescence reaction.

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New Fluorogenic Benzothiadiazole and Benzoselenadiazole Reagents to Yield Environment-sensitive Fluorophores via a Reaction with Amines

Kyoko Kawamoto, Seiichi Uchiyama

2012 Volume 41 Issue 11 Pages 1451-1452
Published: November 05, 2012
Released on J-STAGE: November 03, 2012

DOIhttps://doi.org/10.1246/cl.2012.1451

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We introduce 7-fluoro-4-N,N-dimethylaminosulfonyl-2,1,3-benzothiadiazole and 7-fluoro-4-N,N-dimethylaminosulfonyl-2,1,3-benzoselenadiazole as new fluorogenic reagents for amines. These reagents are nonfluorescent themselves and can easily react with nonfluorescent amines to produce environment-sensitive fluorophores. Herein, we report the synthesis of the new reagents and the fluorescence properties of the reagents and their amine derivatives as well as the reactivity of the new reagents toward amines.

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Supercritical Water Gasification of Organosolv Lignin over a Graphite-supported Ruthenium Metal Catalyst

Masayuki Shirai, Norihito Hiyoshi, Yuka Murakami, Mitsumasa Osada, Osa ...

2012 Volume 41 Issue 11 Pages 1453-1455
Published: November 05, 2012
Released on J-STAGE: November 03, 2012

DOIhttps://doi.org/10.1246/cl.2012.1453

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A graphite-supported ruthenium metal catalyst was highly active for catalytic gasification of organosolv lignin in supercritical water at 673 K because of the easy accessibility of the reaction intermediates to ruthenium metal sites on the graphite surface, compared to a charcoal-supported ruthenium metal catalyst.

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Racemization-free Synthesis of Lactide Using an Onium Salt Catalyst

Yuuki Ishijima, Yasumi Maruta, Atsushi Abiko

2012 Volume 41 Issue 11 Pages 1456-1458
Published: November 05, 2012
Released on J-STAGE: November 03, 2012

DOIhttps://doi.org/10.1246/cl.2012.1456

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Synthesis of LL-lactide with high chemical, diastereomeric, and enantiomeric purities was achieved by depolymerization of oligo(lactic acid) in the presence of an onium salt catalyst.

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Editor’s Choice

Emergence of High-density DNA Origami Network by Dewetting with a Binary Solvent

Yoshiaki Hirano, Kaoru Ojima, Yusuke Miyake, Tomoji Kawai, Takuya Mats ...

2012 Volume 41 Issue 11 Pages 1459-1461
Published: November 05, 2012
Released on J-STAGE: November 03, 2012

DOIhttps://doi.org/10.1246/cl.2012.1459

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We report a novel and convenient method for rapidly preparing and simultaneously immobilizing a homogeneous DNA origami network on a dry mica surface using a binary solvent. This DNA origami network can be easily obtained through a dewetting process using DNA origami species with initial bar structures. This method for inducing the emergence of two-dimensional network structures with high and uniform densities over large areas is highly valuable for quickly building the scaffolding necessary for fabricating molecular nanoscale network devices.

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Letter

Enhanced Gas Permselectivity of Copoly(Hyperbranched Macromonomer) Synthesized by One-pot Simultaneous Copolymerization of Dimethylsilyl-containing Phenylacetylenes

Jun Li, Jianjun Wang, Yu Zang, Toshiki Aoki, Takashi Kaneko, Masahiro ...

2012 Volume 41 Issue 11 Pages 1462-1464
Published: November 05, 2012
Released on J-STAGE: November 03, 2012

DOIhttps://doi.org/10.1246/cl.2012.1462

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Copoly(hyperbranched macromonomer)s, i.e., poly(phenylacetylene)s having many branches were synthesized by one-pot simultaneous copolymerization of two kinds of dimethylsilylphenylacetylenes. Membranes from the copoly(hyperbranched macromonomer)s having several kinds of branches showed higher permselectivities for oxygen and carbon dioxide over nitrogen than those of the corresponding copoly(hyperbranched macromonomer)s without any branches. In particular, the copoly(hyperbranched macromonomer)s having long and rigid branches had both the advantages of poly(phenylacetylene)s and poly(dendron)s. In summary, copoly(hyperbranched macromonomer)s showing good performance as gas-separation membranes were synthesized very easily by the one-pot simultaneous polymerization method. To our knowledge, this is the first synthesis of such complex copolymers showing good performance as gas-separation membranes.

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Odd–Even Effect of Dopant Molecules on Clearing Temperatures of Nematic Liquid-crystal Phases

Keiki Kishikawa, Yuri Haga, Takahiro Inoue, Tomohiro Watanabe, Masahir ...

2012 Volume 41 Issue 11 Pages 1465-1467
Published: November 05, 2012
Released on J-STAGE: November 03, 2012

DOIhttps://doi.org/10.1246/cl.2012.1465

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Nematic liquid-crystal phases doped with the novel dopant compounds 1 (C₆F₅COO(CH)_nOCOC₆F₅, n = 1–7) and 2 (C₆H₅COO(CH)_nOCOC₆H₅, n = 1–7) showed an “opposite odd–even effect” on clearing temperatures. The tendency was exactly opposite to that reported for liquid-crystal dimers. A mechanism is postulated on the basis of the difference in the formation of molecular aggregations of even- and odd-number-dopant molecules in the host liquid-crystal molecules.

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Well-aligned Titanium Dioxide with Very High Length-to-diameter Ratio Synthesized under Magnetic Field

Nursyafreena Attan, Hadi Nur, Jon Efendi, Hendrik Oktendy Lintang, Sie ...

2012 Volume 41 Issue 11 Pages 1468-1470
Published: November 05, 2012
Released on J-STAGE: November 03, 2012

DOIhttps://doi.org/10.1246/cl.2012.1468

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The synthesis of well-aligned titanium dioxide with a very high length-to-diameter ratio is demonstrated for the first time using a sol–gel method under a magnetic field (up to 9.4 T), with cetyltrimethylammonium bromide as a structure-aligning agent.

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Application of Sodium Poly(aspartic acid) as a Binding Phase in the Technique of Diffusive Gradients in Thin Films

Yujing Liu, Hong Chen, Fengling Bai, Jiali Gu, Lianli Liu

2012 Volume 41 Issue 11 Pages 1471-1472
Published: November 05, 2012
Released on J-STAGE: November 03, 2012

DOIhttps://doi.org/10.1246/cl.2012.1471

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Sodium poly(aspartic acid) (PASP) was investigated for application in the diffusive gradients in thin films (DGT) technique as a new binding phase (PASP DGT) for the measurement of Cd²⁺ in waters. The Cd²⁺ uptake of PASP DGT increased linearly with time (r² = 0.9989), with a DGT-labile fraction (Ψ) of 97.57 ± 1.45% in synthetic solution. The Ψ values of Cd²⁺ were measured in spiked river water (48.65 ± 2.26%) and spiked domestic wastewater (26.71 ± 1.25%). The binding capacity of PASP DGT decreased with increasing ionic strength, whereas it remained fairly constant in the pH range 4–10. The stability constant (log K) of PASP with Cd²⁺ was 9.28, indicating that PASP can coordinate strongly with Cd²⁺. The results show that PASP can be used as a binding phase in liquid-type DGT devices for the measurement of Cd²⁺ in waters.

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Efficient Cesium Adsorbent Using Prussian Blue Nanoparticles Immobilized on Cotton Matrices

Akiko Kitajima, Hisashi Tanaka, Nobutsugu Minami, Kazunori Yoshino, To ...

2012 Volume 41 Issue 11 Pages 1473-1474
Published: November 05, 2012
Released on J-STAGE: November 03, 2012

DOIhttps://doi.org/10.1246/cl.2012.1473

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An efficient cesium adsorbent has been developed using Prussian blue nanoparticles immobilized on cotton gauze. A cesium decontamination factor of the order of 10⁶ is achieved by passing cesium solutions through a column filled with 1.81 g of the adsorbent. In this study, two ion-exchange steps were used, i.e., Na⁺ to K⁺ for immobilization of nanoparticles on matrices and K⁺ to Cs⁺ for adsorption. The new cesium adsorbent shows promise for the decontamination of radioactive cesium.

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Thiocarbohydrazides and Oxalyl Dihydrazides Exhibiting Two- to Four-electron Redoxes for Positive Electrode Active Materials in Organic Rechargeable Lithium Batteries

Toyonari Sugimoto, Ken-ichiro Senoo

2012 Volume 41 Issue 11 Pages 1475-1477
Published: November 05, 2012
Released on J-STAGE: November 03, 2012

DOIhttps://doi.org/10.1246/cl.2012.1475

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Thiocarbohydrazides and oxalyl dihydrazides are used as positive electrode active materials for rechargeable lithium batteries with a lithium metal negative electrode. These compounds exhibit a two-electron migration in the positive electrode, yielding very large capacities of 482 and 450 mA h g⁻¹, respectively, by virtue of their small molecular weights (106 and 118, respectively). Additionally, tetramethyl- and diphenyl-substituted derivatives are used; the former compounds exhibit two-electron migrations with capacities of 310 and 300 mA h g⁻¹, while the latter compounds exhibit three- to four-electron migrations with large capacities of both 359 mA h g⁻¹.

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Synthesis, Crystal Structure, and Electrochemical Properties of (Li,Na)_xMn₁₋_yTi_yO₂ (0 < y < 0.49) with O3-type Layered Structure

Naoya Ishida, Hiroshi Hayakawa, Hideka Shibuya, Junichi Imaizumi, Junj ...

2012 Volume 41 Issue 11 Pages 1478-1480
Published: November 05, 2012
Released on J-STAGE: November 10, 2012

DOIhttps://doi.org/10.1246/cl.2012.1478

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O3-type (Li,Na)_xMn₁₋_yTi_yO₂ (0 < y < 0.49) materials were first prepared from Na_0.7Mn₁₋_yTi_yO₂ via Na/Li ion exchange. The substitution of Ti for Mn was confirmed by using XRD and STEM-EDX mapping. The solubility limit of Ti for Mn was estimated to be less than 0.49. The electrochemical measurements between 4.5 and 2.4 V showed that the initial discharge capacity increased from 163 to 191 mA h g⁻¹ with decreasing Ti contents, while the capacity retention rate increased with Ti contents.

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Wavelength Dependence of IR Laser for Dual-laser Shattering of a Water Microdroplet

Akinori Sugiyama, Atsushi Nakajima

2012 Volume 41 Issue 11 Pages 1481-1483
Published: November 05, 2012
Released on J-STAGE: November 10, 2012

DOIhttps://doi.org/10.1246/cl.2012.1481

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For the single- and dual-laser shattering of water microdroplets, the wavelength dependence of an infrared (IR) laser was experimentally examined in the range 2.25–3.75 µm using ion current measurements coupled with time-resolved imaging. Compared to a single IR laser, simultaneous illumination by dual IR lasers effectively compresses the spatial distribution of small fragments around the absorption maximum for the OH-stretching vibration of liquid water (λ = 2.75–3.25 µm). The effect can be explained by the small penetration depth of the IR laser toward water microdroplets.

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CuO Nanoparticles Supported on Silica: A Simple, Efficient, and Recyclable Catalyst for Hydroacylation Reactions of Aldehydes with Azodicarboxylate

Suleman M. Inamdar, Vinod K. More, Sisir K. Mandal

2012 Volume 41 Issue 11 Pages 1484-1486
Published: November 05, 2012
Released on J-STAGE: November 10, 2012

DOIhttps://doi.org/10.1246/cl.2012.1484

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We describe a green and efficient procedure for the hydroacylation of aldehydes with diisopropyl azodicarboxylate, using CuO nanoparticles supported on silica (CuO-np/SiO₂) as a catalyst, in good to excellent yields. A wide range of aldehydes, including aromatic and aliphatic compounds, were considered. The catalyst is found to be truly heterogeneous in the reaction mixture and can be reused without loss of catalytic activity.

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Synthesis of an Amphiphilic Macromonomer Bearing a Terminal Fluorene Moiety and Its Application to the Preparation of Fluorescent Polymer Particles

Jin Motoyanagi, Katsutoshi Nagura, Kohei Sawada, Sadao Miki, Masahiko ...

2012 Volume 41 Issue 11 Pages 1487-1488
Published: November 05, 2012
Released on J-STAGE: November 10, 2012

DOIhttps://doi.org/10.1246/cl.2012.1487

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A new amphiphilic macromonomer MA-PMEEVE-FmPH bearing a methacryloyl group at the α-terminus and a fluorene moiety at the ω-terminus was synthesized by living cationic polymerization and reductive amination, and its application to the preparation of monodisperse polymer particles was studied. It was found that the macromonomer afforded colloidal spheres covered with fluorene moieties, causing it to exhibit fluorescence.

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Editor’s Choice

Photocatalytic Energy Storage over Surface-modified WO₃ Using V⁵⁺/V⁴⁺ Redox Mediator

Yugo Miseki, Hitoshi Kusama, Kazuhiro Sayama

2012 Volume 41 Issue 11 Pages 1489-1491
Published: November 05, 2012
Released on J-STAGE: November 10, 2012

DOIhttps://doi.org/10.1246/cl.2012.1489

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Photocatalytic V⁵⁺ reduction accompanied by O₂ evolution over WO₃ is reported for the first time. Water oxidation reaction utilizing VO₂⁺ ion as an electron acceptor proceeded photocatalytically over WO₃. The activity of WO₃ was remarkably enhanced by the presence of Fe^3+/2+ ion at the ion-exchange site on WO₃ surface, and its apparent quantum yield (AQY) was 22% at 420 nm. Moreover, the AQY was raised to about 78% when a small amount of formic acid was added to reactant solution.

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Letter

Carbon Nanotube–Polypyrrole Hybrid Films as Potentiometric Peroxide Biosensors

Aimin Yu

2012 Volume 41 Issue 11 Pages 1492-1494
Published: November 05, 2012
Released on J-STAGE: November 10, 2012

DOIhttps://doi.org/10.1246/cl.2012.1492

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Nanostructured composite films of multiwalled carbon nanotube/polypyrrole (MWCNT/PPy) were prepared, and their potential as potentiometric biosensors was studied. MWCNT and PPy were alternately assembled on indium tin oxide (ITO) electrodes via a solution-based layer-by-layer self-assembly technique, which provided a good matrix for the immobilization of horseradish peroxidase (HRP). The resulting MWCNT/PPy/HRP composite films exhibited excellent potentiometric response to hydrogen peroxide while the thickness and composition of the multilayer were found to affect the performance of the biosensor.

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Effect of Partial Fluorination in the Myristoyl Groups on Thermal and Interfacial Properties of Dimyristoylphosphatidylcholine

Masaru Yoshino, Hiroshi Takahashi, Toshiyuki Takagi, Teruhiko Baba, Ko ...

2012 Volume 41 Issue 11 Pages 1495-1497
Published: November 05, 2012
Released on J-STAGE: November 10, 2012

DOIhttps://doi.org/10.1246/cl.2012.1495

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A novel partially fluorinated analog of DMPC, diF4H10-PC, was synthesized, and its thermal and interfacial properties were compared with those of DMPC. By fluorine substitution in the terminal butyl segment in the myristoyl group of DMPC, the novel partially fluorinated diF4H10-PC membrane shows higher stability and larger occupied area, while remarkable decrease in the phase transition temperature and more hydrophilic properties in the hydrophilic/hydrophobic interface region were observed.

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Editor’s Choice

Nickel-catalyzed Cycloaddition of α,β-Unsaturated Oximes with Alkynes: Synthesis of Highly Substituted Pyridine Derivatives

Yuji Yoshida, Takuya Kurahashi, Seijiro Matsubara

2012 Volume 41 Issue 11 Pages 1498-1499
Published: November 05, 2012
Released on J-STAGE: November 10, 2012

DOIhttps://doi.org/10.1246/cl.2012.1498

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A nickel-catalyzed cycloaddition of α,β-unsaturated oximes with alkynes to afford 2,3,4,6-tetrasubstituted pyridine derivatives has been developed. The reaction involves oxidative addition of the N–O bond of α,β-unsaturated oximes to Ni(0) and subsequent alkyne insertion to an N–Ni bond, followed by intramolecular cyclization. It was also found that β,γ-unsaturated oximes participate in the nickel-catalyzed reaction with alkynes to furnish pyridine derivatives.

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Letter

Rose Bengal Immobilized on Wool as an Efficiently “Green” Sensitizer for Photooxygenation Reactions

Zhang Yan, Wang Wei, He Xun, Sang Anguo

2012 Volume 41 Issue 11 Pages 1500-1502
Published: November 05, 2012
Released on J-STAGE: November 10, 2012

DOIhttps://doi.org/10.1246/cl.2012.1500

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A new type of supported photosensitizer derived from renewable wool and Rose Bengal is described. The novel sensitizer could efficiently promote the photooxygenation of furan derivatives to the corresponding 5-hydroxy-2-(5H)-furanone in excellent yields, via singlet oxygen, using visible light as the energy source. The sensitizer could be easily recovered from the reaction mixture by a simple filtration. It is discovered that the recovered sensitizer can be reused four times.

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Synthesis of Unsymmetrical Diarylethynes by Pd(0)/Cu(I)-cocatalyzed Sila-Sonogashira–Hagihara Coupling Reactions of Alkynylsilanes with Aryl Tosylates or Mesylates

Yasushi Nishihara, Daisuke Ogawa, Shintaro Noyori, Masayuki Iwasaki

2012 Volume 41 Issue 11 Pages 1503-1505
Published: November 05, 2012
Released on J-STAGE: November 10, 2012

DOIhttps://doi.org/10.1246/cl.2012.1503

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Palladium/copper-cocatalyzed cross-coupling reactions of alkynylsilanes with aryl tosylates or mesylates afforded the corresponding unsymmetrical diarylethynes in moderate to good yields. The optimized reaction conditions to afford higher yields of cross-coupled products were found to be 5 mol % of [PdCl₂(bpy)], 15 mol % of BrettPhos, and 10 mol % of Cu^ICl in DMF as a solvent.

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Editor’s Choice

Effect of Temperature on DNA Chromatographic Separation in Free Solution

Ruonan Li, Lei Liu, Yu Wang, Xiayan Wang

2012 Volume 41 Issue 11 Pages 1506-1508
Published: November 05, 2012
Released on J-STAGE: November 10, 2012

DOIhttps://doi.org/10.1246/cl.2012.1506

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Narrow-bore open capillaries without stationary-phase coatings were used for DNA chromatographic separation in free solution. The retention behaviors of various sizes of DNA fragments were investigated using 1 × TE buffer as the eluent at various temperatures. It was shown that the temperature was an important parameter affecting the speed of DNA separation, with little loss of resolution in narrow-bore open-capillary chromatography.

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Letter

Fabrication of Polycarbonate and Poly(3-hydroxybutyrate-co-3-hydroxyhexanoate) Blend Monolith via Non-solvent-induced Phase Separation Method

Yuanrong Xin, Hiroshi Uyama

2012 Volume 41 Issue 11 Pages 1509-1511
Published: November 05, 2012
Released on J-STAGE: November 10, 2012

DOIhttps://doi.org/10.1246/cl.2012.1509

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A blend monolith of polycarbonate and poly(3-hydroxybutyrate-co-3-hydroxyhexanoate) with a three-dimensional continuous interconnected porous structure is fabricated through a non-solvent-induced phase separation (NIPS) method. By tuning the solvent composition for NIPS, the monolith of the two immiscible polymers is obtained successfully. The blend monolith, with its large surface area and high thermal stability, may find use in various potential applications of porous materials.

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Rapid and High-capacity Adsorption of Glucose Oxidase on Amine-functionalized Mesoporous Silica SBA-15 Platelets

Yi Ding, Guangfu Yin, Xiaoming Liao, Zhongbin Huang, Xianchun Chen, Ya ...

2012 Volume 41 Issue 11 Pages 1512-1514
Published: November 05, 2012
Released on J-STAGE: November 10, 2012

DOIhttps://doi.org/10.1246/cl.2012.1512

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We have synthesized platelet-like SBA-15 particles and functionalized their surfaces with amine groups for use as adsorbent materials in glucose oxidase (GOD) adsorption. The amine-functionalized SBA-15 exhibits very rapid (<20 min to reach equilibrium) and high-capacity (up to 680 mg g⁻¹) adsorption of GOD. It is found that electrostatic interaction is the dominant driving force for GOD adsorption on these mesoporous materials.

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Synthesis and Electrochemical Properties of Porous Titania Prepared by Spray-drying of Titania Nanosheets

Mitsumasa Sakao, Norihito Kijima, Junji Akimoto, Takeshi Okutani

2012 Volume 41 Issue 11 Pages 1515-1517
Published: November 05, 2012
Released on J-STAGE: November 10, 2012

DOIhttps://doi.org/10.1246/cl.2012.1515

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Porous titania was synthesized through the spray-drying of titania nanosheets. SEM-FIB analyses showed that the spray-dried nanosheets were spherical particles with no hollow center. Nitrogen adsorption–desorption isotherms showed that the porous titania had a mesoporous structure composed of slit-shaped pores. The porous titania acted as a rechargeable active material for the lithium battery. Rechargeable capacities of about 200 mA h g⁻¹ (cutoff voltage: 1.0 V) and about 300 mA h g⁻¹ (cutoff voltage: 0.5 V) could be achieved over the first ten cycles.

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Highly Densified Mesoporous Bulk Silica Prepared with Colloidal Mesoporous Silica Nanoparticles toward a New Low-k Material

Norihiro Suzuki, Yu-Tzu Huang, Yoshihiro Nemoto, Atsushi Nakahira, Yus ...

2012 Volume 41 Issue 11 Pages 1518-1519
Published: November 05, 2012
Released on J-STAGE: November 10, 2012

DOIhttps://doi.org/10.1246/cl.2012.1518

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We report the fabrication of highly densified mesoporous bulk silica consisting of colloidal mesoporous silica nanoparticles (MSNs) by using a hydrothermal hot-pressing method. No cracks or voids are found in the synthesized bulk. The mesoporous structure of the bulk is maintained as well as that of the original MSNs. The MSN-based bulk with large pore volume shows potential as a low-k material.

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Selective Extraction of Heavy Rare-earth Metal Ions with a Novel Calix[4]arene-based Diphosphonic Acid

Naoya Morohashi, Tomoko Hayashi, Yuka Nakamura, Takahiro Kobayashi, Sh ...

2012 Volume 41 Issue 11 Pages 1520-1522
Published: November 05, 2012
Released on J-STAGE: November 10, 2012

DOIhttps://doi.org/10.1246/cl.2012.1520

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The selective extraction of heavy rare-earth metal ions is achieved by using a novel calix[4]arenediphosphonic acid 4, in which two phosphono groups are introduced directly at the lower rim of the calix skeleton through the Ullmann-type phosphonation of the 1,3-bistriflate ester of p-tert-butylcalix[4]arene 3 as a key step.

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A Four-spin Cobalt-radical Complex: Structure and Magnetic Properties

Chao Wang, Ya L. Wang, Yue Ma, Qing L. Wang, Li C. Li, Dai Z. Liao

2012 Volume 41 Issue 11 Pages 1523-1525
Published: November 05, 2012
Released on J-STAGE: November 10, 2012

DOIhttps://doi.org/10.1246/cl.2012.1523

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A new complex {[Co(hfac)₂]₂(4P3NIT)₂}·CHCl₃ (1) (hfac: hexafluoroacetylacetonate, 4P3NIT: 2-[3-(4-pyridyl)phenyl]-4,4,5,5-tetramethylimidazoline-1-oxyl-3-oxide) has been synthesized and characterized structurally and magnetically. The single-crystal structure revealed that two 4P3NIT molecules and two [Co(hfac)₂] units construct a four-spin rectangle-like molecule. Effective-spin approach was also employed to evaluate the magnetic coupling J₁ and J₂ within this four-spin unit. The best fitting result gives J₁ = −23.41 cm⁻¹, J₂ = 3.18 cm⁻¹, which indicate the antiferromagnetic interaction between the Co(II) ion and directly bonded radical, and weak ferromagnetic interaction between the central Co(II) ion and organic radical through the pathway of pyridyl and phenyl ring.

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Volume Oscillation in Macroporous Gel

Shingo Maeda, Wahei Oda

2012 Volume 41 Issue 11 Pages 1526-1528
Published: November 05, 2012
Released on J-STAGE: November 10, 2012

DOIhttps://doi.org/10.1246/cl.2012.1526

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We succeeded in synthesizing microphase-separated self-oscillating gel and realized volume oscillation of the gel driven by chemical energy. The novel polymer gels were composed of a non-thermoresponsive polyacrylamide main chain covalently bonded to a ruthenium catalyst for the Belousov–Zhabotinsky (BZ) reaction. By changing the temperature, the displacement and frequency of the volume oscillation in gels were changed. Moreover, we showed that the displacement of the gel has a trade-off relationship with the frequency of the volume oscillation.

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One-pot Chemical Synthesis of Zinc Antimonide Nanoparticles as Building Blocks for Nanostructured Thermoelectric Materials

Nguyen T. Mai, Derrick M. Mott, Koichi Higashimine, Shinya Maenosono

2012 Volume 41 Issue 11 Pages 1529-1531
Published: November 05, 2012
Released on J-STAGE: November 10, 2012

DOIhttps://doi.org/10.1246/cl.2012.1529

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We report a novel one-pot chemical synthesis of zinc antimonide (Zn–Sb) nanoparticles (NPs) via the sequential reduction of metal precursors and subsequent compositional redistribution. Chemically synthesized Zn–Sb NPs are expected to be promising building blocks for nanostructured thermoelectric materials.

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Nonequilibrium Acidic Fluctuations in Room-temperature Ionic Liquid/Water Mixture: N,N-Diethyl-N-methyl-N-(2-methoxyethyl)ammonium Tetrafluoroborate

Masami Aono, Yukitaka Tomita, Hiroshi Abe, Yukihiro Yoshimura

2012 Volume 41 Issue 11 Pages 1532-1534
Published: November 05, 2012
Released on J-STAGE: November 10, 2012

DOIhttps://doi.org/10.1246/cl.2012.1532

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Room-temperature ionic liquid (RTIL)/water mixtures show acidic properties at around 90 mol % H₂O. The RTIL is N,N-diethyl-N-methyl-N-(2-methoxyethyl)ammonium tetrafluoroborate. The pH of the mixture in the nonequilibrium state is sensitive to the quality of the water type: city water (CW), distilled water (DIS), or ultrapure water (UP). At 90 mol % [H₂O]_DIS, rhythmic oscillations of pH are observed. The time periodicity is found to be approximately 20 min. In contrast, 90 mol % [H₂O]_CW and [H₂O]_UP mixtures show no synchronization in the pH.

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Guest-dependent Structural Transformation of Dehydrobenzoannulene Inclusion Crystals Composed of π-Stacked Parallelogram Columnar Motifs

Hajime Shigemitsu, Ichiro Hisaki, Eriko Kometani, Norimitsu Tohnai, Mi ...

2012 Volume 41 Issue 11 Pages 1535-1537
Published: November 05, 2012
Released on J-STAGE: November 10, 2012

DOIhttps://doi.org/10.1246/cl.2012.1535

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Octadehydrotribenzo[14]annulene (DBA) derivative 1 gave inclusion crystals with thirteen kinds of aromatic guest molecules. Heat-induced guest release of the inclusion crystals resulted in the formation of guest-free polymorphs, Forms I and III, which depended on the guest species.

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Editor’s Choice

Formation of Unique Platinum–Silyl Complexes by the Reactions of a Zero-valent Platinum Complex with Various Trisilanes

Hidekazu Arii, Makiko Takahashi, Hideyuki Takahashi, Kunio Mochida, Ta ...

2012 Volume 41 Issue 11 Pages 1538-1540
Published: November 05, 2012
Released on J-STAGE: November 10, 2012

DOIhttps://doi.org/10.1246/cl.2012.1538

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Trisilanes bearing hydrogen atoms at two more silicon atoms reacted with a zero-valent platinum complex [Pt(dppe)(η²-C₂H₄)] to give various types of mononuclear and dinuclear platinum–silyl complexes. Interestingly, in the case of 1,1,2,3,3-pentamethyltrisilane, the Si–Si bond was uniquely activated, resulting in the formation of the diplatinum complex [Pt₂(dppe)₂(µ-1,4-SiMe(SiMe₂)₂SiMe)].

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