Chemistry Letters

Highlight Review

Nanostructure-controlled Materials for Electrochemical Charging–Discharging

Isamu Moriguchi

2014 Volume 43 Issue 6 Pages 740-745
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: March 19, 2014

DOIhttps://doi.org/10.1246/cl.140173

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Down-sizing of Li-host materials is one of the recent research trends to develop high-performance electrode materials. Nanosized materials are expected to show high rate capability and/or high capacities. Nanoporous materials are also candidates for high-performance electrode materials. This review introduces recent studies on nanosized and nanoporous electrode materials toward developing high-performance energy-storage devices.

Down-sizing of Li-host materials is one of the recent research trends to develop high-performance electrode materials. Nanosized materials are expected to show high rate capability and/or high capacities. Nanoporous materials are also one of candidates of the high-performance electrode materials. This review introduces recent studies on nanosized and nanoporous electrode materials toward developing high-performance energy-storage devices. Fullsize Image

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Dynamic Kinetic Resolution of Racemic Allylic Alcohols via Hydrolase–Metal Combo Catalysis: An Effective Method for the Synthesis of Optically Active Compounds

Shuji Akai

2014 Volume 43 Issue 6 Pages 746-754
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: April 04, 2014

DOIhttps://doi.org/10.1246/cl.140223

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This review focuses on the dynamic kinetic resolution (DKR) of racemic allylic alcohols to produce allylic esters in high chemical and optical yields, which was achieved by combining hydrolase-catalyzed kinetic resolution and in situ racemization of the remaining less reactive enantiomers. Two classes of racemization catalysts, e.g., Ru complexes and oxovanadium compounds, are mainly discussed. Typical examples of DKR are shown along with their application in the concise syntheses of optically active compounds as valuable synthetic intermediates. The domino process integrating DKR with the active use of the installed acyl moiety for subsequent intramolecular cyclization is also discussed, which has great potential for the asymmetric syntheses of optically active fused cyclic molecules possessing multiple stereogenic centers.

This review focuses on the dynamic kinetic resolution (DKR) of racemic allylic alcohols to produce allylic esters in high chemical and optical yields, which was achieved by combining the hydrolase-catalyzed kinetic resolution and in situ racemization of the remaining less reactive enantiomers. Two classes of racemization catalysts, e.g., Ru complexes and oxovanadium compounds, are mainly discussed. Some applications of the DKR in the fewer-step syntheses of optically active synthetic intermediates and the further integration of the DKR with the active use of the installed acyl moiety for subsequent intramolecular cyclization are discussed. Fullsize Image

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Letter

Theoretical Study Demonstrating that Silylene Bridging Brings about LUMO Energy Lowering without Increasing the Reorganization Energy for Single Electron Transfer

Eisuke Ohta, Takuya Ogaki, Toru Aoki, Hiroshi Ikeda

2014 Volume 43 Issue 6 Pages 755-757
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: February 08, 2014

DOIhttps://doi.org/10.1246/cl.140023

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Density functional theory calculations were performed on silylene-bridged cyclic tri- and tetrathienylene 1b and 2b. The results show that in comparison to their respective unbridged counterparts 1a and 2a, 1b and 2b have lower LUMO energies but the same reorganization energies for single electron transfer between 1b and 2b and their respective radical anions 1b^•− and 2b^•−. The observations suggest that silylene bridging of π-conjugated systems can serve as a novel strategy for designing materials for n-type organic semiconductors.

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Electrochemical Activity Imaging of Enzymes Immobilized on Substrates Based on a Bio-LSI System

Toshiki Hokuto, Tomoyuki Yasukawa, Ryota Kunikata, Atsushi Suda, Kumi ...

2014 Volume 43 Issue 6 Pages 758-759
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: February 08, 2014

DOIhttps://doi.org/10.1246/cl.140055

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The activities of glucose oxidase (GOx) and lactate oxidase (LOx) immobilized on a substrate were obtained as images of oxidation currents of H₂O₂ using a Bio-LSI system. In the presence of appropriate substrates, the image of the enzyme appeared as lines with a high oxidation current. The time required to obtain the current image was 10 s, a significant decrease from the time required by the scanning method with a miniaturized probe.

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Interaction of Tris(2-aminoethyl)amine-based Ureas and Thiourea with Superoxide Anion and Peroxide Dianion through Multiple Hydrogen Bonding

Natsuru Chikushi, Yuki Nishikami, Hiroyuki Nishide

2014 Volume 43 Issue 6 Pages 760-762
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: February 14, 2014

DOIhttps://doi.org/10.1246/cl.140038

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Tris(2-aminoethyl)amine-based urea and thiourea derivatives interacted with a superoxide anion (O₂⁻) and peroxide dianion (O₂²⁻): The redox potential of oxygen was positively shifted with the molecules through their multiple-hydrogen-bond donor ability.

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Low Resistivity Composite Catalyst for Hybrid Gas Purifier with DC Corona Discharge

Penghao Su, Yimin Zhu, Chunyan Hou, Yingjie Liu

2014 Volume 43 Issue 6 Pages 763-765
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: February 14, 2014

DOIhttps://doi.org/10.1246/cl.140040

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To make titanium tin oxide (TTO) adapted to serve as a catalyst as well as a ground electrode in a DC corona discharge gas purifier, indium tin oxide (ITO) with low resistivity was composited with TTO via the sol–gel method. The resistivity of TTO–ITO composite was reduced to ca. 5 from ca. 10⁴ Ω cm of TTO. The discharge characteristics and the purification performance were promoted by the reduction of resistivity. There was no difference between TTO–ITO and TTO in valence states or crystal phases. We deduced that the hybrid purification mechanism of purifier TTO–ITO was plasma catalysis driven by electrons.

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Highly Diastereoselective Synthesis of Chiral Furans with a Quaternary Carbon Substituent at the 2-Position Using 8-Phenylmenthol as the Chiral Auxiliary

Aki Katori, Yoshiaki Sashihara, Akihisa Iwamoto, Satoshi Kojima, Yohsu ...

2014 Volume 43 Issue 6 Pages 766-768
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: February 14, 2014

DOIhttps://doi.org/10.1246/cl.140052

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The reaction of cis-4-oxo-2-pentenal and 8-phenylmenthyl 2-oxocyclopentane-1-carboxylate in the presence of a fluorinated cosolvent afforded the corresponding furan product with a high diastereoselectivity of up to 96% de. Other cyclic β-ketoesters reacted in a likewise diastereoselective manner.

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Cu²⁺ and Zn²⁺ Ion Adsorption onto a Fluorohectorite Clay–Poly(N-isopropylacrylamide) Nanocomposite Hydrogel

Nagisa Koizumi, Kana Sato, Shin’ichi Ishimaru

2014 Volume 43 Issue 6 Pages 769-771
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: February 15, 2014

DOIhttps://doi.org/10.1246/cl.140026

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Adsorption of Cu²⁺ and Zn²⁺ ions onto clay–poly(N-isopropylacrylamide) nanocomposite with a high clay content was investigated by visible adsorption spectroscopy and atomic absorption spectroscopy. Equilibration time was several hours or more for centimeter-sized specimens but was much shorter for samples with a smaller grain size. Adsorption isotherms of Cu²⁺ could be reproduced well using the Langmuir equation, and the estimated maximum adsorption amount coincided with the cation-exchange capacity of fluorohectorite-type clay contained in the nanocomposite. Results indicated that the effectiveness of using clay as an adsorbent can be improved by nanohybridization with a hydrophilic polymer.

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Structure Directing Agent-free Synthesis of ZSM-5 Zeolite Membranes Using Coal Fly Ash as Alumina Source

Mei-Hua Zhu, Izumi Kumakiri, Zi-Jun Feng, Xue-Mei Hua, Shui-Liang Xia, ...

2014 Volume 43 Issue 6 Pages 772-774
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: February 15, 2014

DOIhttps://doi.org/10.1246/cl.140059

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Hydrophilic ZSM-5 zeolite membranes were successfully prepared using coal fly ash as aluminum source by conventional and microwave-assisted hydrothermal syntheses. As-synthesized membranes had good H₂O selectivity for dehydration of 10 wt % H₂O/organic solution by pervaporation. Microwave-assisted synthesis drastically reduced the membrane synthesis time from 6 to 1 h. Moreover, the flux of the membrane prepared by the microwave-assisted synthesis was about twice the flux of a membrane prepared by a conventional method.

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Selective Liquid–Liquid Extraction of Uranyl Species Using Task-specific Ionic Liquid, Betainium Bis(trifluoromethylsulfonyl)imide

Kotoe Sasaki, Tomoya Suzuki, Takahiro Mori, Tsuyoshi Arai, Koichiro Ta ...

2014 Volume 43 Issue 6 Pages 775-777
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: February 21, 2014

DOIhttps://doi.org/10.1246/cl.140048

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Extraction behavior of U(VI) species from aqueous HNO₃ solution to [Hbet][Tf₂N] or [TMPA][Tf₂N] phase (Hbet: betainium, TMPA: N,N,N-trimethyl-N-propylammonium, Tf₂N: bis(trifluoromethylsulfonyl)imide) has been studied. It was found that the extractability (E) is 62% in the extraction from 0.01 M HNO₃ to [Hbet][Tf₂N] and decreases with an increase in [HNO₃] and that the U(VI) species are not extracted into [TMPA][Tf₂N] phase. These results suggest that the extraction of U(VI) species is due to the complex formation of UO₂²⁺ with the COO⁻ group of deprotonated betaine (bet). Furthermore, other metal species such as Na(I) and Al(III) in 0.01 M HNO₃ solution were found to be hardly extracted.

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Rapid Synthesis of ⁶²Zn-Labeled S-Glycosylated Porphyrin as Positron Emission Tomography Tracers for In Vivo PET Imaging

Masato Tamura, Hirofumi Matsui, Shiho Hirohara, Kiyomi Kakiuchi, Masao ...

2014 Volume 43 Issue 6 Pages 778-780
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: February 21, 2014

DOIhttps://doi.org/10.1246/cl.140056

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Positron emission tomography (PET) with [¹⁸F]-FDG can display cancerous activity depending on glucose uptake. Consequently, different PET tracers with different metabolisms are needed for further indication. We have developed multifunctional PET agents by combining ⁶²Zn²⁺ ion with laserphyrin^® and bisglycosylated 5,10,15,20-tetrakis(pentafluorophenyl)porphyrins (H₂Glccis-2 and H₂Glctrans-2), which can be easily synthesized and have a half-life of 9 h. ⁶²Zn-Labeled chemicals were successfully detected as PET signals in vivo and showed PDT-induced cell death by photoirradiation.

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Preparation of Au-Decorated Ag@C Nanoparticle and Its Biosensing Application

Haiping Huang, Rongjing Cui, Lingjun Yu, Changjie Mao

2014 Volume 43 Issue 6 Pages 781-783
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: February 26, 2014

DOIhttps://doi.org/10.1246/cl.131139

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Novel Ag@C core–shell structural nanospheres were prepared with Au nanoparticles decorated on their surface. The Ag@C nanospheres were first synthesized by a hydrothermal method, and then Au nanoparticles were absorbed onto the surface of the prepared nanospheres via electrostatic effect. In the study of its electrochemical behavior using hemoglobin (Hb) as a model protein, the prepared nanocomposite displayed excellent biocompatibility and high electrical conductivity. When it was used to fabricate a biosensor for H₂O₂ detection, excellent electrocatalytic activity was observed. This study may offer a new approach to expand the syntheses and electrochemical applications of core–shell structural nanospherical composites.

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Chiral Incomplete-cubane-type Mn^III₃O₄ Clusters Containing a µ₃-Methoxido or Hydroxido

Marina Inoue, Takayoshi Suzuki, Yukinari Sunatsuki, Akira Fuyuhiro, Na ...

2014 Volume 43 Issue 6 Pages 784-786
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: February 26, 2014

DOIhttps://doi.org/10.1246/cl.140067

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Two new cluster compounds having chiral incomplete-cubane-type Mn^III₃O₄ cores were synthesized using (2S)-2-hydroxy-4-(salicylideneamino)butyrate (H₂L⁻) and characterized by X-ray analysis as well as magnetic susceptibility and spectroscopic measurements. Compound 1 contains a [Mn^III₃(L)₃(µ₃-OMe)]⁻ cluster anion, while compound 2 prepared in water has a heptanuclear structure bearing two [Mn^III₃(L)₃(µ₃-OH)]⁻ clusters connected by a Mn^II(H₂O)₄ fragment. In both compounds, a moderate intracluster Mn^III···Mn^III ferromagnetic interaction was observed. It was also found that the Mn^III₃O₄ cluster cores are maintained in solution.

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Preparation of Polyimide–Cellulose Composite Using Oligoimide with Ethynyl Terminals

Tomoya Shirata, Tatsuki Kon, Keiko Sasaki, Yoshiyuki Oishi, Yuji Shiba ...

2014 Volume 43 Issue 6 Pages 787-789
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: February 26, 2014

DOIhttps://doi.org/10.1246/cl.140072

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A soluble imide oligomer (IO) (repeating number; 2 and 4) having N-phenylated melamine units and phenylethynyl terminals was prepared, and the application to polyimide composites with cellulose (CEL) crystals derived from pulp (CEL_p) or Halocynthia (CEL_h) with or without a modifier was investigated. The CEL_h additive up to 0.5 wt % was easily dispersed in IO matrix in solution, and thermostable (glass-transition temperature, ca. 285 °C) transparent tough film (tensile strength, ca. 169 MPa; elongation at break, ca. 8.9%; tensile modulus, ca. 4.6 GPa) was obtained, while the addition of a modifier such as cetyltrimethylammonium bromide and poly(ethylene glycol) derivatives was necessary to obtain a similar tough film for the CEL_p additive.

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Efficient CO₂ Adsorption on Amine-impregnated Mesoporous Silica Sorbents: Interpretation of Moderate Amine Loading

Tsuyoshi Watabe, Katsunori Yogo

2014 Volume 43 Issue 6 Pages 790-792
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: February 26, 2014

DOIhttps://doi.org/10.1246/cl.140080

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The CO₂ uptake of amine-impregnated mesoporous MSU-F silica sorbents increased up to 70 wt % amine loading. In terms of the amine-efficiency for CO₂ adsorption (defined as the amount of adsorbed CO₂ per amino group of the sorbent), the amine loadings for the most efficient CO₂ adsorption were 50 wt %. The moderate amine loadings are predictable from the pore volume of the porous support and from the molecular volumes of the impregnated amine and CO₂.

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Microwave-assisted Synthesis of Near-infrared-luminescent Ovalbumin-protected Gold Nanoparticles as a Luminescent Glucose Sensor

Junya Yoshimoto, Naoki Tanaka, Mitsuru Inada, Ryuichi Arakawa, Hideya ...

2014 Volume 43 Issue 6 Pages 793-795
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: February 26, 2014

DOIhttps://doi.org/10.1246/cl.140126

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In this work, highly luminescent ovalbumin-protected Au nanoparticles (OVA–Au NPs) with a quantum yield of 9.3% for emission at 645 nm were demonstrated as a fluorescence probe for sensitive detection of glucose. The fluorescence of the Au NPs originated from the Au(I)–thiol (S) complex on their surfaces, and it was found to be quenched effectively by enzymatically generated hydrogen peroxide (H₂O₂). The OVA–Au NPs allowed the determination of glucose concentrations in the range varying from 1.0 × 10⁻⁴ to 1 × 10⁻² M with a detection limit of 1 × 10⁻⁵ M.

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Controlling the Rotation of Porphyrin Units in Ethynyl-linked Porphyrin Trimers for Dye-sensitized Solar Cells by Anchoring onto TiO₂ Surface

Tomofumi Hamamura, Jotaro Nakazaki, Satoshi Uchida, Takaya Kubo, Hiros ...

2014 Volume 43 Issue 6 Pages 796-798
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: February 27, 2014

DOIhttps://doi.org/10.1246/cl.140087

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An ethynyl-linked porphyrin trimer bearing carboxyphenyl anchoring groups at all the porphyrin units becomes planar upon adsorption onto TiO₂, showing the Q band absorption and IPCE maximum at longer wavelengths.

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Sequential Paired Electrosynthesis of a Diaryl Ether Derivative Using an Electrochemical Microreactor

Tsuneo Kashiwagi, Toshio Fuchigami, Tsuyoshi Saito, Shigeru Nishiyama, ...

2014 Volume 43 Issue 6 Pages 799-801
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: February 28, 2014

DOIhttps://doi.org/10.1246/cl.140046

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A paired electrosynthetic conversion of a phenol to a diaryl ether derivative by using an electrochemical microreactor has been demonstrated. Sequential anodic C–O coupling reaction of phenol 1 to dienone aryl ether 2 and following reduction of 2 took place to give diaryl ether derivative 3 selectively by simply passing an electrolytic solution through the electrochemical microreactor.

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Conjugated Polymer-coated Counter Electrodes for Dye-sensitized Solar Cells Employing Solid Polymer Electrolytes

Moon-Sung Kang

2014 Volume 43 Issue 6 Pages 802-804
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: March 01, 2014

DOIhttps://doi.org/10.1246/cl.140083

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The photovoltaic performances of dye-sensitized solar cells employing solid polymer electrolytes have been greatly improved by the introduction of a chemically doped (p-type) conjugated polymer junction layer onto a conventional platinum-layered counter electrode. The increased energy conversion efficiency would be primarily due to the decrease in the interfacial charge-transfer resistances between the polymer electrolyte and the Pt-layered counter electrode, as confirmed by the results of FE-SEM and impedance spectroscopy.

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Estimation of the Distribution of Excited [2 + 2] Cyclic Reaction Paths through Conical Intersection by CiLC Analysis

Shogo Sakai, Keita Nakamura, Shoko Ito

2014 Volume 43 Issue 6 Pages 805-807
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: March 01, 2014

DOIhttps://doi.org/10.1246/cl.140085

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The excitation of singlet reaction paths through a conical intersection for the [2 + 2] photocycloaddition of two ethylene molecules was studied by the complete active space self-consistent-field method. The electronic states in the conical intersection region were analyzed by the CiLC (CI/LMO/CASSCF) method. Drastic variations in the bond weights observed by CiLC analysis at the circle around the conical intersection corresponded with those observed by dynamic reaction coordinate calculations. The conical intersection was found to have a polarized conformation.

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Light-transmittable Ultrasmooth Gold Film for Gap-mode Tip-enhanced Raman Scattering Spectroscopy

Masahiro Oguchi, Masahito Mochizuki, Taka-aki Yano, Masahiko Hara, Tom ...

2014 Volume 43 Issue 6 Pages 808-810
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: March 01, 2014

DOIhttps://doi.org/10.1246/cl.140093

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We report light-transmittable ultrasmooth gold film enabling gap-mode tip-enhanced Raman scattering (TERS) spectroscopy measurements with extremely low background signals. An ultrasmooth Au substrate was fabricated by introducing a wetting layer of germanium (Ge). We also found that high mechanical and chemical stability of the substrate along with flexibility in chemical modification provides versatile platforms for gap-mode TERS measurements in various environments, such as air, water, and organic solvents.

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A Synthetic Cell Division System: Effect of Nonbilayer-forming Lipid on Division of Liposomal Membranes

Fei Hao, Keishiro Tahara, Jun-ichi Kikuchi

2014 Volume 43 Issue 6 Pages 811-813
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: March 05, 2014

DOIhttps://doi.org/10.1246/cl.140081

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Spontaneous division of lipid bilayer vesicles was observed for giant vesicles formed by a phospholipid mixture containing a nonbilayer-forming lipid, i.e., a nonionic peptide lipid with a quinoyl head moiety. This synthetic cell division involved dynamic sequential processes, including phase separation of mixed lipids in the vesicles, vesicle deformation from a spherical to an elliptical shape, and subsequently fission.

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Application of Cuprous Oxide Nanowires in an Electrochemical Sensor for Ascorbic Acid

Jian-wei Zhao, Zhong-ke Yan, Li-rong Qin, Xi-ning Feng, Ping Wang

2014 Volume 43 Issue 6 Pages 814-816
Published: June 05, 2014
Released on J-STAGE: June 05, 2014

DOIhttps://doi.org/10.1246/cl.131200

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A promising electrochemical sensor of ascorbic acid (AA) was constructed based on cuprous oxide nanowires with coarse surface. The sensor exhibited excellent electrocatalytic performance for AA determination in alkaline medium.

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Regioselective Preparation of 4-Nitro-o-xylene Using Nitrogen Dioxide/Molecular Oxygen over Zeolite Catalysts. Remarkable Enhancement of para-Selectivity

Hongtao Liu, Cheng Ji, Xiongzi Dong, Xinhua Peng, Chunjie Shi

2014 Volume 43 Issue 6 Pages 817-819
Published: June 05, 2014
Released on J-STAGE: June 05, 2014

DOIhttps://doi.org/10.1246/cl.140031

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In the presence of molecular oxygen and zeolite H-β with Si/Al₂ = 500, o-xylene reacted regioselectively with liquid nitrogen dioxide at 35 °C to yield mononitro-o-xylenes as the main product, where the 4-nitro-o-xylene isomer predominated up to 89% and the 4-nitro-/3-nitro-o-xylene isomer ratio improved to 7.8. The process is eco-friendly, less expensive, and the zeolite could be easily regenerated by a simple workup to afford results similar to those obtained with the fresh catalyst.

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Fabrication Process of Silica Hard-shell Microcapsule (HSMC) Containing Phase-change Materials

Takafumi Toyoda, Reishi Narisada, Hiroshi Suzuki, Ruri Hidema, Yoshiyu ...

2014 Volume 43 Issue 6 Pages 820-821
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: March 11, 2014

DOIhttps://doi.org/10.1246/cl.140099

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A fabrication process via the double-emulsion method is proposed for silica hard-shell microcapsules (HSMCs) that contain trimethylolethane (TME) hydrate. The TME-encapsulating silica-HSMCs are promising materials for reusable phase-change materials for latent-heat transportation systems. The obtained silica-HSMCs were visualized by a scanning electron microscope. The amount of TME hydrate inside the capsules was confirmed using a differential scanning calorimeter. The measured latent heat of the TME-encapsulating silica-HSMC was a reasonable fit to the predicted value.

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Amination of Alcohols with Ammonia in Water over Rh–In Catalyst

Tsukasa Takanashi, Yoshinao Nakagawa, Keiichi Tomishige

2014 Volume 43 Issue 6 Pages 822-824
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: March 01, 2014

DOIhttps://doi.org/10.1246/cl.140051

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Amination of various C3 alcohols such as 1,2-propanediol with ammonia was catalyzed by Rh–In/C in water while Rh/C was totally inactive. Activated carbon FAC-10 was the best support in terms of activity and resistance to metal leaching. In the amination of 1,2-propanediol, Rh–In/C produced amino alcohols in 68% total selectivity and 38% conversion. XRD and TEM measurements showed that Rh–In alloy particle with size of 3–4 nm was formed on the carbon support.

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Formation of Thin Molecularly Imprinted Hydrogel Layers with Lectin Recognition Sites on SPR Sensor Chips by Atom Transfer Radical Polymerization

Yoshiaki Kuriu, Akifumi Kawamura, Tadashi Uragami, Takashi Miyata

2014 Volume 43 Issue 6 Pages 825-827
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: March 01, 2014

DOIhttps://doi.org/10.1246/cl.140103

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We prepared lectin-imprinted hydrogel layers on surface plasmon resonance (SPR) sensor chips by atom transfer radical polymerization (ATRP). In a buffer solution with a target protein, the SPR signal and binding constant of the lectin-imprinted hydrogel layer chip were much larger than those of the nonimprinted hydrogel layer chip prepared without using a template lectin. By molecular imprinting with ATRP, recognition sites for the target lectin were formed within thin hydrogel layers on the SPR sensor chips. The lectin-imprinted hydrogel layer chips with recognition sites for target protein are candidates for highly sensitive sensor devices for an SPR sensing system.

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Novel Reddish Yellow-emitting Ce³⁺-Doped Ba₃Sc₄O₉ Phosphors for Blue-light-based White LEDs

Takuya Hasegawa, Sun Woog Kim, Tadashi Ishigaki, Kazuyoshi Uematsu, Hi ...

2014 Volume 43 Issue 6 Pages 828-830
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: March 07, 2014

DOIhttps://doi.org/10.1246/cl.140070

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Novel reddish yellow-emitting Ba₃(Sc₁₋_xCe_x)₄O₉ (0 ≤ x ≤ 0.01) phosphors were synthesized in a single-phase form by a conventional solid-state reaction method. These phosphors exhibited excellent optical absorption in the blue-light region and showed reddish yellow emission with a peak at 583 nm due to the 5d → 4f transition of Ce³⁺ under excitation at 437 nm. By optimizing the Ce³⁺ concentration, the maximum emission intensity was obtained for Ba₃(Sc_0.999Ce_0.001)₄O₉.

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Photochemical Generation of Superbases from Carboxylates Consisting of Phthalimidoacetic Acid Derivatives and Superbases

Koji Arimitsu, Ken Fukuda, Nobuhiko Sakai

2014 Volume 43 Issue 6 Pages 831-833
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: March 11, 2014

DOIhttps://doi.org/10.1246/cl.140073

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We have developed simple and powerful photobase generators capable of highly efficient production of superbases. These photobase generators were prepared by simply mixing phthalimidoacetic acid derivatives with the corresponding superbases. The use of photobase generators enabled anionic UV curing at lower temperatures, in contrast to previous anionic UV curing materials that required heat treatment above 150 °C after UV irradiation. The cured films showed no volume shrinkage.

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Oxidative Desulfurization of Diesel Using Organic Salt of Polyoxometalate as an Efficient and Recoverable Phase-transfer Catalyst

Fengli Yu, Rui Wang

2014 Volume 43 Issue 6 Pages 834-836
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: March 20, 2014

DOIhttps://doi.org/10.1246/cl.140132

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Several organic salts of polyoxometalates were prepared and used initially as effective and recoverable phase-transfer catalysts for the oxidative desulfurization of simulated and real diesels. Meanwhile, the kinetic parameters of the DBT oxidation process were obtained.

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Cyclopentane-condensed Chromones from Marine-derived Fungus Penicillium oxalicum

Jie Bao, Xiao-Yong Zhang, Jie-jie Dong, Xin-ya Xu, Xu-Hua Nong, Shu-Hu ...

2014 Volume 43 Issue 6 Pages 837-839
Published: June 05, 2014
Released on J-STAGE: June 05, 2014

DOIhttps://doi.org/10.1246/cl.140138

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Five new cyclopentane-condensed chromones, coniochaetones G–K (1–5), along with four known compounds—penicillone C (6), penicillanone (7), conioxanthone A (8), and pinselin (9)—were isolated from the crude extract of marine-derived fungus Penicillium oxalicum. The structures of 1–5 were elucidated by NMR, MS, IR, UV, and CD spectra. Metabolites 1–5 were evaluated for cytotoxicity, antibacterial, and antifouling activities.

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Preparation of siRNA Carrier Based on Boronic Acid-functionalized Amphiphilic Poly(γ-glutamic acid) Nanoparticles

Fumiaki Shima, Manami Shudo, Takami Akagi, Mitsuru Akashi

2014 Volume 43 Issue 6 Pages 840-842
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: February 15, 2014

DOIhttps://doi.org/10.1246/cl.140060

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Boronic acid-grafted amphiphilic poly(γ-glutamic acid) was successfully synthesized with carbodiimide. These copolymers could form 200-nm-sized monodispersed nanoparticles (NPs). These NPs were stable in saline and could efficiently load small interfering RNA (siRNA) in a dose-dependent manner at about 80% efficiency. These results demonstrated that the polymer chemistry could contribute to the development of siRNA-based gene therapies.

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Dendritic Tetrathiafulvalene Pentamers Linked by Methylenedithio Spacers

Haruka Kimura, Katsuya Konishi, Shun-ya Muraoka, Takashi Shirahata, Yo ...

2014 Volume 43 Issue 6 Pages 843-845
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: March 05, 2014

DOIhttps://doi.org/10.1246/cl.140092

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Dendritic tetrathiafulvalene (TTF) derivatives linked by methylenedithio groups 3 were synthesized. Cyclic voltammetry and spectroelectrochemistry analyses revealed the presence of considerable mutual interaction among multiple TTF units in the oxidation states.

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Replication of Ordered Mesostructure on the Surface of 2D Hexagonal Mesoporous Silica Film as Exemplified by the Formation of Striped Cu Nanopatterns

Maho Kobayashi, Yosuke Kanno, Kazuyuki Kuroda

2014 Volume 43 Issue 6 Pages 846-848
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: March 06, 2014

DOIhttps://doi.org/10.1246/cl.140071

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The surface of 2D hexagonal mesoporous silica film has been successfully etched with ammonium fluoride to form an uncovered and well-defined mold surface. The surface can be effectively used to replicate striped Cu nanopatterns with the same mesoscale periodicity by vapor deposition of Cu.

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Determination of Chromium Speciation in Tap Water Using Diffusive Gradients in Thin Film Technique

Lianwen Guo, Hong Chen, Yangyang Zhang, Le Bo, Jianrong Li

2014 Volume 43 Issue 6 Pages 849-850
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: March 06, 2014

DOIhttps://doi.org/10.1246/cl.140100

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A dual diffusive gradients in thin film (DGT) device method for in situ fractionation of dissolved inorganic Cr was developed by simultaneously deploying two types of DGT devices with different binding phases in tap water. The concentration of Cr(III) in the tap water determined by a DGT device with sodium poly(aspartic acid) (PASP) solution as the binding phase (PASP DGT) was 3.18 µg L⁻¹, and the recoveries of the spiked Cr(III) were 97.9%–105.3%; the concentration of Cr(VI) in the tap water determined by a DGT device with poly(quaternary ammonium) salt (PQAS) solution as the binding phase (PQAS DGT) was 2.92 µg L⁻¹, and the recoveries of the spiked Cr(VI) were 98.2%–107.7%. The ratios of the total Cr measured by DGT to the total Cr measured by ICP-MS were 102.9%–105.7%.

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A New, Efficient, and Catalyst-free Microwave-assisted Approach for Formation of O-tert-Butoxy Carbonates

Hacène K’tir, Aïcha Amira, Malika Berredjem, Nour-Ed ...

2014 Volume 43 Issue 6 Pages 851-853
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: March 11, 2014

DOIhttps://doi.org/10.1246/cl.140075

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A new simple, efficient, greener, and catalyst-free chemoselective protocol for the O-tert-butoxycarbonylation of various structurally diverse hydroxy compounds was carried out with (Boc)₂O under microwave radiation. The corresponding O-tert-butoxy carbonates were obtained in good to excellent yields in a short reaction time without any side reactions.

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Novel Inorganic Gatekeeper Strategy for Obtaining Controlled Release in Mesoporous Silica Nanoparticles

Ce Peng, Nicol Alec, Miaomiao Zhao, Qiang Cai, Youwei Yao, Xiumei Wang ...

2014 Volume 43 Issue 6 Pages 854-856
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: March 11, 2014

DOIhttps://doi.org/10.1246/cl.140142

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A relatively facile and adjustable approach was investigated to synthesize mesoporous silica nanoparticles (MSNs) with a thin controllable solid silica-cap (sSiO₂) outer layer that prevented unwanted degradation for controlled drug release because the sSiO₂ turned out to degrade gradually. Ibuprofen (IBU) and calcium ions were loaded to evaluate the efficiency of this system. This sSiO₂-capped degradation strategy for controlled release could easily be extended to other pH- or temperature-responsive MSN systems and applications.

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Visually Recognizable Anion Exchange of a Three-dimensional Copper-based Interpenetrated Porous Coordination Polymer

Ryosuke Kotani, Atsushi Kondo, Kazuyuki Maeda

2014 Volume 43 Issue 6 Pages 857-859
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: March 11, 2014

DOIhttps://doi.org/10.1246/cl.140061

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A new three-dimensional copper-based interpenetrated porous coordination polymer (PCP) was synthesized using 1,2-di(4-pyridyl)ethylene (bpe), which is an N-donor neutral organic linker. The PCP has a cationic framework because all counter BF₄⁻ anions present as guest species to compensate the positive charge of the framework. The PCP shows anion-exchange properties for halogen ions, which can be recognized visually.

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Preparation of Modified Mica as an Effective Adsorbent to Remove Cs⁺ from Water

Takahiro Yamamoto, Takuya Fujimura, Tetsuya Shimada, Shinsuke Takagi

2014 Volume 43 Issue 6 Pages 860-861
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: March 11, 2014

DOIhttps://doi.org/10.1246/cl.140089

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The adsorption behavior of Cs⁺ with the modified mica was investigated in aqueous suspension, quantitatively. Phlogopite was used as typical mica. We newly found out that phlogopite treated with BaCl₂ for a short period (2 h) exhibits ability to adsorb Cs⁺, equivalent to phlogopite treated with a conventional reagent such as sodium tetraphenylborate (NaTPB). Since BaCl₂ is a much cheaper reagent than NaTPB and the treatment period is very short, this finding would be valuable to provide a practical method to remove radioactive Cs⁺ from the environment.

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Coordination Oligomers and Polymers of an Oxazole-appended Zinc Chlorophyll Derivative

Yoshinao Shinozaki, Isao Yoshikawa, Koji Araki, Kazuaki Ohara, Kentaro ...

2014 Volume 43 Issue 6 Pages 862-864
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: March 11, 2014

DOIhttps://doi.org/10.1246/cl.140135

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The self-assembled structures of an oxazole-appended zinc chlorophyll derivative in solution and in a crystal are reported. Cyclic oligomers formed in chloroform, while staircase-like coordination polymers formed in the crystal, both mediated by intermolecular axial coordination of the nitrogen atom in the oxazole moiety to the zinc center in another chlorophyll molecule.

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Influence of Trimethylamine N-Oxide (TMAO) on the Three-dimensional Distribution and Alignment of Solvent Molecules in Aqueous Solution

Hideo Doi, Yudai Watanabe, Misako Aida

2014 Volume 43 Issue 6 Pages 865-867
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: March 11, 2014

DOIhttps://doi.org/10.1246/cl.140043

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By means of Monte Carlo simulations together with an ab initio molecular orbital method, we present the influence of trimethylamine N-oxide (TMAO), which is a highly polarized spherical-polyhedron, on the distribution and the alignment of surrounding water molecules. The specific alignment of the average dipole moments of solvent water around TMAO is observed in the MC simulation. The number of water molecules in the first hydration shell from MC simulation was in good agreement with the experimental value. A cluster model of TMAO with 12 water molecules was presented as a representative hydration structure of TMAO.

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Noncovalent Functionalization of Graphene with Spiropyran Molecular Switches via a Specially Designed Perylenediimide Adsorption Anchor

Yawei Song, Jingwen He, Chang Peng, Ding Hu, Encai Ou, Yefei Li, Hua P ...

2014 Volume 43 Issue 6 Pages 868-870
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: March 13, 2014

DOIhttps://doi.org/10.1246/cl.140058

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A spiropyran derivative, which is a well-known photochromic molecule, is attached noncovalently to graphene via a specially designed perylenediimide adsorption anchor group. To explore the feasibility of functionalization, several characterizations were used to prove the π–π interaction between graphene and spiropyran–perylenediimide. This facile and effective noncovalent functionalization strategy provides a new way of introducing various functional molecules to graphene without disturbing its electronic network. The graphene hybrid shows excellent switching ability after modification with spiropyran derivative; furthermore, the switching performance is stable over many cycles. This hybrid has potential application in optical electronic devices and sensors.

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Enhanced Photocatalytic Activity of Titanium Dioxide: Modification with Graphene Oxide and Reduced Graphene Oxide

Xuandong Li, Meirong Kang, Xijiang Han, Jingyu Wang, Ping Xu

2014 Volume 43 Issue 6 Pages 871-873
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: March 13, 2014

DOIhttps://doi.org/10.1246/cl.140063

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In situ growth of TiO₂ nanoparticles on reduced graphene oxide (RGO–TiO₂) exhibits good performance of photocatalytic degradation under visible light. The photocatalytic efficiency of GO–TiO₂ and RGO–TiO₂ in degrading Methyl Orange could reach 99% and 96% within 2 h, respectively. The results showed that the optimum mass ratio of GO or RGO to TiO₂ was 0.15.

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Catalytic Properties of Mn-Modified Hexagonal YbFeO₃: Noble-metal-free Combustion Catalysts

Saburo Hosokawa, Yuichi Masuda, Tatsuya Nishimura, Kenji Wada, Ryu Abe ...

2014 Volume 43 Issue 6 Pages 874-876
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: March 13, 2014

DOIhttps://doi.org/10.1246/cl.140141

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Mn-Modified YbFeO₃ with a metastable hexagonal phase prepared via a solvothermal method exhibited much higher catalytic activity for propane combustion at low temperatures than conventional noble-metal catalyst Pd/Al₂O₃.

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Editor’s Choice

Photocrosslinking of the Exterior of a Fullerene Bilayer that Prevents Vesicle Aggregation

Koji Harano, Akimitsu Narita, Eiichi Nakamura

2014 Volume 43 Issue 6 Pages 877-879
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: March 15, 2014

DOIhttps://doi.org/10.1246/cl.140143

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An amphiphilic molecule bearing a coumarin moiety attached to a water-soluble fullerene via an alkyl linker forms a water-soluble fullerene bilayer vesicle in water that spontaneously agglomerates and fuses upon standing. The agglomeration–fusion ability of the vesicle was endowed probably by the intervesicular interaction between the coumarin group and the fullerene core, as judged by the lack of such ability for the vesicles bearing only alkyl groups and by complete inhibition by conversion of the coumarin group into a photodimer.

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Letter

Theoretical Investigation on the Optical Properties of Diphosphine-protected Au₈ Cluster Complexes

Sachio Hayashi, Kohei Tada, Kohei Sakata, Hiroaki Koga, Shusuke Yamana ...

2014 Volume 43 Issue 6 Pages 880-882
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: March 19, 2014

DOIhttps://doi.org/10.1246/cl.140149

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Herein, we have theoretically investigated the optical properties of the two Au₈ complexes with different shapes of the Au₈ cluster core. From the results of TD-DFT and DFT calculations, it was found that the shape of the Au₈ clusters in the two Au₈ complexes greatly influenced their optical properties, such as absorption and photoluminescence spectra. In particular, the intensities of their photoluminescence spectra are greatly decreased with an increase of the Au–Au bond length variation of the Au core cluster in the S₁ states of the Au₈ complexes.

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Facile Synthesis of 3,3′-Disubstituted 2,2′-Binaphthyls by Transition-metal-catalyzed Double Benzannulation

Rui Umeda, Hiromasa Tabata, Yoshito Tobe, Yutaka Nishiyama

2014 Volume 43 Issue 6 Pages 883-884
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: March 20, 2014

DOIhttps://doi.org/10.1246/cl.140169

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3,3′-Disubstituted 2,2′-binaphthyls were prepared by the Cu- or Re-catalyzed double benzannulation reaction of 2-(phenylethynyl)benzaldehyde with various butadiynes in the presence of trichloroacetic acid, in moderate to good yields. Acceleration of the second benzannulation was clearly observed.

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Comparison between Ion-chromatography and Titration Methods for the Determination of Sulfite in Wastewater Containing Furfural

Yufeng Wang, Kefu Chen, Qiang Wang, Zhibin He, Lei Zheng, Yonghao Ni

2014 Volume 43 Issue 6 Pages 885-886
Published: June 05, 2014
Released on J-STAGE: June 05, 2014

DOIhttps://doi.org/10.1246/cl.140102

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Sulfur-containing species, such as sulfite, are detrimental to the operation of anaerobic systems, therefore, it is critical to determine their concentrations in order to optimize an anaerobic reactor. In this study, the traditional titration method for the determination of sulfite was applied to acid-condensate samples from an acid sulfite pulp mill effluent, and the results showed that they were consistently lower than those from ion chromatography (IC). It was found that the presence of furfural in the acid-condensate samples can interfere with the titration for sulfite, resulting in lower sulfite values; the higher the furfural concentration in the sample, the lower the indicated sulfite concentration by titration. It was concluded that IC method is a reliable method for determining the sulfite concentration for samples containing furfural.

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Oxidative Protonolysis of the Expanded Central C–C Bond in a Di(spiroacridan)-type Hexaphenylethane Derivative Accompanied by UV–vis, FL, and CD Spectral Changes

Takanori Suzuki, Yusuke Kuroda, Kazuhisa Wada, Yuto Sakano, Ryo Katoon ...

2014 Volume 43 Issue 6 Pages 887-889
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: March 25, 2014

DOIhttps://doi.org/10.1246/cl.140192

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Upon electrochemical oxidation of configurationally stable (M)-4,5-dimethyl-9,10-dihydrophenanthrene attached with two spiroacridan units at the C9 and C10 positions [(M)-1c], a three-way-output response by UV–vis, FL, and CD spectra was realized via clean conversion to the corresponding bond-dissociated dication (R_ax)-2c²⁺. Similar gradual changes were induced upon standing of an aerated MeCN solution of (M)-1c after the addition of CF₃CO₂H because the elongated C9–C10 bond was also cleaved by oxidative protonolysis to give (R_ax)-2c²⁺.

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Coordination Programming in the Design of Porous Coordination Polymers: Tuning of the Electronic Activity of Frameworks for Selective Nitrogen Monoxide Trapping

Wataru Kosaka, Kayo Yamagishi, Ryotaro Matsuda, Susumu Kitagawa, Masak ...

2014 Volume 43 Issue 6 Pages 890-892
Published: June 05, 2014
Released on J-STAGE: June 05, 2014
Advance online publication: March 28, 2014

DOIhttps://doi.org/10.1246/cl.140190

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A change of building block from [Ru₂^II,II(p-FPhCO₂)₄] to [Ru₂^II,II(4-F-2-OMePhCO₂)₄] in a phenazine (phz)-bridged [Ru₂^II,II] chain compound led to a high selectivity toward nitrogen monoxide (NO) in the adsorption characteristics. High selectivity was observed despite the fact that electronically negative sites that enable close contact with NO molecules are not present in the pores, in contrast to [Ru₂^II,II(4-Cl-2-OMePhCO₂)₄(phz)], which also exhibited selective NO adsorption.

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