Chemistry Letters

Editor’s Choice

Ratiometric Sensing of D-Glucose in a Combined Approach of Aggregation-induced Emission (AIE) and Dynamic Covalent Bond Formation

Daisuke Yoshihara, Takao Noguchi, Bappaditya Roy, Junji Sakamoto, Tats ...

2016 Volume 45 Issue 7 Pages 702-704
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 06, 2016

DOIhttps://doi.org/10.1246/cl.160240

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A novel saccharide sensing system has been established with an aggregation-induced emission (AIE)-cored probe by utilizing the dynamic covalent bond formation between the diol and boronic acid. Interestingly, this system can selectively sense D-glucose, and the fluorescence spectrum shows a ratiometric change arising from the D-glucose-induced stepwise morphological growth.

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Letter

Preparation of Pd Nanoparticles Supported on Activated Carbon via Glow Discharge Plasma and Their Catalytic Properties for Suzuki Coupling Reactions

Yang Liu, Xuefeng Bai

2016 Volume 45 Issue 7 Pages 705-707
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 09, 2016

DOIhttps://doi.org/10.1246/cl.160219

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Palladium nanoparticles supported on activated carbon were prepared by N₂ glow discharge plasma reduction (PdNPs/C-P) and a chemical reduction method using L-ascorbic acid as the reducing agent (PdNPs/C-V). PdNPs/C-P have a smaller particle size and higher metal dispersion than PdNPs/C-V. PdNPs/C-P afforded a 98% yield for the Suzuki coupling reaction of 4-bromotoluene with phenylboronic acid at a very low loading of Pd (0.5 mmol ‰ Pd) and could be reused five times without an obvious reduction in catalytic activity.

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Fabrication of Porous Si Particles by Barrel Anode Etching

Takashi Yanagishita, Syota Ueno, Keisuke Taniguchi, Hideki Masuda

2016 Volume 45 Issue 7 Pages 708-710
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 09, 2016

DOIhttps://doi.org/10.1246/cl.160248

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Porous Si particles were prepared by the barrel anode etching of small Si particles. The depth of the holes formed on the surface of the Si particles could be controlled by changing the anode etching time. The process reported here allows high-throughput preparation of small porous Si particles with controlled geometrical surface structures. The obtained porous Si particles can be applied in various types of functional devices.

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Facile Biomolecule-assisted Hydrothermal Synthesis of Ag Nanowires with Baseball-like Tips

Weijie Mai, Li Yu, Wenzhong Wang

2016 Volume 45 Issue 7 Pages 711-713
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 09, 2016

DOIhttps://doi.org/10.1246/cl.160268

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We report a facile biomolecule-assisted hydrothermal strategy for controlled synthesis of Ag nanowires (NWs) with baseball-like tips, where the biomolecule rutin is used both as a capping and a reducing agent. The molar ratio of rutin to AgNO₃ was a key factor to form the Ag NWs. The comparative experiments with different reaction times have also been conducted to understand the growth process of Ag NWs. The growth process of Ag NWs was discussed based on the experimental results.

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Low-temperature Process for Fabrication of Porous Nanocrystalline Tin(IV) Oxide Film for Electrochromic Devices

Tamotsu Horiuchi, Keiichiro Yutani, Mamiko Inoue, Tohru Yashiro, Shinj ...

2016 Volume 45 Issue 7 Pages 714-716
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 15, 2016

DOIhttps://doi.org/10.1246/cl.160284

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We report a low-temperature annealing process for the fabrication of an electrochromic device based on a SnO₂ nanocrystalline film. The device exhibits high transmittance and fast response times in the bleached state, and the difference in transmittance between the colored state and the bleached state is higher than that of a TiO₂ film fabricated by low-temperature annealing.

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Improved Performances of Solid Tantalum Electrolytic Capacitors Using EG-treated PEDOT:PSS Conducting Polymer as Cathode Electrodes

Xiaopin Ma, Xiuyu Wang, Mingxiu Li, Tongning Chen, Hao Zhang, Qiang Ch ...

2016 Volume 45 Issue 7 Pages 717-719
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: May 03, 2016

DOIhttps://doi.org/10.1246/cl.160252

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The electrical properties of poly(3,4-ethylenedioxythiophene):poly(styrene sulfonate) (PEDOT:PSS) films were improved by ethylene glycol (EG). Solid tantalum electrolytic capacitors (STEC) fabricated using such EG-treated PEDOT:PSS films as the cathode electrodes exhibited high performances. The equivalent series resistance (ESR) and capacitance–frequency performance of the STEC were significantly improved comparing to those without EG treatment. Particularly, the leakage current (LC) was lowered at the same time.

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Redox-induced Conformational Changes in 1,3-Propylene- and m-Xylylenebis[5-(10-butyl-5,10-dihydrobenzo[a]indolo[2,3-c]carbazole)]: Twin-BIC Donors that Form Sandwich-like Dimeric Cations Exhibiting NIR Absorption

Takanori Suzuki, Wataru Nojo, Yuto Sakano, Ryo Katoono, Yusuke Ishigak ...

2016 Volume 45 Issue 7 Pages 720-722
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 15, 2016

DOIhttps://doi.org/10.1246/cl.160278

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The title electron-donors with two units of a disk-shaped heterocyclic diamine undergo two-stage stepwise one-electron oxidation to the corresponding cation radicals and dication diradicals. They adopt a stacked geometry as in pimers and π-dimers, respectively. In contrast, the third and fourth oxidation processes occur nearly at the same potential, indicating that tricationic/tetracationic species prefer the extended geometry. The similar redox-induced conformational changes were not observed in 1,5-pentylene or o-xylylene derivatives, which prefer the extended geometry irrespective of the oxidation states.

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Effects of NaOH Concentration on the Microstructure and Morphology of TiO₂ Precursor Nanobelts Prepared in a Hydrothermal Process

Ying Chang, Bei Liu, Huihu Wang, Ming Yan, Shijie Dong

2016 Volume 45 Issue 7 Pages 723-725
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 22, 2016

DOIhttps://doi.org/10.1246/cl.160301

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Unlike most previously reported experiments in which nanobelts were prepared using 10 M sodium hydroxide, a series of TiO₂ precursor nanobelts with diameters ranging from 60 to 600 nm were successfully synthesized in our laboratory via a hydrothermal process using different concentrations of NaOH aqueous solutions and a commercial TiO₂ powder (P25) as the raw materials. The reaction temperature was unexpectedly high at 260 °C. The formation process of TiO₂ precursor nanobelts was investigated in terms of the morphological variations during a particle-to-nanobelt transition. Based on the detailed structural analysis of TiO₂ precursor nanobelts, a rational mechanism has been proposed for the growth of the nanobelts. In addition, X-ray diffraction (XRD) of the nanobelts and degradation-efficiency test of a Rhodamine B (RhB) dye solution revealed that the precursor nanobelts should be heat-treated at 650 °C to produce highly crystalline anatase materials.

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Editor’s Choice

Synthesis of Diverse Benzotriazoles from Aryne Precursors Bearing an Azido Group via Inter- and Intramolecular Cycloadditions

Suguru Yoshida, Takamoto Morita, Takamitsu Hosoya

2016 Volume 45 Issue 7 Pages 726-728
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 29, 2016

DOIhttps://doi.org/10.1246/cl.160349

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A diverse range of benzotriazoles were synthesized from various 3-(azidoalkoxy)aryne precursors, which were easily prepared by Mitsunobu etherification. Various bis-1,2,3-triazoles containing a benzotriazole skeleton were obtained via sequential azide–alkyne and azide–aryne cycloadditions. Intramolecular azido–aryne cycloaddition, conducted using the same starting materials, afforded new types of ring-fused benzotriazoles. In the latter case, the reaction proceeded efficiently even though the regioorientation of the azido group was the reverse of that usually observed in intermolecular reactions between 3-alkoxyarynes and an azide.

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Letter

Surface Modification of Titanium Metal Plate Using Alkali Metal Chlorides

Hiromasa Nishikiori, Tetsuya Akaozeki, Taisuke Hizumi, Nobuyuki Zettsu ...

2016 Volume 45 Issue 7 Pages 729-731
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 06, 2016

DOIhttps://doi.org/10.1246/cl.160190

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A titanium metal surface was heated with an alkali metal chloride in order to produce a phase transition from amorphous titania to crystalline titania. The anatase-type titania phase was formed by heating the surface with KCl at 550 °C for 3 h. Further heating and higher temperatures caused a transition to the rutile-type titania. The amorphous titania layer on the surface of the titanium metal was reduced with the assistance of alkali metal chloride and reoxidized to transform into the metastable anatase-type titania phase under certain conditions.

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Facile Synthesis of PdAgCo Trimetallic Nanoparticles for Formic Acid Electrochemical Oxidation

Xinyue Liu, Changqing Dai, Dengfeng Wu, Adrian Fisher, Zhiping Liu, Da ...

2016 Volume 45 Issue 7 Pages 732-734
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 06, 2016

DOIhttps://doi.org/10.1246/cl.160243

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PdAg bimetallic and PdAgCo trimetallic nanoparticles (NPs) are synthesized by a one-pot method in an organic solvent medium. Our results show that the catalytic activity of PdAgCo/C (1133.249 mA mg_Pd⁻¹) for formic acid oxidation (FAO) is ca. 2.4 times larger than commercial Pd/C (483.563 mA mg_Pd⁻¹) and 1.7 times larger than PdAg/C (680.741 mA mg_Pd⁻¹). This study indicates that Co doping in PdAg bimetallic NPs can significantly improve its FAO activity. It is expected that the as-synthesized PdAgCo trimetallic NPs could be used as high-performance catalysts for direct formic acid fuel cells (DFAFCs).

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In-plane Thermal Conductivity Measurement of Conjugated Polymer Films by Membrane-based AC Calorimetry

Hiroaki Ushirokita, Hirokazu Tada

2016 Volume 45 Issue 7 Pages 735-737
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 09, 2016

DOIhttps://doi.org/10.1246/cl.160175

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We investigated the anisotropy in the thermal conductivities of π-conjugated polymer films of poly(3-hexylthiophene-2,5-diyl), poly[2-methoxy-5-(2′-ethylhexyloxy)-p-phenylenevinylene], poly(2,5-bis(3-tetradecylthiophen-2-yl)thieno[3,2-b]thiophene), and poly(3,4-ethylenedioxythiophene):tosylate (PEDOT:Tos). It was found that the in-plane thermal conductivity of the films, measured by membrane-based ac calorimetry, was approximately two times higher than the through-plane one measured by the 3ω method. We also found that the anisotropy of the electronic contribution is not negligible for the PEDOT:Tos films.

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Synthesis of Hydrosilyl-substituted Cyclic Siloxane: New Building Block for Materials

Yasunobu Egawa, Shinji Murakami, Nobuhiro Takeda, Masafumi Unno

2016 Volume 45 Issue 7 Pages 738-739
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 22, 2016

DOIhttps://doi.org/10.1246/cl.160272

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Facile synthesis of cyclotrisiloxane bearing octyl and hydrosilyl moiety was accomplished by the disilazane capping reaction. The synthetic method and spectroscopic data of the product are described.

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Difference in Chiral Recognition Behavior between Ag^I₃M^III₂ and Au^I₃M^III₂ (M = Co, Rh) Anionic Complexes with L-Cysteinate

Pei-Shan Lee, Hou Qun Yuan, Nobuto Yoshinari, Asako Igashira-Kamiyama, ...

2016 Volume 45 Issue 7 Pages 740-742
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 22, 2016

DOIhttps://doi.org/10.1246/cl.160280

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Treatment of the racemic isomer (ΔΔ/ΛΛ) of the cationic Co^III₃ trinuclear complex that includes 2-aminoethanethiolate (aet), ΔΔ/ΛΛ-[Co₃(aet)₆]³⁺, with the Δ_LLLΔ_LLL isomer of the anionic Ag^I₃M^III₂ pentanuclear complex that includes L-cysteinate (L-cys), Δ_LLLΔ_LLL-[Ag₃M₂(L-cys)₆]³⁻ (M = Co, Rh), in water produced a 1:1 complex salt of [Co₃(aet)₆][Ag₃M₂(L-cys)₆] in which only the ΔΔ isomer of [Co₃(aet)₆]³⁺ was incorporated. A similar treatment with the analogous Au^I₃M^III₂ complex, Δ_LLLΔ_LLL-[Au₃M₂(L-cys)₆]³⁻, also produced the 1:1 complex salt, but it incorporated both the ΔΔ and ΛΛ isomers of [Co₃(aet)₆]³⁺.

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Effects of Natural Chalcone–Tannin Hybrids Protecting Mesenchymal Stem Cells against ROS-mediated Oxidative Damage and Indexes for Antioxidant Mechanisms

Xican Li, Jingjing Liu, Zhong-xiang Zhao, Tingting Wang, Jian Lin, Don ...

2016 Volume 45 Issue 7 Pages 743-745
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 02, 2016

DOIhttps://doi.org/10.1246/cl.160177

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As antioxidants and potential beneficial agents in cell transplantation, natural chalcone–tannin hybrids can protect mesenchymal stem cells against ROS-mediated damage. In their antioxidant abilities, galloyl moiety, 4-OH, and 2′-OH present antioxidant indexes of 0.58:0.13:0.29. The galloyl moiety enhances antioxidant levels of chalcone–tannin hybrids. Their antioxidant mechanisms may include Fe²⁺-chelating and direct radical scavenging, which comprises at least one electron transfer (ET). The Fe²⁺-chelating and ET may mainly occur in the galloyl moiety, while 4-OH without H-bonding interference prefers to donate H atom.

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Semisynthesis of (−)-Barbatusol, (+)-Demethylsalvicanol, and (+)-Rosmaridiphenol from (+)-Pisiferic Acid

Eri Nisigaki, Kazuhiro Sugamoto, Misaki Nishida, Yoh-ichi Matsushita

2016 Volume 45 Issue 7 Pages 746-748
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 06, 2016

DOIhttps://doi.org/10.1246/cl.160221

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(+)-Pisiferic acid (1) was converted into (+)-12-O-methoxymethylpisiferol (5c) in 3 steps. The rearrangement of 5c with trifluoromethanesulfonic anhydride in pyridine provided (−)-12-O-methoxymethylpisiferin (6c), which was converted into icetexane phenols 6a, 11, and 14. The ortho-selective oxygenation of 6a and 14 with stabilized 2-iodoxybenzoic acid (SIBX), followed by the reduction of intermediary quinones afforded (−)-barbatusol (2) and (+)-rosmaridiphenol (4) in 49% and 35%, respectively. The oxygenation of 11 using potassium 5-methyl-2-iodobenzenesulfonate (pre-MIBS) with Oxone^® followed by reduction gave (+)-demethylsalvicanol (3) in 59% yield.

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Staphylococcus aureus Detection by Fluorescent Silica Nanoparticles Modified with Metal–Dipicolylamine Complexes

Yuna Kasai, Hiroyuki Kobayashi, Yuji Tsuchido, Takeshi Hashimoto, Nobu ...

2016 Volume 45 Issue 7 Pages 749-751
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 20, 2016

DOIhttps://doi.org/10.1246/cl.160261

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We have developed a new method for Staphylococcus aureus (S. aureus) detection, which employs fluorescent silica nanoparticles (FSiNPs) modified with metal–dipicolylamine complex (M-dpa-HCC). Among the M-dpa-HCC/FSiNP complexes, Cu-dpa-HCC/FSiNP formed large aggregates with S. aureus in 10 min, which were easily observed by the naked eye. The antibacterial activity of Cu-dpa-HCC/FSiNP was also confirmed.

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A Typical NEDDA Cycloaddition Strategy between C-3- and N-Substituted Indoles and Butadienes Using Silica-supported Copper Triflate as an Efficient Catalytic System: A Correlative Experimental and Theoretical Study

Monika Ahuja, Gagandeep Kour Reen, Ashok Kumar, Pratibha Sharma

2016 Volume 45 Issue 7 Pages 752-754
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 22, 2016

DOIhttps://doi.org/10.1246/cl.160155

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The present paper elicits a [4+2] Diels–Alder cycloaddition strategy between C-3- and N-substituted indoles I-1 to I-6 with two dienes of different nucleophilicity using silica-supported Cu(OTf)₂. Theoretical studies computed at the B3LYP/6-311G(d) level of theory reveal that all the indoles undertaken behave as electron-poor dienophiles and, therefore, prefer to participate through a normal electron demand Diels–Alder (NEDDA) pathway. The analysis of the local reactivity descriptors further ascertained the completely regioselective outcome of the reaction profile.

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ZnSe Nanowires and Partially Hollow Nanotubes Synthesized by Femtosecond Laser Ablation in Liquid

Chao Yang, Jiajia Yin, Jiangyun Dai, Shutong Wang, Hua Zhang, Guoying ...

2016 Volume 45 Issue 7 Pages 755-757
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 29, 2016

DOIhttps://doi.org/10.1246/cl.160297

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Hexagonal ZnSe nanowires were synthesized by the self-assembly of nanoparticles prepared by femtosecond laser ablation in deionized water. With introduction of air, partially hollow ZnSe nanotubes were also obtained. The nature of the ZnSe nanowires was characterized by scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy-dispersive X-ray spectrometry mapping (EDS-Mapping), and X-ray diffraction (XRD). Possible self-assembly and hydrolysis mechanisms for the formation of nanowires and partially hollow nanotubes were discussed.

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Linear Polystyrene-stabilized Pt Nanoparticles Catalyzed Indole Synthesis in Water via Aerobic Alcohol Oxidation

Atsushi Ohtaka, Mao Kozono, Kazuhiro Takahashi, Go Hamasaka, Yasuhiro ...

2016 Volume 45 Issue 7 Pages 758-760
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 29, 2016

DOIhttps://doi.org/10.1246/cl.160331

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The one-pot synthesis of indole in water by aerobic alcohol oxidation and subsequent cyclization was achieved using linear polystyrene-stabilized Pt nanoparticles as a catalyst. The catalyst could be reused, although a slight increase in particle size was observed by TEM analysis of the recovered catalyst.

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Photocatalytic Activity of Perovskite-type BaTbO₃ Containing Tetravalent Lanthanide Ions under Blue LED Irradiation

Nobuyuki Taira, Yasuki Yoshida

2016 Volume 45 Issue 7 Pages 761-763
Published: July 05, 2016
Released on J-STAGE: July 05, 2016

DOIhttps://doi.org/10.1246/cl.160307

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In this study, we investigated the photocatalytic properties of perovskite-type oxides BaLnO₃ (Ln = Ce, Pr, and Tb). Both Pt-loaded BaCeO₃ and Pt-loaded BaPrO₃ show no photocatalytic activity under blue LED irradiation; however, Pt-loaded BaTbO₃ shows photocatalytic activity for H₂ evolution. Although the rate of H₂ evolution was very low, this is the first example of a perovskite-type BaTbO₃ showing photocatalytic activity for H₂ evolution from an aqueous methanol solution under blue LED irradiation.

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Effect of Ag Ion Insertion on Electron Transport through Au Ion Wires

Shintaro Fujii, Sougin Kanae, Madoka Iwane, Tomoaki Nishino, Takafumi ...

2016 Volume 45 Issue 7 Pages 764-766
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: May 03, 2016

DOIhttps://doi.org/10.1246/cl.160286

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Atomic-scale charge-transport properties of Au–Ag ion clusters aligned as wires in host molecular cages were measured by a scanning tunneling microscopy-based break junction method. The Au–Ag ion wires were prepared by doping guest Ag ions into Au ion wires through a self-assembly process. We demonstrated that the electronic conductance of the Au ion wires can be modulated by 10 times by doping the guest Ag ion based on statistical analysis of the electronic investigations.

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Ribonuclease A as Effective Promoter for Unimolecular Invasion of Peptide Nucleic Acid to Double-stranded DNA

Makiko Tanaka, Narumi Shigi, Makoto Komiyama

2016 Volume 45 Issue 7 Pages 767-769
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: May 03, 2016

DOIhttps://doi.org/10.1246/cl.160340

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With the use of ribonuclease A (RNase A) as promoter, only one strand of peptide nucleic acid (PNA) efficiently invades double-stranded DNA (dsDNA), according to the Watson–Crick rule. The RNase A locally rewinds the dsDNA to facilitate unimolecular invasion, which otherwise hardly occurs. Furthermore, the single-stranded portion, formed at the invasion site in the dsDNA, is trapped by the protein.

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Thermally Activated Delayed Fluorescence from Pentacarbazorylbenzonitrile

Shuho Tanimoto, Takatsugu Suzuki, Hajime Nakanotani, Chihaya Adachi

2016 Volume 45 Issue 7 Pages 770-772
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: May 03, 2016

DOIhttps://doi.org/10.1246/cl.160290

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A benzonitrile derivative substituted by five carbazoles (5CzBN), which emits thermally activated delayed fluorescence (TADF), was synthesized and evaluated. The organic light-emitting diode (OLED) containing 5CzBN demonstrated light-blue electroluminescence and a high external quantum efficiency of 14.8%.

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Synthesis, Hollow Spherical Aggregation, and Crystallization of an Adamantane-derived Azacyclophane Containing Triazine Rings

Masahide Tominaga, Aika Noda, Kazuaki Ohara, Kentaro Yamaguchi, Tsutom ...

2016 Volume 45 Issue 7 Pages 773-775
Published: July 05, 2016
Released on J-STAGE: July 05, 2016

DOIhttps://doi.org/10.1246/cl.160347

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An adamantane-derived azacyclophane containing triazine rings was synthesized by the S_NAr reaction of a disubstituted adamantane with amino groups and cyanuric chloride. X-ray analysis of the macrocycle reveals a nearly rectangular structure. The macrocycles self-assembled into hollow spherical aggregates bearing a multilayer membrane in aqueous solution, which fused into disordered aggregates and eventually formed single crystals.

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Development of a Granulation Method for Prussian Blue by Thin-film Polymer Gel Coating

Yusuke Inaba, Yusuke Sakai, Keita Kanazawa, Miki Harigai, Hiroshi Oaki ...

2016 Volume 45 Issue 7 Pages 776-778
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 06, 2016

DOIhttps://doi.org/10.1246/cl.160167

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We introduce a new granulation method for Prussian blue (PB) based on thin-film polymer gel coating. PB particles were strongly supported on a hydrophilic polymer gel porous carrier. Scanning electron microscope (SEM) images confirmed that the PB supported on silica (PBS) samples was thinly covered with the polymer gel containing PB, whereas electron probe microanalysis (EPMA) confirmed that the PB particles mainly existed on the PBS surface. PBS is suitable as a column material for adsorbing low concentrations of Cs.

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Novel pH-responsive Liquid Marble as Microfluidic Responder for Controlled Release

Yifan Si, Zhiguang Guo

2016 Volume 45 Issue 7 Pages 779-781
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: May 03, 2016

DOIhttps://doi.org/10.1246/cl.160362

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A novel pH-responsive liquid marble covered by thiol-modified copper powders has been demonstrated via a facile one-step self-assemble method. The wettability of the modified copper powders can change with the outside environment pH. This multifunctional liquid marble can be applied to act as a micro-gas responder and microfluidic controllable-release system with high sensitivity.

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Synthesis and Characterization of Ethynylated Germa[4]pericyclyne

Hiroki Tanimoto, Tomohiko Nagao, Satomi Hosokawa, Taro Fujiwara, Yasuh ...

2016 Volume 45 Issue 7 Pages 782-784
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: May 11, 2016

DOIhttps://doi.org/10.1246/cl.160332

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This paper presents the synthesis and characterization of (TMS-ethynyl)-substituted germa[4]pericyclyne composed of acetylene moieties and germanium atoms. Characterization was performed by X-ray crystallography, UV–vis absorption, and photoluminescence spectroscopy. DFT calculations suggested interactions between the side chain alkynes and the ring-forming acetylenes through germanium vertex atoms.

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Magnetic-field Sensitivity for Magnetic Elastomers with Various Elasticities

Jinta Nanpo, Mika Kawai, Tetsu Mitsumata

2016 Volume 45 Issue 7 Pages 785-786
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: June 03, 2016

DOIhttps://doi.org/10.1246/cl.160363

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The effect of plasticizer content on the magnetic-field sensitivity for magnetic elastomers has been investigated while maintaining the concentration of magnetic particles at 70 wt %. The magnetic-field dependence of the storage modulus for magnetic elastomers was measured by dynamic viscoelastic measurements under magnetic fields with a sweep rate of 3.7 mT s⁻¹. The magnetic-field sensitivity, determined by the initial slope of the storage modulus using an exponential function, increased from 1.0 × 10⁻³ to 1.8 × 10⁻² mT⁻¹ with increasing plasticizer content.

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Effect of Hexylthiophene and Hexyloxy Substituents on Triphenylamine-based DSSCs after TiCl₄ Treatment

Jianhui Qiao, Cheng Zhong, Qunliang Song, Fei Wu, Linna Zhu

2016 Volume 45 Issue 7 Pages 787-789
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 06, 2016

DOIhttps://doi.org/10.1246/cl.160242

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Three organic dyes were synthesized and characterized for application in dye-sensitized solar cells. It turned out that the performances of dyes Q1 and Q2 significantly increased when the TiO₂ anode film was treated by TiCl₄. However, the efficiency of dye Q3 containing two hexylthiophene groups was almost unchanged after the anode film was treated. This should be originated from their structure differences.

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Palladium-catalyzed Coupling of Benzoyl Halides with Aryltrifluorosilanes Leading to Diaryl Ketones

Yohei Ogiwara, Yuki Maegawa, Daisuke Sakino, Norio Sakai

2016 Volume 45 Issue 7 Pages 790-792
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 06, 2016

DOIhttps://doi.org/10.1246/cl.160223

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Acyl–aryl Hiyama coupling of acyl halides with arylsilanes has been achieved by employing a palladium/phosphine catalyst system. A variety of acyl chlorides and fluorides can be applied for coupling with arylsilicon reagents, and unsymmetrical benzophenone derivatives can be prepared using this protocol.

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Fabrication of Poly(methyl methacrylate)-block-Poly(methacrylic acid) Diblock Copolymer as a Self-embrittling Strippable Coating for Radioactive Decontamination

Ren-Long Liu, Yin-Tao Li, Yuan-Lin Zhou, Hui-Yan Zhang, Quan-Ping Zhan ...

2016 Volume 45 Issue 7 Pages 793-794
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 09, 2016

DOIhttps://doi.org/10.1246/cl.160195

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The poly(methyl methacrylate)-block-poly(methacrylic acid) diblock copolymer with different monomer compositions was synthesized via reversible addition–fragmentation chain transfer polymerization. Meanwhile, a novel self-embrittling strippable coating was prepared using the diblock copolymers, which is proposed to be used as radioactive decontamination agents without manual operation. Furthermore, the decontamination efficiencies of self-embrittling strippable coatings for radioactive contamination on glass, marble, and stainless steel surfaces were studied.

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Higher-order-structure Formation in Liquid Crystal Epoxy Thermosets Investigated by Synchrotron Radiation–Wide-angle X-ray Diffraction

Rina Maeda, Kenta Okuhara, Akihiro Nakamura, Teruaki Hayakawa, Yasushi ...

2016 Volume 45 Issue 7 Pages 795-797
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 09, 2016

DOIhttps://doi.org/10.1246/cl.160249

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We report the investigation of the mesophase transformations of a liquid crystalline molecule with terminal epoxy groups from the initial stages of curing with a diamine compound. The ordered arrangement of molecules within the smectic layers in the thermoset formed at the end of the curing process was characterized by synchrotron radiation–wide-angle X-ray diffraction (SR-WAXD). Data from this experiment helps us understand the phase transitions from the nematic to smectic phases of curing liquid crystalline epoxies.

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Palladium-catalyzed Asymmetric Allylic Alkylation Using C₂-symmetric Chiral Bidentate Bis(N-heterocyclic carbene) Ligands with the o-Xylylene Framework

Yoshitaka Yamaguchi, Yasutomo Suzuki, Sawako Matsumoto, Satoshi Anezak ...

2016 Volume 45 Issue 7 Pages 798-800
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 15, 2016

DOIhttps://doi.org/10.1246/cl.160235

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An asymmetric allylic alkylation reaction of 1,3-diphenylprop-2-en-1-yl acetate with dimethyl malonate was examined using C₂-symmetric chiral bidentate bis(N-heterocyclic carbene)-based palladium catalysts. The alkylated product was obtained in 96% yield with good enantioselectivity (80% ee).

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Formation of Lactones by Decarboxylation of Aromatic Diacids via TiO₂-mediated Photocatalytic Reactions in Acetonitrile Solution

Ryusei Oketani, Teruyuki Miyake, Seihou Jinnai, Takuya Fukui, Hidetaka ...

2016 Volume 45 Issue 7 Pages 801-803
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 15, 2016

DOIhttps://doi.org/10.1246/cl.160237

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Aromatic diacids such as diphenic acid and (E)-2-(2-carboxyvinyl)benzoic acid were converted into the corresponding lactones with high selectivity by decarboxylation via TiO₂-photocatalytic reactions in acetonitrile solution containing 10% (v/v) water and molecular oxygen.

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Electrical Conductance of a Single 1,2-Ethanedithiol Molecular Junction Prepared in Ultrahigh Vacuum

Elena Bedogni, Satoshi Kaneko, Shintaro Fujii, Tomoaki Nishino, Manabu ...

2016 Volume 45 Issue 7 Pages 804-806
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 15, 2016

DOIhttps://doi.org/10.1246/cl.160238

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We have studied the electrical conductance of the single 1,2-ethanedithiol molecular junction prepared in ultrahigh vacuum (UHV). The single molecular junction was fabricated by breaking the Au contacts with mechanically controllable break junction technique in the presence of 1,2-ethanedithiol. The conductance of the single 1,2-ethanedithiol molecular junction was 0.13 G₀ (2e²/h), larger than the value expected for the single molecular junction fabricated in the molecular solution. The present study revealed that the molecular junctions created in UHV exhibited lower contact resistances due to the clean vacuum environment.

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Controllable Synthesis of Homogeneous Mesoporous Alumina by Reaction Crystallization

Tian-hua Chen, Li Zhong, Dong-ping Duan

2016 Volume 45 Issue 7 Pages 807-809
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 20, 2016

DOIhttps://doi.org/10.1246/cl.160304

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Homogeneous mesoporous alumina (HMA) was synthesized by reaction–crystallization from supersaturated sodium aluminate solution and sodium bicarbonate solution, using methylcellulose as a template. The novel HMA material showed properties of mesoporous alumina and sandy alumina. Effects of synthesis conditions on the structure and characteristics of the HMA material were investigated. The mechanism of the synthesis process for HMA material was revealed.

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Investigation of State-of-charge Distributions for LiCoO₂ Composite Positive Electrodes in All-solid-state Lithium Batteries by Raman Imaging

Misae Otoyama, Yusuke Ito, Akitoshi Hayashi, Masahiro Tatsumisago

2016 Volume 45 Issue 7 Pages 810-812
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 22, 2016

DOIhttps://doi.org/10.1246/cl.160299

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Composite positive electrodes for all-solid-state lithium batteries were prepared by mixing LiCoO₂ and Li₂S-P₂S₅ solid electrolytes particles. Two different sizes of solid electrolyte particles were used. Raman mapping was conducted for each positive electrode before and after the charge–discharge tests to examine local state-of-charge (SOC) distribution. Mapping images indicated that the charge–discharge reaction proceeded uniformly in the positive electrode with smaller solid electrolyte particles.

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Highly Selective Photocyclic Aromatization (SCAT)-GPC Method for Quantitative Determination of Microstructures of Copoly(substituted acetylenes) Backbone

Guanwu Yin, Lijia Liu, Toshiki Aoki, Takeshi Namikoshi, Masahiro Terag ...

2016 Volume 45 Issue 7 Pages 813-815
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: April 22, 2016

DOIhttps://doi.org/10.1246/cl.160357

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Highly selective photocyclic aromatization (SCAT) of poly(substituted acetylene)s, which can quantitatively yield the corresponding 1,3,5-trisubstituted benzene derivative, was applied to quantitative determination of the microstructures of copoly(substituted acetylene)s. By GPC analysis of the SCAT products of the copolymers of two substituted acetylenes having substituents whose molecular weights were greatly different, some clear information regarding the microstructures, such as sequence (triad) distribution and composition, which could not be obtained from NMR because of their broad peaks, could be obtained successfully under a mild condition.

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In Situ Generation of Trichloromethyl Anion and Efficient Reaction with Benzaldehyde in an Electrochemical Flow Microreactor

Yoshimasa Matsumura, Yoshiyuki Yamaji, Hiroyuki Tateno, Tsuneo Kashiwa ...

2016 Volume 45 Issue 7 Pages 816-818
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: May 03, 2016

DOIhttps://doi.org/10.1246/cl.160337

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We demonstrated in situ preparation of unstable trichloromethyl anion and its reaction with benzaldehyde in an electrochemical flow microreactor at ambient temperature. The trichloromethyl anion was prepared by the reaction of chloroform with an electrogenerated base. The generated unstable anion was rapidly used for following reaction with benzaldehyde before decomposition, and 2,2,2-trichloro-1-phenylethanol was obtained in a reasonable yield.

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Enhanced Stability of CH₃NH₃PbI₃ Thin Films Deposited on FTZO

Wenlong Jiang, Tieying Yang, Yanmin Gao, Xingyu Gao

2016 Volume 45 Issue 7 Pages 819-821
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: May 03, 2016

DOIhttps://doi.org/10.1246/cl.160281

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Fluorine (F) and tin (Sn) codoped ZnO (FTZO) nanoparticles (NPs) were synthesized by sol–gel technique on indium tin oxide (ITO). The structural changes arising from CH₃NH₃PbI₃ deposited on FTZO NPs layer during its degradation were characterized via in situ grazing incidence X-ray diffraction (GIXRD). It was indicated that the FTZO NPs layer helped reduce the degradation of the perovskite film during the annealing process. This film also exhibited enhanced crystallization and preferred in-plane orientation of the (110) plane after annealing.

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Effects of Gas Blowing Condition on Formation of Perovskite Layer on Organic Scaffolds

Takeshi Gotanda, Shigehiko Mori, Akihiro Matsui, Haruhi Oooka

2016 Volume 45 Issue 7 Pages 822-824
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: May 03, 2016

DOIhttps://doi.org/10.1246/cl.160298

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We confirmed that the gas blowing condition during perovskite formation is suitable for fabricating large-scale cells composed of a PEDOT:PSS layer as a scaffold. Gas blowing minimized the defects at the interface between the perovskite and PEDOT:PSS and created a flat perovskite layer. The crystallization process by which the perovskite layer grew was different from one-step spin-coating. Gas blowing led to a perovskite layer with orientation along the (310) plane.

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Copper-catalyzed Phosphorylation of Coumarins with Trialkyl Phosphites

Shengmei Guo, Jiuhan Gong, Zheng Zhu, Linhai Yu, Yufeng Wang, Lin Huan ...

2016 Volume 45 Issue 7 Pages 825-827
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: May 03, 2016

DOIhttps://doi.org/10.1246/cl.160305

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A copper-catalyzed phosphorylation of coumarins has been developed. Different from previous reports, this catalytic system involved the use of copper as a catalyst and trialkyl phosphonates as phosphorus sources with moderate to good yields, which provides an alternative way to prepare coumarins containing phosphates.

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Synthesis of Tetramethoxysilane from Silica and Methanol Using Carbon Dioxide and an Organic Dehydrating Reagent

Norihisa Fukaya, Seong Jib Choi, Toshio Horikoshi, Hiroshi Kumai, Mino ...

2016 Volume 45 Issue 7 Pages 828-830
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: May 03, 2016

DOIhttps://doi.org/10.1246/cl.160329

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A new efficient method of synthesizing tetramethoxysilane (TMOS) directly from silica (SiO₂) and methanol was developed using a base catalyst and 2,2-dimethoxypropane (acetal) as an organic dehydrating reagent. Carbon dioxide significantly accelerated the reaction. TMOS was obtained in good yield from SiO₂ in 24 h using stoichiometric or excess amounts of the acetal with a good material balance. The TMOS synthesis from a natural silica substrate, such as rice hull ash is described.

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Production of Bio-based 1,3-Butadiene by Highly Selective Dehydration of 2,3-Butanediol over SiO₂-supported Cesium Dihydrogen Phosphate Catalyst

Daijiro Tsukamoto, Satoshi Sakami, Masateru Ito, Katsushige Yamada, Te ...

2016 Volume 45 Issue 7 Pages 831-833
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: May 11, 2016

DOIhttps://doi.org/10.1246/cl.160309

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We investigated the catalyst that promotes the selective dehydration of 2,3-butanediol to 1,3-butadiene. We found that the SiO₂-supported CsH₂PO₄ catalyst showed the highest 1,3-butadiene selectivity (>90%) with the single-bed catalyst system. The present process was successfully applied to bio-based 1,3-butadiene production from 2,3-butanediol produced by the microbial fermentation of biomass resources.

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Chemical Modification of a [2]Rotaxane Composed of Dithiacrown Ether and Dialkylammonium with Organic and Inorganic Compounds

Hiroyuki Nagai, Yuji Suzaki, Kohtaro Osakada

2016 Volume 45 Issue 7 Pages 834-836
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: May 11, 2016

DOIhttps://doi.org/10.1246/cl.160345

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The complexation of Pd with dithia[24]crown-8-ether (DTC) and decomplexation by PPh₃ addition led to reversible shuttling of the [2]rotaxane, which is composed of DTC and dialkylammonium whose shuttling behavior is different from that induced by N-acetylation of the ammonium moiety of the axle component causing irreversible structural change.

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N-Heterocyclic Carbene Coordinated Heterogeneous Pd Nanoparticles as Catalysts for Suzuki–Miyaura Coupling

Hyemin Min, Hiroyuki Miyamura, Shu Kobayashi

2016 Volume 45 Issue 7 Pages 837-839
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: May 11, 2016

DOIhttps://doi.org/10.1246/cl.160369

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Palladium nanoparticle (Pd NP) catalysts immobilized in a polymer with an N-heterocyclic carbene (NHC) moiety (PICB-NHC-Pd) have been developed, wherein the NHC moiety plays dual roles as a crosslinker and a ligand to activate the Pd NPs. The presence of both Pd NPs and NHC was confirmed by STEM/EDS and SR-MAS NMR analyses, respectively. This PICB-NHC-Pd catalyst showed excellent activity in the Suzuki–Miyaura coupling reaction without leaching of Pd. Excellent results were obtained in gram-scale synthesis, and catalyst recovery/reuse experiments were completed without loss of catalyst activity.

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Study on Branched Structure–Physiological Activity Relationship of Fucoidan

Yoshiaki Yuguchi, Bui Minh Ly, Bui Van Nguyen, Tran Thi Thanh Van, Tha ...

2016 Volume 45 Issue 7 Pages 840-842
Published: July 05, 2016
Released on J-STAGE: July 05, 2016
Advance online publication: May 11, 2016

DOIhttps://doi.org/10.1246/cl.160189

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The cytotoxicity for cancer cells of fucoidans isolated from 6 brown seaweed species was investigated. All fucoidans showed cytotoxic activity against the RD (Rhabdomyosarcoma) and HepG2 (hepatocellular carcinoma) cells. From small-angle X-ray scattering (SAXS) measurements, fucoidans have a branched structure, as indicated by the R_gc values ranging from 0.78 to 1.51 nm. Our results supported the branched architecture with many sulfate groups reveals bioactivity of fucoidan but the relationship between the length of the branch and the level of bioactivity was not clear.

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Aqueous Oxidation of Sugars into Sugar Acids Using Hydrotalcite-supported Gold Nanoparticle Catalyst under Atmospheric Molecular Oxygen

Ravi Tomar, Jatin Sharma, Shun Nishimura, Kohki Ebitani

2016 Volume 45 Issue 7 Pages 843-845
Published: July 05, 2016
Released on J-STAGE: July 05, 2016

DOIhttps://doi.org/10.1246/cl.160364

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Hydrotalcite-supported gold nanoparticles show good activity as a heterogeneous catalyst for the oxidation of monosaccharides (xylose, ribose, galactose and mannose) and disaccharides (lactose and cellobiose) into the corresponding sugar acids under external base-free conditions in water solvent using atmospheric pressure of molecular oxygen. The produced sugar acids were thoroughly identified by ¹H-, ¹³C-, and HMQC-NMR and ESI-FT-ICR MS spectroscopic techniques.

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