Faculty Profiles - OSHIKI Toshiyuki

Papers - OSHIKI Toshiyuki

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Control of the electronic and optical properties of aminoxyl radicals via boron complexation. Reviewed International journal

Takuma Kuroda, Peiyuan Yang, Marika Nakamura, Risa Hyakutake, Hiroki Fukumoto, Toshiyuki Oshiki, Yuta Nishina, Koichiro Masada, Takahiro Sasamori, Yosihiyuki Mizuhata, Kazuya Kubo, Ryo Inoue, Tomohiro Agou

Dalton transactions (Cambridge, England : 2003) 2024.11

Language：English Publishing type：Research paper (scientific journal)

Stable radicals have attracted increasing attention in recent years because of their unique electronic and optical characteristics. Aminoxyl radicals are one of the most widely studied stable radicals to date, but their applications in opto-functional materials have yet to be explored in detail. Our group previously reported the boron complexes of aminoxyl radicals exhibit near-infrared (NIR) absorption. In this work, an aminoxyl radical without boron-complexation was synthesized to elucidate the effects of boron coordination on the properties of the aminoxyl radicals. The results of electron spin resonance spectroscopy, ultraviolet-visible-NIR absorption measurements, and density functional theory calculations indicated that boron complexation facilitated spin delocalization over the radical π-frameworks. Furthermore, a π-extended aminoxyl radical-boron complex exhibited a significant wavelength-shift to longer wavelengths in the NIR-II absorption region, thereby reflecting its larger π-conjugated radical skeleton.

DOI： 10.1039/d4dt02973a

PubMed

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Origin of the Two Major Types of Repeating Units in Poly(β-pinene) Obtained by Cationic Polymerization Reviewed

Oluwaseyi Aderemi Ajala, Shogo Nakaichi, Toshiyuki Oshiki, Yuushou Nakayama, Takeshi Shiono, Ryo Tanaka

Macromolecules 57 ( 19 ) 9257 - 9264 2024.9

Synthesis and Optical Properties of Dithieno-1,4-Thiaborins Bearing Electron-Donating Amino Groups Reviewed

Tomohiro Agou, Shota Hayama, Naoya Takano, Shigeyuki Yamada, Tsutomu Konno, Toshiyuki Oshiki, Hidehito Komatsuzaki, Hiroki Fukumoto

Bulletin of the Chemical Society of Japan 2024.2

Publishing type：Research paper (scientific journal) Publisher：Oxford University Press (OUP)

Abstract

Dibenzo-1,4-heteraborins and their π-extended derivatives have been paid increased attention to because of their potential as optical and electronic functional materials such as organic electroluminescence emitters. Meanwhile, 1,4-heteraborin compounds with heteroaromatic ring systems have remained scarce, even though Liu et al. recently reported the synthesis, properties and functionalization of dithieno-1,4-thiaborins (DTTBs). In this work, DTTBs with 10H-phenothiazine-10-yl (Pz), 9H-carbazol-9-yl (Cz), and p-(Ph2N)C6H4 groups as electron-donating amino groups at the α-positions of the thiophene moieties were synthesized using palladium-catalyzed coupling reactions. X-Ray crystallographic analysis revealed the molecular structure of a DTTB substituted with Pz groups. This analysis showed that the two Pz moieties adopted extra- (quasi-axial) conformations. The Cz and p-(Ph2N)C6H4 substituted DTTBs showed red-shifted absorption and emission when compared to the original DTTBs. This shift is due to donor–acceptor interactions between the amino groups and the DTTB cores. The Pz-substituted DTTB exhibited dual fluorescence emissions, originating from the locally-excited (LE) and twisted intramolecular charge transfer (TICT) states. The intensity and nature of these emissions varied based on solvent polarity, temperature, and viscosity, suggesting the potential of the Pz-substituted DTTB to act as a fluorescent environment sensor.

DOI： 10.1093/bulcsj/uoae014

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A Practical Method for the Measurement of 183W NMR Signals in Solution: Challenge to Multinuclear Solution NMR Invited

Toshiyuki Oshiki

58 ( 1 ) 2023.7

A Practical Method for the Measurement of 183W NMR Signals in Solution: Challenge to Multinuclear Solution NMR Invited

55 ( 1 ) 16 - 23 2023.6

Synthesis and characterization of a polystyrene-type polymer bearing a cyclic perfluoroalkylene group Reviewed

Tatsuro Hisa, Yasunori Kanno, Tomohiro Shirai, Toshiyuki Oshiki, Yoshiyuki Mizuhata, Norihiro Tokitoh, Hiroki Fukumoto, Tomohiro Agou

Polymer 265 125588 - 125588 2022.12

Synthesis of perfluoroalkylene-vinylene-arylene copolymers via the Mizoroki-Heck co-polymerization of 1,4-divinylperfluorobutane and 1,6-divinylperfluorohexane with dihalogenated arylene monomers Reviewed

Hiroto Tsukada, Tatsuro Hisa, Tomohiro Shirai, Toshiyuki Oshiki, Yoshiyuki Mizuhata, Norihiro Tokitoh, Hiroki Fukumoto, Tomohiro Agou

Journal of Fluorine Chemistry 261-262 110033 - 110033 2022.9

Presence of Microplastics in Four Types of Shellfish Purchased at Fish Markets in Okayama City, Japan. Reviewed

Kenichi Yamamoto, Toshiyuki Oshiki, Hiroko Kagawa, Masayoshi Namba, Masakiyo Sakaguchi

Acta medica Okayama 75 ( 3 ) 381 - 384 2021.6

Language：English Publishing type：Research paper (scientific journal)

The worldwide microplastic pollution in our environment is a matter of great concern. Harmful effects of plastics have been reported in various types of organisms including murine animals. We examined the presence of microplastics in four types of shellfish purchased from fish markets in Okayama, Japan and served to the public: short-neck clam (Ruditapes philippinarum, asari in Japanese), hard-shell clam (Meretrix lusoria, hamaguri), brackishwater clam (Cyrenidae, shijimi), and oyster (Crassostrea gigas, kaki). Our analyses demonstrated that approx. 3 pieces of microplastics were present per single shellfish, based on the division of the total number of pieces of microplastic obtained from all 4 types of shellfish by the total number of shellfish examined. Since health problems in humans due to microplastics have not yet been confirmed, further examinations of the effects of ingested microplastics are needed.

DOI： 10.18926/AMO/62234

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Alcohol Extracts from Plastic Wrap induces Cytotoxic Effect on Culture cells

山本健一, TAN Xian Wen, 有元佐賀恵, 押木俊之, 難波正義, 阪口政清

組織培養研究(Web) 39 ( 1 ) 2021

Cytotoxic Effects of Alcohol Extracts from a Plastic Wrap (Polyvinylidene Chloride) on Human Cultured Liver Cells and Mouse Primary Cultured Liver Cells. Reviewed

Ken-Ichi Yamamoto, Hiroko Kagawa, Sakae Arimoto, Xian Wen Tan, Kento Yasui, Toshiyuki Oshiki, Masakiyo Sakaguchi

Acta medica Okayama 74 ( 4 ) 327 - 334 2020.8

Language：English Publishing type：Research paper (scientific journal)

An increasing accumulation of microplastics and further degraded nanoplastics in our environment is suspected to have harmful effects on humans and animals. To clarify this problem, we tested the cytotoxicity of two types of plastic wrap on human cultured liver cells and mouse primary cultured liver cells. Alcohol extracts from plastic wrap, i.e., polyvinylidene chloride (PVDC), showed cytotoxic effects on the cells. Alcohol extracts of polyethylene (PE) wrap were not toxic. The commercially available PVDC wrap consists of vinylidene chloride, epoxidized soybean oil, epoxidized linseed oil as a stiffener and stabilizer; we sought to identify which component(s) are toxic. The epoxidized soybean oil and epoxidized linseed oil exerted strong cytotoxicity, but the plastic raw material itself, vinylidene chloride, did not. Our findings indicate that plastic wraps should be used with caution in order to prevent health risks.

DOI： 10.18926/AMO/60371

PubMed

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微生物が生み出す安全で鮮やかな赤色顔料と固体触媒

中西真, 押木俊之, 田村勝徳, 高田潤

塗装工学 54 ( 2 ) 2019

Structural Characterization and Unique Catalytic Performance of Silyl-Group-Substituted Geminal Dichromiomethane Complexes Stabilized with a Diamine Ligand Reviewed

Masahito Murai, Ryuji Taniguchi, Naoki Hosokawa, Yusuke Nishida, Hiroko Mimachi, Toshiyuki Oshiki, Kazuhiko Takai

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 139 ( 37 ) 13184 - 13192 2017.9

Language：English Publishing type：Research paper (scientific journal) Publisher：AMER CHEMICAL SOC

Stabilization by a silyl group on the methylene carbon and a diamine ligand led to the isolation of gem-dichromiomethane species. X-ray crystallography confirmed the identity of the structure of this rare example of reactive gem-dimetalloalkane species. The isolated gem-dichromiomethane complex acted as a storable silylmethylidene carbene equivalent, with reactivity that could be changed dramatically upon addition of a Lewis acid (ZnCl2) and a base (TMEDA) to promote both silylalkylidenation of polar aldehydes and silylcyclopropanation of nonpolar alkenes. Identification of a key reactive species also identified the catalytic version of these transformations and provided insights into the reaction mechanism. In contrast to Simmons-Smith cyclopropanation, the real reactive species for the current cyclopropanation was a chromiocarbene species, not a chromium carbenoid species.

DOI： 10.1021/jacs.7b07487

Web of Science

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Industrial Application and Olefin Metathesis Catalyst Technologies for Reaction Injection Molding of Dicyclopentadiene Reviewed

Michiru Kamada, Toshiyuki Oshiki

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN 75 ( 2 ) 19 - 28 2017.2

Language：Japanese Publishing type：Research paper (scientific journal) Publisher：SOC SYNTHETIC ORGANIC CHEM JPN

Current technologies of DCP-RIM (reaction injection molding of dicyclopentadiene) are reviewed from an industrial point of view. The DCP-RIM provides high-impact, heat resistant, and insulating poly (dicyclopentadiene) thermoset resin via catalytic olefin metathesis. Control of chemical reactivities of the catalysts is one of the most important technologies for the DCP-RIM. The key properties of the catalysts are their good solubility in dicyclopentadiene and latency.
Suitable tungsten or molybdenum-based catalyst systems have been developed and used for over 30 years. These catalyst systems are comprised of inorganic tungsten (or molybdenum) salt and an air-sensitive organoaluminum as an activator. In contrast, robust Grubbs type ruthenium-alkylidene catalysts are attracted great interest in the field of the DCP-RIM. Detailed structure and reactivities of the ruthenium catalysts for the DCP-RIM are summarized.

DOI： 10.5059/yukigoseikyokaishi.75.111

Web of Science

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New Catalyst Technology for Industrial Production of Polydicyclopentadiene Molding

押木俊之, 鎌田満, 鎌田満, 西岡直樹

山陽技術雑誌 61 10 - 14 2014.4

革新的プロセス開発の新展開産業界と連携した革新性ある錯体触媒プロセスの開発

押木俊之

ケミカルエンジニヤリング 59 ( 2 ) 93 - 100 2014.2

PH effect on properties of surfactant-free oil-in-water emulsion prepared with oleic acid Reviewed

Yuta Akizuki, Mikio Yoshida, Naoyuki Ishida, Toshiyuki Oshiki, Jun Oshitani

Chemistry Letters 43 ( 5 ) 604 - 606 2014

Language：English Publishing type：Research paper (scientific journal) Publisher：Chemical Society of Japan

Size distribution, potential, and yield of surfactant-free oil-in-water (O/W) emulsion prepared with oleic acid were measured at various pHs after seven days from the emulsification. We found that the size distribution is almost the same regardless of pH from 9 to 3. The magnitude of potential and yield remains constant at pH from 9 to 6, and decreases at pH from 6 to 3. There is a correlation between the potential and the yield, but no correlation between the potential and the size, suggesting that the potential relates to stability of oleic acid droplets in water rather than their size. © 2014 The Chemical Society of Japan.

DOI： 10.1246/cl.131209

Web of Science

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Preparation of Magnetic Ionic Liquids Composed of Hybrid-Type Anions Reviewed

Yumiko Takagi, Yoriko Kusunoki, Yukihiro Yoshida, Hirofusa Tanaka, Gunzi Saito, Kosuke Katagiri, Toshiyuki Oshiki

AUSTRALIAN JOURNAL OF CHEMISTRY 65 ( 11 ) 1557 - 1560 2012

Language：English Publishing type：Research paper (scientific journal) Publisher：CSIRO PUBLISHING

1-Ethyl-3-methylimidazolium ethylsulfate ([C(2)mim][EtSO4]) was mixed with iron(III) chloride center dot 6H(2)O to give a magnetic ionic liquid composed of the hybrid-type anion, [C(2)mim][FeCl3 center dot EtSO4], which showed a slightly different magnetic property than [C(2)mim][FeCl4]. On the other hand, reaction of [C(2)mim][EtSO4] with cobalt(II) chloride hydrate formed [C(2)mim](2)[(CoCl4)-Cl-II], the structure of which was characterised by X-ray crystallographic analysis.

DOI： 10.1071/CH12331

Web of Science

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Iridium complexes for the catalytic hydration of acrylonitrile

Oshiki Toshiyuki, Kawakami Yukiko, Muranaka Makoto

Proceeding of Annual/Fall Meetings of the Japan Petroleum Institute 42nd 133 - 133 2012

2-Diphenylphosphanyl-4-pyridyl(dimethyl) amine as an effective ligand for the ruthenium(II) complex catalyzed homogeneous hydration of nitriles under neutral conditions Reviewed

Makoto Muranaka, Isao Hyodo, Wataru Okumura, Toshiyuki Oshiki

CATALYSIS TODAY 164 ( 1 ) 552 - 555 2011.4

Language：English Publishing type：Research paper (scientific journal) Publisher：ELSEVIER SCIENCE BV

New homogeneous catalyst comprised of [Ru(methallyl)(2)(cod)] (cod = 1,5-cyclooctadiene) (1) and 2-diphenylphosphanyl-4-pyridyl(dimethyl) amine (2) is shown to efficiently catalyze the hydration of various nitriles under neutral conditions. The hydration proceeds in the presence of 0.5 mol% of the ruthenium catalyst at 80 degrees C in 1,2-dimethoxyethane solution and the corresponding amide is obtained within few hours without the formation of by products. Comparison of some phosphine ligands for the hydration reveals that the dimethylamino moiety of 2 improves the catalytic performance dramatically. (C) 2010 Elsevier B. V. All rights reserved.

DOI： 10.1016/j.cattod.2010.11.050

問われる日本の研究開発力問われる産と学の決断と勇気

押木俊之

化学経済 58 ( 2 ) 50-55 - 55 2011.2

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