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  2. 川瀬 毅

川瀬 毅

Takeshi Kawase

基本情報

所属
兵庫県立大学 工学部 応用化学工学科 兵庫県立大学大学院工学研究科応用化学専攻 教授
学位
理学博士
J-GLOBAL ID
200901016785202220
researchmap会員ID
1000031598
外部リンク

研究キーワード

 2

研究分野

 3

経歴

 8
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学歴

 4

委員歴

 6
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受賞

 2

論文

 108
  • Takeru Inoue, Yuuka Matsuura, Koki Horii, Akihito Konishi, Jun-ichi Nishida, Makoto Yasuda, Takeshi Kawase
    Chemical Communications 2024年  
    N-di(isopropyl)phenyl-2-azaphenalenyl radical cations were obtained as a dark brown air-sensitive crystalline compound. The high HOMA values and the ACID calculation indicate relatively high aromatic character of a 5,8-di-tert-butyl derivative, and...
  • Hiroshi Nishimoto, Tomofumi Kadoya, Takeshi Kawase, Jun‐ichi Nishida
    Asian Journal of Organic Chemistry 12(12) 2023年12月4日  
    Abstract Despite having an asymmetric structure, 2‐(thiopyran‐4‐ylidene)‐1,3‐benzodithiole (TP‐BT) is a good p‐type semiconductor containing isotropic three‐dimensional (3D) intermolecular interactions. Moreover, its π‐extended analogs can potentially work as organic electronic materials. Herein, a fused‐type π‐extended analog containing an extra benzene ring on the benzodithiole unit, i. e., 2‐(thiopyran‐4‐ylidene)‐1,3‐naphtho[2,3‐d]dithiole (TP‐NT), and three σ‐bonded‐type π‐extended analogs, i. e., phenyl‐, naphthyl‐, and anthryl‐substituted analogs (Ph‐TP‐BT, Nap‐TP‐BT, and Ant‐TP‐BT, respectively), were prepared and their molecular arrangements and organic field‐effect transistor (OFET) properties were investigated. TP‐NT formed a herringbone arrangement with 3D intermolecular interactions similar to that of the parent TP‐BT. Meanwhile, Ant‐TP‐BT formed a bilayer‐type layered herringbone arrangement. Since the highest occupied molecular orbital and the lowest unoccupied molecular orbital are located on the TP‐BT and anthracene units, respectively, a unique donor–acceptor separated network was formed. In OFETs prepared via a vapor deposition method using the σ‐bonded‐type analogs, slightly lower mobilities (0.1 to 8×10−3 cm2/Vs) than that of TP‐NT (0.1 cm2/Vs) were observed. Upon photo‐irradiation, the OFET of Ant‐TP‐BT exhibited a larger threshold voltage shift and an increase in the off current compared with TP‐NT. The σ‐bonded‐type analogs showed a larger photo‐response effect than TP‐NT derived from the donor–acceptor molecular structure.
  • K. Oda, H. Nishiyama, J. Nishida, T. Kawase
    ChemPlusChem 2023 e202200360 2023年2月  査読有り最終著者責任著者
  • Hiroshi Nishimoto, Takeshi Kawase, Jun-ichi Nishida
    CrystEngComm 25(34) 4856-4863 2023年  
    We report the synthesis of aryl-substituted TP-BT derivatives and their OFET properties. 4-Pyridyl substituted TP-BT shows switching characteristics by photo-irradiation.
  • K. Katayama, Y. Matsuura, C. Kitamura, J. Nishida, T. Kawase
    ChemPhotoChem 2022 e202200013 2022年3月  査読有り最終著者責任著者
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MISC

 83
  • Takeshi Kawase
    SYNLETT (17) 2609-2626 2007年10月  
    Strained phenylacetylene macrocycles, cyclic [3]- and [4]metaphenylacetylenes ([n]CMPAs) and methoxy derivatives, and cyclic [5]- to [9]paraphenylacetylenes ([n]CPPAs) were prepared using a strategy based on the McMurry coupling reaction. The physicochemical and supramolecular properties of these substances were determined. Interestingly, apart from [3]CMPAs, compounds in these series possess preorganized three-dimensional cavities. 1 Introduction 2 Theoretical Optimized Structures 3 Synthesis 4 Properties and Structures of Cyclic Metaphenylacetylenes 5 Properties and Structures of Carbon Nanorings 6 Outlook.
  • Takeshi Kawase
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN 65(9) 888-896 2007年9月  
    The pi-pi interaction between curved conjugated systems is important for the formation and properties of new carbon materials such as carbon nanotubes, bucky onions and fullerene peapods. However, the nature has been little understood so far. Recently we have designed and synthesized cyclic [n]paraphenyleneacetylenes ([n]CPPAs) and the related compounds. They have smooth belt-shaped structures similar to a cut piece of carbon nanotubes, and thus may be termed "carbon nanorings". The carbon nanorings having an appropriate cavity size form stable inclusion complexes with fullerenes in solution as well as in the solid state. The high affinity suggests that the considerably strong attractive interactions are operative between the curved conjugated systems. This review provides an insight into the noncovalent interaction between the concave and convex pi surfaces.
  • Hiroyuki Kurata, Seiji Muro, Tetsuya Enomoto, Takeshi Kawase, Masaji Oda
    Bulletin of the Chemical Society of Japan 80(2) 349-357 2007年  
  • H Kurata, Y Takehara, K Matsumoto, T Kawase, M Oda
    CHEMISTRY LETTERS 34(12) 1660-1661 2005年12月  
    The extended-qui none derivative of cyclopent[fg]acenaphthylene-1,2-dione (pyracyloquinone) is first synthesized and characterized. An X-ray analysis exhibits the non-planar structure involving bent of two 3,5-di-tert-butyl-4-oxo-cyclohexadienylidene units, and bond alternation along the molecular periphery. The facile formation of trianion radical on cyclic voltammetry reflects high-electron affinity enhanced by antiaromatic character of the formed pyracylene moiety on the dianion state.
  • H Kurata, Y Takehara, K Matsumoto, T Kawase, M Oda
    CHEMISTRY LETTERS 34(12) 1660-1661 2005年12月  
    The extended-qui none derivative of cyclopent[fg]acenaphthylene-1,2-dione (pyracyloquinone) is first synthesized and characterized. An X-ray analysis exhibits the non-planar structure involving bent of two 3,5-di-tert-butyl-4-oxo-cyclohexadienylidene units, and bond alternation along the molecular periphery. The facile formation of trianion radical on cyclic voltammetry reflects high-electron affinity enhanced by antiaromatic character of the formed pyracylene moiety on the dianion state.
  • H Kurata, Y Oki, K Matsumoto, T Kawase, M Oda
    CHEMISTRY LETTERS 34(7) 910-911 2005年7月  
    The parent tetrakis (2-furyl)methane is first synthesized using aromatic nucleophilic substitution on 2-chlorofurans as a key reaction. X-ray analysis reveals the shortest bond length between the central methane carbon and furyl ipso-carbons among known tetraarylmethanes. Successful tetrabromination and tetralithiation promise its high synthetic utility.
  • H Kurata, Y Oki, K Matsumoto, T Kawase, M Oda
    CHEMISTRY LETTERS 34(7) 910-911 2005年7月  
    The parent tetrakis (2-furyl)methane is first synthesized using aromatic nucleophilic substitution on 2-chlorofurans as a key reaction. X-ray analysis reveals the shortest bond length between the central methane carbon and furyl ipso-carbons among known tetraarylmethanes. Successful tetrabromination and tetralithiation promise its high synthetic utility.
  • T Kawase, Y Minami, N Nishigaki, S Okano, H Kurata, M Oda
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 44(2) 316-319 2005年  
  • Angew. Chem. Int. Ed. 43, 7334-7336 2005年  査読有り責任著者
  • T Kawase, Y Minami, N Nishigaki, S Okano, H Kurata, M Oda
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 44(2) 316-319 2005年  
  • T Kawase, N Nishigaki, H Kurata, M Oda
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 3090 - 3096(14) 3090-3096 2004年7月  
    Treatment of 2,6-di-tert-butyl-4-ethynylphenol with 2 equivalents of nBuLi, followed by addition of diaryl ketones, afforded the corresponding p-quinopropadienes 2a-f upon appropriate dehydrative treatments. These compounds are fairly stable, orange to purple, crystalline substances, exhibiting intense absorptions at longer wavelengths. In particular, the bis(dimethylamino) derivative 2a absorbs across the whole of the visible spectrum and into the near infrared. Unlike the quinone methides 1, compounds 2 exhibited irreversible oxidation waves together with irreversible reduction waves on cyclic voltammetry. The very small E-sum(1) value of 2a also indicates the highly amphoteric redox properties of 2a; however, both the anion and cation radicals of 2 are highly reactive. The molecular structures of 2a and 2e exhibit relatively small dihedral angles between two aromatic ring planes (2a for 47degrees and 2e for 52degrees), and each has a short central double bond and long side double bonds. The short central double bond (2a for 1.228 Angstrom and 2e for 1.235 Angstrom) indicates the importance of the resonance contribution of the dipolar structure with an acetylenic bond. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).
  • T Kawase, N Nishigaki, H Kurata, M Oda
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 3090-3096(14) 3090-3096 2004年7月  
    Treatment of 2,6-di-tert-butyl-4-ethynylphenol with 2 equivalents of nBuLi, followed by addition of diaryl ketones, afforded the corresponding p-quinopropadienes 2a-f upon appropriate dehydrative treatments. These compounds are fairly stable, orange to purple, crystalline substances, exhibiting intense absorptions at longer wavelengths. In particular, the bis(dimethylamino) derivative 2a absorbs across the whole of the visible spectrum and into the near infrared. Unlike the quinone methides 1, compounds 2 exhibited irreversible oxidation waves together with irreversible reduction waves on cyclic voltammetry. The very small E-sum(1) value of 2a also indicates the highly amphoteric redox properties of 2a; however, both the anion and cation radicals of 2 are highly reactive. The molecular structures of 2a and 2e exhibit relatively small dihedral angles between two aromatic ring planes (2a for 47degrees and 2e for 52degrees), and each has a short central double bond and long side double bonds. The short central double bond (2a for 1.228 Angstrom and 2e for 1.235 Angstrom) indicates the importance of the resonance contribution of the dipolar structure with an acetylenic bond. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).
  • Kouzou Matsumoto, Masaki Kannami, Daisuke Inokuchi, Hiroyuki Kurata, Takeshi Kawase, Masaji Oda
    Organic Letters 9(15) 2903-2906 2004年6月  
  • T Kawase, K Tanaka, N Shiono, Y Seirai, M Oda
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 43(13) 1722-1724 2004年3月  
  • T Kawase, K Tanaka, N Shiono, Y Seirai, M Oda
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 43(13) 1722-1724 2004年3月  
  • T Kawase, N Fujiwara, M Tsutumi, M Oda, Y Maeda, T Wakahara, T Akasaka
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 43(38) 5060-5062 2004年  
  • Angew. Chem. Int. Ed. 43, 4396 - 4398 2004年  
  • K Matsumoto, H Minami, T Kawase, M Oda
    ORGANIC & BIOMOLECULAR CHEMISTRY 2(16) 2323-2326 2004年  
    The McMurry coupling of 2,7-diformylfluorene affords a dimer, anti-[2.2](2,7)-fluorenophanediene, and a trimer, [2.2.2](2,7)-fluorenophanetriene, as cyclic oligomers. X-Ray crystallography of the dimer establishes its strained, layered structure with anti- conformation. While the fluorenyl groups of the dimer do not show any sign of rotation in the variable temperature H-1 NMR spectra up to 120degreesC, those of the trimer are fast rotating even at -50degreesC. Treatment of the dimer and trimer with KH in DMSO furnished the respective dianion and trianion that are stable at room temperature in the solutions. While the trianion shows substantial conjugation through the etheno bridges, the dianion shows little conjugation through the etheno bridges and almost no proton-deuterium exchange of the fluorenyl C9-H with the solvent DMSO-d(6) probably due to stereospecific protonation-deprotonation associated with the tightly layered structure.
  • T Kawase, N Fujiwara, M Tsutumi, M Oda, Y Maeda, T Wakahara, T Akasaka
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 43(38) 5060-5062 2004年  
  • Angew. Chem. Int. Ed. 43, 4396-4398 2004年  
  • K Matsumoto, H Minami, T Kawase, M Oda
    ORGANIC & BIOMOLECULAR CHEMISTRY 2(16) 2323-2326 2004年  
    The McMurry coupling of 2,7-diformylfluorene affords a dimer, anti-[2.2](2,7)-fluorenophanediene, and a trimer, [2.2.2](2,7)-fluorenophanetriene, as cyclic oligomers. X-Ray crystallography of the dimer establishes its strained, layered structure with anti- conformation. While the fluorenyl groups of the dimer do not show any sign of rotation in the variable temperature H-1 NMR spectra up to 120degreesC, those of the trimer are fast rotating even at -50degreesC. Treatment of the dimer and trimer with KH in DMSO furnished the respective dianion and trianion that are stable at room temperature in the solutions. While the trianion shows substantial conjugation through the etheno bridges, the dianion shows little conjugation through the etheno bridges and almost no proton-deuterium exchange of the fluorenyl C9-H with the solvent DMSO-d(6) probably due to stereospecific protonation-deprotonation associated with the tightly layered structure.
  • T Kawase, T Okada, T Enomoto, T Kikuchi, Y Miyake, M Oda
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN 76(9) 1793-1799 2003年9月  
    Upon heating at 200 degreesC in o-dichlorobenzene, 2,5-bis(dicyanomethylene)bicyclo[4.2.0]octa-3,7-diene gave rise to 2,6-bis(dicyanomethylene)bicyclo[3.3.0]octa-3,7-diene by a rearrangement as a sole isolable product in modest yield, and no trace of 5,8-bis(dicyanomethylene)cycloocta-1,3,6-triene, the expected product, was detected. On the other hand., 2,5-bis(dicyanomethylene)bicyclo[4.2.0]octa-7-ene underwent a thermal reaction at lower temperature (110 degreesC in toluene) to give 5,8-bis(dicyanomethylene)-1,3-cyclooctadiene, the normal ring-opened product, and 2,6-bis(dicyanomethylene)bicyclo[3.3.0]octa-1(5)-ene, a rearranged product, in about 1: 1 ratio. The rearranged product has a planar 1, 1,6,6-tetracyanohexatriene structure (X-ray analysis), and shows a considerably lower electron affinity than that of tetracyanoethylene and 7,7,8,8-tetracyano-p-quinodimethane. The electron acceptor also formed a crystalline 1: 1 charge transfer complex with tetrathiafulvalene, of which electronic conductivity was near insulating (1.1 X 10(-7) S cm(-1)). We have proposed a possible mechanism for the rearangements involving the zwitterionic intermediates.
  • H Kurata, Y Takehara, T Kawase, M Oda
    CHEMISTRY LETTERS 32(6) 538-539 2003年6月  
    A dibenzo-ortho-terphenoquinone derivative, the first o-terquinone derivative, is largely deviated from coplanarity, is in a slight equilibrium with its diradical form, displays an easy rotation of the exocyclic double bonds, and shows photoresponsive switching property traceable by ESR spectroscopy.
  • H Kurata, Y Takehara, T Kawase, M Oda
    CHEMISTRY LETTERS 32(6) 538-539 2003年6月  
    A dibenzo-ortho-terphenoquinone derivative, the first o-terquinone derivative, is largely deviated from coplanarity, is in a slight equilibrium with its diradical form, displays an easy rotation of the exocyclic double bonds, and shows photoresponsive switching property traceable by ESR spectroscopy.
  • H Kurata, K Haruki, H Nakaminami, T Kawase, M Oda
    CHEMISTRY LETTERS 32(5) 422-423 2003年5月  
    The McMurry coupling of tris(5-formyl-2-thienyl)methane afforded an unsubstituted, etheno-bridged trithienylmethanophane which was in turn transformed to novel cage-molecular monocation, dication, and dianion of substantial stability. The latter two species are the first examples of fully conjugated ionic cyclophane cage molecule.
  • H Kurata, K Haruki, H Nakaminami, T Kawase, M Oda
    CHEMISTRY LETTERS 32(5) 422-423 2003年5月  
    The McMurry coupling of tris(5-formyl-2-thienyl)methane afforded an unsubstituted, etheno-bridged trithienylmethanophane which was in turn transformed to novel cage-molecular monocation, dication, and dianion of substantial stability. The latter two species are the first examples of fully conjugated ionic cyclophane cage molecule.
  • Keiichiro Utsumi, Takeshi Kawase, Masaji Oda
    Chemistry Letters 32(4) 412-413 2003年4月5日  
    The title cyclophanes as a potential fragment of double-helical π-conjugated system were synthesized, and the spectroscopic and crystallographic characterization shows the strained nature of the π-system variable-temperature NMR spectra also reveal that the cyclophanes exist as an equilibrium mixture between the meso- and dl-forms in solution.
  • K Utsumi, T Kawase, M Oda
    CHEMISTRY LETTERS 32(4) 412-413 2003年4月  
    The title cyclophanes as a potential fragment of double-helical pi-conjugated system were synthesized, and the spectroscopic and crystallographic characterization shows the strained nature of the pi-system; variable-temperature NMR spectra also reveal that the cyclophanes exist as an equilibrium mixture between the meso- and dl-forms in solution.
  • T Kawase, T Iwata, M Oda
    CHEMISTRY LETTERS 32(4) 322-323 2003年4月  
    Treatment of 3-lithiophenyldicyanomethide ions with Michler's ketone afforded the title compounds as stable crystals upon weak-acidic work-up. The molecular structure and spectroscopic data reveal the zwitterionic nature of the compounds.
  • T Kawase, T Iwata, M Oda
    CHEMISTRY LETTERS 32(4) 322-323 2003年4月  
    Treatment of 3-lithiophenyldicyanomethide ions with Michler's ketone afforded the title compounds as stable crystals upon weak-acidic work-up. The molecular structure and spectroscopic data reveal the zwitterionic nature of the compounds.
  • T Kawase, K Tanaka, Y Seirai, N Shiono, M Oda
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 42(45) 5597-5600 2003年  
  • T Kawase, K Tanaka, N Fujiwara, HR Darabi, M Oda
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 42(14) 1624-1628 2003年  
  • T Kawase, Y Seirai, HR Darabi, M Oda, Y Sarakai, K Tashiro
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 42(14) 1621-1624 2003年  
  • T Kawase, K Tanaka, Y Seirai, N Shiono, M Oda
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 42(45) 5597-5600 2003年  
  • Takeshi Kawase, Tomoaki Okada, Tetsuya Enomoto, Takayuki Kikuchi, Yoji Miyake, Masaji Oda
    Bulletin of the Chemical Society of Japan 76(9) 1793-1799 2003年  
    Upon heating at 200 °C in o-dichlorobenzene, 2,5-bis(dicyanomethylene)bicyclo[4.2.0]octa-3,7-diene gave rise to 2,6-bis(dicyanomethylene)bicyclo[3.3.0]octa-3,7-diene by a rearrangement as a sole isolable product in modest yield, and no trace of 5,8-bis(dicyanomethylene)cycloocta-1,3,6-triene, the expected product, was detected. On the other hand, 2,5-bis(dicyanomethylene)bicyclo[4.2.0]octa-7-ene underwent a thermal reaction at lower temperature (110 °C in toluene) to give 5,8-bis(dicyanomethylene)-1,3-cyclooctadiene, the normal ring-opened product, and 2,6-bis(dicyanomethylene)bicyclo[3.3.0]octa-1(5)-ene, a rearranged product, in about 1:1 ratio. The rearranged product has a planar 1,1,6,6-tetracyanohexatriene structure (X-ray analysis), and shows a considerably lower electron affinity than that of tetracyano-ethylene and 7,7,8,8-tetracyano-p-quinodimethane. The electron acceptor also formed a crystalline 1:1 charge transfer complex with tetrathiafulvalene, of which electronic conductivity was near insulating (1.1 × 10-7 S cm-1). We have proposed a possible mechanism for the rearangements involving the zwitterionic intermediates.
  • T Kawase, K Tanaka, N Fujiwara, HR Darabi, M Oda
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 42(14) 1624-1628 2003年  
  • T Kawase, Y Seirai, HR Darabi, M Oda, Y Sarakai, K Tashiro
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 42(14) 1621-1624 2003年  
  • K Matsumoto, Y Harada, T Kawase, M Oda
    CHEMICAL COMMUNICATIONS 4,324-325(4) 324-325 2002年  
    The titled [3]radialenes are the first, water-soluble hexaaryl[3]radialenes with considerably high electron affinity, their alkali metal reduction giving rise to anion-radicals and dianions stepwise as fairly stable species in degassed tetrahydrofuran.
  • K Matsumoto, Y Harada, T Kawase, M Oda
    CHEMICAL COMMUNICATIONS 4,324-325(4) 324-325 2002年  
    The titled [3]radialenes are the first, water-soluble hexaaryl[3]radialenes with considerably high electron affinity, their alkali metal reduction giving rise to anion-radicals and dianions stepwise as fairly stable species in degassed tetrahydrofuran.
  • Y Hosokawa, T Kawase, M Oda
    CHEMICAL COMMUNICATIONS 19,1948-1949(19) 1948-1949 2001年10月  
    The titled cyclophane (cyclic [6]metaphenylacetylene) with six methoxy groups inside the cavity has a nearly planar carbon framework, forms open-channel structures in the crystal, and exhibits an ammonium-selective ionophoric property in spite of the considerably large cavity.
  • Y Hosokawa, T Kawase, M Oda
    CHEMICAL COMMUNICATIONS 19,1948-1949(19) 1948-1949 2001年10月  
    The titled cyclophane (cyclic [6]metaphenylacetylene) with six methoxy groups inside the cavity has a nearly planar carbon framework, forms open-channel structures in the crystal, and exhibits an ammonium-selective ionophoric property in spite of the considerably large cavity.
  • T Kawase, N Ueda, K Tanaka, Y Seirai, M Oda
    TETRAHEDRON LETTERS 42(32) 5509-5511 2001年8月  
    Treatment of stilbenedialdehyde derivatives with low-valent titanium generated in a mixed solvent of DME and toluene favored reductive cyclo-oligomerization to give macrocyclic cyclophanepolyenes in relatively good yields leading to improved or new synthesis of a series of cyclic paraphenylacetylenes ([6] to [9]CPPAs). (C) 2001 Elsevier Science Ltd. All rights reserved.
  • H Kurata, T Shimoyama, K Matsumoto, T Kawase, M Oda
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN 74(7) 1327-1332 2001年7月  
    Adamantane-2,4-bis(p-quinone methide) and -2,6-bis(p-quinone methide) were synthesized by the reaction of adamantane-2,4-dione and -2,6-dione, respectively, with lithium 4-lithio-2,6-di-t-butylphenoxide, followed by dehydration. Their structures were established by spectroscopic and X-ray crystallographic analyses. Having a distance (2.47 Angstrom) between C2 and C4 longer than that (ca. 1.9 Angstrom) between C1 and C3 of cyclobutane-1,3-bis(p-quinone methide)s, adamantane-2,4-bis(p-quinone methide) was found to show a clear through-space interaction (homoconjugation) and to form a sigma -bond at its bis(anion radical) stage upon both chemical and electrochemical reduction. On the other hand, adamantane-2,6-bis(p-quinone methide), which has a long distance and near orthogonal arrangement between the quinone methide chromophores, shows a through-bond interaction, though it is weak.
  • H Kurata, H Nakaminami, K Matsumoto, T Kawase, M Oda
    CHEMICAL COMMUNICATIONS (6) 529-530 2001年  
    The McMurry coupling of tris(5-formyl-2-thienyl)methanes affords novel cage molecules which are bicapped with tris(2-thienyl)methanes and where all the sulfur atoms of thienyl groups direct inward.
  • T Enomoto, N Nishigaki, H Kurata, T Kawase, M Oda
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN 73(9) 2109-2114 2000年9月  
    A number of hexaphenyl[3]radialene derivatives were synthesized in modest to good yields by the reaction of tetrachlorocyclopropene with diarylmethyl anion followed by oxidation with oxygen. That the acidity of diarylmethane is higher than that of diphenylmethane is found to be an important factor for the successful synthesis. Lithiation and protonation of hexa(4-iodophenyl)[3]radialene thus obtained leads to the first synthesis of hexaphenyl[3]radialene. These hexaaryl[3]radialenes are stable, orange to red, crystalline substances. An X-ray crystallographic analysis of hexa(4-cyanophenyl)[3]radialene reveals a double three-bladed propeller conformation. The effects of substituents in the phenyl groups on their properties are most clearly seen in their electrochemical reduction potentials; among hexaphenyl[3]radialenes here obtained, hexa (4-nitrophenyl)[3]radialene (E-1(red) = -0.30 V, E-2(red) = -0.45 V) is found to be a good electron acceptor stronger than p-benzoquinone.
  • T Kawase, Y Hosokawa, H Kurata, M Oda
    CHEMISTRY LETTERS (8) 745-746 1999年8月  
    The title cyclophane has a preorganized cavity with about 1.2 Angstrom in diameter surrounded by four oxygen atoms (X-ray analysis); however, solvent extraction experiments using alkali metal picrates revealed the unexpectedly flexible nature of the cavity that forms 1:1 complexes with various alkali metal ions with considerably large association constants.
  • R Suzuki, H Kurata, T Kawase, M Oda
    CHEMISTRY LETTERS (7) 571-572 1999年7月  
    Unannelated thioquinone methides were first synthesized as labile but isolable substances with aid of steric protection; they exhibit higher dipolar properties and stronger electron affinity than the corresponding quinone methides.
  • 小田雅司, 川瀬 毅
    化学と工業 52(5) 578-581 1999年5月  最終著者
  • H Kurata, M Monden, T Kawase, M Oda
    TETRAHEDRON LETTERS 39(39) 7135-7138 1998年9月  
    Tetrakis(2-thienyl)allene was synthesized as an acid-sensitive tetraarylallene by dehydration of the corresponding tetrathienylallyl alcohol with anhydrous copper(II) sulfate. This electron-rich allene forms a remarkably stable tetrathienylallyl cation by protonation, undergoes Diels-Alder reaction with tetracyanoethylene, and is capable of tetrafold lithiation and functionalization. (C) 1998 Elsevier Science Ltd. All rights reserved.
  • Masaji Oda, Takeshi Kawase, Hiroyuki Kurata, Tetsuya Enomoto
    Reactive Organometallics 289-292 1998年  

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 6
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 22
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