研究者データベース

宋 志毅(ソン ツイ)
触媒科学研究所 高分子機能科学研究部門
准教授

基本情報

所属

  • 触媒科学研究所 高分子機能科学研究部門

職名

  • 准教授

学位

  • 理学博士(中国南開大学)

ホームページURL

J-Global ID

研究キーワード

  • organic synthesis   organometal   early transition metal   C-C bond cleavage   C-C bong formation   フルオレン誘導体   インデン誘導体   シクロペンタジエニル   有機合成   遷移金属   がカップリング   

研究分野

  • ナノテク・材料 / 有機合成化学

職歴

  • 2017年07月 - 現在 北海道大学 触媒科学研究所 准教授
  • 2011年03月 - 現在 北海道大学
  • 2011年03月 - 2017年06月 北海道大学 触媒化学研究センター 助教
  • 2004年07月 - 2006年06月 Beijing University Postdoctoral researcher

学歴

  • 2001年09月 - 2004年06月   Nankai University
  • 2001年09月 - 2004年06月   南開大学   化学学院   有機化学

所属学協会

  • 日本化学会   

研究活動情報

論文

  • Zhiyi Song, a, Hiroyasu Sato, Adriana Pietropaolo, Qingyu Wang, Shuhei Shimoda, Heshuang Dai, Yoshitane Imai, Hayato Toda, Takunori Harada, Yukatsu Shichibu, Katsuaki Konishi, Masayoshi Bando, Naofumi Naga, Tamaki Nakano
    Chem. Commun., 58 7 1029 - 1032 2022年01月 [査読有り]
     
    Optically active linear polyurethane and a cyclic dimer were synthesized from 2,7-diisocyanatofluorene and 2,2 '-dihydroxy-1,1 '-binaphthyl. The circular dichroism (CD) spectral intensity of the polymer was amplified at a higher concentration through aggregate formation, while circularly polarized light (CPL) emission was not enhanced. The cyclic dimer's CPL emission was largely amplified (g(lum) 1.1 x 10(-2)) due to intermolecular excimer formation through aggregation, while the CD intensity was not affected.
  • Yuehui Yuan, Zhiyi Song, Masayoshi Bando, Tamaki Nakano
    Polymer 226 123769 - 123769 2021年06月
  • Yuting Wang, Nabin Maity, Liming Zhao, Maximilian Krämer, Jun-ya Hasegawa, Yukatsu Shichibu, Katsuaki Konishi, Xiaoyuan Wang, Zhiyi Song, Masayoshi Bando, Tamaki Nakano
    Chemistry Letters 2021年04月
  • Sambhav Vishwakarma, Archana Kumari, Kheyanath Mitra, Shikha Singh, Zhiyi Song, Masayoshi Bando, Tamaki Nakano, Susanta Kumar Sen Gupta, Biswajit Ray
    Materials Today Communications 26 101705 - 101705 2021年03月
  • Yuting Wang, Koji Yazawa, Qingyu Wang, Takunori Harada, Shuhei Shimoda, Zhiyi Song, Masayoshi Bando, Naofumi Naga, Tamaki Nakano
    Chemical Communications 57 62 7681 - 7684 2021年 

    Preferred-handed twist was induced by CPL to covalent organic frameworks (COF’s) and hyperbranched polymers where the internal rotation rate in the COF’s estimated by solid-state NMR was found to affect the chirality induction efficiency.

  • Zhaoming Zhang, Takunori Harada, Adriana Pietropaolo, Yuting Wang, Yue Wang, Xiao Hu, Xuehan He, Hui Chen, Zhiyi Song, Masayoshi Bando, Tamaki Nakano
    Chemical Communications 57 14 1794 - 1797 2021年01月 

    Single-handed propeller structure was induced by circularly polarized light irradiation to three molecules with a flat core moiety and twisted periphery groups (wings). The molecules exhibited efficient blue circularly polarized luminescence.

  • Elsayed Elbayoumy, Yuting Wang, Jamil Rahman, Claudio Trombini, Masayoshi Bando, Zhiyi Song, Mostafa A. Diab, Farid S. Mohamed, Naofumi Naga, Tamaki Nakano
    Catalysts 11 1 137 - 137 2021年01月 
    Four vinyl polymer gels (VPGs) were synthesized by free radical polymerization of divinylbenzene, ethane-1,2-diyl dimethacrylate, and copolymerization of divinylbenzene with styrene, and ethane-1,2-diyl dimethacrylate with methyl methacrylate, as supports for palladium nanoparticles. VPGs obtained from divinylbenzene and from divinylbenzene with styrene had spherical shapes while those obtained from ethane-1,2-diyl dimethacrylate and from ethane-1,2-diyl dimethacrylate with methyl methacrylate did not have any specific shapes. Pd(OAc)2 was impregnated onto VPGs and reduced to form Pd0 nanoparticles within VPGs. The structures of Pd0-loaded VPGs were analyzed by XRD, TEM, and nitrogen gas adsorption. Pd0-loaded VPGs had nanocrystals of Pd0 within and on the surface of the polymeric supports. Pd0/VPGs efficiently catalyzed the oxidation/disproportionation of benzyl alcohol into benzaldehyde/toluene, where activity and selectivity between benzaldehyde and toluene varied, depending on the structure of VPG and the weight percentage loading of Pd0. The catalysts were stable and Pd leaching to liquid phase did not occur. The catalysts were separated and reused for five times without any significant decrease in the catalytic activity.
  • Yuting Wang, Nino Zavradashvili, Yue Wang, Adriana Pietropaolo, Zhiyi Song, Masayoshi Bando, Ramaz Katsarava, Tamaki Nakano
    Macromolecules 53 22 9916 - 9928 2020年12月
  • Synthesis of CF2H-Containing Oxime Ethers Derivatives from ClCF2H, tert-Butyl Nitrile and Indoles
    2020年02月
  • Heshuang Dai, Yukatsu Shichibu, Yoshitane Imai, Nobuyuki Hara, Katsuaki Konishi, Yue Wang, Zhiyi Song, Tamaki Nakano
    POLYMER CHEMISTRY 11 6 1134 - 1144 2020年02月 
    Polyaddition between 2,2'-dihydroxy-1,1'-binaphthyl (BINOL) and 1,4-diisocyanatobenzene (14DIB) and that between BINOL and 1,3-diisocyanatobenzene (13DIB) were conducted leading to optically active, helical polyurethanes, poly(BINOL-alt-14DIB) and poly(BINOL-alt-13DIB), respectively. In BINOL-14DIB systems, cyclic dimers were formed along with helical, linear poly(BINOL-alt-14DIB) where the content of dimers was higher at a lower ee of BINOL and the yield of higher-molar-mass, linear polymers was higher at a higher ee of BINOL in feed. (R,R)-, (R,S)-, and (S, S)-Cyclic dimers were completely resolved and separated by chiral HPLC. The (R,S)-cyclic dimer was preferred over (R,R)-and (S, S)-cyclic dimers, while in the reaction using racemic BINOL, the (R,R)-cyclic dimer was preferred over the other isomers at 25-75% ee of (R)-BINOL in feed. Poly(BINOL-alt-14DIB) is proposed to be composed of sequences with rather contiguous (R)-BINOL units as the majority component with rather sporadically incorporated (S)-units as the minor component. Helical sense excess appears to be greater than expected from the ee of BINOL units in the chain, suggesting that (S)-BINOL units sporadically incorporated in a rather contiguous (R)-BINOL unit sequence become a part of the left-handed helical conformation controlled by the chiral influence of contiguous (R)-BINOL units. In addition, the chiral conformation of poly (BINOL-alt-14DIB) and BINOL-14DIB cyclic dimers appeared to be stabilized or enhanced in the solid state. The BINOL-13DIB systems produced linear dimers as major components of the dimer whose content was almost constant regardless of the ee of BINOL in feed. Poly(BINOL-alt-13DIB) is proposed to be composed of sequences with rather randomly distributed (R)- and (S)-BINOL units and may be characterized by sharp, left-handed turns based on BINOL chirality forming a longer-pitched, left-handed helix.
  • Cu-Catalyzed C-N Bond Cleavage of 3-Aminoindazoles for C-H Arylation of Enamines
    2019年11月
  • Polymerization of Bulky of Oxirane Monomers Leading to Polyethers Exhibiting Intramolecular Charge Transfer Interactions
    2019年11月
  • Masayoshi Bando, Kiyohiko Nakajima, Zhiyi Song, Tamotsu Takahashi
    Dalton Transactions 48 37 13912 - 13915 2019年08月 

    Homocoupling of stannyl- and alkyl-substituted alkynes with Cp2TiBu2 gave unsymmetrical titanacyclopentadienes with >95% regioselectivities, whereas the coupling with Cp2ZrBu2 provided symmetrical zirconacyclopentadienes with >93% selectivities.

  • Synthesis and photo-induced stereomutation of helical, π-stacked copolymers of dibenzofulvene and menthyl methacrylate
    2019年05月
  • Masayoshi Bando, Kiyohiko Nakajima, Zhiyi Song, Tamotsu Takahashi
    Organometallics 38 4 731 - 734 2019年02月
  • Zhiying Jia, Kiyohiko Nakajima, Ken-Ichiro Kanno, Zhiyi Song, Tamotsu Takahashi
    ChemistrySelect 3 16 4298 - 4302 2018年04月30日 [査読有り][通常論文]
     
    Substituted pentacene derivatives, 1,4,6,13-tetrabutyl-2,3-bis(methoxycarbonyl)pentacene 1 and 1,2,3,4,6,8,9,10,11,13-decapropylpentacene 2, occurred Diels-Alder reaction with most dienophiles at the central-ring. The second ring adduct was obtained only in the case of TCNE or chloranil probably due to the steric hindrance of such dienophiles. On the other hand, reaction of substituted dihydropentacene derivatives with dienophiles was followed by aromatization gave second-ring adducts in perfect selectivity.
  • Yanqing Wang, Kiyohiko Nakajima, Zhiyi Song, Tamotsu Takahashi
    Chemical Communications 54 10 1265 - 1268 2018年 [査読有り][通常論文]
     
    Dibromodihydropentacene compound 1 was palladated and then lithiated to give a lithiated-palladated intermediate. Both of the lithium moiety and the palladium complex moiety on dihydropentacene unexpectedly survived in the solution. The Li and Pd moieties reacted with electrophiles and nucleophiles respectively to give the substituted dihydropentacene products. Aromatization of these dihydropentacenes gave substituted pentacene derivatives.
  • Masayoshi Bando, Yuki Mizukami, Kiyohiko Nakajima, Zhiyi Song, Tamotsu Takahashi
    DALTON TRANSACTIONS 46 47 16408 - 16411 2017年12月 [査読有り][通常論文]
     
    The treatment of titanacyclopentadienes with bismuth(III) chloride gave spiro compounds in moderate yields. Two carbon atoms of the diene moiety of the titanacyclopentadiene were connected to one carbon atom of the Cp ligand. This is in sharp contrast to the formation of dihydroindene derivatives, where two carbon-carbon bonds were formed between the diene moiety and the adjacent two carbon atoms of the Cp ligand.
  • Formation A Spiro[4,4]nona-1,3,6-triene by the Reaction of Bis(cyclopentadienyl)titanacyclopentadienes with Bismuth(III) Chloride
    宋志毅
    Dalton Transactions 46 16408 - 16411 2017年 [査読有り][通常論文]
  • Ken-ichiro Kanno, Efi Igarashi, Yuki Mizukami, Kiyohiko Nakajima, Zhiyi Song, Tamotsu Takahashi
    ORGANIC LETTERS 18 24 6217 - 6219 2016年12月 [査読有り][通常論文]
     
    The highly selective synthesis of triene derivatives was achieved by a zirconocene-mediated three component coupling reaction, and the trienes were efficiently subjected to 7-endo mode cyclization. The reaction of unsymmetrical zirconacyclopentadienes prepared from two different alkynes with N-bromosuccinimide (NBS) followed by treatment with allyl halides in the presence of CuCl afforded the corresponding heptatrienes in good yields. When the trienes reacted with an organolithium reagent, 7-endo mode cyclization occurred smoothly to give the corresponding cycloheptadiene.
  • Zhiyi Song, Yi-Fang Hsieh, Kiyohiko Nakajima, Ken-ichiro Kanno, Tamotsu Takahashi
    ORGANOMETALLICS 35 8 1092 - 1097 2016年04月 [査読有り][通常論文]
     
    Five carbons linearly aligned in a dihydroindene titanium complex were separated into a two-carbon group and a three-carbon group on titanium when the complex was treated with 2-aminopyridine. The protonolysis product, dihydroindene with two alkyl groups at both bridge-head positions, was obtained in high yield.
  • Yuki Mizukami, Zhiyi Song, Tamotsu Takahashi
    ORGANIC LETTERS 17 24 5942 - 5945 2015年12月 [査読有り][通常論文]
     
    The halogen exchange reaction of aliphatic fluorine compounds with organic halides as the halogen source was achieved. Treatment of alkyl fluorides (primary, secondary, or tertiary fluorides) with a catalytic amount of titanocene dihalides, trialkyl aluminum, and polyhalomethanes (chloro or bromo methanes) as the halogen source gave the corresponding alkyl halides in excellent yields under mild conditions. In the case of a fluorine/iodine exchange, no titanocene catalyst is needed. Only C-F bonds are selectively activated under these conditions, whereas alkyl chlorides, bromides, and iodides are tolerant to these reactions.
  • Yuki Mizukami, Haijun Li, Kiyohiko Nakajima, Zhiyi Song, Tamotsu Takahashi
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 53 34 8899 - 8903 2014年08月 [査読有り][通常論文]
     
    Titanacyclopentadienes, prepared from [Cp2TiBu2] and either two equivalents of an alkyne or a diyne, were treated with PMe3 (3 equiv) at 50 degrees C for 3 h and then with azobenzene at room temperature for 12 h to give 4,5,6-trisubstituted indene derivatives with the loss of one substituent in good yields. This reaction contrasts sharply with our previously reported reaction for the formation of 4,5,6,7-tetrasubstituted indene derivatives without the loss of substituents by the treatment of titanacyclopentadienes with azobenzene without PMe3. C-13 NMR spectroscopy of the product derived from a C-13-enriched complex revealed that the five carbon atoms originating from a Cp ligand were arranged linearly in the trisubstituted indene derivatives, in contrast to the 4,5,6,7-tetrasubsituted indene derivatives, in which the corresponding five carbon atoms are arranged in a ring.
  • Sicheng Zhang, Yanqing Wang, Zhiyi Song, Kiyohiko Nakajima, Tamotsu Takahashi
    CHEMISTRY LETTERS 42 7 697 - 699 2013年07月 [査読有り][通常論文]
     
    Dimerization of 2-hydroxyanthracene was investigated with 5 mol % of various catalysts that are efficient catalysts for the dimerization of 2-naphthol. Catalysts such as Cu(OH)Cl center dot TMEDA, [Mn(acac)(3)], and [Mn(acac)(2)] did not give satisfactory results. However, MnI2, which gave only trace amounts of dimerization product of 2-naphthol under the same conditions, afforded 2,2'-dihydroxy-1,1'-bianthracene in 74% yield.
  • Zhiying Jia, Shi Li, Kiyohiko Nakajima, Ken-ichiro Kanno, Zhiyi Song, Tamotsu Takahashi
    HETEROCYCLES 86 2 1495 - 1506 2012年12月 [査読有り][通常論文]
     
    Iodination of zirconacyclopentadiene derivative gave diiododiene derivative. The product was lithiated with t-BuLi and treated with diiodonaphthalene successively to afford 6,13-bis(trimethylsilyl)-5,14-dihydropentacene. A 6,13-diiodo-5,14-dihydropentacene was synthesized by iodination of 6,13-bis(trimethylsilyl)-5,14-dihydropentacene with ICl. This diiododihydropentacene was used for the introduction of substituent at 6 and 13 positions by the cross-coupling reactions with Pd catalyst. After aromatization by a combination of DDQ and gamma-terpinene or triethylamine, 6,13-disubstituted pentacene derivatives were synthesized.
  • Debabrata Payra, Zhiyi Song, Ken-ichiro Kanno, Tamotsu Takahashi
    CHEMISTRY LETTERS 40 12 1447 - 1449 2011年12月 [査読有り][通常論文]
     
    For the formation of oligothiophenes or thiophene co-oligomers, a preconnected method using zirconacyclopentadienes was demonstrated. Oligoynes of 4,4-bis(butoxymethyl)-1,6-heptadiyne linked through bithiophene were prepared where all components and diyne moieties were connected in advance before converting to zirconacyclopentadiene-containing precursors. Treatment of the reactive zirconacyclopentadienes in the preconnected precursors with acid, dimethyl acetylenedicarboxylate or sulfur monochloride afforded different oligothiophenes or thiophene co-oligomer derivatives.
  • Zhiyi Song, Yi-Fang Hsieh, Ken-ichiro Kanno, Kiyohiko Nakajima, Tamotsu Takahashi
    ORGANOMETALLICS 30 4 844 - 851 2011年02月 [査読有り][通常論文]
     
    Coupling reactions of a cyclopentadienyl (Cp) ligand with a dienyl or alkenyl ligand on dienyl- or alkenyltitanocenes proceeded to give dienylcyclopentadiene or alkenylcyclopentadiene derivatives in good to high yields. Dienyltitanocene derivatives were prepared by protonation of bis(cyclopentadienyl)titanacyclopentadienes with carboxylic acids. Chlorodienyltitanocene derivatives were formed by the reaction of titanacyclopentadienes with NCS. Alkenyltitanocene derivatives were prepared by the reaction of titanacyclopentene, which were prepared from Cp(2)TiEt(2), and alkynes, with t-BuOH. The structure of the alkenyltitanocene (in the case of 1,2-cliphenylethenyl) was determined by X-ray analysis of the single crystal. These dienyl-, chlorodienyl-, or alkenyltitanocenes were treated with azobenzene at 50 degrees C for 6 h, and the corresponding dienylcyclopcntadienes, chlorodienylcyclopentadienes, and alkenylcyclopentadiene derivatives were obtained in good to high yields. This result supports the existence of the stepwise mechanism for the coupling reaction of a Cp ligand with a diene moiety of titanacyclopentadienes, giving indene derivatives in the presence of azobenzene.
  • Tamotsu Takahashi, Zhiyi Song, Yi-Fang Hsieh, Kiyohiko Nakajima, Ken-ichiro Kanno
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 130 46 15236 - + 2008年11月 [査読有り][通常論文]
     
    The once cleaved carbon-carbon bond of the Cp moiety in 2 was recombined in indene products. Aslo, we propose a novel mechanism for the cleavage of the carbon-carbon bond of the Cp moiety.
  • Juyan Liu, Jie Han, Zhiyi Song, Yongheng Wei, Meili Pang, Jiben Meng
    JOURNAL OF MOLECULAR STRUCTURE 891 1-3 214 - 220 2008年11月 [査読有り][通常論文]
     
    Three indenone derivatives (1: 2-[3'-hydroxy-3'-(2-thienyl)indanone-2'-yl]-3-(2-thienyl)indenone; 2: trans-anti-3,3'-(2-thienyl)-3,3'-dihydroxy-[2,2'-bi-1H-indene]-1,1'dione and 3: trans-syn-3,3'-(2-thienyl)-3,3'-dihydroxy-[2,2'-bi-1H-indene]-1,1'-dione) were obtained in a one-pot reaction of 2,2'-biindanylidene-1,1',3,3'-tetraone with 2-thienylmagnesium bromide. Their structures were characterized by means of IR, (1)H NMR, MS, elemental analysis, and X-ray crystallography. The photochromic and photoinduced radical behaviors of these compounds were investigated by means of solid UV-vis spectroscopy and electron spin resonance (ESR) spectroscopy. The results show that compounds 2 and 3 exhibit photochromism in the solid state, whereas compound I does not. The relationship between the crystal structures and photochemical properties is also discussed. Based on the formation and product distribution of compounds 1, 2, and 3, a plausible pathway is suggested for the reaction of 2,2'-biindanylidene-1,1',3,3'-tetraone with 2-thienylmagnesium bromide. The findings obtained in this study also provide new insights into the addition-oxidation mechanism for the reaction of 2,2'-biindanylidene-1,1',3,3'-tetraone with Grignard reagent. (C) 2008 Elsevier B.V. All rights reserved.
  • Shi Li, Lishan Zhou, Zhiyi Song, Fengyu Bao, Ken-Ichiro Kanno, Tamotsu Takahashi
    HETEROCYCLES 73 1 519 - + 2007年12月 [査読有り][通常論文]
     
    Effects of substituents at 1,4-positions of polycyclic aromatic compounds were investigated in the case of reduction of 2,3-bis(alkoxycarbonyl)arenes with the LiAIH(4)/AlCl3 system. 2,3-Bis(alkoxycarbonyl)dihydronaphthacenes and dihydropentacenes 1 were treated with a mixture of LiAlH4 and AlCl3. The products were dependent on the substituents at 1,4-positions. Similar type of influence of the substituents at 1,4-positions was observed in the oxidation of diols 2 to dialdehydes 4. Without substituents at 1,4-positions, dialdehydes 4 were conveniently obtained. However, with substituents at 1,4-positions, dialdehydes 4 were not obtained. Instead, 1,3-dihydroisobenzofuran-1,3-diol or 1,3-dihydroisobenzofuran-1-ol derivatives 5, 6 were obtained in good yields. Preparation of pentacene imides and pentacene carboxylic acid anhydride was also reported.
  • Tamotsu Takahashi, Zhiyi Song, Kimihiko Sato, Yuichi Kuzuba, Kiyohiko Nakajima, Ken-ichiro Kanno
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 129 38 11678 - + 2007年09月 [査読有り][通常論文]
     
    Reaction of titanacyclopentadienes 1 with TiCl4 afforded 1-chloro-4,5,6,7-tetrasubstituted dihydroindene derivatives 8 in high yields.

書籍

  • 合成の科学、知識のアップデート
    宋志毅 高橋保 (担当:共著範囲:Grignard Reactions with Transition Metals)
    Georg Thieme Verlag KG 2013年01月

教育活動情報

主要な担当授業

  • 大学院共通授業科目(一般科目):自然科学・応用科学
    開講年度 : 2021年
    課程区分 : 修士課程
    開講学部 : 大学院共通科目
    キーワード : Photofunctional molecules, Semiconductor, Quantum chemical calculation, Nanomaterial, Catalyst, Energy source, Diffusion, Reaction
  • 総合化学特論Ⅰ(Modern Trends in Physical and Material Chemistry)
    開講年度 : 2021年
    課程区分 : 修士課程
    開講学部 : 総合化学院
    キーワード : Photofunctional molecules, Semiconductor, Quantum chemical calculation, Nanomaterial, Catalyst, Energy source, Diffusion, Reaction
  • 先端総合化学特論Ⅰ
    開講年度 : 2021年
    課程区分 : 博士後期課程
    開講学部 : 総合化学院
    キーワード : Photofunctional molecules, Semiconductor, Quantum chemical calculation, Nanomaterial, Catalyst, Energy source, Diffusion, Reaction
  • 環境と人間
    開講年度 : 2021年
    課程区分 : 学士課程
    開講学部 : 全学教育
    キーワード : 触媒、化学物質、環境とエネルギー、持続的な社会発展


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