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2013 Fiscal Year Final Research Report

Development of purely organic single-component conductors

Research Project

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Project/Area Number 23550155
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Functional materials chemistry
Research InstitutionEhime University

Principal Investigator

MISAKI Yohji  愛媛大学, 理工学研究科, 教授 (90202340)

Co-Investigator(Renkei-kenkyūsha) SHIRAHATA Takashi  愛媛大学, 大学院理工学研究科, 講師 (40360565)
Project Period (FY) 2011 – 2013
Keywords分子性導体 / 多段階酸化還元 / サイクリックボルタンメトリー / ドナー・アクセプター系分子 / 電子構造
Research Abstract

Several derivatives of brand-new donor-acceptor (D-A) systems 1-5 composed of DT-TTF and dicyanomethylidene and dicyanoquinodimethane groups were synthesized. Cyclic voltammetry revealed that the compound 1 and 3 exhibited multi-stage of oxidation and one-stage of reduction processes. The IR spectra of 1 and 3 demonstrated considerable contribution of polarized structures. Electronic spectra and theoretical calculation (DFT method) suggested that the absorption maximum of 1 at around 900 nm was due to intramolecular charge-transfer. The D-A system 1 exhibited conductivity of 10E-5 S/cm on a single crystal in spite of a single-component material.

  • Research Products

    (55 results)

All 2014 2013 2012 2011 Other

All Journal Article (24 results) (of which Peer Reviewed: 24 results) Presentation (27 results) Book (1 results) Remarks (3 results)

  • [Journal Article] Dendritic Tetrathiafulvalene Pentamers Linked by Methylenedithio Spacers2014

    • Author(s)
      Haruka Kimura, Katsuya Konishi, Shun-ya Muraoka, Takashi Shirahata, Yohji Misaki
    • Journal Title

      Chem. Lett.

      Volume: 43(6) Pages: 843-845

    • DOI

      10.1246/cl.140092

    • Peer Reviewed
  • [Journal Article] Cyclic TTF Tetramer Linked by Methylenedithio Spacers2014

    • Author(s)
      Ken-ichi Nakamura, Yuuki Okada, Takashi Shirahata, Yohji Misaki
    • Journal Title

      Chem. Lett.

      Volume: 43(5) Pages: 708-710

    • DOI

      10.1246/cl.140092

    • Peer Reviewed
  • [Journal Article] A Pentakis-fused Tetrathiafulvalene System Extended by Cyclohexene-1,4-diylidenes : A New Positive Electrode Material for Rechargeable Batteries Utilizing Ten-electrons Redox2014

    • Author(s)
      Minami Kato, Ken-ichiro Senoo, Masatu Yao, Yohji Misaki
    • Journal Title

      J. Mater. Chem. A

      Volume: 2(19) Pages: 6747-6754

    • DOI

      10.1039/c3ta14920j

    • Peer Reviewed
  • [Journal Article] 電子供与性[n]デンドラレン類の合成,構造と性質(Synthesis, Structures and Properties of [n]Dendralens Substituted with Electron-Donating Groups)2013

    • Author(s)
      長谷川真士,渡邊美穂,御崎洋二(Masashi Hasegawa, Miho Watanabe, Yohji Misaki)
    • Journal Title

      有機合成化学協会誌(J. Synth. Org. Chem. Jpn.)

      Volume: 71(12) Pages: 1268-1281

    • DOI

      10.5059/yukigoseikyokaishi.71.1268

    • Peer Reviewed
  • [Journal Article] A Tris-fused Tetrathiafulvalene Extended with Cyclohexene-1,4-diylidene : A New Positive Electrode Material for Organic Rechargeable Batteries2013

    • Author(s)
      Minami Kato, Daisuke Ogi, Masaru Yao, Yohji Misaki
    • Journal Title

      Chem. Lett.

      Volume: 42(12) Pages: 1556-1558

    • DOI

      10.1246/cl.130841

    • Peer Reviewed
  • [Journal Article] A New Bis-fusedπ-Electron Donor Composed of Tetrathiafulvalene and 2-(Xanthen-9-ylidene)-1,3-dithiole2013

    • Author(s)
      Minami Kato, Takashi Shirahata, Yohji Misaki
    • Journal Title

      Chem. Lett.

      Volume: 42(12) Pages: 1548-1550

    • DOI

      10.1246/cl.130822

    • Peer Reviewed
  • [Journal Article] [5]Radialene-Fused Tetrathiafulvalenes Exihibiting a Simultaneous Four- or Eight- Electron Transfer2013

    • Author(s)
      Masafumi Ueda, Yohji Misaki
    • Journal Title

      Org. Lett.

      Volume: 15(15) Pages: 3824-3827

    • DOI

      10.1021/ol401350c

    • Peer Reviewed
  • [Journal Article] Oxidation States of [5]Radialene with Five 1,3-Dithiol-2-ylidenes and Its Oxygen Adduct2013

    • Author(s)
      Masafumi Ueda, Takashi Shirahata, Yohji Misaki
    • Journal Title

      Chem. Lett.

      Volume: 42(5) Pages: 565-567

    • DOI

      10.1246/cl.2013.565

    • Peer Reviewed
  • [Journal Article] Synthesis and Properties of Novel [5]Radialenes Substituted with Multiple 1,3-Dithiol-2-yildenes2013

    • Author(s)
      Masafumi Ueda, Yui Ogura, Yohji Misaki
    • Journal Title

      Chem. Lett.

      Volume: 42(5) Pages: 562-564

    • DOI

      10.1246/cl.2013.562

    • Peer Reviewed
  • [Journal Article] Construction of Rechargeable Batteries Using Multifused Tetrathiafulvalene Systems as Cathode Materials2013

    • Author(s)
      Yuu Inatomi, Nobuhiko Hojo, Taisuke Yamamoto, Sho-ichiro Watanabe, Yohji Misaki
    • Journal Title

      ChemPlusChem

      Volume: 77(11) Pages: 973-976

    • DOI

      10.1002/cplu.201200197

    • Peer Reviewed
  • [Journal Article] Synthesis, Structures and Properties of Molecular Conductors Based on Bis-Fused Donors Composed of (Thio)Pyran-4-ylidene- 1,3-dithiole and Tetraselenafulvalene2012

    • Author(s)
      Ken-ichi Ishidzu, Minoru Ashizawa, Masaki Watanabe, Takashi Shirahata, Yohji Misaki
    • Journal Title

      Crystals

      Volume: 2(3) Pages: 1091-1107

    • DOI

      10.3390/cryst2031092

    • Peer Reviewed
  • [Journal Article] Structural Transitions from Triangular to Square Molecular Arrangements in the Quasi-One-Dimensional Molecular Conductors (DMEDO-TTF)_2XF_6 (X = P, As, and Sb2012

    • Author(s)
      Takashi Shirahata, Keita Shiratori, Shouhei Kumeta, Tadashi Kawamoto, Tadahiko Ishikawa, Shin-ya Koshihara, Yoshiaki Nakano, Hideki Yamochi, Yohji Misaki, Takehiko Mori
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 134(32) Pages: 13330–13340

    • DOI

      10.1021/ja303435n

    • Peer Reviewed
  • [Journal Article] Synthesis and Properties of Tris-Fused Tetrathiafulvalene Analogues Possessing [3]Dendralene Moieties2012

    • Author(s)
      Yoshihiro Kajiwara, Shojun Hino, Yohji Misaki
    • Volume
      85(7)
    • Pages
      830-835
    • DOI

      10.1246/bcsj.20120063

    • Peer Reviewed
  • [Journal Article] Synthesis of bis-fused tetrathiafulvalene with mono- and dicarboxylic acids2012

    • Author(s)
      Takeshi Terauchi, Yuka Kobayashi, Yohji Misaki
    • Journal Title

      Tetrahedron Lett.

      Volume: 53(26) Pages: 3277-3280

    • DOI

      10.1016/j.tetlet.2012.04.064

    • Peer Reviewed
  • [Journal Article] Synthesis and Properties of 2-Alkylidene-1,3-dithiolo[4,5-d]-4,5-ethylene diselenotetrathiafulvalene Derivatives and Crystal Structures of Their Cation Radical Salts2012

    • Author(s)
      Keisuke Furuta, Shuhei Kohno, Takashi Shirahata, Koya Yamasaki, Shojun Hino, Yohji Misaki
    • Journal Title

      Crystals

      Volume: 2(2) Pages: 393-412

    • DOI

      10.3390/cryst2020393

    • Peer Reviewed
  • [Journal Article] Structures and electrical properties of a new molecular conductor, (BSM-TTP)_4(PF_6)_3(C_6H_5Cl)_22012

    • Author(s)
      Hiroya Tsuji, Misaki Yasuda, Takashi Shirahata, Hideki Fujiwara, Toyonari Sugimoto, Yohji Misaki
    • Journal Title

      Phys. Status Solidi C

      Volume: 9(5) Pages: 1149-1151

    • DOI

      10.1002/pssc.201100690

    • Peer Reviewed
  • [Journal Article] Synthesis of a new donor, MOET-TTP, and the crystal structure, electrical, and magnetic properties of (MOET-TTP)_2MCl_4 (M = Fe and Ga)2012

    • Author(s)
      Takashi Shirahata, Tetsuya Ito, Shinya Toki, Yohji Misaki
    • Journal Title

      Phys. Status Solidi B

      Volume: 249(5) Pages: 929-932

    • DOI

      10.1002/pssb.201100674

    • Peer Reviewed
  • [Journal Article] Probing the metal-insulator phase transition in the (DMEDO-EBDT)_2PF_6 single crystal by optical measurements2012

    • Author(s)
      Tadahiko Ishikawa, Makoto Kitayama, Aya Chono, Ken Onda, Yoichi Okimoto, Shin-ya Koshihara, Yoshiaki Nakano, Hideki Yamochi, Toru Morikawa, Takashi Shirahata, Yohji Misaki
    • Journal Title

      J. Phys.: Condens. Matter

      Volume: 24(19) Pages: 195501/1-9

    • DOI

      10.1088/0953-8984/24/19/195501

    • Peer Reviewed
  • [Journal Article] Synthesis and properties of a new donor-acceptor diad composed of DT-TTF and dicyanomethylidene group2011

    • Author(s)
      Ken-ichi Nakamura, Takashi Shirahata, Hisakazu Miyamoto, Yohji Misaki
    • Journal Title

      Heterocycles

      Volume: 83(9) Pages: 2115-2126

    • DOI

      10.3987/COM-11-12277

    • Peer Reviewed
  • [Journal Article] Synthesis and properties of new trimeric and tetrameric tetrathiafulvalenes with alternate links2011

    • Author(s)
      Ken-ichi Nakamura, Tomomi Hashimoto, Takashi Shirahata, Shojun Hino, Masashi Hasegawa, Yasuhiro Mazaki, Yohji Misaki
    • Journal Title

      Chem. Lett.

      Volume: 40(8) Pages: 883-885

    • DOI

      10.1246/cl.2011.883

    • Peer Reviewed
  • [Journal Article] Dimeric and trimeric tetrathiafulvalenes with strong intramolecular interactions in the oxidized states2011

    • Author(s)
      Ken-ichi Nakamura, Tsuyoshi Takashima, Takashi Shirahata, Shojun Hino, Masashi Hasegawa, Yasuhiro Mazaki, Yohji Misaki
    • Journal Title

      Org. Lett.

      Volume: 13(12) Pages: 3122-3125

    • DOI

      10.1021/ol201025g

    • Peer Reviewed
  • [Journal Article] Synthesis and properties of 1,3-dithiole[4]dendralenes, in which two thiophene rings are inserted2011

    • Author(s)
      Masataka Nishiwaki, Mami Tezuka, Takashi Shirahata, Yohji Misaki
    • Journal Title

      Chem. Lett.

      Volume: 40(5) Pages: 467-469

    • DOI

      10.1246/cl.2011.467

    • Peer Reviewed
  • [Journal Article] Novel molecular conductors based on cyclopenteno-TTP showing strong self-aggregation2011

    • Author(s)
      Masataka Nishiwaki, Ken-ichi Nakamura, Takashi Shirahata, Yohji Misaki
    • Journal Title

      Chem. Lett.

      Volume: 40(5) Pages: 452-454

    • DOI

      10.1246/cl.2011.452

    • Peer Reviewed
  • [Journal Article] New Molecular Conductors with Effectively Half-Filled Electronic State Based on TTF Derivative Condensed with 2-Isopropylidene-1,3-dithiole Ring

    • Author(s)
      Keisuke Furuta, Shuhei Kohno, Takashi Shirahata, Yohji Misaki
    • Journal Title

      Eur. J. Inorg. Chem.

      Volume: (in press)

    • DOI

      10.1002/ejic.201402006

    • Peer Reviewed
  • [Presentation] 融合型1,3-ジチオール[5]ラジアレン二量体の合成と性質2014

    • Author(s)
      松田孝司,上田将史,白旗崇,御崎洋二
    • Organizer
      2014年日本化学会第94春季年会
    • Place of Presentation
      名古屋大学東山キャンパス(名古屋)
    • Year and Date
      2014-03-28
  • [Presentation] 1,3-ジチオール[5]ラジアレンおよびその酸化種の結晶構造と電子状態2014

    • Author(s)
      上田将史,白旗崇,御崎洋二
    • Organizer
      2014年日本化学会第94春季年会
    • Place of Presentation
      名古屋大学東山キャンパス(名古屋)
    • Year and Date
      2014-03-28
  • [Presentation] 立体障害を導入したDT-DSDTF導体の構造と物性2014

    • Author(s)
      古田圭介,河野秀平,白旗崇,御崎洋二
    • Organizer
      2014年日本化学会第94春季年会
    • Place of Presentation
      名古屋大学東山キャンパス(名古屋)
    • Year and Date
      2014-03-27
  • [Presentation] ペンタセンキノイド部位を有する新規融合型TTFの合成と性質2013

    • Author(s)
      尾木大祐,白旗崇,御崎洋二
    • Organizer
      第7回有機π電子系シンポジウム
    • Place of Presentation
      高崎ビューホテル(高崎)
    • Year and Date
      2013-12-13
  • [Presentation] DA型電荷移動錯体による新規純有機超伝導体の開拓2013

    • Author(s)
      白旗崇,樋原康浩,古田圭介,川本正,森健彦,賣市幹大,御崎洋二
    • Organizer
      2013年日本化学会中国四国支部大会
    • Place of Presentation
      広島大学東広島キャンパス(東広島)
    • Year and Date
      2013-11-17
  • [Presentation] キサンテン部を有するテトラチアペンタレン系ドナーの合成と性質2013

    • Author(s)
      加藤南,白旗崇,御崎洋二
    • Organizer
      第22回有機結晶シンポジウム
    • Place of Presentation
      北海道大学札幌キャンパス(札幌)
    • Year and Date
      2013-10-30
  • [Presentation] 一段階多電子移動を示す1,3-ジチオール[5]ラジアレン誘導体の合成と性質2013

    • Author(s)
      上田将史,白旗崇,御崎洋二
    • Organizer
      第24回基礎有機化学討論会
    • Place of Presentation
      学習院大学目白キャンパス(東京)
    • Year and Date
      2013-09-06
  • [Presentation] Charge-discharge Properties of Organic Rechargeable Batteries Using Ten-Electron Redox System2013

    • Author(s)
      Minami Kato, Ken-ichiro Senoo, Yohji Misaki
    • Organizer
      15th International Symposium on Novel Aromatic Compounds (ISNA-15)
    • Place of Presentation
      Taipei (Taiwan)
    • Year and Date
      2013-07-30
  • [Presentation] 純有機超伝導体(EtDTET)(TCNQ)の構造と物性2013

    • Author(s)
      白旗崇,樋原康浩,古田圭介,川本正,森健彦,御崎洋二
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学びわこ・くさつキャンパス(草津)
    • Year and Date
      2013-03-22
  • [Presentation] フラン環が挿入された1,3-ジチオール[n]デンドラレン類の合成と性質2012

    • Author(s)
      渡部友紀,白旗崇,御崎洋二
    • Organizer
      第39回有機典型元素化学討論会
    • Place of Presentation
      いわて県民情報交流センター(盛岡)
    • Year and Date
      2012-12-07
  • [Presentation] New Donor-Acceptor Type Organic Superconductor (EtDTET)(TCNQ)2012

    • Author(s)
      Takashi Shirahata, Yasuhiro Hibara, Keisuke Furuta, Tadashi Kawamoto, Takehiko Mori, Yohji Misaki
    • Organizer
      International Symposium Material Science Opened by Molecular Degree of Freedom
    • Place of Presentation
      Miyazaki (Japan)
    • Year and Date
      2012-12-02
  • [Presentation] Synthesis and Properties of Dimeric 1,3-dithiole[5]radialenes2012

    • Author(s)
      Masafumi Ueda, Yohji Misaki
    • Organizer
      The Twelfth International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      Kyoto (Japan)
    • Year and Date
      2012-11-15
  • [Presentation] Synthesis and Properties of Origomeric TTP Donors2012

    • Author(s)
      Haruka Kimura, Yohji Misaki
    • Organizer
      The Twelfth International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-12)
    • Place of Presentation
      Kyoto (Japan)
    • Year and Date
      2012-11-14
  • [Presentation] BDT-TTPから成る様々なオリゴマーの合成と性質2012

    • Author(s)
      木村晴佳,白旗崇,御崎洋二
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都テルサ(京都)
    • Year and Date
      2012-09-21
  • [Presentation] シクロヘキセン環を挿入した融合型TTFオリゴマーの合成と性質2012

    • Author(s)
      加藤南,妹尾健一郎,御崎洋二
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都テルサ(京都)
    • Year and Date
      2012-09-19
  • [Presentation] TTF部位が融合した1,3-ジチオール[5]ラジアレンの合成と性質2012

    • Author(s)
      上田将史,御崎洋二
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都テルサ(京都)
    • Year and Date
      2012-09-19
  • [Presentation] フランをスペーサーとした1,3-ジチオール[4]デンドラレンの酸化還元挙動2012

    • Author(s)
      渡邊美穂,御崎洋二
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都テルサ(京都)
    • Year and Date
      2012-09-19
  • [Presentation] アントラキノイドをスペーサーとする新規融合型TTFオリゴマーの合成と性質2012

    • Author(s)
      尾木大祐,白旗崇,御崎洋二
    • Organizer
      第23回基礎有機化学討論会
    • Place of Presentation
      京都テルサ(京都)
    • Year and Date
      2012-09-19
  • [Presentation] セレン原子を有するメトキシ基置換TTP導体の合成、構造と物性2012

    • Author(s)
      白旗崇,村上直弥,土岐慎也,伊藤鉄也,御崎洋二
    • Organizer
      第6回分子科学討論会
    • Place of Presentation
      東京大学本郷キャンパス(東京)
    • Year and Date
      2012-09-18
  • [Presentation] フランを挿入した1,3-ジチオール[n]デンドラレン誘導体の酸化還元挙動2012

    • Author(s)
      渡邊美穂,白旗崇,御崎洋二
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応大学日吉キャンパス(横浜)
    • Year and Date
      2012-03-27
  • [Presentation] 1,3-ジチオール環を有する[5]ラジアレンオリゴマーの合成と性質2012

    • Author(s)
      上田将史,白旗崇,御崎洋二
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応大学日吉キャンパス(横浜)
    • Year and Date
      2012-03-27
  • [Presentation] アントラキノイドを挿入したTTF二量体の合成と性質2012

    • Author(s)
      加藤南,尾木大祐,白旗崇,御崎洋二
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応大学日吉キャンパス(横浜)
    • Year and Date
      2012-03-26
  • [Presentation] チオフェン環を挿入した1,3-ジチオール[4]デンドラレン類の合成と性質2011

    • Author(s)
      西脇匡崇,手塚真未,白旗崇,御崎洋二
    • Organizer
      第38回有機典型元素化学討論会
    • Place of Presentation
      石川県立音楽堂邦楽ホール(金沢)
    • Year and Date
      2011-12-08
  • [Presentation] 芳香環を挿入した1,3-ジチオール[n]デンドラレン類の合成,構造と性質2011

    • Author(s)
      御崎洋二
    • Organizer
      第5回有機π電子系シンポジウム
    • Place of Presentation
      ホテルアウィーナ大阪(大阪)
    • Year and Date
      2011-11-25
  • [Presentation] アントラキノイドで拡張されたテトラチアペンタレン系ドナーの合成と性質2011

    • Author(s)
      加藤南,藤田悠介,白旗崇,御崎洋二
    • Organizer
      第5回有機π電子系シンポジウム
    • Place of Presentation
      ホテルアウィーナ大阪(大阪)
    • Year and Date
      2011-11-25
  • [Presentation] ベンゼン環をスペーサーとした交差共役型ドナーの合成と性質2011

    • Author(s)
      萬代知子,堀内裕章,白旗崇,御崎洋二
    • Organizer
      第5回有機π電子系シンポジウム
    • Place of Presentation
      ホテルアウィーナ大阪(大阪)
    • Year and Date
      2011-11-25
  • [Presentation] 新しいTTPオリゴマーの合成と性質2011

    • Author(s)
      木村晴佳,白旗崇,御崎洋二
    • Organizer
      第22回基礎有機化学討論会
    • Place of Presentation
      つくば国際会議場(つくば)
    • Year and Date
      2011-09-22
  • [Book] "融合型TTFオリゴマーの合成と有機蓄電池活物質材料への展開"『次世代蓄電池の【最新】材料技術と性能評価』第8章第8節2013

    • Author(s)
      御崎洋二
    • Publisher
      技術情報協会
  • [Remarks] 『大学院理工学研究科の御崎洋二教授らの論文がJournal of Materials Chemistry A誌のBack cover(2巻19号/平成26年5月発行)に選出されました』

    • URL

      http://www.ehime-u.ac.jp/research/news/detail.html?new_rec=11648

  • [Remarks] 『大学院理工学研究科の御崎洋二教授らの論文がChemistry Letters誌のEditor's Choice(42巻12号/平成25年12月発行)に選出されました』

    • URL

      http://www.ehime-u.ac.jp/research/news/detail.html?new_rec=11305

  • [Remarks] 研究室ホームページ

    • URL

      http://www.misaki-lab.jp

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Published: 2015-07-16  

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