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Maximization of Intermolecular Interactions for Condensed Conjugation

Planned Research

Project AreaCondensed Conjugation Molecular Physics and Chemistry: Revisiting "Electronic Conjugation" Leading to Innovative Physical Properties of Molecular Materials
Project/Area Number 20H05865
Research Category

Grant-in-Aid for Transformative Research Areas (A)

Allocation TypeSingle-year Grants
Review Section Transformative Research Areas, Section (II)
Research InstitutionOsaka University

Principal Investigator

久保 孝史  大阪大学, 理学研究科, 教授 (60324745)

Co-Investigator(Kenkyū-buntansha) 瀧宮 和男  東北大学, 理学研究科, 教授 (40263735)
芥川 智行  東北大学, 多元物質科学研究所, 教授 (60271631)
Project Period (FY) 2020-11-19 – 2025-03-31
Project Status Granted (Fiscal Year 2022)
Budget Amount *help
¥176,670,000 (Direct Cost: ¥135,900,000、Indirect Cost: ¥40,770,000)
Fiscal Year 2022: ¥38,220,000 (Direct Cost: ¥29,400,000、Indirect Cost: ¥8,820,000)
Fiscal Year 2021: ¥32,370,000 (Direct Cost: ¥24,900,000、Indirect Cost: ¥7,470,000)
Fiscal Year 2020: ¥30,940,000 (Direct Cost: ¥23,800,000、Indirect Cost: ¥7,140,000)
Keywords高密度共役 / X-conjugation / 分子間相互作用 / 分子積層 / 熱運動抑制 / 分子集積
Outline of Research at the Start

有機化合物が集合化してできる分子性固体では,分子間に働く相互作用が弱いことから分子が緩やかに結合した状態にあり,分子間には多くの隙間が存在する。本研究課題では,不対電子間相互作用,静電相互作用,カルコゲン結合などの分子間相互作用を徹底的に活用することで,分子間空隙を極端に排除した高密度の分子集積状態を達成し,熱による分子の運動を極限まで抑制し制御することと,分子の波動関数を物質全体に広げることで,“分子”を超越した新しい電子状態“X”-conjugation を物質内に固定化することを目指す。

Outline of Annual Research Achievements

有機化合物が集合化してできる分子性固体では分子間に働く相互作用が弱いことから,分子が緩やかに結合した状態にある。そのため,室温程度の低いエネルギーであっても,電気伝導や超伝導などの巨視的物性を妨げる要因となる。また,緩やかな結合状態であるために分子間の波動関数の重なりが大きくならず,分子の個性を大きく超える物理現象を発現させるのが難しいという欠点にもつながる。このような有機物質の“常識”を覆すには,分子を著しく密集させることで常態からの脱却を図る必要がある。本研究課題では,分子間に働く相互作用を極大化することで,分子間空隙を極端に排除した高密度の分子集積状態を達成し,熱による分子の運動を限りなく抑制することと,分子の波動関数を物質全体に広げることで,分子を超越した新しい電子状態“X”-conjugationが備わる物質を生み出すことを目指している。
2021年度は,不対電子間相互作用,静電相互作用,カルコゲン結合を利用した高密度共役実現のための分子合成を行った。具体的には,ハロゲン原子を導入したフェナレニルラジカル誘導体の合成,アニオン性n型半導体材料であるNDI誘導体の分子集合体の構築,セレノメチル基を導入したピレン系半導体化合物の合成,メチルカルコゲノ基を有するベンゾジカルコゲノフェン誘導体(計9種)の合成,の成果を得た。また,合成した化合物や分子集合体の物性評価を行った。得られた研究成果は,高密度共役を実現するための重要な知見を与えるものとなった。

Current Status of Research Progress
Current Status of Research Progress

2: Research has progressed on the whole more than it was originally planned.

Reason

2021年度の成果を以下に述べる。
1)不対電子間相互作用を用いた分子間空隙の極小化・固定化(久保):π平面同士が極限まで密着・固定化された分子集積体を得るため,分子骨格周辺部にハロゲン原子を導入したフェナレニルラジカル誘導体の合成に挑んだ。既知化合物であるフェナレノンを出発物質として7段階でトリブロモフェナレノンの合成・単離に至った。今後は還元,脱水素反応により,目的のラジカルの生成を行う。また,フェナレニルラジカルを分子内に3個有するプロペラ状化合物の合成・単離に至った。この成果はラジカル二次元集積体の構築につながる重要な知見である。
2)静電相互作用を用いた分子間空隙の極小化・固定化(芥川):多彩な分子間相互作用が共存する分子集合体では,静電相互作用と多点van der Waals相互作用のバランスが,優れた電子輸送特性の実現に重要であった。結晶格子の熱的な揺らぎが小さくする最適な対カチオン鎖長が存在し,その設計指針の提出に成功した。
3)カルコゲン結合を用いた分子間空隙の極小化・固定化(瀧宮):カルコゲン原子相互作用が固体状態における分子間相互作用に与える影響を検討するため,ヘテロアセン系有機半導体やカルコゲノメチル基をもつ種々の有機半導体の開発に成功した。また,量子化学計算,分子動力学シミュレーションなど,カルコゲン原子が分子固体中で如何なる効果を持つか検討するための計算化学的な手法を検討し,種々の含カルコゲン有機半導体に適用できる準備を整えることができた。さらに,単結晶トランジスタによる低温での評価が可能なセットアップを構築し,移動度の温度依存性評価を行えるようになるなど,今後の研究のための新たな手法を確立できた。

Strategy for Future Research Activity

分子間空隙を極小化し固定化するには,分子軌道の広がりや結晶中における分子同士の相対配置などが重要であることから,かなり緻密な分子設計が要求される。これまでの研究で,強い分子間相互作用に関する知見はある程度得られているものの,著しく接近した距離でπ平面同士を固定化するには不十分であることから,新たな分子設計指針に資する知見を得る必要がある。そこで,全研究期間の前半においては,強い相互作用を生み出す基本分子骨格や,置換基の種類・位置・数などを多角的に検討し,有望な分子をいくつか選出することを目標とする。
2022度は前年度に引き続き,全体計画の一部を継続的に実施する。
1)不対電子間相互作用を用いた分子間空隙の極小化・固定化(久保):フェナレニルラジカルにハロゲン原子を導入した化合物の合成を引き続き行う。また,不対電子の数を増やすことでπ平面同士が極限まで密着・固定化された分子集積体を得るため,マルチラジカル性を有する新規分子の合成を行う。
2)静電相互作用を用いた分子間空隙の極小化・固定化(芥川):アニオン性n型有機半導体材料であるNDI骨格のさらなる分子設計を試みる。高い電子移動度を示す高密度共役を実現するために,アニオン部位の構造自由度を増加させたエチルスルフォネート置換誘導体における検討を進める。
3)カルコゲン結合を用いた分子間空隙の極小化・固定化(瀧宮):今年度確立したメチルセレノ基の効率的導入法,縮合多環芳香族の選択的置換基導入法などを用い,種々の含カルコゲン有機半導体を合成するとともに,計算化学を用いた解析を実施し,高密度共役を実現しうる分子設計法を導出すべく,分子構造ー結晶構造ー電気的特性の相関を明らかにしつつ研究を進める。また,分子間相互作用の評価を出発点とする結晶構造予測についても検討を行う。

Report

(2 results)
  • 2021 Annual Research Report
  • 2020 Annual Research Report

Research Products

(81 results)

All 2022 2021 2020 Other

All Int'l Joint Research (3 results) Journal Article (52 results) (of which Int'l Joint Research: 8 results,  Peer Reviewed: 51 results,  Open Access: 14 results) Presentation (22 results) (of which Int'l Joint Research: 4 results,  Invited: 12 results) Remarks (4 results)

  • [Int'l Joint Research] Aalto University School of Science(フィンランド)

    • Related Report
      2020 Annual Research Report
  • [Int'l Joint Research] University of Pisa(イタリア)

    • Related Report
      2020 Annual Research Report
  • [Int'l Joint Research] Tampere University(フィンランド)

    • Related Report
      2020 Annual Research Report
  • [Journal Article] Mechanism and Kinetics of Fluorescence Quenching of Fluorene-Endcapped Butatriene: A Microspectroscopic Study of the Discrete State Constructed in Microcrystals2022

    • Author(s)
      Hirao Yasukazu、Ihara Keiji、Ishibashi Yukihide、Tiu Elisha Gabrielle、Asahi Tsuyoshi、Kubo Takashi
    • Journal Title

      The Journal of Physical Chemistry C

      Volume: 126 Pages: 1196-1203

    • DOI

      10.1021/acs.jpcc.1c09163

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 1,2,3‐Tri(9‐anthryl)benzene: Photophysical Properties and Solid‐State Intermolecular Interactions of Radially Arranged, Congested Aromatic π‐Planes**2022

    • Author(s)
      Nishiuchi Tomohiko、Sotome Hikaru、Shimizu Kazuto、Miyasaka Hiroshi、Kubo Takashi
    • Journal Title

      Chem. Eur. J.

      Volume: 28

    • DOI

      10.1002/chem.202104245

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A strong hydride donating, acid stable and reusable 1,4-dihydropyridine for selective aldimine and aldehyde reductions2022

    • Author(s)
      Hirao Yasukazu、Eto Hajime、Teraoka Mitsuru、Kubo Takashi
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 20 Pages: 1671-1679

    • DOI

      10.1039/d1ob02358f

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis, properties and chemical modification of a persistent triisopropylsilylethynyl substituted tri(9-anthryl)methyl radical2022

    • Author(s)
      Nishiuchi Tomohiko、Ishii Daisuke、Aibara Seito、Sato Hiroyasu、Kubo Takashi
    • Journal Title

      Chemical Communications

      Volume: 58 Pages: 3306-3309

    • DOI

      10.1039/d2cc00548d

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Molecular and Spin Structures of a Through‐Space Conjugated Triradical System2022

    • Author(s)
      Kodama Takuya、Aoba Mitsuya、Hirao Yasukazu、Rivero Samara Medina、Casado Juan、Kubo Takashi
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 61

    • DOI

      10.1002/anie.202200688

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Heterospin frustration in a metal-fullerene-bonded semiconductive antiferromagnet2022

    • Author(s)
      Shen Yongbing、Cui Mengxing、Takaishi Shinya、Kawasoko Hideyuki、Sugimoto Kunihisa、Tsumuraya Takao、Otsuka Akihiro、Kwon Eunsang、Yoshida Takefumi、Hoshino Norihisa、Kawachi Kazuhiko、Kasama Yasuhiko、Akutagawa Tomoyuki、Fukumura Tomoteru、Yamashita Masahiro
    • Journal Title

      Nature Commun.

      Volume: 13 Pages: 495-495

    • DOI

      10.1038/s41467-022-28134-w

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Insight into the Gd–Pt Bond: Slow Magnetic Relaxation of a Heterometallic Gd–Pt Complex2022

    • Author(s)
      Yoshida Takefumi、Shabana Ahmed、Zhang Haitao、Izuogu David Chukwuma、Sato Tetsu、Fuku Kentaro、Abe Hitoshi、Horii Yoji、Cosquer Goulven、Hoshino Norihisa、Akutagawa Tomoyuki、Thom Alex J. W.、Takaishi Shinya、Yamashita Masahiro
    • Journal Title

      Bull. Chem. Soc. Jpn.

      Volume: 95 Issue: 3 Pages: 513-521

    • DOI

      10.1246/bcsj.20210429

    • ISSN
      0009-2673, 1348-0634
    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Chalcogen Bond versus Halogen Bond: Changing Contributions in Determining the Crystal Packing of Dihalobenzochalcogenadiazoles2022

    • Author(s)
      Ishigaki Yusuke、Shimomura Kai、Asai Kota、Shimajiri Takuya、Akutagawa Tomoyuki、Fukushima Takanori、Suzuki Takanori
    • Journal Title

      Bull. Chem. Soc. Jpn.

      Volume: 95 Issue: 3 Pages: 522-531

    • DOI

      10.1246/bcsj.20220008

    • ISSN
      0009-2673, 1348-0634
    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Simple Molecular Ferroelectrics: N,N′-Dialkylterephthalamide Derivatives in the Solid Phase2022

    • Author(s)
      Moeko Kawana, Ryohei Mizoue Ryohei, Takashi Takeda, Norihisa Hoshino, Tomoyuki Akutagawa
    • Journal Title

      Journal of Materials Chemistry C

      Volume: 10 Pages: 4208-4217

    • DOI

      10.1039/d1tc05001j

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ferroelectrics Coupled with Unidirectional Rotation in Liquid Crystals2022

    • Author(s)
      Jianyun Wu, Takashi Takeda, Norihisa Hoshino, Tomoyuki Akutagawa
    • Journal Title

      The Journal of Physical Chemistry C

      Volume: 126 Pages: 3864-3871

    • DOI

      10.1021/acs.jpcc.1c10313

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Solid‐State Fluorescence of Excited‐State Cation-Anion Intermolecular Proton Transfer in 2‐(2‐Hydroxypyridyl)benzothiazole2022

    • Author(s)
      Takahashi Keigo、Sambe Kohei、Kasahara Yotaro、Takeda Takashi、Hoshino Norihisa、Sakai Ken‐ichi、Akutagawa Tomoyuki
    • Journal Title

      Advanced Optical Materials

      Volume: 2200134 Pages: 2200134-2200134

    • DOI

      10.1002/adom.202200134

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Thermal Conductivities and Figures of Merit of Tetracyanoquinodimethane-Based Thermoelectric Materials Consisting of Cations Exhibiting Order-Disorder Transitions2022

    • Author(s)
      Hoshino Norihisa、Akutagawa Tomoyuki
    • Journal Title

      Crystal Growth & Design

      Volume: ASAP

    • DOI

      10.1021/acs.cgd.2c00161

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Dielectric response of 1,1-difluorosumanene caused by an in-plane motion2022

    • Author(s)
      Li Minghong、Wu JianYun、Sambe Kohei、Yakiyama Yumi、Akutagawa Tomoyuki、Kajitani Takashi、Fukushima Takanori、Matsuda Kazunari、Sakurai Hidehiro
    • Journal Title

      Materials Chemistry Frontiers

      Volume: ASAP

    • DOI

      10.1039/d2qm00134a

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Packing structures of (trialkylsilyl)ethynyl-substituted dinaphtho[2,3-b:2′,3′-f]thieno[3,2-b]thiophenes (DNTTs): effects of substituents on crystal structures and transport properties2022

    • Author(s)
      Takimiya Kazuo、Usui Sayaka、Sato Aoi、Kanazawa Kiseki、Kawabata Kohsuke
    • Journal Title

      Journal of Materials Chemistry C

      Volume: 10 Pages: 2775-2782

    • DOI

      10.1039/d1tc04312a

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantiopure 2-(2-ethylhexyl)dinaphtho[2,3-b:2′,3′-f]thieno[3,2-b]thiophenes: synthesis, single-crystal structure and a surprising lack of influence of stereoisomerism on thin-film structure and electronic properties2022

    • Author(s)
      Sumitomo Kenta、Sudo Yuta、Kanazawa Kiseki、Kawabata Kohsuke、Takimiya Kazuo
    • Journal Title

      Materials Horizons

      Volume: 9 Pages: 444-451

    • DOI

      10.1039/d1mh01119g

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Bandlike versus Temperature-Independent Carrier Transport in Isomeric Diphenyldinaphtho[2,3-b:2′,3′-f]thieno[3,2-b]thiophenes2022

    • Author(s)
      Takimiya Kazuo、Bulgarevich Kirill、Horiuchi Shingo、Sato Aoi、Kawabata Kohsuke
    • Journal Title

      ACS Materials Letters

      Volume: 4 Pages: 675-681

    • DOI

      10.1021/acsmaterialslett.2c00084

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Biradicaloid Behavior of a Twisted Double Bond2021

    • Author(s)
      Hamamoto Yosuke, Hirao Yasukazu, Kubo Takashi
    • Journal Title

      The Journal of Physical Chemistry Letters

      Volume: 12 Pages: 4729-4734

    • DOI

      10.1021/acs.jpclett.1c00664

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Spin-Spin Interactions in One‐Dimensional Assemblies of a Cumulene‐Based Singlet Biradical2021

    • Author(s)
      Hirao Yasukazu、Daifuku Yoko、Ihara Keiji、Kubo Takashi
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 60 Pages: 21319-21326

    • DOI

      10.1002/anie.202105740

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Long Carbon-Carbon Bonding beyond 2Å in Tris(9-fluorenylidene)methane2021

    • Author(s)
      Kubo Takashi、Suga Yuki、Hashizume Daisuke、Suzuki Hiroki、Miyamoto Tatsuya、Okamoto Hiroshi、Kishi Ryohei、Nakano Masayoshi
    • Journal Title

      Journal of the American Chemical Society

      Volume: 143 Pages: 14360-14366

    • DOI

      10.1021/jacs.1c07431

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Syntheses and Properties of Open-Shell π-Conjugated Molecules2021

    • Author(s)
      Kubo Takashi
    • Journal Title

      Bull. Chem. Soc. Jpn.

      Volume: 94 Issue: 9 Pages: 2235-2244

    • DOI

      10.1246/bcsj.20210224

    • NAID

      130008103595

    • ISSN
      0009-2673, 1348-0634
    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Optical nature of non‐substituted triphenylmethyl cation: Crystalline state emission, thermochromism, and phosphorescence2021

    • Author(s)
      Nishiuchi Tomohiko、Sotome Hikaru、Fukuuchi Risa、Kamada Kenji、Miyasaka Hiroshi、Kubo Takashi
    • Journal Title

      Aggregate

      Volume: 2

    • DOI

      10.1002/agt2.126

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Ferroelectric columnar assemblies from the bowl-to-bowl inversion of aromatic cores2021

    • Author(s)
      Furukawa Shunsuke、Wu Jianyun、Koyama Masaya、Hayashi Keisuke、Hoshino Norihisa、Takeda Takashi、Suzuki Yasutaka、Kawamata Jun、Saito Masaichi、Akutagawa Tomoyuki
    • Journal Title

      Nature Communications

      Volume: 12 Pages: 768-768

    • DOI

      10.1038/s41467-021-21019-4

    • Related Report
      2021 Annual Research Report 2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Dynamic structural reconstruction of (guanidinium+)2(benzene-1,4-disulfonate2) host crystal by guest adsorption2021

    • Author(s)
      Abe Haruka、Kobayashi Takahiro、Hoshino Norihisa、Takeda Takashi、Suzuki Yasutaka、Kawamata Jun、Akutagawa Tomoyuki
    • Journal Title

      CrystEngComm

      Volume: 23 Pages: 1149-1157

    • DOI

      10.1039/d0ce01616k

    • Related Report
      2021 Annual Research Report 2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chemical Design and Physical Properties of Dynamic Molecular Assemblies2021

    • Author(s)
      Akutagawa Tomoyuki
    • Journal Title

      Bull. Chem. Soc. Jpn.

      Volume: 94 Issue: 4 Pages: 1400-1420

    • DOI

      10.1246/bcsj.20200384

    • NAID

      130008037401

    • ISSN
      0009-2673, 1348-0634
    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chalcogen Bond versus Weak Hydrogen Bond: Changing Contributions in Determining the Crystal Packing of [1,2,5]-Chalcogenadiazole-Fused Tetracyanonaphthoquinodimethanes2021

    • Author(s)
      Ishigaki Yusuke、Asai Kota、Shimajiri Takuya、Akutagawa Tomoyuki、Fukushima Takanori、Suzuki Takanori
    • Journal Title

      Organic Materials

      Volume: 03 Pages: 090-096

    • DOI

      10.1055/s-0041-1725046

    • Related Report
      2021 Annual Research Report 2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Substituent Effect on Molecular Motions of m-Halogenated Anilinium/Dibenzo[18]crown-6 Supramolecular Cations in [Ni(dmit)2]- Crystals2021

    • Author(s)
      Kubo Kazuya、Takahashi Kiyonori、Nakagawa Shota、Sakai Ken-ichi、Noro Shin-ichiro、Akutagawa Tomoyuki、Nakamura Takayoshi
    • Journal Title

      Crystal Growth Design

      Volume: 21 Pages: 2340-2347

    • DOI

      10.1021/acs.cgd.0c01739

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Fluorescent Molecular Glass Based on Hexadehydrotribenzo[12]annulene2021

    • Author(s)
      Yotaro Kasahara, Ichiro Hisaki, Tomoyuki Akutagawa, Takashi Takeda
    • Journal Title

      Chemical Communications

      Volume: 57 Pages: 5374-5377

    • DOI

      10.1039/d1cc01356d

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Effective Na+ Binding Ability and Molecular Assembly of an Alkylamide-Substituted Penta(ethylene)glycol Derivative2021

    • Author(s)
      Shinya Seto, Takashi Takeda, Norihisa Hoshino, Tomoyuki Akutagawa
    • Journal Title

      The Journal of Physical Chemistry B

      Volume: 125 Pages: 6349-6358

    • DOI

      10.1021/acs.jpcb.1c03188

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Photoinduced Generation of the π-Conjugated Zwitterionic State in the ESIPT Fluorophore of 2,4-Bisimidazolylphenol2021

    • Author(s)
      Sakai Ken-ichi、Miyamoto Naoya、Ogawa Mayu、Kawano Keiichi、Akutagawa Tomoyuki
    • Journal Title

      The Journal of Physical Chemistry A

      Volume: 125 Pages: 4784-4792

    • DOI

      10.1021/acs.jpca.1c02353

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Color-Tunable Arylaminoanthraquinone Dyes through Hydrogen-Bond-Assisted Charge Transfer Interaction2021

    • Author(s)
      Takashi Takeda, Yotaro Kasahara, Tomoyuki Akutagawa
    • Journal Title

      RSC Advances

      Volume: 11 Pages: 24217-24231

    • DOI

      10.1039/d1ra03985g

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Further investigations of the crystal-to-crystal phase transition of a [2]pseudorotaxane composed of ferrocene-terminated dialkylammonium and dibenzo[24]crown-8-ether2021

    • Author(s)
      Suzaki Yuji、Fukuchi Yugo、Tadami Hiroko、Koizumi Take-aki、Osakada Kohtaro、Ide Tomohito、Horie Masaki、Hoshino Norihisa、Akutagawa Tomoyuki
    • Journal Title

      CrystEngCommun

      Volume: 23 Pages: 5942-5952

    • DOI

      10.1039/d1ce00457c

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Ferroelectricity of Hydrogen-Bonded Azobenzene Derivatives2021

    • Author(s)
      Jianyun Wu, Qingyang Zhu, Takashi Takeda, Norihisa Hoshino, Tomoyuki Akutagawa
    • Journal Title

      ACS Applied Electronic Materials

      Volume: 3 Pages: 3521-3529

    • DOI

      10.1021/acsaelm.1c00462

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Dynamics of Proton, Ion, Molecule, and Crystal Lattice in Functional Molecular Assemblies2021

    • Author(s)
      Tomoyuki Akutagawa, Takashi Takeda, Norihisa Hoshino
    • Journal Title

      Chemical Communications

      Volume: 57 Pages: 8378-8401

    • DOI

      10.1039/d1cc01586a

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Dipole fluctuation and structural phase transition in hydrogen-bonding molecular assemblies of mononuclear CuII complexes with polar fluorobenzoate ligands2021

    • Author(s)
      Takahashi Kiyonori、Miyazaki Yuji、Noro Shin-ichiro、Nakano Motohiro、Nakamura Takayoshi、Akutagawa Tomoyuki
    • Journal Title

      Dalton Transactions

      Volume: 50 Pages: 13680-13685

    • DOI

      10.1039/d1dt02118d

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Electrostatic versus van der Waals Interactions in an n-Type Semiconducting Dianionic Naphthalenediimide Derivative with CnH2n+1NH3+ (n = 1-16)2021

    • Author(s)
      Ayumi Kawasaki, Takashi Takeda, Norihisa Hoshino, Wakana Matsuda, Shu Seki, Tomoyuki Akutagawa
    • Journal Title

      The Journal of Physical Chemistry C

      Volume: 125 Pages: 21595-21606

    • DOI

      10.1021/acs.jpcc.1c05176

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Crystal Structures and Physical Properties of (M+)(Crown Ethers)x(TCNQ)y Salts with M+ = Li+, Na+, K+, Rb+, and Cs+2021

    • Author(s)
      Kohei Sambe, Norihisa Hoshino, Takashi Takeda, Takayoshi Nakamura, Tomoyuki Akutagawa
    • Journal Title

      Crystal Growth & Design

      Volume: 21 Pages: 5928-5942

    • DOI

      10.1021/acs.cgd.1c00812

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Ionic Conductivities Induced by the Partial Solvent Molecule Removal from Diruthenium(II,III) Adamantanecarboxylate Salts2021

    • Author(s)
      Hoshino Norihisa、Akutagawa Tomoyuki
    • Journal Title

      Crystal Growth & Design

      Volume: 21 Pages: 4640-4646

    • DOI

      10.1021/acs.cgd.1c00496

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Donor-Type Nickel-Dithiolene Complexes Fused with Bulky Cycloalkane Substituents and Their Application in Molecular Conductors2021

    • Author(s)
      Kubo Kazuya、Sadahiro Mamoru、Arata Sonomi、Hoshino Norihisa、Kadoya Tomofumi、Akutagawa Tomoyuki、Kato Reizo、Yamada Jun-ichi
    • Journal Title

      Crystals

      Volume: 11 Pages: 1154-1154

    • DOI

      10.3390/cryst11101154

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ion Polarisation-Assisted Hydrogen-Bonded Ferroelectrics in Liquid Crystalline Domains2021

    • Author(s)
      Guohao Yuan, Yuko Kimura Yuko, Takayuki Kobayashi, Takashi Takeda, Norihisa Hoshino, Tomoyuki Akutagawa
    • Journal Title

      Chemical Science

      Volume: 12 Pages: 13520-13529

    • DOI

      10.1039/d1sc03301h

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 私の自慢「ダイナミックな分子集合体の研究 脇道に寄り道することを楽しむ」2021

    • Author(s)
      芥川智行
    • Journal Title

      化学と工業

      Volume: 74 Pages: 674-676

    • Related Report
      2021 Annual Research Report
  • [Journal Article] Crystal Structures of β-Methylchalcogenated Tetrathienoacenes: From One-Dimensional π-Stacking to Sandwich Pitched π-Stacking Structure2021

    • Author(s)
      Takimiya Kazuo、Kanazawa Kiseki、Kawabata Kohsuke
    • Journal Title

      Crystal Growth & Design

      Volume: 21 Pages: 4055-4063

    • DOI

      10.1021/acs.cgd.1c00347

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] “Manipulation” of Crystal Structure by Methylthiolation Enabling Ultrahigh Mobility in a Pyrene‐Based Molecular Semiconductor2021

    • Author(s)
      Takimiya Kazuo、Bulgarevich Kirill、Abbas Mamatimin、Horiuchi Shingo、Ogaki Takuya、Kawabata Kohsuke、Ablat Abduleziz
    • Journal Title

      Advanced Materials

      Volume: 33 Pages: 2102914-2102914

    • DOI

      10.1002/adma.202102914

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Highly Electron‐Donating Bipyranylidene Derivatives: Potential n‐Type Dopants for Organic Thermoelectrics2021

    • Author(s)
      Matsuo Takaya、Kawabata Kohsuke、Takimiya Kazuo
    • Journal Title

      Advanced Energy and Sustainability Research

      Volume: 2 Pages: 2100084-2100084

    • DOI

      10.1002/aesr.202100084

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis of Anthracene‐Based Cyclic π‐Clusters and Elucidation of their Properties Originating from Congested Aromatic Planes2021

    • Author(s)
      Tomohiko Nishiuchi, Kazuki Kisaka, Takashi Kubo
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 60 Pages: 5400-5406

    • DOI

      10.1002/anie.202013349

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Quantitative analysis of the formation mechanism of tightly bound rubber by using carbon-coated alumina nanoparticles as a model filler2021

    • Author(s)
      Hoshikawa Yasuto, Kawaguchi Rei, Nomura Keita, Akahane Hidenobu, Ishii Takafumi, Ando Mariko, Hoshino Norihisa, Akutagawa Tomoyuki, Yamada Hiroshi, Kyotani Takashi
    • Journal Title

      Carbon

      Volume: 173 Pages: 870-879

    • DOI

      10.1016/j.carbon.2020.11.074

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Low-Temperature Removal of Dissociated Bromine by Silicon Atoms for an On-Surface Ullmann Reaction2020

    • Author(s)
      Sun Kewei、Nishiuchi Tomohiko、Sahara Keisuke、Kubo Takashi、Foster Adam S.、Kawai Shigeki
    • Journal Title

      The Journal of Physical Chemistry C

      Volume: 124 Pages: 19675-19680

    • DOI

      10.1021/acs.jpcc.0c06188

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Chiral Tetraarylmethane Derivative with Metal‐Coordinating Ability2020

    • Author(s)
      Matsumoto Kouzou、Miki Kaori、Tanaka Rina、Matsuda Takahiro、Nehira Tatsuo、Hirao Yasukazu、Kurata Hiroyuki、Pescitelli Gennaro、Kubo Takashi
    • Journal Title

      Asian Journal of Organic Chemistry

      Volume: 9 Pages: 652-659

    • DOI

      10.1002/ajoc.201900760

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Switching of Electron and Ion Conductions by Reversible H2O Sorption in n-Type Organic Semiconductors2020

    • Author(s)
      Abe Haruka, Kawasaki Ayumi, Takeda Takashi, Hoshino Norihisa, Matsuda Wakana, Seki Shu, Akutagawa Tomoyuki
    • Journal Title

      ACS Applied Materials & Interfaces

      Volume: 12 Pages: 37391-37399

    • DOI

      10.1021/acsami.0c09501

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Interfacial Nanostructuring of Poly(vinylidene fluoride) Homopolymer with Predominant Ferroelectric Phases2020

    • Author(s)
      Fu Chang, Zhu Huie, Hoshino Norihisa, Akutagawa Tomoyuki, Mitsuishi Masaya
    • Journal Title

      Langmuir

      Volume: 36 Pages: 14083-14091

    • DOI

      10.1021/acs.langmuir.0c02667

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Contrasting temperature dependences of isostructural one-dimensional ferroelectric crystals NH4HSO4 and RbHSO4 in terms of thermal conductivities2020

    • Author(s)
      Hoshino Norihisa, Akutagawa Tomoyuki
    • Journal Title

      J. Chem. Phys.

      Volume: 153 Pages: 194503-194503

    • DOI

      10.1063/5.0028153

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Room-Temperature Pentacene Fluids: Oligoethylene Glycol Substituent-Controlled Morphologies and Singlet Fission2020

    • Author(s)
      Yoshino Keisuke、Sakai Hayato、Shoji Yoshiaki、Kajitani Takashi、Anetai Hayato、Akutagawa Tomoyuki、Fukushima Takanori、Tkachenko Nikolai V.、Hasobe Taku
    • Journal Title

      J. Phys. Chem. B.

      Volume: 124 Pages: 11910-11918

    • DOI

      10.1021/acs.jpcb.0c09754

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Crystal Lattice Design of H2O-Tolerant n-Type Semiconducting Dianionic Naphthalenediimide Derivatives2020

    • Author(s)
      Abe Haruka, Kawasaki Ayumi, Takeda Takashi, Hoshino Norihisa, Matsuda Wakana, Seki Shu, Akutagawa Tomoyuki
    • Journal Title

      Journal of the American Chemical Society

      Volume: 143 Pages: 1046-1060

    • DOI

      10.1021/jacs.0c11545

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Presentation] 有機材料が形成する多様な分子集合体構造と機能発現2022

    • Author(s)
      芥川 智行
    • Organizer
      2021年度アライアンス合同分科会
    • Related Report
      2021 Annual Research Report
    • Invited
  • [Presentation] フェナレニルラジカルの高密度共役化2021

    • Author(s)
      久保 孝史
    • Organizer
      第11回化学フェスタ(2021年度)
    • Related Report
      2021 Annual Research Report
    • Invited
  • [Presentation] 高密度共役を生み出す物質の開発2021

    • Author(s)
      久保 孝史
    • Organizer
      第14回 物性科学領域横断研究会
    • Related Report
      2021 Annual Research Report
    • Invited
  • [Presentation] 結合と非結合の狭間で:一重項ビラジカル種に関する最近の研究2021

    • Author(s)
      久保 孝史
    • Organizer
      2021年度有機合成化学北陸セミナー
    • Related Report
      2021 Annual Research Report
    • Invited
  • [Presentation] Duality of Reactivity Characterized by Closed-Shell and Open-Shell Electronic Structure2021

    • Author(s)
      Takashi Kubo
    • Organizer
      PACIFICHEM2021
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 静電相互作用を用いたn型有機半導体材料の高密度共役制御2021

    • Author(s)
      芥川 智行
    • Organizer
      第11回化学フェスタ(2021年度)
    • Related Report
      2021 Annual Research Report
    • Invited
  • [Presentation] Molecular sensing by ESIPT fluorescent chromism2021

    • Author(s)
      Tomoyuki Akutagawa
    • Organizer
      International Conference on Aggregate Science-20th Anniversary of AIE Research
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 有機半導体の「制御」と熱電・太陽電池応用 ~有機半導体の設計と合成~2021

    • Author(s)
      瀧宮 和男
    • Organizer
      日本学術振興会 R025 先進薄膜表面機能創成委員会 第5回研究会
    • Related Report
      2021 Annual Research Report
    • Invited
  • [Presentation] 結晶構造制御によるピレン系有機半導体の高移動度化2021

    • Author(s)
      瀧宮 和男
    • Organizer
      第31回基礎有機化学討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] "Manipulation” of crystal structures of pyrene-based organic semiconductors enabling ultrahigh mobility2021

    • Author(s)
      Kazuo Takimiya
    • Organizer
      The international Conference on Flexible and Printed Electronics
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 分子性半導体の結晶構造制御 ~高密度共役を目指して~2021

    • Author(s)
      瀧宮 和男
    • Organizer
      第11回化学フェスタ(2021年度)
    • Related Report
      2021 Annual Research Report
  • [Presentation] Manipulation of crystal structures of pyrene-based organic semiconductors enabling ultrahigh mobility2021

    • Author(s)
      Kazuo Takimiya
    • Organizer
      IDW ’21
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 長い炭素間結合を二つ有する化合物の合成検討2021

    • Author(s)
      藤井匠平、久保孝史
    • Organizer
      第14回有機π電子系シンポジウム
    • Related Report
      2020 Annual Research Report
  • [Presentation] アントラセン骨格を基盤としたラダー状πクラスター分子の合成と物性2021

    • Author(s)
      赤澤勇樹、西内智彦、久保孝史
    • Organizer
      日本化学会 第101回春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] トリ-tert-ブチルトリインデニルの合成とその性質2021

    • Author(s)
      宮川奈那子、西内智彦、久保孝史
    • Organizer
      日本化学会 第101回春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] フルオレニル骨格を用いた長い炭素間結合を二つ有する化合物の合成検討2021

    • Author(s)
      藤井匠平、久保孝史
    • Organizer
      日本化学会 第101回春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 水素結合性C8-BTBT-X (X = PO3H2およびCOOH)の分子集合体構造と物性制御2021

    • Author(s)
      三部 宏平、武田 貴志、星野 哲久、松田 若菜、関 修平、芥川 智行
    • Organizer
      日本化学会 第101回春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] β位にメチルカルコゲノ基を有するテトラチエノアセン誘導体の結晶構造と分子間相互作用2021

    • Author(s)
      金澤輝石、川畑公輔、瀧宮和男
    • Organizer
      日本化学会 第101回春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Syntheses and Properties of Open-Shell π-Conjugated Molecules2021

    • Author(s)
      久保孝史
    • Organizer
      日本化学会 第101回春季年会
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Presentation] 水の吸脱着に伴う電子移動度スイッチングを示すナフタレンジイミド誘導体2020

    • Author(s)
      阿部春花、川崎渉、武田貴志、星野哲久、松田若菜、関修平、芥川智行
    • Organizer
      第14回分子科学討論会2020
    • Related Report
      2020 Annual Research Report
  • [Presentation] M+ (クラウンエーテル)-TCNQ錯体の構造・物性に対するアルカリ金属とクラウンエーテルのサイズ効果2020

    • Author(s)
      三部宏平、星野哲久、武田貴志、中村貴義、芥川智行
    • Organizer
      第14回分子科学討論会2020
    • Related Report
      2020 Annual Research Report
  • [Presentation] 分子性材料におけるダイナミクスの設計と機能発現2020

    • Author(s)
      芥川智行
    • Organizer
      第1回東北大学材料ウエビナー
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Remarks] 研究室ホームページ(久保孝史)

    • URL

      http://www.chem.sci.osaka-u.ac.jp/lab/kubo/

    • Related Report
      2021 Annual Research Report
  • [Remarks] 研究室ホームページ(芥川智行)

    • URL

      http://www2.tagen.tohoku.ac.jp/lab/akutagawa/html/Homepage2010/index-j.html

    • Related Report
      2021 Annual Research Report
  • [Remarks] 研究室ホームページ(瀧宮和男)

    • URL

      http://web.tohoku.ac.jp/ogchmii/index.html

    • Related Report
      2021 Annual Research Report
  • [Remarks] Twitter (Condensed Conjugation)

    • URL

      https://twitter.com/CConjugation

    • Related Report
      2020 Annual Research Report

URL: 

Published: 2020-11-24   Modified: 2022-12-28  

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