Maximization of Intermolecular Interactions for Condensed Conjugation

• Project Area: Condensed 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 Type: Single-year Grants
• Review Section: Transformative Research Areas, Section (II)
• Research Institution: Osaka University
• Principal Investigator: 久保 孝史 大阪大学, 大学院理学研究科, 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 2024)
• Budget Amount: ¥176,670,000 (Direct Cost: ¥135,900,000、Indirect Cost: ¥40,770,000); Fiscal Year 2024: ¥36,920,000 (Direct Cost: ¥28,400,000、Indirect Cost: ¥8,520,000); Fiscal Year 2023: ¥38,220,000 (Direct Cost: ¥29,400,000、Indirect Cost: ¥8,820,000); 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

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。

Research Products

• [Int'l Joint Research] Aalto University School of Science(フィンランド)
• [Int'l Joint Research] University of Pisa(イタリア)
• [Int'l Joint Research] Tampere University(フィンランド)
• [Journal Article] Mechanism and Kinetics of Fluorescence Quenching of Fluorene-Endcapped Butatriene: A Microspectroscopic Study of the Discrete State Constructed in Microcrystals (2022)
  • 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 Issue: 2 Pages: 1196-1203
  • DOI: 10.1021/acs.jpcc.1c09163
  • 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: Chemistry - A European Journal Volume: 28 Issue: 5 Pages: 202104245-202104245
  • DOI: 10.1002/chem.202104245
  • Peer Reviewed
• [Journal Article] A strong hydride donating, acid stable and reusable 1,4-dihydropyridine for selective aldimine and aldehyde reductions (2022)
  • Author(s): Hirao Yasukazu、Eto Hajime、Teraoka Mitsuru、Kubo Takashi
  • Journal Title: Organic & Biomolecular Chemistry Volume: 20 Issue: 8 Pages: 1671-1679
  • DOI: 10.1039/d1ob02358f
  • Peer Reviewed
• [Journal Article] Synthesis, properties and chemical modification of a persistent triisopropylsilylethynyl substituted tri(9-anthryl)methyl radical (2022)
  • Author(s): Nishiuchi Tomohiko、Ishii Daisuke、Aibara Seito、Sato Hiroyasu、Kubo Takashi
  • Journal Title: Chemical Communications Volume: 58 Issue: 20 Pages: 3306-3309
  • DOI: 10.1039/d2cc00548d
  • Peer Reviewed / Open Access
• [Journal Article] Molecular and Spin Structures of a Through‐Space Conjugated Triradical System (2022)
  • Author(s): Kodama Takuya、Aoba Mitsuya、Hirao Yasukazu、Rivero Samara Medina、Casado Juan、Kubo Takashi
  • Journal Title: Angewandte Chemie International Edition Volume: 61 Issue: 14 Pages: 202200688-202200688
  • DOI: 10.1002/anie.202200688
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Heterospin frustration in a metal-fullerene-bonded semiconductive antiferromagnet (2022)
  • 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 Communications Volume: 13 Issue: 1 Pages: 495-495
  • DOI: 10.1038/s41467-022-28134-w
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Insight into the Gd-Pt Bond: Slow Magnetic Relaxation of a Heterometallic Gd-Pt Complex (2022)
  • 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: Bulletin of the Chemical Society of Japan Volume: 95 Issue: 3 Pages: 513-521
  • DOI: 10.1246/bcsj.20210429
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Chalcogen Bond versus Halogen Bond: Changing Contributions in Determining the Crystal Packing of Dihalobenzochalcogenadiazoles (2022)
  • Author(s): Ishigaki Yusuke、Shimomura Kai、Asai Kota、Shimajiri Takuya、Akutagawa Tomoyuki、Fukushima Takanori、Suzuki Takanori
  • Journal Title: Bulletin of the Chemical Society of Japan Volume: 95 Issue: 3 Pages: 522-531
  • DOI: 10.1246/bcsj.20220008
  • Peer Reviewed / Open Access
• [Journal Article] Simple Molecular Ferroelectrics: N,N′-Dialkylterephthalamide Derivatives in the Solid Phase (2022)
  • Author(s): Moeko Kawana, Ryohei Mizoue Ryohei, Takashi Takeda, Norihisa Hoshino, Tomoyuki Akutagawa
  • Journal Title: Journal of Materials Chemistry C Volume: 10 Issue: 11 Pages: 4208-4217
  • DOI: 10.1039/d1tc05001j
  • Peer Reviewed
• [Journal Article] Ferroelectrics Coupled with Unidirectional Rotation in Liquid Crystals (2022)
  • Author(s): Jianyun Wu, Takashi Takeda, Norihisa Hoshino, Tomoyuki Akutagawa
  • Journal Title: The Journal of Physical Chemistry C Volume: 126 Issue: 8 Pages: 3864-3871
  • DOI: 10.1021/acs.jpcc.1c10313
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Solid‐State Fluorescence of Excited‐State Cation-Anion Intermolecular Proton Transfer in 2‐(2‐Hydroxypyridyl)benzothiazole (2022)
  • Author(s): Takahashi Keigo、Sambe Kohei、Kasahara Yotaro、Takeda Takashi、Hoshino Norihisa、Sakai Ken‐ichi、Akutagawa Tomoyuki
  • Journal Title: Advanced Optical Materials Volume: 2200134 Issue: 11 Pages: 2200134-2200134
  • DOI: 10.1002/adom.202200134
  • Peer Reviewed
• [Journal Article] Thermal Conductivities and Figures of Merit of Tetracyanoquinodimethane-Based Thermoelectric Materials Consisting of Cations Exhibiting Order-Disorder Transitions (2022)
  • Author(s): Hoshino Norihisa、Akutagawa Tomoyuki
  • Journal Title: Crystal Growth & Design Volume: ASAP Issue: 5 Pages: 3359-3364
  • DOI: 10.1021/acs.cgd.2c00161
  • Peer Reviewed
• [Journal Article] Dielectric response of 1,1-difluorosumanene caused by an in-plane motion (2022)
  • 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 Issue: 13 Pages: 1752-1758
  • DOI: 10.1039/d2qm00134a
  • Peer Reviewed / Int'l Joint Research
• [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 properties (2022)
  • Author(s): Takimiya Kazuo、Usui Sayaka、Sato Aoi、Kanazawa Kiseki、Kawabata Kohsuke
  • Journal Title: Journal of Materials Chemistry C Volume: 10 Issue: 7 Pages: 2775-2782
  • DOI: 10.1039/d1tc04312a
  • 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 properties (2022)
  • Author(s): Sumitomo Kenta、Sudo Yuta、Kanazawa Kiseki、Kawabata Kohsuke、Takimiya Kazuo
  • Journal Title: Materials Horizons Volume: 9 Issue: 1 Pages: 444-451
  • DOI: 10.1039/d1mh01119g
  • Peer Reviewed
• [Journal Article] Bandlike versus Temperature-Independent Carrier Transport in Isomeric Diphenyldinaphtho[2,3-b:2′,3′-f]thieno[3,2-b]thiophenes (2022)
  • Author(s): Takimiya Kazuo、Bulgarevich Kirill、Horiuchi Shingo、Sato Aoi、Kawabata Kohsuke
  • Journal Title: ACS Materials Letters Volume: 4 Issue: 4 Pages: 675-681
  • DOI: 10.1021/acsmaterialslett.2c00084
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Biradicaloid Behavior of a Twisted Double Bond (2021)
  • Author(s): Hamamoto Yosuke, Hirao Yasukazu, Kubo Takashi
  • Journal Title: The Journal of Physical Chemistry Letters Volume: 12 Issue: 19 Pages: 4729-4734
  • DOI: 10.1021/acs.jpclett.1c00664
  • Peer Reviewed
• [Journal Article] Spin-Spin Interactions in One‐Dimensional Assemblies of a Cumulene‐Based Singlet Biradical (2021)
  • Author(s): Hirao Yasukazu、Daifuku Yoko、Ihara Keiji、Kubo Takashi
  • Journal Title: Angewandte Chemie International Edition Volume: 60 Issue: 39 Pages: 21319-21326
  • DOI: 10.1002/anie.202105740
  • Peer Reviewed
• [Journal Article] Long Carbon-Carbon Bonding beyond 2Å in Tris(9-fluorenylidene)methane (2021)
  • 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 Issue: 35 Pages: 14360-14366
  • DOI: 10.1021/jacs.1c07431
  • Peer Reviewed / Open Access
• [Journal Article] Syntheses and Properties of Open-Shell π-Conjugated Molecules (2021)
  • Author(s): Kubo Takashi
  • Journal Title: Bulletin of the Chemical Society of Japan Volume: 94 Issue: 9 Pages: 2235-2244
  • DOI: 10.1246/bcsj.20210224
  • NAID: 130008103595
  • Peer Reviewed / Open Access
• [Journal Article] Optical nature of non‐substituted triphenylmethyl cation: Crystalline state emission, thermochromism, and phosphorescence (2021)
  • Author(s): Nishiuchi Tomohiko、Sotome Hikaru、Fukuuchi Risa、Kamada Kenji、Miyasaka Hiroshi、Kubo Takashi
  • Journal Title: Aggregate Volume: 2 Issue: 6 Pages: 126-126
  • DOI: 10.1002/agt2.126
  • Peer Reviewed / Open Access
• [Journal Article] Ferroelectric columnar assemblies from the bowl-to-bowl inversion of aromatic cores (2021)
  • 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 Issue: 1 Pages: 768-768
  • DOI: 10.1038/s41467-021-21019-4
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Dynamic structural reconstruction of (guanidinium+)2(benzene-1,4-disulfonate2) host crystal by guest adsorption (2021)
  • Author(s): Abe Haruka、Kobayashi Takahiro、Hoshino Norihisa、Takeda Takashi、Suzuki Yasutaka、Kawamata Jun、Akutagawa Tomoyuki
  • Journal Title: CrystEngComm Volume: 23 Issue: 5 Pages: 1149-1157
  • DOI: 10.1039/d0ce01616k
  • Peer Reviewed
• [Journal Article] Chemical Design and Physical Properties of Dynamic Molecular Assemblies (2021)
  • Author(s): Akutagawa Tomoyuki
  • Journal Title: Bulletin of the Chemical Society of Japan Volume: 94 Issue: 4 Pages: 1400-1420
  • DOI: 10.1246/bcsj.20200384
  • NAID: 130008037401
  • Peer Reviewed
• [Journal Article] Chalcogen Bond versus Weak Hydrogen Bond: Changing Contributions in Determining the Crystal Packing of [1,2,5]-Chalcogenadiazole-Fused Tetracyanonaphthoquinodimethanes (2021)
  • Author(s): Ishigaki Yusuke、Asai Kota、Shimajiri Takuya、Akutagawa Tomoyuki、Fukushima Takanori、Suzuki Takanori
  • Journal Title: Organic Materials Volume: 03 Issue: 02 Pages: 090-096
  • DOI: 10.1055/s-0041-1725046
  • 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]- Crystals (2021)
  • 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 Issue: 4 Pages: 2340-2347
  • DOI: 10.1021/acs.cgd.0c01739
  • Peer Reviewed / Open Access
• [Journal Article] Fluorescent Molecular Glass Based on Hexadehydrotribenzo[12]annulene (2021)
  • Author(s): Yotaro Kasahara, Ichiro Hisaki, Tomoyuki Akutagawa, Takashi Takeda
  • Journal Title: Chemical Communications Volume: 57 Issue: 44 Pages: 5374-5377
  • DOI: 10.1039/d1cc01356d
  • Peer Reviewed
• [Journal Article] Effective Na+ Binding Ability and Molecular Assembly of an Alkylamide-Substituted Penta(ethylene)glycol Derivative (2021)
  • Author(s): Shinya Seto, Takashi Takeda, Norihisa Hoshino, Tomoyuki Akutagawa
  • Journal Title: The Journal of Physical Chemistry B Volume: 125 Issue: 23 Pages: 6349-6358
  • DOI: 10.1021/acs.jpcb.1c03188
  • Peer Reviewed
• [Journal Article] Photoinduced Generation of the π-Conjugated Zwitterionic State in the ESIPT Fluorophore of 2,4-Bisimidazolylphenol (2021)
  • Author(s): Sakai Ken-ichi、Miyamoto Naoya、Ogawa Mayu、Kawano Keiichi、Akutagawa Tomoyuki
  • Journal Title: The Journal of Physical Chemistry A Volume: 125 Issue: 22 Pages: 4784-4792
  • DOI: 10.1021/acs.jpca.1c02353
  • Peer Reviewed
• [Journal Article] Color-Tunable Arylaminoanthraquinone Dyes through Hydrogen-Bond-Assisted Charge Transfer Interaction (2021)
  • Author(s): Takashi Takeda, Yotaro Kasahara, Tomoyuki Akutagawa
  • Journal Title: RSC Advances Volume: 11 Issue: 39 Pages: 24217-24231
  • DOI: 10.1039/d1ra03985g
  • 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-ether (2021)
  • Author(s): Suzaki Yuji、Fukuchi Yugo、Tadami Hiroko、Koizumi Take-aki、Osakada Kohtaro、Ide Tomohito、Horie Masaki、Hoshino Norihisa、Akutagawa Tomoyuki
  • Journal Title: CrystEngComm Volume: 23 Issue: 34 Pages: 5944-5952
  • DOI: 10.1039/d1ce00457c
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Ferroelectricity of Hydrogen-Bonded Azobenzene Derivatives (2021)
  • Author(s): Jianyun Wu, Qingyang Zhu, Takashi Takeda, Norihisa Hoshino, Tomoyuki Akutagawa
  • Journal Title: ACS Applied Electronic Materials Volume: 3 Issue: 8 Pages: 3521-3529
  • DOI: 10.1021/acsaelm.1c00462
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Dynamics of Proton, Ion, Molecule, and Crystal Lattice in Functional Molecular Assemblies (2021)
  • Author(s): Tomoyuki Akutagawa, Takashi Takeda, Norihisa Hoshino
  • Journal Title: Chemical Communications Volume: 57 Issue: 68 Pages: 8378-8401
  • DOI: 10.1039/d1cc01586a
  • Peer Reviewed
• [Journal Article] Dipole fluctuation and structural phase transition in hydrogen-bonding molecular assemblies of mononuclear CuII complexes with polar fluorobenzoate ligands (2021)
  • Author(s): Takahashi Kiyonori、Miyazaki Yuji、Noro Shin-ichiro、Nakano Motohiro、Nakamura Takayoshi、Akutagawa Tomoyuki
  • Journal Title: Dalton Transactions Volume: 50 Issue: 39 Pages: 13680-13685
  • DOI: 10.1039/d1dt02118d
  • 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 Issue: 39 Pages: 21595-21606
  • DOI: 10.1021/acs.jpcc.1c05176
  • 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 Issue: 10 Pages: 5928-5942
  • DOI: 10.1021/acs.cgd.1c00812
  • Peer Reviewed / Open Access
• [Journal Article] Ionic Conductivities Induced by the Partial Solvent Molecule Removal from Diruthenium(II,III) Adamantanecarboxylate Salts (2021)
  • Author(s): Hoshino Norihisa、Akutagawa Tomoyuki
  • Journal Title: Crystal Growth & Design Volume: 21 Issue: 8 Pages: 4640-4646
  • DOI: 10.1021/acs.cgd.1c00496
  • Peer Reviewed
• [Journal Article] Donor-Type Nickel-Dithiolene Complexes Fused with Bulky Cycloalkane Substituents and Their Application in Molecular Conductors (2021)
  • Author(s): Kubo Kazuya、Sadahiro Mamoru、Arata Sonomi、Hoshino Norihisa、Kadoya Tomofumi、Akutagawa Tomoyuki、Kato Reizo、Yamada Jun-ichi
  • Journal Title: Crystals Volume: 11 Issue: 10 Pages: 1154-1154
  • DOI: 10.3390/cryst11101154
  • Peer Reviewed
• [Journal Article] Ion Polarisation-Assisted Hydrogen-Bonded Ferroelectrics in Liquid Crystalline Domains (2021)
  • Author(s): Guohao Yuan, Yuko Kimura Yuko, Takayuki Kobayashi, Takashi Takeda, Norihisa Hoshino, Tomoyuki Akutagawa
  • Journal Title: Chemical Science Volume: 12 Issue: 40 Pages: 13520-13529
  • DOI: 10.1039/d1sc03301h
  • 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
• [Journal Article] Crystal Structures of β-Methylchalcogenated Tetrathienoacenes: From One-Dimensional π-Stacking to Sandwich Pitched π-Stacking Structure (2021)
  • Author(s): Takimiya Kazuo、Kanazawa Kiseki、Kawabata Kohsuke
  • Journal Title: Crystal Growth & Design Volume: 21 Issue: 7 Pages: 4055-4063
  • DOI: 10.1021/acs.cgd.1c00347
  • Peer Reviewed
• [Journal Article] “Manipulation” of Crystal Structure by Methylthiolation Enabling Ultrahigh Mobility in a Pyrene‐Based Molecular Semiconductor (2021)
  • Author(s): Takimiya Kazuo、Bulgarevich Kirill、Abbas Mamatimin、Horiuchi Shingo、Ogaki Takuya、Kawabata Kohsuke、Ablat Abduleziz
  • Journal Title: Advanced Materials Volume: 33 Issue: 32 Pages: 2102914-2102914
  • DOI: 10.1002/adma.202102914
  • Peer Reviewed / Open Access / Int'l Joint Research
• [Journal Article] Highly Electron‐Donating Bipyranylidene Derivatives: Potential n‐Type Dopants for Organic Thermoelectrics (2021)
  • Author(s): Matsuo Takaya、Kawabata Kohsuke、Takimiya Kazuo
  • Journal Title: Advanced Energy and Sustainability Research Volume: 2 Issue: 11 Pages: 2100084-2100084
  • DOI: 10.1002/aesr.202100084
  • Peer Reviewed / Open Access
• [Journal Article] Synthesis of Anthracene‐Based Cyclic π‐Clusters and Elucidation of their Properties Originating from Congested Aromatic Planes (2021)
  • Author(s): Tomohiko Nishiuchi, Kazuki Kisaka, Takashi Kubo
  • Journal Title: Angewandte Chemie International Edition Volume: 60 Issue: 10 Pages: 5400-5406
  • DOI: 10.1002/anie.202013349
  • Peer Reviewed / Open Access
• [Journal Article] Quantitative analysis of the formation mechanism of tightly bound rubber by using carbon-coated alumina nanoparticles as a model filler (2021)
  • 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
  • Peer Reviewed
• [Journal Article] Low-Temperature Removal of Dissociated Bromine by Silicon Atoms for an On-Surface Ullmann Reaction (2020)
  • 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 Issue: 36 Pages: 19675-19680
  • DOI: 10.1021/acs.jpcc.0c06188
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Chiral Tetraarylmethane Derivative with Metal‐Coordinating Ability (2020)
  • 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 Issue: 4 Pages: 652-659
  • DOI: 10.1002/ajoc.201900760
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Switching of Electron and Ion Conductions by Reversible H2O Sorption in n-Type Organic Semiconductors (2020)
  • Author(s): Abe Haruka, Kawasaki Ayumi, Takeda Takashi, Hoshino Norihisa, Matsuda Wakana, Seki Shu, Akutagawa Tomoyuki
  • Journal Title: ACS Applied Materials & Interfaces Volume: 12 Issue: 33 Pages: 37391-37399
  • DOI: 10.1021/acsami.0c09501
  • Peer Reviewed
• [Journal Article] Interfacial Nanostructuring of Poly(vinylidene fluoride) Homopolymer with Predominant Ferroelectric Phases (2020)
  • Author(s): Fu Chang, Zhu Huie, Hoshino Norihisa, Akutagawa Tomoyuki, Mitsuishi Masaya
  • Journal Title: Langmuir Volume: 36 Issue: 46 Pages: 14083-14091
  • DOI: 10.1021/acs.langmuir.0c02667
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Contrasting temperature dependences of isostructural one-dimensional ferroelectric crystals NH4HSO4 and RbHSO4 in terms of thermal conductivities (2020)
  • Author(s): Hoshino Norihisa, Akutagawa Tomoyuki
  • Journal Title: The Journal of Chemical Physics Volume: 153 Issue: 19 Pages: 194503-194503
  • DOI: 10.1063/5.0028153
  • Peer Reviewed
• [Journal Article] Room-Temperature Pentacene Fluids: Oligoethylene Glycol Substituent-Controlled Morphologies and Singlet Fission (2020)
  • Author(s): Yoshino Keisuke、Sakai Hayato、Shoji Yoshiaki、Kajitani Takashi、Anetai Hayato、Akutagawa Tomoyuki、Fukushima Takanori、Tkachenko Nikolai V.、Hasobe Taku
  • Journal Title: The Journal of Physical Chemistry B Volume: 124 Issue: 52 Pages: 11910-11918
  • DOI: 10.1021/acs.jpcb.0c09754
  • Peer Reviewed / Int'l Joint Research
• [Journal Article] Crystal Lattice Design of H2O-Tolerant n-Type Semiconducting Dianionic Naphthalenediimide Derivatives (2020)
  • 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 Issue: 2 Pages: 1046-1060
  • DOI: 10.1021/jacs.0c11545
  • 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
  • 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）
  • 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
  • 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
  • Invited
• [Presentation] Duality of Reactivity Characterized by Closed-Shell and Open-Shell Electronic Structure (2021)
  • Author(s): Takashi Kubo
  • Organizer: PACIFICHEM2021
  • 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）
  • Invited
• [Presentation] Molecular sensing by ESIPT fluorescent chromism (2021)
  • Author(s): Tomoyuki Akutagawa
  • Organizer: International Conference on Aggregate Science-20th Anniversary of AIE Research
  • 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
  • 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
• [Presentation] "Manipulation” of crystal structures of pyrene-based organic semiconductors enabling ultrahigh mobility (2021)
  • Author(s): Kazuo Takimiya
  • Organizer: The international Conference on Flexible and Printed Electronics
  • 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）
• [Presentation] Manipulation of crystal structures of pyrene-based organic semiconductors enabling ultrahigh mobility (2021)
  • Author(s): Kazuo Takimiya
  • Organizer: IDW ’21
  • 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
• [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
• [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
• [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
• [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
• [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
• [Presentation] Syntheses and Properties of Open-Shell π-Conjugated Molecules (2021)
  • Author(s): 久保孝史
  • Organizer: 日本化学会 第101回春季年会
  • 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
• [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
• [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
  • 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/
• [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
• [Remarks] 研究室ホームページ（瀧宮和男）
  • URL: http://web.tohoku.ac.jp/ogchmii/index.html
• [Remarks] Twitter (Condensed Conjugation)
  • URL: https://twitter.com/CConjugation