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2022 Fiscal Year Annual Research Report

前駆体法を基盤とするπ共役拡張芳香族化合物の創成

Research Project

Project/Area Number 20H00379
Research InstitutionNara Institute of Science and Technology

Principal Investigator

山田 容子  奈良先端科学技術大学院大学, 先端科学技術研究科, 教授 (20372724)

Co-Investigator(Kenkyū-buntansha) 林 宏暢  奈良先端科学技術大学院大学, 先端科学技術研究科, 助教 (00736936)
松尾 恭平  奈良先端科学技術大学院大学, 先端科学技術研究科, 助教 (00778904)
Project Period (FY) 2020-04-01 – 2023-03-31
Keywords前駆体 / ポルフィリン / ポルフィリン / 有機半導体 / シクラセン
Outline of Annual Research Achievements

本申請課題では、“前駆体法”を最大限に活用し、合成法の開発と結晶構造制御の2つの側面からπ共役拡張芳香族化合物の化学に貢献するため、①前人未到の超高次アセン・シクラセンの金基板上合成と電子構造の解明、単結晶トランジスタへの挑戦;②置換基エンジニアリングによる低分子有機半導体開発と塗布プロセスによる結晶構造制御、を目的として研究を行なった。
① シクラセン前駆体の合成方法の確立と精製に成功し、その構造を単結晶X線構造解析により決定した(Eur. J. Org. Chem. 2022, 38, e202200621)。これらは、シクラセン合成の鍵化合物として期待される。また、芳香族分子骨格にリン元素を含むフォスファアセンの合成と有機トランジスタ特性の評価に成功した(Chem. Commun. 2022, 58, 13576)。前駆体法を用いる高次アセンの合成と物性に関する総説をまとめた(Photochem. Photobiol. Sci. 2022, 21, 1511)。
②薄膜の結晶構造に対する置換基効果を評価するために、長鎖アルキル基を導入した5,15-置換テトラベンゾポルフィリンを系統的に合成し、溶液プロセスにより成膜し有機トランジスタ特性を評価した。熱安定性の高い薄膜作成に成功し、その正孔移動度は4.1 cm2/Vsを達成した(ACS Appl. Mater. Interfaces, 2022, 14, 32319)。置換基構造と結晶構造、電荷移動度の相関について詳細に検討した。また、浙江大学Li教授との共同研究により、5,15-TIPS-BP単結晶FETにおける残存溶媒の影響について明らかにした(Adv. Electron. Mater. 2022,02200158)。

Research Progress Status

令和4年度が最終年度であるため、記入しない。

Strategy for Future Research Activity

令和4年度が最終年度であるため、記入しない。

  • Research Products

    (36 results)

All 2023 2022 Other

All Int'l Joint Research (4 results) Journal Article (23 results) (of which Int'l Joint Research: 6 results,  Peer Reviewed: 20 results,  Open Access: 3 results) Presentation (8 results) (of which Int'l Joint Research: 6 results,  Invited: 8 results) Remarks (1 results)

  • [Int'l Joint Research] ETH/EMPA(スイス)

    • Country Name
      SWITZERLAND
    • Counterpart Institution
      ETH/EMPA
  • [Int'l Joint Research] IMDEA Nanoscience(スペイン)

    • Country Name
      SPAIN
    • Counterpart Institution
      IMDEA Nanoscience
  • [Int'l Joint Research] Jiangsu University/Zhejiang University(中国)

    • Country Name
      CHINA
    • Counterpart Institution
      Jiangsu University/Zhejiang University
  • [Int'l Joint Research] University Toulouse III - Paul Sabatier(フランス)

    • Country Name
      FRANCE
    • Counterpart Institution
      University Toulouse III - Paul Sabatier
  • [Journal Article] Synthesis and properties of 10,20-bis(triisopropylsilylethynyl)-tetrabenzo-5,15-diazaporphine2023

    • Author(s)
      Sugano Yuki、Matsuo Kyohei、Hayashi Hironobu、Aratani Naoki、Yamada Hiroko
    • Journal Title

      Journal of Porphyrins and Phthalocyanines

      Volume: 27 Pages: 136-144

    • DOI

      10.1142/S1088424622500766

    • Peer Reviewed
  • [Journal Article] A Series of Soluble Planar Oligorylenes up to Hexarylene2023

    • Author(s)
      Fujita Ryuichi、Yoshida Shoko、Kano Haruka、Matsuo Kyohei、Hayashi Hironobu、Yamada Hiroko、Aratani Naoki
    • Journal Title

      Chinese Journal of Chemistry

      Volume: 41 Pages: 1023~1027

    • DOI

      10.1002/cjoc.202200692

    • Peer Reviewed
  • [Journal Article] Diazazethrene bisimide: a strongly electron-accepting π-system synthesized via the incorporation of both imide substituents and imine-type nitrogen atoms into zethrene2023

    • Author(s)
      Tajima Keita、Matsuo Kyohei、Yamada Hiroko、Fukui Norihito、Shinokubo Hiroshi
    • Journal Title

      Chemical Science

      Volume: 14 Pages: 635~642

    • DOI

      10.1039/D2SC05992D

    • Peer Reviewed / Open Access
  • [Journal Article] Possibilities and Limitations in Monomer Combinations for Ternary Two-Dimensional Covalent Organic Frameworks2023

    • Author(s)
      Suzuki Mitsuharu、Miura Masashi、Ohkubo Enzo、Karimata Haru、Aizawa Naoya、Yamada Hiroko、Nakayama Ken-ichi
    • Journal Title

      Journal of the American Chemical Society

      Volume: 145 Pages: 3008~3015

    • DOI

      10.1021/jacs.2c11520

    • Peer Reviewed
  • [Journal Article] An Atropisomerism Study of Large Cycloarylenes: [n]Cyclo‐4,10‐Pyrenylenes’ Case2023

    • Author(s)
      Kurosaki Ryo、Morimoto Hirofumi、Matsuo Kyohei、Hayashi Hironobu、Yamada Hiroko、Aratani Naoki
    • Journal Title

      Chemistry - A European Journal

      Volume: - Pages: e202203848

    • DOI

      10.1002/chem.202203848

  • [Journal Article] Enhanced Four‐Electron Oxygen Reduction Selectivity of Clamp‐Shaped Cobalt(II) Porphyrin(2.1.2.1) Complexes2023

    • Author(s)
      Xue Songlin、Ryan Osterloh W.、Lv Xiaojuan、Liu Ningchao、Gao Yimei、Lei Haitao、Fang Yuanyuan、Sun Zhongti、Mei Peifeng、Kuzuhara Daiki、Aratani Naoki、Yamada Hiroko、Cao Rui、Kadish Karl M.、Qiu Fengxian
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 62 Pages: e202218567

    • DOI

      10.1002/anie.202218567

  • [Journal Article] Synthesis of polyacene by using a metal-organic framework2023

    • Author(s)
      Takashi Kitao, Takumi Miura, Ryo Nakayama, Yusuke Tsutsui, Yee Seng Chan, Hironobu Hayashi, Hiroko Yamada, Shu Seki, Taro Hitosugi, Takashi Uemura
    • Journal Title

      Nature Synthesis

      Volume: 2023 Pages: -

  • [Journal Article] Reversible Photoluminescence Control of Azobenzene Crystals by Light and Heat Stimulation2022

    • Author(s)
      Yamauchi Mitsuaki、Okaji Miho、Aratani Naoki、Yamada Hiroko、Masuo Sadahiro
    • Journal Title

      ChemPhotoChem

      Volume: 6 Pages: e202100301

    • DOI

      10.1002/cptc.202100301

    • Peer Reviewed
  • [Journal Article] Synthesis, Characterization, and Electrochemistry of Copper Dibenzoporphyrin(2.1.2.1) Complexes2022

    • Author(s)
      Liu Ningchao、Osterloh W. Ryan、Huang Hongliang、Tang Xinyue、Mei Peifeng、Kuzuhara Daiki、Fang Yuanyuan、Pan Jianming、Yamada Hiroko、Qiu Fengxian、Kadish Karl M.、Xue Songlin
    • Journal Title

      Inorganic Chemistry

      Volume: 61 Pages: 3563~3572

    • DOI

      10.1021/acs.inorgchem.1c03596

    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Cross-conjugated isothianaphthene quinoids: a versatile strategy for controlling electronic structures2022

    • Author(s)
      Yamamoto Keitaro、Quintero Sergio Moles、Jinnai Seihou、Jeong Eunjeong、Matsuo Kyohei、Suzuki Mitsuharu、Yamada Hiroko、Casado Juan、Ie Yutaka
    • Journal Title

      Journal of Materials Chemistry C

      Volume: 10 Pages: 4424~4433

    • DOI

      10.1039/D1TC05794D

    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Effect of Aromatic Solvents Residuals on Electron Mobility of Organic Single Crystals2022

    • Author(s)
      Xue Guobiao、Peng Boyu、Ye Tao、Wu Jiake、Zhao Yujie、Liu Yujing、Yamada Hiroko、Chen Hongzheng、Li Hanying
    • Journal Title

      Advanced Electronic Materials

      Volume: 8 Pages: 2200158~2200158

    • DOI

      10.1002/aelm.202200158

    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Facile Post-synthesis and Redox Behavior of π-Expanded Ferrocene and ansa-Ferrocene2022

    • Author(s)
      Morimoto Hirofumi、Matsuo Kyohei、Hayashi Hironobu、Yamada Hiroko、Aratani Naoki
    • Journal Title

      Chemistry Letters

      Volume: 51 Pages: 428~430

    • DOI

      10.1246/cl.220011

    • Peer Reviewed
  • [Journal Article] Synthesis of porphyrin(2.1.2.1) with embedded naphthalene2022

    • Author(s)
      Lv Xiaojuan、Liu Ningchao、Xiao Bentian、Morimoto Hirofumi、Kuzuhara Daiki、Aratani Naoki、Yamada Hiroko、Qiu Fengxian、Xue Songlin
    • Journal Title

      Journal of Porphyrins and Phthalocyanines

      Volume: 26 Pages: 510~516

    • DOI

      10.1142/S1088424622500390

    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] A porphyrin(2.1.2.1) bis-boron complex as a deep-red AIE luminophore induced by intermolecular F-π interaction2022

    • Author(s)
      Liu Ningchao、Lv Xiaojuan、Xiao Bentian、Kuzuhara Daiki、Mei Peifeng、Aratani Naoki、Yamada Hiroko、Qiu Fengxian、Pan Jianming、Xue Songlin
    • Journal Title

      Dalton Transactions

      Volume: 51 Pages: 9606~9610

    • DOI

      10.1039/d2dt01289h

    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Exploration of Alkyl Group Effects on the Molecular Packing of 5,15-Disubstituted Tetrabenzoporphyrins toward Efficient Charge-Carrier Transport2022

    • Author(s)
      Jeong Eunjeong、Ito Tatsuya、Takahashi Kohtaro、Koganezawa Tomoyuki、Hayashi Hironobu、Aratani Naoki、Suzuki Mitsuharu、Yamada Hiroko
    • Journal Title

      ACS Applied Materials & Interfaces

      Volume: 14 Pages: 32319~32329

    • DOI

      10.1021/acsami.2c07313

    • Peer Reviewed
  • [Journal Article] Gram‐Scale Diversity‐Oriented Synthesis of Dinaphthothiepine Bisimides as Soluble Precursors for Perylene Bisimides2022

    • Author(s)
      Tanaka Yuki、Matsuo Kyohei、Yamada Hiroko、Fukui Norihito、Shinokubo Hiroshi
    • Journal Title

      European Journal of Organic Chemistry

      Volume: - Pages: e202200770

    • DOI

      10.1002/ejoc.202200770

    • Peer Reviewed
  • [Journal Article] Synthesis of Planar meso-Aryl Rosarins: A Reversible Antiaromatic/Aromatic Interconversion2022

    • Author(s)
      Liu Ningchao、Morimoto Hirofumi、Wu Fan、Lv Xiaojuan、Xiao Bentian、Kuzuhara Daiki、Pan Jianming、Qiu Fengxian、Aratani Naoki、Shen Zhen、Yamada Hiroko、Xue Songlin
    • Journal Title

      Organic Letters

      Volume: 24 Pages: 3609~3613

    • DOI

      10.1021/acs.orglett.2c01147

    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Polyazaacene and Cyclazaacene Precursors Synthesized by Dehydration Condensation from a Versatile Bis‐α‐diketone Unit Having an Anthracene Skeleton2022

    • Author(s)
      Chan Yee Seng、Hayashi Hironobu、Sato Shizuka、Kasahara Shoma、Matsuo Kyohei、Aratani Naoki、Yamada Hiroko
    • Journal Title

      European Journal of Organic Chemistry

      Volume: - Pages: e202200621

    • DOI

      10.1002/ejoc.202200621

    • Peer Reviewed
  • [Journal Article] On-surface synthesis of hydroxy-functionalized graphene nanoribbons through deprotection of methylenedioxy groups2022

    • Author(s)
      Ohtomo Manabu、Hayashi Hironobu、Shiotari Akitoshi、Kawamura Mayu、Hayashi Ryunosuke、Jippo Hideyuki、Yamaguchi Junichi、Ohfuchi Mari、Aratani Naoki、Sugimoto Yoshiaki、Yamada Hiroko、Sato Shintaro
    • Journal Title

      Nanoscale Advances

      Volume: 4 Pages: 4871~4879

    • DOI

      10.1039/d2na00031h

    • Peer Reviewed
  • [Journal Article] Phosphaacene as a structural analogue of thienoacenes for organic semiconductors2022

    • Author(s)
      Matsuo Kyohei、Okumura Rina、Hayashi Hironobu、Aratani Naoki、Jinnai Seihou、Ie Yutaka、Saeki Akinori、Yamada Hiroko
    • Journal Title

      Chemical Communications

      Volume: 58 Pages: 13576~13579

    • DOI

      10.1039/D2CC05122B

    • Peer Reviewed / Open Access
  • [Journal Article] Nonpolymer Organic Solar Cells: Microscopic Phonon Control to Suppress Nonradiative Voltage Loss via Charge-Separated State2022

    • Author(s)
      Nagatomo Takaaki、Vats Ajendra K.、Matsuo Kyohei、Oyama Shinya、Okamoto Naoya、Suzuki Mitsuharu、Koganezawa Tomoyuki、Fuki Masaaki、Masuo Sadahiro、Ohta Kaoru、Yamada Hiroko、Kobori Yasuhiro
    • Journal Title

      ACS Physical Chemistry Au

      Volume: 3 Pages: 207~221

    • DOI

      10.1021/acsphyschemau.2c00049

    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis of oligoacenes using precursors for evaluation of their electronic structures2022

    • Author(s)
      Yamada Hiroko、Hayashi Hironobu
    • Journal Title

      Photochemical & Photobiological Sciences

      Volume: 21 Pages: 1511~1532

    • DOI

      10.1007/s43630-022-00235-x

    • Peer Reviewed
  • [Journal Article] Microscopic Structures, Dynamics, and Spin Configuration of the Charge Carriers in Organic Photovoltaic Solar Cells Studied by Advanced Time-Resolved Spectroscopic Methods2022

    • Author(s)
      Ohta Kaoru、Tominaga Keisuke、Ikoma Tadaaki、Kobori Yasuhiro、Yamada Hiroko
    • Journal Title

      Langmuir

      Volume: 38 Pages: 7365~7382

    • DOI

      10.1021/acs.langmuir.2c00290

    • Peer Reviewed
  • [Presentation] ベンゼン環はどこまで伸ばせるか? 光反応による高次アセン合成への挑戦2023

    • Author(s)
      山田容子
    • Organizer
      “光”機到来!Qコロキウム@唐津
    • Invited
  • [Presentation] Metalation Effect on Diketopyrrolopyrrole-tetrabenzoporphyrin Conjugate as p-Type Material in BHJ Organic Photovoltaics2022

    • Author(s)
      Ajendra Kumar Vats, Kyohei Matsuo, Hiroko Yamada
    • Organizer
      241st ECS Meeting
    • Int'l Joint Research / Invited
  • [Presentation] On-surface Synthesis of Higher Acenes using Precursors2022

    • Author(s)
      Hiroko Yamada and Hironobu Hayashi
    • Organizer
      241st ECS Meeting
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis of 10,20-substituted-tetrabenzo-5,15-diazaporphyrins and evaluation of their application to organic semiconductors2022

    • Author(s)
      Hiroko Yamada, Yuki Sugano, Kyohei Matsuo
    • Organizer
      The 12th international conference on porphyrins and phthalocyanines (ICPP-12)
    • Int'l Joint Research / Invited
  • [Presentation] Small bandgap in atomically precise 17-atom-wide armchair-edged graphene nanoribbons.2022

    • Author(s)
      Hiroko Yamada, Hironobu Hayashi, Junichi Yamaguchi, Hideyuki Jippo, Akitoshi Shiotari, Manabu Ohtomo, Mitsuaki Sakakura, Nao Hieda, Naoki Aratani, Mari Ohfuchi, Yoshiaki Sugimoto, Shintaro Sato
    • Organizer
      International Workshop On-Surface Synthesis (OSS22)
    • Int'l Joint Research / Invited
  • [Presentation] On-surface Synthesis of Higher Acenes using Precursors2022

    • Author(s)
      Hiroko Yamada
    • Organizer
      Kyoto-Bordeaux Symposium on Organic Chemistry and Photochemistry
    • Int'l Joint Research / Invited
  • [Presentation] Polyazaacene and cyclazaacene precursor synthesis2022

    • Author(s)
      H. Hayashi, and H. Yamada
    • Organizer
      11th singapore international chemical conference
    • Int'l Joint Research / Invited
  • [Presentation] 基板上合成による高次アセンの合成と グラフェンナノリボンへの展開2022

    • Author(s)
      山田容子
    • Organizer
      第33回万有仙台シンポジウム
    • Invited
  • [Remarks] 奈良先端科学技術大学院大学機能有機化学研究室

    • URL

      https://mswebs.naist.jp/LABs/env_photo_greenmat/index3.html

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Published: 2023-12-25  

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