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2018 Fiscal Year Annual Research Report

Development of aromatic functional materials by "precursor method", control of thin film structure and development to organic devices

Research Project

Project/Area Number 16H02286
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) 葛原 大軌  岩手大学, 理工学部, 助教 (00583717)
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)
中山 健一  大阪大学, 工学研究科, 教授 (20324808)
鈴木 充朗  大阪大学, 工学研究科, 准教授 (20724959)
Project Period (FY) 2016-04-01 – 2019-03-31
Keywords機能材料 / 有機半導体 / 薄膜構造制御 / 光反応 / アセン / ポルフィリン
Outline of Annual Research Achievements

塗布型有機半導体や近赤外吸収発光材料をターゲットに、独自に展開してきた『前駆体法』により、材料開発を行った。『前駆体法』とは、光、熱、酸などの刺激により、溶液・薄膜・固体・結晶状態で化合物の構造変化を引き起こし、それに伴いin-situで物理的性質の発現やナノ構造制御を行う手法である。具体的には次の3点に焦点を絞り研究を展開した。
1)有機薄膜トランジスタ・太陽電池を志向した塗布型低分子有機半導体材料や近赤外吸収発光色素の開発:有機薄膜太陽電池の短絡電流(Jsc)、開放電圧(Voc)、フィルファクター(FF)それぞれの値を向上させるための因子を明らかにすることで、光電変換効率(PCE)向上に取り組んだ。
2)溶液プロセスによる有機薄膜ナノ構造制御と、高性能有機薄膜電子デバイス作製法の確立:簡便な溶液プロセスであるディップコート法に適した、ベンゾポルフィリン誘導体の合成を行い、成膜法の確立と有機薄膜トランジスタの作製を行い、置換基構造やポルフィリンの中心金属と薄膜構造、電荷移動度の相関について明らかにした。
3)分子性ナノグラフェン合成・ナノリボンボトムアップ合成・ナノ構造体の構築などを志向した新しい前駆体法の開発:ノナセンまでの高次アセンの基板上合成と、HOMO-LUMOエネルギーの見積もりから、ノナセンが金基板上では開殻ビラジカル構造であることを明らかにした。また、ポルフィリン類縁体をユニット構造に用いたポルフィリンナノベルトの合成に成功するなど、分子性ナノベルトの合成に取り組んだ。

Research Progress Status

平成30年度が最終年度であるため、記入しない。

Strategy for Future Research Activity

平成30年度が最終年度であるため、記入しない。

  • Research Products

    (26 results)

All 2019 2018 Other

All Int'l Joint Research (2 results) Journal Article (13 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 13 results,  Open Access: 1 results) Presentation (8 results) (of which Int'l Joint Research: 5 results,  Invited: 8 results) Book (1 results) Remarks (1 results) Patent(Industrial Property Rights) (1 results)

  • [Int'l Joint Research] EMPA(スイス)

    • Country Name
      SWITZERLAND
    • Counterpart Institution
      EMPA
  • [Int'l Joint Research] UCSB(米国)

    • Country Name
      U.S.A.
    • Counterpart Institution
      UCSB
  • [Journal Article] Photoconversion of 6, 13-α-Diketopentacene Single Crystals Exhibiting Light Intensity-Dependent Morphological Change2019

    • Author(s)
      Mitsuaki Yamauchi, Yuya Miyamoto, Mitsuharu Suzuki, Hiroko Yamada, Sadahiro Masuo*
    • Journal Title

      Physical Chemistry Chemical Physics

      Volume: 21 Pages: 6348~6355

    • DOI

      10.1039/c8cp06594b

    • Peer Reviewed
  • [Journal Article] On-surface light-induced generation of higher acenes and elucidation of their open-shell character2019

    • Author(s)
      Jos_ I. Urgel, Shantanu Mishra, Hironobu Hayashi, Jan Wilhelm, Carlo A. Pignedoli, Marco Di Giovannantonio, Masataka Yamashita, Nao Hieda, Pascal Ruffieux, Hiroko Yamada,* and Roman Fasel*
    • Journal Title

      Nature Communications

      Volume: 10 Pages: 861/1~9

    • DOI

      10.1038/s41467-019-08650-y

    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis of a Porphyrin(2.1.2.1) Nanobelt and its Ability to Bind Fullerene2019

    • Author(s)
      Songlin Xue, Daiki Kuzuhara,* Naoki Aratani, Hiroko Yamada*
    • Journal Title

      Organic Letters

      Volume: 21 Pages: 2069~2072

    • DOI

      10.1021/acs.orglett.9b00329

    • Peer Reviewed
  • [Journal Article] Photophysical Properties and Structural Analysis of Modified Methylene Blues as Near Infrared Dyes2018

    • Author(s)
      Akira Tamoto, Naoki Aratani,* Hiroko Yamada*
    • Journal Title

      J. Photochem. Photobiol. A: Chemistry.

      Volume: 358 Pages: 441~446

    • DOI

      doi.org/10.1016/j.jphotochem.2017.10.031

    • Peer Reviewed
  • [Journal Article] Transient Photocurrent Elucidating Carrier Dynamics and Potential of Bulk Heterojunction Solar Cells Fabricated by Thermal Precursor Approach2018

    • Author(s)
      Kudo Naoki、Uchida Ken、Ikoma Tadaaki、Takahashi Kohtaro、Kuzuhara Daiki、Suzuki Mitsuharu、Yamada Hiroko、Kumagai Daichi、Yamaguchi Yuji、Nakayama Ken-Ichi
    • Journal Title

      Solar RRL

      Volume: 2 Pages: 1700234~1700234

    • DOI

      10.1002/solr.201700234

    • Peer Reviewed
  • [Journal Article] An Anomalous Antiaromaticity That Arises from the Cycloheptatrienyl Anion Equivalent2018

    • Author(s)
      Uehara Keiji、Mei Peifeng、Murayama Tomohisa、Tani Fumito、Hayashi Hironobu、Suzuki Mitsuharu、Aratani Naoki、Yamada Hiroko
    • Journal Title

      European Journal of Organic Chemistry

      Volume: - Pages: 4508~4511

    • DOI

      doi.org/10.1002/ejoc.201800769

    • Peer Reviewed
  • [Journal Article] 1,3-Phenylene-bridged naphthalene wheels synthesized by one-pot Suzuki?Miyaura coupling and the complex of the hexamer with C602018

    • Author(s)
      Mei Peifeng、Matsumoto Akinobu、Hayashi Hironobu、Suzuki Mitsuharu、Aratani Naoki、Yamada Hiroko
    • Journal Title

      RSC Advances

      Volume: 8 Pages: 20872~20876

    • DOI

      10.1039/C8RA03601B

    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] A photochemical layer-by-layer solution process for preparing organic semiconducting thin films having the right material at the right place2018

    • Author(s)
      Suzuki Mitsuharu、Yamaguchi Yuji、Uchinaga Kensuke、Takahira Katsuya、Quinton Cassandre、Yamamoto Shinpei、Nagami Naoto、Furukawa Mari、Nakayama Ken-ichi、Yamada Hiroko
    • Journal Title

      Chemical Science

      Volume: 9 Pages: 6614~6621

    • DOI

      10.1039/C8SC01799A

    • Peer Reviewed
  • [Journal Article] [30]Hexaphyrin(2.1.2.1.2.1) as Aromatic Planar Ligand and Its Trinuclear Rhodium(I) Complex2018

    • Author(s)
      Xue Songlin、Kuzuhara Daiki、Aratani Naoki、Yamada Hiroko
    • Journal Title

      Inorganic Chemistry

      Volume: 57 Pages: 9902~9906

    • DOI

      10.1021/acs.inorgchem.8b00977

    • Peer Reviewed
  • [Journal Article] An ethynylene-bridged pentacene dimer: two-step synthesis and charge transport property2018

    • Author(s)
      Koki Kawano, Hironobu Hayashi*, Shinya Yoshimoto, Naoki Aratani, Mitsuharu Suzuki, Jun Yoshinobu*, Hiroko Yamada*
    • Journal Title

      Chemistry -A European Journal

      Volume: 24 Pages: 14916~14920

    • DOI

      10.1002/chem.201803002

    • Peer Reviewed
  • [Journal Article] Improvement in Interlayer Structure of p_i_n-Type Organic Solar Cells with Use of Fullerene-Linked Tetrabenzoporphyrin as Additive2018

    • Author(s)
      Yuto Tamura, Mitsuharu Suzuki, Takaki Nakagawa, Tomoyuki Koganezawa, Sadahiro Masuo, Hironobu Hayashi, Naoki Aratani, Hiroko Yamada*
    • Journal Title

      RSC Advances

      Volume: 8 Pages: 35237~35245

    • DOI

      10.1039/C8RA07398H

    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Interpolymer self-assembly of bottom-up graphene nanoribbons fabricated from fluorinated precursors.2018

    • Author(s)
      Manabu Ohtomo,* Hideyuki Jippo, Hironobu Hayashi, Jun-ichi Yamaguchi,
    • Journal Title

      ACS Applied Materials & Interfaces

      Volume: 10 Pages: 31623~31630

    • DOI

      10.1021/acsami.8b11017

    • Peer Reviewed
  • [Journal Article] Semiconducting pi-Extended Tetrathiafulvalene Derivatives2018

    • Author(s)
      Hiroko Yamada,* Masataka Yamashita, Hironobu Hayashi, Mitsuharu Suzuki, Naoki Aratani
    • Journal Title

      Chemistry - A European Journal

      Volume: 12 Pages: 18601~18612

    • DOI

      doi.org/10.1002/chem.201802744

    • Peer Reviewed
  • [Presentation] Development of pi-Extended Aromatic Materials Using Precursor Approach2019

    • Author(s)
      山田 容子
    • Organizer
      日本化学会第99春季年会
    • Invited
  • [Presentation] 前駆体法による機能性材料開発2018

    • Author(s)
      山田 容子
    • Organizer
      ハリス理化学研究所イブニングセミナー
    • Invited
  • [Presentation] グラフェンナノリボンの基板上合成2018

    • Author(s)
      山田 容子
    • Organizer
      産研テクノサロン
    • Invited
  • [Presentation] Hexaphyrin(2.1.2.1.2.1): Synthesis, Metal Complexes, and Substituent Effect2018

    • Author(s)
      Hiroko Yamada, Songlin Xue, Naoki Aratani, Daiki Kuzuhara
    • Organizer
      10th International Symposium on porphyrins and Phthalocianines (ICPP10)
    • Int'l Joint Research / Invited
  • [Presentation] Constructions of Dimeric Triphyrin(2.1.1) and Porphyrin(2.1.2.1) Nanobelt2018

    • Author(s)
      Daiki Kuzuhara,a Songlin Xue,b Naoki Aratani,b Hiroko Yamada
    • Organizer
      10th International Symposium on porphyrins and Phthalocianines(ICPP10)
    • Int'l Joint Research / Invited
  • [Presentation] Benzoporphyrin-conjugated Dyes with Near-Infrared Absorption2018

    • Author(s)
      Naoki Aratani, Keiji Uehara, Peifeng Mei, Kohtaro Takahashi, Mitsuharu Suzuki, and Hiroko Yamada
    • Organizer
      10th International Symposium on porphyrins and Phthalocianines(ICPP10)
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis and Characterization of Large Acenes and Porphyrin(2.1.2.1) Nanobelt2018

    • Author(s)
      Hiroko Yamada
    • Organizer
      The third international symposium on the synthesis and applications of curved organic pi-molecules & materials (Curo-pi3)
    • Int'l Joint Research / Invited
  • [Presentation] On-Surface Synthesis of Self-Assembled Graphene Nanoribbon from Partially Fluorinated Precursors2018

    • Author(s)
      Hironobu Hayashi, Hiroko Yamada
    • Organizer
      International workshop On-Surface Synthesis (OSS18)
    • Int'l Joint Research / Invited
  • [Book] Light - Active Functional Organic Materials2019

    • Author(s)
      Hiroko Yamada, Shiki Yagai
    • Total Pages
      224
    • Publisher
      Pan Stanford Publishing.
    • ISBN
      978-981-4800-15-0
  • [Remarks] 奈良先端科学技術大学院大学先端科学技術研究科有機光分子科学研究室

    • URL

      http://mswebs.naist.jp/LABs/env_photo_greenmat/

  • [Patent(Industrial Property Rights)] シクラセン前駆体およびその製造方法、並びに、 ヘテロシクラセン前駆体およびその製造方法2019

    • Inventor(s)
      林 宏暢、山田 容子、大友 悟、佐藤 静香
    • Industrial Property Rights Holder
      奈良先端科学技術大学院大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      特願2019-037006

URL: 

Published: 2019-12-27  

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