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Exploration of pi-electron systems with optoelectronic functions based on the characteristics of sulfur

Research Project

Project/Area Number 17H04869
Research Category

Grant-in-Aid for Young Scientists (A)

Allocation TypeSingle-year Grants
Research Field Organic chemistry
Research InstitutionKyoto University (2018-2019)
Nagoya University (2017)

Principal Investigator

Fukazawa Aiko  京都大学, 高等研究院, 教授 (70432234)

Project Period (FY) 2017-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥24,830,000 (Direct Cost: ¥19,100,000、Indirect Cost: ¥5,730,000)
Fiscal Year 2019: ¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2018: ¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2017: ¥14,690,000 (Direct Cost: ¥11,300,000、Indirect Cost: ¥3,390,000)
Keywordsπ電子系 / 典型元素 / 硫黄 / 反芳香族 / 有機半導体 / 近赤外蛍光 / 不斉酸化 / 中員環 / 動的速度論分割 / 近赤外吸収色素 / π共役 / 構造有機化学 / 有機元素化学 / 光機能 / 蛍光 / パイ電子系 / 発光機能
Outline of Final Research Achievements

In this study, we proposed new concepts for the use of sulfur for the molecular design of π-electron systems that exhibits attractive optical and electronic functions. The major findings are summarized as follows: (1) stabilization of highly reactive π-electron systems by taking advantage of the weak aromaticity of thiophene, (2) development of novel electron-accepting π-electron systems based on thioesters, and (3) exploring of solubilizing substituents without electron-donating character based on the suppression of n-π interactions.

Academic Significance and Societal Importance of the Research Achievements

学術的な観点での本研究の最大の特色および独創的な点は,硫黄の特徴を様々な角度から引き出すための分子設計にある.従来の機能性有機材料における硫黄の使い方は,n-π相互作用の利用による電子供与性π電子系の創製である.一方,本研究では,n-π相互作用の本質的な弱さや硫黄の誘起効果に着目した相補的な分子設計により硫黄の潜在的な特徴を多角的に引き出すことに成功したものであり,典型元素化学,構造有機化学,機能物質科学分野に基礎的かつ新たな知見を与えたと位置付けられる.

Report

(5 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Annual Research Report
  • 2017 Annual Research Report
  • Products Report
  • Research Products

    (36 results)

All 2022 2021 2020 2019 2018 2017 Other

All Journal Article (6 results) (of which Peer Reviewed: 6 results) Presentation (26 results) (of which Int'l Joint Research: 7 results,  Invited: 13 results) Remarks (2 results) Patent(Industrial Property Rights) (2 results) (of which Overseas: 1 results)

  • [Journal Article] Late-stage modification of π-electron systems based on asymmetric oxidation of a medium-sized sulfur-containing ring2022

    • Author(s)
      Hayakawa Masahiro、Horike Satoshi、Hijikata Yuh、Yasui Kosuke、Yamaguchi Shigehiro、Fukazawa Aiko
    • Journal Title

      Chemical Communications

      Volume: 58 Issue: 15 Pages: 2548-2551

    • DOI

      10.1039/d1cc06996a

    • Related Report
      Products Report
    • Peer Reviewed
  • [Journal Article] Thiophene-fused 1,4-Diazapentalene: A Stable C=N-Containing π-Conjugated System with Restored Antiaromaticity2021

    • Author(s)
      J. Usuba, A. Fukazawa
    • Journal Title

      Chem. Eur. J.

      Volume: 27 Issue: 65 Pages: 16127-16134

    • DOI

      10.1002/chem.202103122

    • Related Report
      Products Report
    • Peer Reviewed
  • [Journal Article] Extended π-Electron Delocalization in Quinoid-Based Conjugated Polymers Boosts Intrachain Charge Carrier Transport2021

    • Author(s)
      Mikie Tsubasa、Hayakawa Masahiro、Okamoto Kenta、Iguchi Keitaro、Yashiro Shuhei、Koganezawa Tomoyuki、Sumiya Masatomo、Ishii Hiroyuki、Yamaguchi Shigehiro、Fukazawa Aiko、Osaka Itaru
    • Journal Title

      Chemistry of Materials

      Volume: 33 Issue: 21 Pages: 8183-8193

    • DOI

      10.1021/acs.chemmater.1c02072

    • Related Report
      Products Report
    • Peer Reviewed
  • [Journal Article] Dithieno[a,e]pentalenes: Highly Antiaromatic Yet Stable π-Electron Systems without Bulky Substituents2021

    • Author(s)
      J. Usuba, M. Hayakawa, S. Yamaguchi, A. Fukazawa
    • Journal Title

      Chem. Eur. J.

      Volume: 27 Issue: 5 Pages: 1638-1647

    • DOI

      10.1002/chem.202004244

    • Related Report
      Products Report
    • Peer Reviewed
  • [Journal Article] End-Capping π-Conjugated Systems with Medium-Sized Sulfur-Containing Rings: A Route Towards Solution-Processable Air-Stable Semiconductors2018

    • Author(s)
      Fukazawa Aiko、Toda Yusuke、Hayakawa Masahiro、Sekioka Anna、Ishii Hiroyuki、Okamoto Toshihiro、Takeya Jun、Hijikata Yuh、Yamaguchi Shigehiro
    • Journal Title

      Chemistry - A European Journal

      Volume: 24 Issue: 44 Pages: 11503-11510

    • DOI

      10.1002/chem.201802656

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A New Infrared Dye that Undergoes Multiple Interconversions through Acid-Base Equilibria and Reversible Redox Processes2017

    • Author(s)
      Kengo Asai, Aiko Fukazawa, Shigehiro Yamaguchi
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 56 Issue: 24 Pages: 6848-6852

    • DOI

      10.1002/anie.201702140

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Presentation] Renaissance of Nonbenzenoid π-Conjugated Systems toward Functional Materials2020

    • Author(s)
      Aiko Fukazawa
    • Organizer
      The SPIRITS International Symposium “Shaping Self-Assembled Mesoscale (Bio)Materials with Microengineering”
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] チエニル基を導入したジチエノ[a,e]ペンタレンの分子間相互作用と会合体形成2020

    • Author(s)
      薄葉純一,山口茂弘,深澤愛子
    • Organizer
      日本化学会第100春季年会講演要旨集 2C3-29
    • Related Report
      2019 Annual Research Report
  • [Presentation] 硫黄を含む中員環で片側末端をエンドキャップした液晶性π共役系の物性2020

    • Author(s)
      早川雅大,山口茂弘,深澤愛子
    • Organizer
      日本化学会第100春季年会講演要旨集 2C3-28
    • Related Report
      2019 Annual Research Report
  • [Presentation] Synthesis of Thiophene-Containing Triarylmethine Dyes Bridged with Phosphoryl Group and Its Conversion to Stable Organic Radicals2020

    • Author(s)
      Stanley Surya Winata Oey,Shigehiro Yamaguchi,Aiko Fukazawa
    • Organizer
      日本化学会第100春季年会講演要旨集
    • Related Report
      2019 Annual Research Report
  • [Presentation] 硫黄の特性を生かしたπ電子系の新展開2019

    • Author(s)
      深澤愛子
    • Organizer
      大阪府立大学 有機化学研究会(白鷺セミナー)第86回講演会
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] 第3周期典型元素の特性を生かした新奇π電子系の創製と機能開拓2019

    • Author(s)
      深澤愛子
    • Organizer
      万有札幌シンポジウム
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] Synthesis, Structures and Properties of Dithieno[a,e]pentalenes without Bulky Substituents2019

    • Author(s)
      Junichi Usuba, Aiko Fukazawa, and Shigehiro Yamaguchi
    • Organizer
      The 18th International Symposium on Novel Aromatic Compounds (ISNA-18)
    • Related Report
      2019 Annual Research Report
  • [Presentation] Exploration of Sulfur-Containing π-Electron Systems toward Unusual Yet Stable Functional Materials2019

    • Author(s)
      Aiko Fukazawa
    • Organizer
      The 2nd JGP Chem&ChemEn International Workshop “Sustainability-Oriented Organic Synthesis”
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] 硫黄を含む中員環の不斉酸化を利用したπ電子系の構造修飾2019

    • Author(s)
      早川雅大,深澤愛子,山口茂弘
    • Organizer
      第30回基礎有機化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Exploration of Novel π-Electron Systems toward Unusual Yet Stable Functional Materials2019

    • Author(s)
      Aiko Fukazawa
    • Organizer
      18th Asian Chemical Congress
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] Exploration of Novel Sulfur-Containing pi-Systems toward Unusual Yet Stable Functional Materials2018

    • Author(s)
      Aiko Fukazawa
    • Organizer
      The 10th Singapore International Chemistry Conference (SICC-10)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] End-Capping pi-Conjugated Systems with Medium-Sized Sulfur-Containing Rings towards Solution-Processable Air-Stable Semiconductors2018

    • Author(s)
      Aiko Fukazawa, Yusuke Toda, Masahiro Hayakawa, Anna Sekioka, Hiroyuki Ishii, Toshihiro Okamoto, Jun Takeya, Yuh Hijikata, and Shigehiro Yamaguchi
    • Organizer
      The 14th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-14)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 硫黄を含む中員環でエンドキャップしたπ電子系の合成とその物性2018

    • Author(s)
      早川雅大,深澤愛子,戸田雄佑,関岡杏奈,石井宏幸,岡本敏弘,竹谷純一,土方 優,山口茂弘
    • Organizer
      中部化学関係学協会支部連合秋季大会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Exploring New Concept for the Use of Sulfur in the Molecular Design of Functional マ?-Electron Materials2018

    • Author(s)
      Aiko Fukazawa
    • Organizer
      The 9th RSC-CSJ Workshop
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 含硫黄π電子系の新展開2018

    • Author(s)
      深澤愛子
    • Organizer
      有機合成セミナー
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] End-Capping of pi-Conjugated Skeletons with Medium-Sized Sulfur-Containing Rings2018

    • Author(s)
      Masahiro Hayakawa, Aiko Fukazawa, Yusuke Toda, Anna Sekioka, Hiroyuki Ishii, Toshihiro Okamoto, Jun Takeya, Yuh Hijikata, Shigehiro Yamaguchi
    • Organizer
      28th International Symposium on the Organic Chemistry of Sulfur (ISOCS-28)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Exploring New Sulfur-Containing pi-Skeletons for Functional Materials2018

    • Author(s)
      Aiko Fukazawa
    • Organizer
      28th International Symposium on the Organic Chemistry of Sulfur (ISOCS-28)
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Exploring New Sulfur-Containing pi-Skeletons for Functional Materials2018

    • Author(s)
      Aiko Fukazawa
    • Organizer
      2nd From Carbon-Rich Molecules to Carbon-Based Materials Conference
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 嵩高い置換基をもたないジチエノ[a,e]ペンタレンの合成,構造および分子間相互作用2018

    • Author(s)
      薄葉純一,深澤愛子,山口茂弘
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 硫黄を含む中員環でエンドキャップしたフェニレン-チエニレンオリゴマーの合成と光物性2018

    • Author(s)
      早川雅大,深澤愛子,山口茂弘
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] End-Capped Oligothiophenes with Sulfur-Containing Medium Rings2017

    • Author(s)
      Aiko Fukazawa, Yusuke Toda, Masahiro Hayakawa, Anna Sekioka, Toshihiro Okamoto, Jun Takeya, Shigehiro Yamaguchi
    • Organizer
      The 17th International Symposium on Novel Aromatics (ISNA2017)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 第3周期元素の特性を生かした機能性π電子系の創製2017

    • Author(s)
      深澤愛子
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 硫黄を含む中員環が縮環したチオフェンによるπ電子系の分子配向制御2017

    • Author(s)
      早川雅大, 深澤愛子, 戸田雄佑,山口茂弘
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 硫黄を含むπ電子系の化学の新展開2017

    • Author(s)
      深澤愛子
    • Organizer
      第7回CSJ化学フェスタ,JST 特別企画:ACT-C プログラムが生み出す未来の科学技術
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] チオラクトンを基本骨格とする拡張π電子系の合成と近赤外蛍光特性2017

    • Author(s)
      竹腰麻由,近藤美希,WANG Chenguang,深澤愛子,山口茂弘
    • Organizer
      第7回CSJ化学フェスタ
    • Related Report
      2017 Annual Research Report
  • [Presentation] チオフェンの低い芳香族性を生かした分子変換による新奇π電子系の創製2017

    • Author(s)
      深澤愛子
    • Organizer
      有機合成化学協会中国四国支部 第76回パネル討論会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Remarks] 深澤研究室公式ウェブサイト

    • URL

      https://fukazawa.icems.kyoto-u.ac.jp/

    • Related Report
      2018 Annual Research Report
  • [Remarks]

    • URL

      http://orgreact.chem.nagoya-u.ac.jp/olddocs/Fukazawa-CV.html

    • Related Report
      2017 Annual Research Report
  • [Patent(Industrial Property Rights)] ジベンゾペンタフルバレンオリゴマー及びその製造方法2022

    • Inventor(s)
      中愛子(深澤愛子)、砂山尚之、早川雅大
    • Industrial Property Rights Holder
      京都大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2022-033643
    • Filing Date
      2022
    • Related Report
      Products Report
    • Overseas
  • [Patent(Industrial Property Rights)] ジチエノホスホリン化合物、並びにそれを用いた無色近赤外吸収材料及び エレクトロクロミック材料2020

    • Inventor(s)
      中 愛子,ウィー・ステンリー・スルヤ・ウィナタ
    • Industrial Property Rights Holder
      国立大学法人京都大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2020-037129
    • Filing Date
      2020
    • Related Report
      2019 Annual Research Report

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Published: 2017-04-28   Modified: 2023-03-30  

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