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Toward construction of crystalline nanoporous organic frameworks via photodimerization of acenes

Research Project

Project/Area Number 26600004
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Nanostructural chemistry
Research InstitutionNara Institute of Science and Technology

Principal Investigator

Suzuki Mitsuharu  奈良先端科学技術大学院大学, 物質創成科学研究科, 助教 (20724959)

Project Period (FY) 2014-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2015: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2014: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Keywords自己組織化 / 共有結合性有機構造体 / 結晶性多孔質材料
Outline of Final Research Achievements

This project aims at the construction of chemically stable covalent organic frameworks (COFs) by photo-dimerization of acenes. During this grant period, mainly examined was the synthesis of macrocyclic compounds that can serve as COF monomers. Systematic investigation has led to successful formation of macrocycles through one-step connection of three each of o-phenylenediamine and boronic acid units (six molecular units in total). The diazaborole motif, which is formed by the dehydration condensation between o-phenylenediamine and boronic acid, can be formed under thermodynamic control and relatively stable to hydrolysis, being ideal for the purpose of this project. The present work paves the way toward the synthesis of COFs through photodimerization of acenes. In addition, the reaction conditions optimized for the macrocycle synthesis might be directly applied to the synthesis of a new class of COFs assembled via the diazaborole linkage.

Report

(3 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • Research Products

    (23 results)

All 2016 2015 2014 Other

All Journal Article (6 results) (of which Peer Reviewed: 6 results,  Open Access: 4 results,  Acknowledgement Compliant: 4 results) Presentation (16 results) (of which Int'l Joint Research: 4 results,  Invited: 2 results) Remarks (1 results)

  • [Journal Article] Photoprecursor Approach Enables Preparation of Well-Performing Bulk-Heterojunction Layers2016

    • Author(s)
      M. Suzuki, Y. Yamaguchi, K. Takahashi, K. Takahara, T. Koganezawa, S. Masuo, K. Nakayama, and H. Yamada
    • Journal Title

      ACS Appl. Mater. Interfaces

      Volume: 8 Issue: 13 Pages: 8644-8651

    • DOI

      10.1021/acsami.6b00345

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Evaluation of semiconducting molecular thin films solution-processed via the photoprecursor approach: the case of hexyl-substituted thinoanthracenes2015

    • Author(s)
      C. Quinton, M. Suzuki, Y. Kaneshige, Y. Tatenaka, C. Katagiri, Y. Yamaguchi, D. Kuzuhara, N. Aratani, K. Nakayama, H. Yamada,
    • Journal Title

      J. Mater. Chem. C

      Volume: 3 Issue: 23 Pages: 5995-6005

    • DOI

      10.1039/c5tc00794a

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Evaluation of the charge transfer efficiency of organic thin-film photovoltaic devices fabricated using a photoprecursor approach2015

    • Author(s)
      S. Masuo, W. Sato, Y. Yamaguchi, M. Suzuki, K. Nakayama, and H. Yamada
    • Journal Title

      Photochem. Photobiol. Sci

      Volume: - Issue: 5 Pages: 883-890

    • DOI

      10.1039/c4pp00477a

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] An Optically and Thermally Switchable Electronic Structure Based on an Anthracene--BODIPY Conjugate2015

    • Author(s)
      T. Aotake,M. Suzuki, K. Tahara, D. Kuzuhara, N. Aratani, N. Tamai, H. Yamada*
    • Journal Title

      Chem. Eur. J.

      Volume: 21 Issue: 13 Pages: 4966-4974

    • DOI

      10.1002/chem.201406384

    • NAID

      120006334983

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] 9,9’-Anthryl-Anthroxyl Radicals: Strategic Stabilization of Highly Reactive Phenoxyl Radicals2015

    • Author(s)
      Tatsuya Aotake, Mitsuharu Suzuki, Naoki Aratani, Junpei Yuasa, Daiki Kuzuhara, Hironobu Hayashi, Haruyuki Nakano, Tsuyoshi Kawai, Jishan Wu Hiroko Yamada
    • Journal Title

      Chem. Commun.

      Volume: 51 Issue: 31 Pages: 6734-6737

    • DOI

      10.1039/c4cc10104a

    • NAID

      120006334970

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Photoprecursor approach as an effective means for preparing multilayer organic semiconducting thin films by solution processes2014

    • Author(s)
      Y. Yamaguchi, M. Suzuki, T. Motoyama, S. Sugii, C. Katagiri, K. Takahira, S. Ikeda, H. Yamada*, K. Nakayama*
    • Journal Title

      Sci. Rep.

      Volume: 4 Issue: 1 Pages: 7151-7151

    • DOI

      10.1038/srep07151

    • NAID

      120005716846

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Presentation] 塗布光変換型フラーレン材料の合成と有機薄膜太陽電池への応用2016

    • Author(s)
      川尻 和己,川ノ上 貴裕,大和 雅樹,寺井 健悟,山口 裕二,鈴木 充朗,中山 健一,山田 容子
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス(京都府京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] 積層型有機光電変換層への応用を志向した塗布光変換型p型半導体材料の開発2016

    • Author(s)
      永見 直斗,内永 憲佑,C. Quinton,高平 勝也,山口 裕二,鈴木 充朗,中山 健一,山田 容子
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス(京都府京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Photoprecursor approach towards efficient solution-processed organic solar cells2015

    • Author(s)
      M. Suzuki, Y. Yamaguchi, K. Nakayama, H. Yamada
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Hawaii Convention Center (Honolulu, Hawaii, USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Controlling vertical composition profile in organic photovoltaic active layers through the photoprecursor approach2015

    • Author(s)
      M. Suzuki, Y. Yamaguchi, K. Nakayama, H. Yamada
    • Organizer
      2015 MRS Fall Meeting & Exhibit
    • Place of Presentation
      Hynes Convention Center (Boston, Massachusetts, USA)
    • Year and Date
      2015-11-29
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Optimizing the morphology of organic bulk heterojunction films using solvent additives in the photoprecursor approach2015

    • Author(s)
      Y. Yamaguchi, M. Suzuki, T. Koganezawa, H. Yamada, K. Nakayama
    • Organizer
      2015 MRS Fall Meeting & Exhibit
    • Place of Presentation
      Hynes Convention Center (Boston, Massachusetts, USA)
    • Year and Date
      2015-11-29
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Solution-processable photoprecursors of narrow band gap molecular semiconductors for organic photovoltaic applications2015

    • Author(s)
      M. Suzuki, Y. Yamaguchi, K. Nakayama, H. Yamada
    • Organizer
      International Symposium for Photo- and Electro-Molecular Machines
    • Place of Presentation
      CEMES-CNRS Research Laboratory (Toulose, France)
    • Year and Date
      2015-10-06
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 光前駆体法を用いた積層型光電変換層の構築2015

    • Author(s)
      鈴木充朗,山口裕二,中山健一,山田容子
    • Organizer
      2015年光化学討論会
    • Place of Presentation
      大阪市立大(大阪府大阪市)
    • Year and Date
      2015-09-09
    • Related Report
      2015 Annual Research Report
  • [Presentation] ジケトピロロピロール骨格をもつp型有機半導体分子の可溶性光前駆体:合成と性質および塗布型太陽電池への応用2015

    • Author(s)
      内永憲佑,山口裕二,高平勝也,鈴木充朗,中山健一,山田容子
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス(千葉県船橋市)
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] 溶液塗布型有機薄膜太陽電池を指向したピラジノ[2,3-g]キノキサリン誘導体の合成2015

    • Author(s)
      青竹達也,鈴木充朗,山田容子
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス(千葉県船橋市)
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] アンスラセン-ベンゾチアジアゾール連結分子の光前駆体の合成と塗布型有機薄膜太陽電池への応用2015

    • Author(s)
      山本秦平,山口裕二,高平勝也,鈴木充朗,中山健一,山田容子
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス(千葉県船橋市)
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] 積層型有機薄膜太陽電池への応用を志向した塗布光変換型ホール輸送材料の合成2015

    • Author(s)
      仲内阿季,鈴木充朗,荒谷直樹,山田容子
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス(千葉県船橋市)
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] アントラセンのα-ジケトン型光前駆体を連結したフラーレン誘導体の合成と性質2015

    • Author(s)
      川ノ上貴裕,鈴木充朗,荒谷直樹,山田容子
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部船橋キャンパス(千葉県船橋市)
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] 光脱離型可溶化ユニットをもつジケトピロロピロール誘導体の合成と塗布変換型有機薄膜太陽電池への応用2014

    • Author(s)
      内永憲佑,山口裕二,鈴木充朗,高平勝也,中山健一,山田容子
    • Organizer
      2014年光化学討論会
    • Place of Presentation
      北海道大学札幌キャンパス(北海道札幌市)
    • Year and Date
      2014-10-11 – 2014-10-13
    • Related Report
      2014 Research-status Report
  • [Presentation] ベンゾチアジアゾール-アントラセン連結化合物の光前駆体の合成と塗布型有機薄膜太陽電池への応用2014

    • Author(s)
      山本秦平,山口裕二,高平勝也,鈴木充朗,中山健一,山田容子
    • Organizer
      2014年光化学討論会
    • Place of Presentation
      北海道大学札幌キャンパス(北海道札幌市)
    • Year and Date
      2014-10-11 – 2014-10-13
    • Related Report
      2014 Research-status Report
  • [Presentation] Photovoltaic performance of bulk heterojunction thin films prepared through the photoprecursor approach2014

    • Author(s)
      M. Suzuki, Y. Yamaguchi, S. Yamamoto, K. Takahira, K. Nakayama, H. Yamada
    • Organizer
      NIMS Conference 2014
    • Place of Presentation
      エポカルつくば(茨城県つくば市)
    • Year and Date
      2014-07-01 – 2014-07-03
    • Related Report
      2014 Research-status Report
  • [Presentation] Solution-processed organic photovoltaic cells fabricated via the photoprecursor aproach using a-diketone derivatives of acenes2014

    • Author(s)
      M. Suzuki, Y. Yamaguchi, K. Uchinaga, S. Yamamoto, K. Nakayama, H. Yamada
    • Organizer
      225th ECS Meeting
    • Place of Presentation
      Hilton Bonnet Creek, Orland (USA)
    • Year and Date
      2014-05-11 – 2014-05-15
    • Related Report
      2014 Research-status Report
    • Invited
  • [Remarks]

    • URL

      http://mswebs.naist.jp/LABs/env_photo_greenmat/Yamada_Research_Group/index.html

    • Related Report
      2014 Research-status Report

URL: 

Published: 2014-04-04   Modified: 2017-05-10  

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