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Creation of novel large quinoidal conjugated molecular material toward organic electronics

Research Project

Project/Area Number 26810024
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Organic chemistry
Research InstitutionKyushu University

Principal Investigator

Ishida Masatoshi  九州大学, 分子システムデバイス国際リーダー教育センター, 助教 (60706951)

Project Period (FY) 2014-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2015: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2014: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywordsπ共役 / ポルフィリン / テトラチアフルバレン / ラジカル / 酸化還元 / 金属錯体 / 電子移動 / 超分子錯体
Outline of Final Research Achievements

We have synthesized novel nonaromatic π-conjugated macrocycle based on various tetrathiafulvalene-derived structures. The formation of supramolecular ensembles composing of two dicationic porphyrin-bridged extended TTF derivative and a tetraanionic porphyrin derivatives were characterized and achieved the extremely long-lived photoinduced charge separated states (τCS ~ 83 ms). In a case of TTF-annulated expanded porphyrin, the protonation-induced thermal charge separation between the porphyrin and TTF units was observed.
In a similar design principle, we have also succeeded in the preparation of stable π radical complex based on a contracted N-confused hexaphyrin derivatives.

Report

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

    (46 results)

All 2016 2015 2014 Other

All Int'l Joint Research (4 results) Journal Article (16 results) (of which Int'l Joint Research: 8 results,  Peer Reviewed: 16 results,  Acknowledgement Compliant: 8 results,  Open Access: 4 results) Presentation (25 results) (of which Int'l Joint Research: 3 results,  Invited: 4 results) Book (1 results)

  • [Int'l Joint Research] Yonsei University/Kangwon National University(韓国)

    • Related Report
      2015 Annual Research Report
  • [Int'l Joint Research] National University of Singapore(シンガポール)

    • Related Report
      2015 Annual Research Report
  • [Int'l Joint Research] The University of Texas at Austin(米国)

    • Related Report
      2015 Annual Research Report
  • [Int'l Joint Research] East China University(中国)

    • Related Report
      2015 Annual Research Report
  • [Journal Article] Breaking aggregation in a tetrathiafulvalene-fused zinc porphyrin by metal-ligand coodination to form a donor-acceptor hybrid for ultrafast charge separation and charge stabilization2015

    • Author(s)
      Atanu Jana, Habtom B. Gobeze, Masatoshi Ishida, Toshiyuki Mori, Katsuhiko Ariga, Jonathan P. Hill and Francis D’Souza
    • Journal Title

      Dalton Trans

      Volume: 44 Issue: 1 Pages: 359-367

    • DOI

      10.1039/c4dt03157a

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Near-infrared luminescent Sn(IV) complexes of N-confused tetraphenylporphyrin: Effect of axial anion coordination2015

    • Author(s)
      Arghya Basu, Motoki Kitamura, Shigeki Mori, Masatoshi Ishida, Yongshu Xie, Hiroyuki Furuta
    • Journal Title

      J. Porphyrins Phthalocyanines

      Volume: 19 Issue: 01-03 Pages: 361-371

    • DOI

      10.1142/s1088424615500212

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Spectroscopic and Theoretical Studies of Acid-Base Behaviors of N-Confused Porphyrins: Effects of meso-Aryl Substituents2015

    • Author(s)
      Ryuichi Sakashita, Masatoshi Ishida, Hiroyuki Furuta
    • Journal Title

      J. Phys. Chem. A.

      Volume: 119 Issue: 6 Pages: 1013-1022

    • DOI

      10.1021/jp512229k

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Phenalenyl-fused porphyrins with different ground states2015

    • Author(s)
      W. Zeng, S. Lee, M. Son, M. Ishida, K. Furukawa, P. Hu, Z. Sun, D. Kim, J. Wu
    • Journal Title

      Chem. Sci.

      Volume: 6 Issue: 4 Pages: 2427-2433

    • DOI

      10.1039/c4sc03866e

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] β-Functionalized push-pull porphyrin sensitizers in dye-sensitized solar cells: π-Conjugated spacer effect2015

    • Author(s)
      Masatoshi Ishida, Daesub Hwang, Zhan Zhang, Young Bean Koo, Juwon Oh, Vincent M. Lynch, Dong Young Kim, Jonanthan L. Sessler, Dongho Kim
    • Journal Title

      ChemSusChem

      Volume: 8 Issue: 17 Pages: 2967-2977

    • DOI

      10.1002/cssc.201500085

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Intramolecular charge transfer character in tetrathiafulvalene-annulated porphyrinoids: Effects on core modification and protonation2015

    • Author(s)
      Ramababu Bolligarla, Masatoshi Ishida, Vijayendra S. Shetti, Kazuhisa Yamasumi, Hiroyuki Furuta, Chang-Hee Lee
    • Journal Title

      Phys. Chem. Chem. Phys.

      Volume: 17 Issue: 14 Pages: 8699-8705

    • DOI

      10.1039/c4cp05385k

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Near-infrared-induced electron transfer of an uranyl macrocyclic complex without energy transfer to dioxygen2015

    • Author(s)
      Christina M. Davis, Kei Ohkubo, I-Ting Ho, Zhan Zhang, Masatoshi Ishida, Yuanyuan Fang, Vincent M. Lynch, Karl M. Kadish, Jonathan L. Sessler, Shunichi Fukuzumi
    • Journal Title

      Chem. Commun.

      Volume: 51 Issue: 31 Pages: 6757-6760

    • DOI

      10.1039/c5cc00903k

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Stable π-Radical from a Contracted Doubly N-Confused Hexaphyrin by Bis-Palladium Metallation2015

    • Author(s)
      Y. Hisamune, K. Nishimura, K. Isakari, M. Ishida, S. Mori, Satoru. Karasawa, T. Kato, Sangsu L., D.Kim, and H. Furuta,
    • Journal Title

      Angew. Chem., Int. Ed. Engl.

      Volume: 54 Issue: 25 Pages: 7323-7327

    • DOI

      10.1002/anie.201502285

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Formation of Ground State Triplet Diradicals from Annulated Rosarin Derivatives by Triprotonation2015

    • Author(s)
      Ohkubo K et al.
    • Journal Title

      JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

      Volume: 137 Issue: 31 Pages: 9780-9783

    • DOI

      10.1021/jacs.5b05309

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Synthesis of a Neo-Confused Octaphyrin and the Formation of Its Mononuclear Complexes2015

    • Author(s)
      Zhang, K.; Zhang, J.; Li, X.; Guo, R.; Agren, H.; Ou, Z.; Ishida, M.; Furuta, H.; Xie, Y.
    • Journal Title

      Org. Lett.

      Volume: 17 Issue: 19 Pages: 4806-4809

    • DOI

      10.1021/acs.orglett.5b02363

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Doubly N-Confused Isophlorin: Synthesis, Structure and Copper Coordination2014

    • Author(s)
      Yan, J.; Takakusaki, M.; Yang, Y.; Mori, S.; Zhang, B.; Feng, Y.; Ishida, M.; Furuta, H.
    • Journal Title

      Chem. Commun

      Volume: 50 Issue: 93 Pages: 14593-14596

    • DOI

      10.1039/c4cc06259k

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] N-confused phlorin: a stable dihydroporphyrin isomer containing a confused pyrrole ring2014

    • Author(s)
      M. Ishida, K. Nakahara, R. Sakashita, T. Ishizuka, M. Watanabe, H. Uno, A. Osuka, and H. Furuta
    • Journal Title

      J. Porphyrins Phthalocyanines

      Volume: 18 Issue: 10n11 Pages: 909-919

    • DOI

      10.1142/s1088424614500692

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Stepwise π-Extension of meso-Alkylidenyl Porphyrins through Sequential 1,3-Dipolar Cycloaddition and Redox Reactions2014

    • Author(s)
      D. Park, S. D. Jeong, M. Ishida, C.-H. Lee
    • Journal Title

      Chem Commun.

      Volume: 50 Issue: 66 Pages: 9277-9280

    • DOI

      10.1039/c4cc04283b

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Long-Lived Charge-Separated States Produced in Supramolecular Complexes between Anionic and Cationic Porphyrins2014

    • Author(s)
      Bill, N. L.; Ishida, M.; Kawashima, Y.; Ohkubo, K.; Sung, Y. M.; Lynch, V. M.; Lim, J. M.; Kim, D.; Sessler, J. L.; Fukuzumi, S.
    • Journal Title

      Chem. Sci.

      Volume: 5 Issue: 10 Pages: 3888-3896

    • DOI

      10.1039/c4sc00803k

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Cyclo[6]pyridine[6]pyrrole: A Dynamic, Twisted Mcrocycle with no Meso Bridges2014

    • Author(s)
      Z. Zhang, W.-Y. Cha, N. Williams, E. Rush, M. Ishida, V. Lynch, D. Km, J. L. Sessler
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 136 Issue: 21 Pages: 7591-7594

    • DOI

      10.1021/ja503451m

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Turning on the Biradical State of Tetracyano- Perylene and Quaterrylenequinodimethanes by Incorporation of Additional Thiophene Rings2014

    • Author(s)
      Z. Zeng, S. Lee, J. Zafra, M. Ishida, N. Bao, R. Webster, N. López, T. Juan, J. Ding, J. Casado, D. Kim, J. Wu
    • Journal Title

      Chem. Sci.

      Volume: 5 Issue: 8 Pages: 3072-3080

    • DOI

      10.1039/c4sc00659c

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Presentation] N-混乱ポルフィリンを用いた機能性MOFの合成と物性2016

    • Author(s)
      楊雨峰、石田真敏、古田弘幸
    • Organizer
      日本化学会 第96春季年会
    • Place of Presentation
      同志社大学
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Bis-metal Complexes of Doubly N-Confused Hexaphyrins: Low-band Gap and Open-Shell Molecules2016

    • Author(s)
      Masatoshi Ishida
    • Organizer
      4th International Symposium of Molecular Systems
    • Place of Presentation
      Kyushu University
    • Year and Date
      2016-03-22
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Doubly N-Confused Hexaphyrin Bis-metal Complexes for Near IR Optical Materials2016

    • Author(s)
      Masatoshi Ishida, Koki Ogasahara, Hiroyuki Furuta
    • Organizer
      251st American Chemical Society National Meeting & Exposition
    • Place of Presentation
      San Diego
    • Year and Date
      2016-03-13
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Highly Porous N-confused Porphyrin-based Metal-Organic Frameworks2016

    • Author(s)
      Yang Yufeng, Masatoshi Ishida, Hiroyuki Furuta
    • Organizer
      251st American Chemical Society National Meeting & Exposition
    • Place of Presentation
      San Diego
    • Year and Date
      2016-03-13
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ~魅力ある新奇有機π電子系の構築に向けて~ピリジン環を構成骨格に含んだハイブリッドシクロピロール誘導体の合成と物性2015

    • Author(s)
      石田真敏
    • Organizer
      有機合成協会九州山口支部・第2回講演会
    • Place of Presentation
      住友化学大分工場
    • Year and Date
      2015-11-20
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] N-混乱”環拡張ポルフィリノイドの配位化学~構造・光物性・磁気特性~2015

    • Author(s)
      石田真敏
    • Organizer
      構造有機化学若手研究者 ミニシンポジウム
    • Place of Presentation
      九州大学
    • Year and Date
      2015-08-31
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] 24π共役サーキットを有する二重N-混乱ヘキサフィリン(1,1,0,1,1,0)の合成と物性2015

    • Author(s)
      下村恵人、石田真敏、古田弘幸
    • Organizer
      第26回基礎有機化学会討論会
    • Place of Presentation
      愛媛大学・松山大学
    • Year and Date
      2015-08-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] 二重N-混乱ヘキサフィリン(1,1,1,1,1,0)銅二核錯体の合成と磁気物性2015

    • Author(s)
      山角和久、西村啓一、久宗穣、石田真敏、古田 弘幸
    • Organizer
      第26回基礎有機化学会討論会
    • Place of Presentation
      愛媛大学・松山大学
    • Year and Date
      2015-08-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] 二重N-混乱ヘキサフィリン二核金属錯体の合成と光学特性2015

    • Author(s)
      小笠原光紀、ゴクルナス サバパッチ、石田真敏、古田 弘幸
    • Organizer
      第26回基礎有機化学会討論会
    • Place of Presentation
      愛媛大学・松山大学
    • Year and Date
      2015-08-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] 二重N-混乱ヘキサフィリン(1,1,0,1,1,0)の合成と物性2015

    • Author(s)
      下村恵人、石田真敏、古田弘幸
    • Organizer
      第52回化学関連支部合同九州大会
    • Place of Presentation
      北九州国際会議場
    • Year and Date
      2015-06-27
    • Related Report
      2015 Annual Research Report
  • [Presentation] 二重N-混乱ヘキサフィリン(1,1,1,1,1,0)銅二核錯体の合成と物性2015

    • Author(s)
      山角和久、西村啓一、久宗穣、石田真敏、古田弘幸
    • Organizer
      第52回化学関連支部合同九州大会
    • Place of Presentation
      北九州国際会議場
    • Year and Date
      2015-06-27
    • Related Report
      2015 Annual Research Report
  • [Presentation] FORMATION OF STABLE ORGANIC RADICAL SPECIES BASED ON BIS-PD COMPLEX OF DOUBLY N-CONFUSED HEXAPHYRIN2014

    • Author(s)
      Hisamune, Yutaka; Nishimura, Keiichi; Ishida, Masaroshi; Furuta, Hiroyuki
    • Organizer
      8th Singapore International Chemistry Conference
    • Place of Presentation
      Singapore
    • Year and Date
      2014-12-14 – 2014-12-17
    • Related Report
      2014 Research-status Report
  • [Presentation] SYNTHESIS AND PHOTOPHYSICAL PROPERTIES OF DOUBLY N-CONFUSED HEXAPHYRIN BIS METAL COMPLEXES2014

    • Author(s)
      Ogasahara, Koki; Gokulnath, Sabapathi; Ishida, Masatoshi; Furuta, Hiroyuki
    • Organizer
      8th Singapore International Chemistry Conference
    • Place of Presentation
      Singapore
    • Year and Date
      2014-12-14 – 2014-12-17
    • Related Report
      2014 Research-status Report
  • [Presentation] MULTIPLE REDOX AND ELECTRONIC STATES OF PORPHYRINOID MACROCYCLES: STRUCTURE-PROPERTY RELATIONSHIP BETWEEN AROMATIC, ANTIAROMATIC AND NONAROMATIC RADICAL SPECIES2014

    • Author(s)
      MASATOSHI ISHIDA, DONGHO KIM, JONATHAN L. SESSLER, HIROYUKI FURUTA
    • Organizer
      8th Singapore International Chemistry Conference
    • Place of Presentation
      Singapore
    • Year and Date
      2014-12-14 – 2014-12-17
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] Stabilization of Organic Radical in the Bis-Pd Complexes of Doubly N-Confused Hexaphyrin(1.1.1.1.1.0)2014

    • Author(s)
      Yutaka Hisamune, Keiichi Nishimura, Masatoshi Ishida, Hiroyuki Furuta
    • Organizer
      Curved Organic π-Molecules and Materials
    • Place of Presentation
      京都
    • Year and Date
      2014-10-19 – 2014-10-21
    • Related Report
      2014 Research-status Report
  • [Presentation] 二重N-混乱[26]ヘキサフィリン二核金属錯体の合成と光学特性2014

    • Author(s)
      小笠原光紀、Gokulnath Sabapathi、石田真敏、古田弘幸
    • Organizer
      第31 回有機合成化学セミナー
    • Place of Presentation
      福岡
    • Year and Date
      2014-09-17 – 2014-09-19
    • Related Report
      2014 Research-status Report
  • [Presentation] 小笠原光紀、Gokulnath Sabapathi、石田真敏、古田弘幸2014

    • Author(s)
      二重N-混乱[26]ヘキサフィリン二核金属錯体の合成と光学特性
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      仙台
    • Year and Date
      2014-09-07 – 2014-09-09
    • Related Report
      2014 Research-status Report
  • [Presentation] Synthesis and Metallation of Trans-Doubly N-Confused Isophlorin bearing Arylthio Groups2014

    • Author(s)
      Jiaying Yan, Makoto Takakusaki, Masatoshi Ishida, Hiroyuki Furuta
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      仙台
    • Year and Date
      2014-09-07 – 2014-09-09
    • Related Report
      2014 Research-status Report
  • [Presentation] 二重N-混乱ヘキサフィリンパラジウム二核錯体を基体とする安定有機中性ラジカル種の生成2014

    • Author(s)
      久宗穣、西村啓一、石田真敏、古田弘幸
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      仙台
    • Year and Date
      2014-09-07 – 2014-09-09
    • Related Report
      2014 Research-status Report
  • [Presentation] N-混乱フロリンの合成と物性2014

    • Author(s)
      坂下竜一・仲原健介・大須賀篤弘・石田真敏・古田弘幸
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      仙台
    • Year and Date
      2014-09-07
    • Related Report
      2014 Research-status Report
  • [Presentation] 二重N-混乱[26]ヘキサフィリン二核金属錯体の合成2014

    • Author(s)
      小笠原光紀、Gokulnath Sabapathi、石田真敏、古田弘幸
    • Organizer
      第51回化学関連支部合同九州大会
    • Place of Presentation
      北九州
    • Year and Date
      2014-06-28
    • Related Report
      2014 Research-status Report
  • [Presentation] N-連結コロールイリジウム(III)錯体の合成と光物性2014

    • Author(s)
      石川喬浩、川部泰典、石田真敏、戸叶基樹、古田弘幸
    • Organizer
      第51回化学関連支部合同九州大会
    • Place of Presentation
      北九州
    • Year and Date
      2014-06-28
    • Related Report
      2014 Research-status Report
  • [Presentation] 楊雨峰、晏佳エイ、高草木誠、石田真敏、古田弘幸2014

    • Author(s)
      トランス二重N-混乱イソフロリンとその金属錯体の合成と性質
    • Organizer
      第51回化学関連支部合同九州大会
    • Place of Presentation
      北九州
    • Year and Date
      2014-06-28
    • Related Report
      2014 Research-status Report
  • [Presentation] β-Functionalized Push-Pull Structured Porphyrin Sensitizers for Dye-sensitized Solar Cells2014

    • Author(s)
      Masatoshi Ishida, Daesub Hwang, Honathan L. Sessler, Dongho Kim
    • Organizer
      8th International Conference on Porphyrins and Phthalocyanines
    • Place of Presentation
      Istanbul
    • Year and Date
      2014-06-23 – 2014-06-29
    • Related Report
      2014 Research-status Report
  • [Presentation] Synthesis and Properties of Trans Doubly N-Confused Porphyrins and Their Metal Complexes2014

    • Author(s)
      Jiaying Yan, Makoto Takakusaki, Masatoshi Ishida, Bao Zhang, Yaqing Feng ,Hiroyuki Furuta
    • Organizer
      8th International Conference on Porphyrins and Phthalocyanines
    • Place of Presentation
      Istanbul
    • Year and Date
      2014-06-23 – 2014-06-29
    • Related Report
      2014 Research-status Report
  • [Book] Chemical Science of pi-Electron Systems2015

    • Author(s)
      Akasaka, T., Osuka, A., Fukuzumi, S., Kandori, H., Aso, Y.
    • Total Pages
      777
    • Publisher
      Springer
    • Related Report
      2015 Annual Research Report

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Published: 2014-04-04   Modified: 2022-02-01  

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