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Monomer/oigomer switching upon reversible formation of stable 1,4-diyl dicationic species

Research Project

Project/Area Number 16K13968
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Functional solid state chemistry
Research InstitutionHokkaido University

Principal Investigator

Takanori Suzuki  北海道大学, 理学研究院, 教授 (70202132)

Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2018: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2017: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2016: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Keywords酸化還元 / カチオン / 色素 / オリゴマー / エレクトロクロミズム / 近赤外吸収 / 炭素陽イオン / 脱重合
Outline of Final Research Achievements

Dications with the butan-1,4-diyl unit are highly reactive species and thus only used the reactive intermediates. Our successful design to stabilize such species enabled us to use those class of compounds as novel dicationic dyes. Based on the ditopic-chromophore approach, their redox reactions caused novel switching between monomers and oligomers, which was established in this work based on the electrochemical analyses on a sereis of newly synthesized compounds. It is noteworthy that not only stability but also solubility in water were attained by attaching the hydrophilic substituents on the electon donating amino group.

Academic Significance and Societal Importance of the Research Achievements

シアニン色素に代表される有機π共役型カチオンは、可視領域での大きな吸収や水中での会合能など材料科学的に魅力的なモチーフであり、そのようなカチオン部位が一定の間隔で配列されたポリマーポリカチオンには、集約された状況下で発現する複合的な特性も期待されるものの、その詳細は未だに明らかにされていなかった。本研究は、そのようなa) ポリマーポリカチオンを安定な化学種として発生させる方法論を提供するばかりでなく、b)出発物となるモノマーへの可逆な脱重合が可能な系を確立した。

Report

(4 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • 2016 Research-status Report
  • Research Products

    (35 results)

All 2019 2018 2017 2016 Other

All Int'l Joint Research (2 results) Journal Article (27 results) (of which Int'l Joint Research: 5 results,  Peer Reviewed: 27 results,  Open Access: 9 results,  Acknowledgement Compliant: 6 results) Presentation (6 results) (of which Invited: 6 results)

  • [Int'l Joint Research] Nanjing University(中国)

    • Related Report
      2018 Annual Research Report
  • [Int'l Joint Research] BIO-HPC, UCAM(スペイン)

    • Related Report
      2016 Research-status Report
  • [Journal Article] Selective Formation of a Mixed‐valence State from Linearly‐bridged Oligo(aromatic diamines): Drastic Structural Change into a Folded Columnar Stack for Half‐filled Polycations**2019

    • Author(s)
      Nojo Wataru、Ishigaki Yusuke、Takeda Takashi、Akutagawa Tomoyuki、Suzuki Takanori
    • Journal Title

      Chemistry A European Journal

      Volume: - Issue: 32 Pages: 7759-7765

    • DOI

      10.1002/chem.201901272

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chiral diversification through the assembly of achiral phenylacetylene macrocycles with a two-fold bridge2019

    • Author(s)
      Katoono Ryo、Kusaka Keiichi、Saito Yuki、Sakamoto Kazuki、Suzuki Takanori
    • Journal Title

      Chemical Science

      Volume: - Issue: 18 Pages: 4782-4791

    • DOI

      10.1039/c9sc00972h

    • NAID

      120006709315

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis of the cyclohexene segment of portimine2019

    • Author(s)
      T. Saito, K. Fujiwara, Y. Kondo, U. Akiba, T. Suzuki
    • Journal Title

      Tetrahedron Letters

      Volume: 60 Issue: 4 Pages: 386-389

    • DOI

      10.1016/j.tetlet.2018.12.063

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Two-way Chromic Systems Based on Tetraarylanthraquinodimethanes: Electrochromism in Solution and Mechanofluorochromism in a Solid State.2019

    • Author(s)
      Y. Ishigaki, K. Sugawara, M. Yoshida, M. Kato, T. Suzuki
    • Journal Title

      Bull. Chem. Soc. Jpn。

      Volume: - Issue: 7 Pages: 1211-1217

    • DOI

      10.1246/bcsj.20190094

    • NAID

      130007679358

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Dual dynamic chirality generated in the assembly of three achiral rods through the three-fold twisting of a macrocycle2019

    • Author(s)
      Katoono Ryo、Sakamoto Kazuki、Suzuki Takanori
    • Journal Title

      Chemical Communications

      Volume: - Issue: 38 Pages: 5503-5506

    • DOI

      10.1039/c9cc02226k

    • NAID

      120006843069

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total synthesis of kehokorins A and B2019

    • Author(s)
      K. Fujiwara, R. Motousu, D. Sato, Y. Kondo, U. Akiba, T. Suzuki, T. Tokiwano
    • Journal Title

      Tetrahedron Letters

      Volume: 60 Issue: 18 Pages: 1299-1301

    • DOI

      10.1016/j.tetlet.2019.04.011

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Engineering of Electrochromic Materials as Activatable Probes for Molecular Imaging and Photodynamic Therapy2018

    • Author(s)
      Wu Luyan、Sun Yidan、Sugimoto Keisuke、Luo Zhiliang、Ishigaki Yusuke、Pu Kanyi、Suzuki Takanori、Chen Hong-Yuan、Ye Deju
    • Journal Title

      Journal of the American Chemical Society

      Volume: 140 Issue: 47 Pages: 16340-16352

    • DOI

      10.1021/jacs.8b10176

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Direct synthesis of aryl-annulated [c]carbazoles by gold(I)-catalysed cascade reaction of azide-diynes and arenes2018

    • Author(s)
      Yuiki Kawada, Shunsuke Ohmura, Misaki Kobayashi, Wataru Nojo, Masaki Kondo, Yuka Matsuda, Junpei Matsuoka, Shinsuke Inuki, Shinya Oishi, Chao Wang, Tatsuo Saito, Masanobu Uchiyama, Takanori Suzuki, Hiroaki Ohno
    • Journal Title

      Chem. Sci.

      Volume: 9 Issue: 44 Pages: 8416-8416

    • DOI

      10.1039/c8sc03525c

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Expandability of a long C-O bond by a scissor effect in acenaphthofuran2018

    • Author(s)
      Uchimura Yasuto、Shimajiri Takuya、Ishigaki Yusuke、Katoono Ryo、Suzuki Takanori
    • Journal Title

      Chemical Communications

      Volume: 54 Issue: 73 Pages: 10300-10303

    • DOI

      10.1039/c8cc05998e

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Molecular Wires with Controllable π-Delocalization Incorporating Redox-Triggered π-Conjugated Switching Units2018

    • Author(s)
      Nojo Wataru、Tamaoki Hitomi、Ishigaki Yusuke、Katoono Ryo、Fujiwara Kenshu、Fukushima Takanori、Suzuki Takanori
    • Journal Title

      ChemPlusChem

      Volume: ー Issue: 6 Pages: 634-642

    • DOI

      10.1002/cplu.201800341

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Transmission of Point Chirality to Axial Chirality for Strong Circular Dichroism in Triarylmethylium-o,o-dimers2018

    • Author(s)
      Suzuki Takanori、Ishigaki Yusuke、Iwai Tomohiro、Hayashi Yuki、Nagaki Aiichiro、Katoono Ryo、Fujiwara Kenshu、Yoshida Jun-ichi
    • Journal Title

      Synlett

      Volume: 29 Issue: 16 Pages: 2147-2154

    • DOI

      10.1055/s-0037-1610190

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Double bond formation based on nitroaldol reaction and radical elimination: A prototype segment connection method for the total synthesis of nigricanoside A dimethyl ester2018

    • Author(s)
      Tsunoda Takayuki、Fujiwara Kenshu、Okamoto Satoshi、Kondo Yoshihiko、Akiba Uichi、Ishigaki Yusuke、Katoono Ryo、Suzuki Takanori
    • Journal Title

      Tetrahedron Letters

      Volume: 59 Issue: 19 Pages: 1846-1850

    • DOI

      10.1016/j.tetlet.2018.03.091

    • Related Report
      2018 Annual Research Report 2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Narrower HOMO-LUMO gap attained by conformational switching through peripheral polyarylation in 1,4,5,8-tetraaza-9,10-anthraquinodimethanes2018

    • Author(s)
      Suzuki Takanori、Ishigaki Yusuke、Sugawara Kazuma、Umezawa Yu、Katoono Ryo、Shimoyama Atsushi、Manabe Yoshiyuki、Fukase Koichi、Fukushima Takanori
    • Journal Title

      Tetrahedron

      Volume: 74 Issue: 18 Pages: 2239-2244

    • DOI

      10.1016/j.tet.2018.03.041

    • Related Report
      2018 Annual Research Report 2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] An improved synthesis of the C42-C52 segment of ciguatoxin 3C2018

    • Author(s)
      Saito Takafumi、Fujiwara Kenshu、Sano Yusuke、Sato Takuto、Kondo Yoshihiko、Akiba Uichi、Ishigaki Yusuke、Katoono Ryo、Suzuki Takanori
    • Journal Title

      Tetrahedron Letters

      Volume: 59 Issue: 14 Pages: 1372-1376

    • DOI

      10.1016/j.tetlet.2018.02.052

    • Related Report
      2018 Annual Research Report 2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Enhanced circular dichroism at elevated temperatures through complexation-induced transformation of a three-layer cyclophane with dualistic dynamic helicity2018

    • Author(s)
      Katoono Ryo、Obara Yudai、Fujiwara Kenshu、Suzuki Takanori
    • Journal Title

      Chemical Science

      Volume: 9 Issue: 8 Pages: 2222-2229

    • DOI

      10.1039/c7sc05242a

    • NAID

      120006473606

    • Related Report
      2018 Annual Research Report 2017 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Supramolecular chiroptical switching of helical-sense preferences through the two-way intramolecular transmission of a single chiral source2018

    • Author(s)
      Katoono Ryo、Kusaka Keiichi、Tanaka Yuki、Fujiwara Kenshu、Suzuki Takanori
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 16 Issue: 7 Pages: 1167-1171

    • DOI

      10.1039/c7ob03057f

    • NAID

      120006558997

    • Related Report
      2018 Annual Research Report 2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Longest C-C Single Bond among Neutral Hydrocarbons with a Bond Length beyond 1.8A2018

    • Author(s)
      Ishigaki Yusuke、Shimajiri Takuya、Takeda Takashi、Katoono Ryo、Suzuki Takanori
    • Journal Title

      Chem

      Volume: 2018 Issue: 4 Pages: 795-806

    • DOI

      10.1016/j.chempr.2018.01.011

    • Related Report
      2018 Annual Research Report 2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Dynamic or undynamic chirality generated by helical arrangement of a shape-persistent ring and rod doubly bridged in a molecule2018

    • Author(s)
      Katoono Ryo、Obara Yudai、Kusaka Keiichi、Suzuki Takanori
    • Journal Title

      Chemical Communications

      Volume: 54 Issue: 7 Pages: 735-738

    • DOI

      10.1039/c7cc09485j

    • NAID

      120006549167

    • Related Report
      2018 Annual Research Report 2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] 9,10-Dihydrophenanthrene with Two Spiro(dibenzocycloheptatriene) Units: A Highly Strained Caged Hydrocarbon Exhibiting Reversible Electrochromic Behavior2017

    • Author(s)
      Ishigaki Yusuke、Hayashi Yuki、Sugawara Kazuma、Shimajiri Takuya、Nojo Wataru、Katoono Ryo、Suzuki Takanori
    • Journal Title

      Molecules

      Volume: 22 Issue: 11 Pages: 1900-1900

    • DOI

      10.3390/molecules22111900

    • NAID

      120006383818

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Stereoselecive Encapsulation for a Triarylmethylium o,o-Dimer by Natural gamma-Cyclodextrin: Origin of Chiral Recogntion For the Acially Chiral Dicationic Guest2017

    • Author(s)
      T. Suzuki, J. P. Cerón-Carrasco, H. Tamaoki, Y. Ishigaki, R. Katoono, T. Fukushima, H. Pérez-Sánchez,
    • Journal Title

      Heterocycles

      Volume: - Issue: 6 Pages: 1123-1123

    • DOI

      10.3987/com-17-13674

    • Related Report
      2017 Research-status Report 2016 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Organic Molecular Layer with High Electrochemical Bistability: Synthesis, Structure, and Properties of a Dynamic Redox System with Lipoate Units for Binding to Au(111),2017

    • Author(s)
      E. Ohta, H. Uehara, Y. Han, K. Wada, H. Noguchi, R. Katoono, Y. Ishigaki, H. Ikeda, K. Uosaki, T. Suzuki
    • Journal Title

      ChemPlusChem

      Volume: - Issue: 7 Pages: 1043-1047

    • DOI

      10.1002/cplu.201600649

    • Related Report
      2017 Research-status Report 2016 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] xidative Desulfurization of Electron-Donating 5,5,7,7-Tetraaryl-5,7-dihydrodibenzo[c,e]thiepins and the Related Heterocycles: Generation of Dicationic Dyes upon Two-Electron Oxidation2017

    • Author(s)
      T. Suzuki, T. Kuroda, H. Tamaoki, S. Higasa, T. Nehira, R. Katoono, Y. Ishigaki, K. Fujiwara, T. Fukushima, H. Yamada
    • Journal Title

      Heterocycles

      Volume: 95(2), Issue: 2 Pages: 816-829

    • DOI

      10.3987/com-16-s(s)50

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Bis(diarylethenyl)thiophenes, -bithiophenes, and -terthiophenes: A New Series of Electrochromic Systems that Exhibit a Fluorescence Response2016

    • Author(s)
      Y. Ishigaki, H. Kawai, R. Katoono, K. Fujiwara, H. Higuchi, H. Kikuchi, T. Suzuki
    • Journal Title

      Can. J. Chem.

      Volume: 95(3) Issue: 3 Pages: 243-252

    • DOI

      10.1139/cjc-2016-0222

    • Related Report
      2017 Research-status Report 2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Redox-induced conformational changes in 1,3-propylene- and m-xylylenebis[5-(10-butyl-5,10-dihydrobenzo[a]indolo[2,3-c]carbazole)]: Twin-BIC donors that form sandwich-like dimeric cations exhibiting NIR absorption2016

    • Author(s)
      T. Suzuki, W. Nojo, Y. Sakano, R. Katoono, Y. Ishigaki, H. Ohno, K. Fujiwara,
    • Journal Title

      Chem. Lett.

      Volume: 45 Issue: 7 Pages: 2582-2586

    • DOI

      10.1246/cl.160278

    • NAID

      130005253001

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Dynamic helical cyclophanes with two quadruply-bridged planes arranged in an “obverse and/or reverse” relation2016

    • Author(s)
      R. Katoono, S. Kawai, T. Suzuki
    • Journal Title

      Chem. Sci

      Volume: 7 Issue: 5 Pages: 3240-3247

    • DOI

      10.1039/c5sc04673d

    • NAID

      120006220021

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Assembly of an Axially Chiral Dynamic Redox System with a Perfluorobiphenyl Skeleton into Dumbbell- or Tripod-type Electron Donors2016

    • Author(s)
      H. Tamaoki, R. Katoono, K. Fujiwara, T. Suzuki
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 55(7) Issue: 7 Pages: 2582-2586

    • DOI

      10.1002/anie.201510935

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Planar chiral desymmetrization of a two-layered cyclophane and control of dynamic helicity through the arrangement of two nonstereogenic centers2016

    • Author(s)
      Ryo Katoono* and Takanori Suzuki
    • Journal Title

      Chemical Communications

      Volume: 52 Issue: 5 Pages: 1029-1031

    • DOI

      10.1039/c5cc09069e

    • NAID

      120005866833

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access
  • [Presentation] Studies on Dynamic Redox Systems: Construction of Record-breaking Strained Compounds and Development of Unimolecular Memory2019

    • Author(s)
      鈴木孝紀
    • Organizer
      第99回日本化学会春季年会(受賞講演)
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] 超結合:共有結合の限界を超えた化学2019

    • Author(s)
      鈴木孝紀
    • Organizer
      第99回日本化学会春季年会(特別企画)
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] 有機酸化還元系設計の愉しみ: 世界一の構造から単一分子メモリまで2018

    • Author(s)
      鈴木孝紀
    • Organizer
      日本化学会第98春季年会特別企画招待講演
    • Related Report
      2017 Research-status Report
    • Invited
  • [Presentation] Dynamic redox system that can form an organic molecular layer : Toward the realization of molecular-based data storage devices2017

    • Author(s)
      Takanori Suzuki
    • Organizer
      17th International Symposium on Novel Aromatic Compounds (ISNA-17)
    • Related Report
      2017 Research-status Report
    • Invited
  • [Presentation] Toward the realization of molecular-based data storage Devices: An apporach from the organic chemistry based on dynamic redox systems2017

    • Author(s)
      Takanori Suzuki
    • Organizer
      The 18th RIES-Hokudai International Symposium
    • Related Report
      2017 Research-status Report
    • Invited
  • [Presentation] 単一分子メモリユニットとしての動的酸化還元系:発想とプロトタイプ構築2017

    • Author(s)
      鈴木孝紀
    • Organizer
      第41回有機電子移動化学討論会
    • Related Report
      2017 Research-status Report
    • Invited

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Published: 2016-04-21   Modified: 2020-03-30  

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