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2013 Fiscal Year Final Research Report

Multicolor Macromolecular Architectures by Multiple Click Reactions

Research Project

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Project/Area Number 22685023
Research Category

Grant-in-Aid for Young Scientists (A)

Allocation TypeSingle-year Grants
Research Field Polymer/Textile materials
Research InstitutionTokyo Institute of Technology

Principal Investigator

MICHINOBU Tsuyoshi  東京工業大学, 理工学研究科, 准教授 (80421410)

Project Period (FY) 2010-04-01 – 2014-03-31
Keywords高分子合成 / 合成化学 / クリックケミストリー / 色彩化学
Research Abstract

A wide variety of colorful organic polymers are synthesized by using high-yielding addition reactions between electron-rich alkynes and cyano-acceptors. The three primary colors of red, yellow, and blue are successfully constructed, and accordingly, it is thought that this new synthetic method for producing polymer-based organic dyes and pigments is highly useful in industry. Also, the combined use of other efficient addition reactions allows for the production of complex macromolecular architectures in remarkably high yields. Furthermore, when cyano-acceptors are added to the electron-rich alkynes integrated into conjugated polymers, the energy levels of the precursor polymers are lowered. This result suggests the conversion of the polymer characteristics from p-type into n-type semiconductors.

  • Research Products

    (53 results)

All 2014 2013 2012 2011 2010 Other

All Journal Article (26 results) (of which Peer Reviewed: 26 results) Presentation (23 results) Book (3 results) Remarks (1 results)

  • [Journal Article] Novel Design of Organic Donor-Acceptor Dyes without Carboxylic Acid Anchoring Groups for Dye-Sensitized Solar Cells2014

    • Author(s)
      T. Michinobu, N. Satoh, J. Cai, Y. Li, L. Han
    • Journal Title

      J. Mater. Chem. C

      Volume: Vol.2, No.17 Pages: 3367-3372

    • DOI

      10.1039/C3TC32165G

    • Peer Reviewed
  • [Journal Article] Attempted Inversion of Semiconducting Features of Platinum Polyyne Polymers : A New Approach for All-Polymer Solar Cells2013

    • Author(s)
      Y. Yuan, T. Michinobu, J. Oguma, T. Kato, K. Miyake
    • Journal Title

      Macromol. Chem. Phys

      Volume: Vol.214, No.13 Pages: 1465-1472

    • DOI

      10.1002/macp.201300245

    • Peer Reviewed
  • [Journal Article] イオン認識能を有する機能性高分子のクリック合成2013

    • Author(s)
      道信剛志
    • Journal Title

      有機合成化学協会誌

      Volume: Vol.71, No.2 Pages: 149-157

    • DOI

      10.5059/yukigoseikyokaishi.71.149

    • Peer Reviewed
  • [Journal Article] Polymeric Ion Sensors with Multiple Detection Modes Achieved by a New Type of Click Chemistry Reactions2013

    • Author(s)
      T. Michinobu, Y. Li, T. Hyakutake
    • Journal Title

      Phys. Chem. Chem. Phys

      Volume: Vol.15, No.8 Pages: 2623-2631

    • DOI

      10.1039/c2cp43203j

    • Peer Reviewed
  • [Journal Article] Sequential and Click-Type Postfunctionalization of Regioregular Poly(3-hexylthiophene) for Realization of n-Doped Multiplet State2013

    • Author(s)
      Y. Yuan, W. Choi, H. Nishide, T. Michinobu
    • Journal Title

      Chem. Sci

      Volume: Vol.4, No.1 Pages: 345-350

    • DOI

      10.1039/c2sc21334f

    • Peer Reviewed
  • [Journal Article] Synthesis and Postfunctionalization of Rod-Coil Diblock and Coil-Rod-Coil Triblock Copolymers Composed of Poly(3-hexylthiophene) and Poly(4-(4' -N, N-dihexylaminophenylethynyl)styre ne) Segments2012

    • Author(s)
      H. Fujita, T. Michinobu, M. Tokita, M. Ueda, T. Higashihara
    • Journal Title

      Macromolecules

      Volume: Vol.45, No.24 Pages: 9643-9656

    • DOI

      10.1021/ma301692b

    • Peer Reviewed
  • [Journal Article] Colorimetric Sensing of Cations and Anions by Clicked Polystyrenes Bearing Side Chain Donor-Acceptor Chromophores2012

    • Author(s)
      Y. Li, M. Ashizawa, S. Uchida, T. Michinobu
    • Journal Title

      Polym. Chem

      Volume: Vol.3, No.8 Pages: 1996-2005

    • DOI

      10.1039/c2py20230a

    • Peer Reviewed
  • [Journal Article] Effects of Click Postfunctionalization on Thermal Stability and Field Effect Transistor Performances of Aromatic Polyamines2012

    • Author(s)
      T. Michinobu, C. Seo, K. Noguchi, T. Mori
    • Journal Title

      Polym. Chem

      Volume: Vol.3, No.6 Pages: 1427-1435

    • DOI

      10.1039/c2py20079a

    • Peer Reviewed
  • [Journal Article] Construction of Donor-Acceptor Chromophores in Platinum Polyyne Polymer by [2+2] Cycloaddition or Organic Acceptor2012

    • Author(s)
      Y. Yuan, T. Michinobu
    • Journal Title

      Macromol. Chem. Phys

      Volume: Vol.213, No.20 Pages: 2114-2119

    • DOI

      10.1002/macp.201200316

    • Peer Reviewed
  • [Journal Article] Multi-coloration of polyurethane derivatives through click postfunctionalization, electrochemical oxidation, and Ag+ ion complexation2012

    • Author(s)
      Y. Li, T. Michinobu
    • Journal Title

      J. Mater. Chem

      Volume: Vol.22, No.19 Pages: 9513-9521

    • DOI

      10.1039/C2JM30298E

    • Peer Reviewed
  • [Journal Article] Click Synthesis and Reversible Electrochromic Behaviors of Novel Polystyrenes Bearing Aromatic Amine Units2012

    • Author(s)
      Y. Li, T. Michinobu
    • Journal Title

      J. Polym. Sci., Part A : Polym. Chem

      Volume: Vol.50, No.11 Pages: 2111-2120

    • DOI

      10.1002/pola.25990

    • Peer Reviewed
  • [Journal Article] Synthesis and Photovoltaic Properties of 1, 8-Carbazole-Based Donor-Acceptor Type Conjugated Polymers2012

    • Author(s)
      H. Fujita, T. Michinobu
    • Journal Title

      Macromol. Chem. Phys

      Volume: Vol.213, No.4 Pages: 447-457

    • DOI

      10.1002/macp.201100591

    • Peer Reviewed
  • [Journal Article] A Novel Polymeric Chemosensor : Dual Colorimetric Detection of Metal Ions Through Click Synthesis2011

    • Author(s)
      Y. Li, M. Ashizawa, S. Uchida, T. Michinobu
    • Journal Title

      Macromol. Rapid Commun

      Volume: Vol.32, No.22 Pages: 1804-1808

    • DOI

      10.1002/marc.201100397

    • Peer Reviewed
  • [Journal Article] Multicolor Emission and Thin Film Transistor Properites of 1, 8-Diethynylcarbazole-Based Conjugated Copolymers2011

    • Author(s)
      T. Michinobu, H. Osako, C. Seo, K. Murata, T. Mori, K. Shigehara
    • Journal Title

      Polymer

      Volume: Vol.52, No.25 Pages: 5756-5763

    • DOI

      10.1016/j.polymer.2011.10.028

    • Peer Reviewed
  • [Journal Article] Electrical Memory Characteristics of Nitrogen-Linked Poly(2, 7-carbazole)s2011

    • Author(s)
      S. G. Hahm, T. J. Lee, D. M. Kim, W. Kwon, Y.-K. Ko, T. Michinobu, M. Ree
    • Journal Title

      J. Phys. Chem. C

      Volume: Vol.115, No.44 Pages: 21954-21962

    • DOI

      10.1021/jp207211e

    • Peer Reviewed
  • [Journal Article] Photochemical control of a highly efficient addition reaction between electron-rich alkynes and tetracyanoethylene2011

    • Author(s)
      M. Morimoto, K. Murata, T. Michinobu
    • Journal Title

      Chem. Commun

      Volume: Vol.47, No.35 Pages: 9819-9821

    • DOI

      10.1039/c1cc13476k

    • Peer Reviewed
  • [Journal Article] High-Yielding Alkyne-Tetracyanoethylene Addition Reactions : A Powerful Tool for Analyzing Alkyne-Linked Conjugated Polymer Structures, Macromol2011

    • Author(s)
      H. Fujita, K. Tsuboi, T. Michinobu
    • Journal Title

      Chem. Phys

      Volume: Vol.212, No.16 Pages: 1785-1766

    • DOI

      10.1002/macp.201100198

    • Peer Reviewed
  • [Journal Article] Oxygen Permeability Change of Polyphenylacetylene Derivatives by Postfunctional TCNE Addition2011

    • Author(s)
      Y. Li, T. Hyakutake, T. Michinobu
    • Journal Title

      Chem. Lett

      Volume: Vol.40, No.6 Pages: 570-572

    • DOI

      10.1246/cl.2011.570

    • Peer Reviewed
  • [Journal Article] Adapting semiconducting polymer doping techniques to create new types of click postfunctionalization2011

    • Author(s)
      T. Michinobu
    • Journal Title

      Chem. Soc. Rev

      Volume: Vol.40, No.5 Pages: 2306-2316

    • DOI

      10.1039/c0cs00205d

    • Peer Reviewed
  • [Journal Article] Application of Alkyne-TCNQ Addition Reaction to Polymerization2011

    • Author(s)
      Y. Washino, T. Michinobu
    • Journal Title

      Macromol. Rapid Commun

      Volume: Vol.32, No.8 Pages: 644-648

    • DOI

      10.1002/marc.201100025

    • Peer Reviewed
  • [Journal Article] Creation of persistent charge-transfer interactions in TCNQ polyester2011

    • Author(s)
      Y. Washino, K. Murata, M. Ashizawa, S. Kawauchi, T. Michinobu
    • Journal Title

      Polym. J

      Volume: Vol. 43, No. 4 Pages: 364-369

    • DOI

      10.1038/pj.2011.2

    • Peer Reviewed
  • [Journal Article] Microwave-Assisted TCNE/TCNQ Addition to Poly(thienyleneethynylene) Derivative for Construction of Donor-Acceptor Chromophores2011

    • Author(s)
      Y. Yuan, T. Michinobu, M. Ashizawa, T. Mori
    • Journal Title

      J. Polym. Sci., Part A : Polym. Chem

      Volume: Vol.49, No.4 Pages: 1013-1020

    • DOI

      10.1002/pola.24515

    • Peer Reviewed
  • [Journal Article] Energy Level Tuning of Polythiophene Derivative by Click Chemistry-Type Post-Functionalization of Side Chain Alkynes2011

    • Author(s)
      Y. Yuan, T. Michinobu
    • Journal Title

      J. Polym. Sci., Part A : Polym. Chem

      Volume: Vol.49, No.1 Pages: 225-233

    • DOI

      10.1002/pola.24443

    • Peer Reviewed
  • [Journal Article] One-Step Synthesis of Ladder-Type Fused Poly(benzopentalene) Derivatives with Tunable Energy Levels by Variable Substituents2011

    • Author(s)
      D. Wang, T. Michinobu
    • Journal Title

      J. Polym. Sci., Part A : Polym. Chem

      Volume: Vol.49, No.1 Pages: 72-81

    • DOI

      10.1002/pola.24419

    • Peer Reviewed
  • [Journal Article] Click Synthesis of Donor-Acceptor Type Aromatic Polymers2010

    • Author(s)
      T. Michinobu
    • Journal Title

      Pure Appl. Chem

      Volume: Vol.82, No.4 Pages: 1001-1009

    • DOI

      10.1351/PAC-CON-09-09-09

    • Peer Reviewed
  • [Journal Article] Double Click Synthesis and Second-Order Nonlinearities of Polystyrenes Bearing Donor-Acceptor Chromophores2010

    • Author(s)
      Y. Li, K. Tsuboi, T. Michinobu
    • Journal Title

      Macromolecules

      Volume: Vol.43, No.12 Pages: 5277-5286

    • DOI

      10.1021/ma100869m

    • Peer Reviewed
  • [Presentation] Covalently-Bonded Layer-by-Layer Thin Films by High-Yielding Alkyne-Acceptor Addition Reactions2013

    • Author(s)
      T. Michinobu, H. Fujita
    • Organizer
      第62回高分子討論会
    • Place of Presentation
      金沢大学
    • Year and Date
      2013-09-12
  • [Presentation] クリックケミストリーを用いた高分子の機能化とセンサー特性2013

    • Author(s)
      道信剛志, 百武壮
    • Organizer
      平成25年度繊維学会秋季研究発表会
    • Place of Presentation
      金沢大学
    • Year and Date
      2013-09-12
  • [Presentation] ポリ(3-ヘキシルチオフェン)から成るロッド‐コイル型ブロック共重合体の合成と有機薄膜太陽電池への応用2013

    • Author(s)
      藤田弘幸, 道信剛志, 戸木田雅利, 上田充, 東原知哉
    • Organizer
      平成25年度繊維学会年次大会
    • Place of Presentation
      タワーホール船堀
    • Year and Date
      2013-06-12
  • [Presentation] Chemosensor and Photovoltaic Applications of Polymer-Based Organic Donor-Acceptor Dyes2013

    • Author(s)
      T. Michinobu
    • Organizer
      The Polymer Society of Korea Spring Meeting
    • Place of Presentation
      Daejeon (Korea)
    • Year and Date
      2013-04-12
  • [Presentation] Click synthesis of novel biomass-based polymers from lignin-derived stable metabolic intermediate2012

    • Author(s)
      T. Michinobu
    • Organizer
      E-MRS 2012 Fall Meeting
    • Place of Presentation
      Warsaw Univ. Technol. (Poland)
    • Year and Date
      2012-09-20
  • [Presentation] Covalently Bonded Layer-by-Layer Films by High-Yielding Addition Reaction between Electron-Rich Alkynes and Tetracyanoquinodimethane2012

    • Author(s)
      H. Fujita, T. Michinobu
    • Organizer
      244th ACS National Meeting
    • Place of Presentation
      Philadelphia (USA)
    • Year and Date
      2012-08-23
  • [Presentation] Click Synthesis of Low Band Gap Semiconducting Polymers2012

    • Author(s)
      H. Fujita, T. Michinobu
    • Organizer
      244th ACS National Meeting
    • Place of Presentation
      Philadelphia (USA)
    • Year and Date
      2012-08-19
  • [Presentation] Redox-active multilayer thin films by alkyne-acceptor click chemistry2012

    • Author(s)
      T. Michinobu, H. Fujita
    • Organizer
      14th International Conference on Organized Molecular Films
    • Place of Presentation
      Paris (France)
    • Year and Date
      2012-07-13
  • [Presentation] 高い立体規則性を有するポリチオフェン誘導体の還元とポリアニオンラジカルの基底状態に関する研究2012

    • Author(s)
      道信剛志, 原宇平, 山田亮, 川内進
    • Organizer
      平成24年度繊維学会年次大会
    • Place of Presentation
      タワーホール船堀
    • Year and Date
      2012-06-08
  • [Presentation] 高分子の化学修飾によるイオン認識能の付与2012

    • Author(s)
      道信剛志, 李永榮
    • Organizer
      平成24年度繊維学会年次大会
    • Place of Presentation
      タワーホール船堀
    • Year and Date
      2012-06-06
  • [Presentation] Polystyrenes Bearing Donor-Acceptor Chromophores as Colorimetric Probe for Anions and Cations2012

    • Author(s)
      T. Michinobu, Y. Li
    • Organizer
      第61回高分子学会年次大会
    • Place of Presentation
      パシフィコ横浜
    • Year and Date
      2012-05-31
  • [Presentation] Postfunctionalization of P3HT : Regioregular and Narrow Band Gap Polythiophenes2011

    • Author(s)
      Y. Yuan, T. Michinobu
    • Organizer
      The 12th Pacific Polymer Conference
    • Place of Presentation
      Jeju (Korea)
    • Year and Date
      2011-11-16
  • [Presentation] Double click syntheses of highly-colored polymers2011

    • Author(s)
      T. Michinobu, Y. Li, Y. Washino
    • Organizer
      The 12th Pacific Polymer Conference
    • Place of Presentation
      Jeju (Korea)
    • Year and Date
      2011-11-16
  • [Presentation] Luminescent sensory polymer coating for crack inspection2011

    • Author(s)
      T. Hyakutake, I. Nishizaki, T. Michinobu
    • Organizer
      The 12th Pacific Polymer Conference
    • Place of Presentation
      Jeju (Korea)
    • Year and Date
      2011-11-15
  • [Presentation] ポリチオフェン誘導体のポスト機能化による電子状態の変化2011

    • Author(s)
      道信剛志, 原宇平
    • Organizer
      第60回高分子討論会
    • Place of Presentation
      岡山大学
    • Year and Date
      2011-09-29
  • [Presentation] Oxygen permeability control of polyphenylacetylene derivatives by postfunctionalization using alkyne-TCNE click chemistry2011

    • Author(s)
      Y. Li, T. Hyakutake, T. Michinobu
    • Organizer
      242nd ACS National Meeting
    • Place of Presentation
      Denver (USA)
    • Year and Date
      2011-08-29
  • [Presentation] Origin of Second-Order Nonlinear Optical Effects of Nonpoled Donor-Acceptor Chromophores on Surface2010

    • Author(s)
      T. Michinobu, Y. Li, Y. Washino, K. Murata, K. Tsuboi
    • Organizer
      International Symposium on Optical Memory 2010
    • Place of Presentation
      Taiwan
    • Year and Date
      2010-10-26
  • [Presentation] ラダー型共役高分子の一段階合成とポスト機能化2010

    • Author(s)
      道信剛志, 王冬
    • Organizer
      第59回高分子討論会
    • Place of Presentation
      北海道大学
    • Year and Date
      2010-09-15
  • [Presentation] Click Chemistry-Type Postfunctionalization of Aromatic Polymers for Organic Electronic Applications2010

    • Author(s)
      T. Michinobu
    • Organizer
      MACRO2010
    • Place of Presentation
      Glasgow (UK)
    • Year and Date
      2010-07-13
  • [Presentation] Click-Type Postfunctionalization of Aromatic Polymers2010

    • Author(s)
      T. Michinobu
    • Organizer
      ICSM2010
    • Place of Presentation
      京都国際会議場
    • Year and Date
      2010-07-06
  • [Presentation] N-Type Semiconducting Polythiophene Derivatives Prepared by Click-Type Postfunctionalization2010

    • Author(s)
      Y. Yuan, C. Seo, J.-i. Inoue, T. Mori, T. Michinobu
    • Organizer
      ICSM2010
    • Place of Presentation
      京都国際会議場
    • Year and Date
      2010-07-05
  • [Presentation] ラダー型共役高分子の一段階合成と性質2010

    • Author(s)
      道信剛志, 王冬
    • Organizer
      平成22年度繊維学会年次大会
    • Place of Presentation
      タワーホール船堀
    • Year and Date
      2010-06-18
  • [Presentation] クリックケミストリーによる新規囗共役高分子の開発2010

    • Author(s)
      道信剛志
    • Organizer
      第59回高分子学会年次大会
    • Place of Presentation
      パシフィコ横浜
    • Year and Date
      2010-05-27
  • [Book] Polymer Ion Sensors Based on Intramolecular Charge-Transfer Interactions, in Optical Properties of Functional Polymers and Nano Engineering Applications, V. Jain, A. Kokil Eds2014

    • Author(s)
      T. Michinobu, T. Hyakutake
    • Publisher
      CMC Press - Taylor & Francis(印刷中)
  • [Book] All-Polymer Solar Cells, in Organometallics for Energy Conversion, R. W. Y. Wong Ed2014

    • Author(s)
      T. Michinobu
    • Publisher
      Springer(印刷中)
  • [Book] アルキンとシアノ基含有アクセプター間のClick 反応, in クリックケミストリー -基礎から実用まで-, 高田十志和, 小山靖人, 深瀬浩一編2014

    • Author(s)
      道信剛志
    • Publisher
      シーエムシー社(印刷中)
  • [Remarks]

    • URL

      http://www.op.titech.ac.jp/lab/michinobu/jp/index.html

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Published: 2015-07-16  

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