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Novel Crystal Engineering Strategies for High Performance Semiconducting Thienoacenes

Research Project

Project/Area Number 17K14478
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Functional solid state chemistry
Research InstitutionInstitute of Physical and Chemical Research

Principal Investigator

WANG CHENGYUAN  国立研究開発法人理化学研究所, 創発物性科学研究センター, 特別研究員 (20772932)

Project Period (FY) 2017-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2018: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Fiscal Year 2017: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywordsβ-Alkylthionation / Thienoacene / Crystal engineering / OFETs / Thienoacenes / Alkylthionation / Packing / Molecular Orientation / Crystal Engineering / Semiconductors
Outline of Final Research Achievements

In this research project firstly efficient chemistry was established to straightforwardly introduce alkylthio groups at the β-position of various thienoacenes, through which the targeted thienoacene-based organic semiconductors were successfully developed. The packing structures of the as-synthesized materials were studied by single-crystal XRD analysis. The study revealed that by attaching certain alkylthio groups at the β-position of linear thienoacenes, the corresponding crystal structures could be generally and selectively altered into the rubrene-like packing structure, in which efficient frontier orbital overlap could be realized.
Single-crystal and thin-film OFETs were fabricated based on the as-developed materials, and some of them showed excellent performance even rivaling rubrene. The study manifested that the packing design through β-alkylthionation in thienoacenes could be a real rational material design strategy to develop high performance organic semiconductors.

Academic Significance and Societal Importance of the Research Achievements

The research project is the first systematic study of crystal engineering of thienoacenes by alkylthionation to develop high performance organic semiconductors for OFETs, which opens a new door to rationally design materials applied in organic electronics by control of intermolcular interactions.

Report

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

    (7 results)

All 2019 2018 2017

All Journal Article (2 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 2 results) Presentation (5 results) (of which Int'l Joint Research: 3 results)

  • [Journal Article] Thiacycle-fused benzo[1,2-b:4,5-b′]dithiophenes (BDTs): synthesis, packing, molecular orientation and semiconducting properties2018

    • Author(s)
      Chengyuan Wang, Hiroshi Nakamura, Hiroyoshi Sugino, Kazuo Takimiya
    • Journal Title

      Journal of Materials Chemistry C

      Volume: 6 Issue: 14 Pages: 3604-3612

    • DOI

      10.1039/c7tc05317g

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Methylthionated benzo[1,2-b:4,5-b′]dithiophenes: a model study to control packing structures and molecular orientation in thienoacene-based organic semiconductors2017

    • Author(s)
      Chengyuan Wang, Hiroshi Nakamura, Hiroyoshi Sugino, Kazuo Takimiya
    • Journal Title

      Chemical Communications

      Volume: 53 Issue: 69 Pages: 9594-9597

    • DOI

      10.1039/c7cc04998f

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Presentation] Rational Packing Design to Approach Thienoacene-based Organic Semiconductors Rivaling Rubrene2019

    • Author(s)
      Chengyuan Wang, Kazuo Takimiya
    • Organizer
      The 99th Annual Meeting of the Chemical Society of Japan
    • Related Report
      2018 Annual Research Report
  • [Presentation] Alkylthionation of Thienoacenes to Tune the Packing, Molecular Orientation & Semiconducting Properties2018

    • Author(s)
      Chengyuan Wang, Hiroshi Nakamura, Kazuo Takimiya
    • Organizer
      2018 MRS Spring Meeting & Exhibit
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Alkylthionation of Thienoacenes to Tune the Packing, Molecular Orientation & Semiconducting Properties2018

    • Author(s)
      Chengyuan Wang, Hiroshi Nakamura, Hiroyoshi Sugino, Kazuo Takimiya
    • Organizer
      The 14th International Conference on Organic Electronics
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Alkylthionation of Thienoacenes to Tune the Packing, Molecular Orientation and Semiconducting Properties2018

    • Author(s)
      Chengyuan Wang, Hiroshi Nakamura, Kazuo Takimiya
    • Organizer
      The 98th Annual Meeting of the Chemical Society of Japan
    • Related Report
      2017 Research-status Report
  • [Presentation] Alkylthionation of Thienoacenes to Tune Their Packing, Molecular Orientation and Semiconducting Properties2018

    • Author(s)
      Chengyuan Wang, Hiroshi Nakamura, Kazuo Takimiya
    • Organizer
      CEMS International Symposium on Supramolecular Chemistry & Functional Materials 2018
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research

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Published: 2017-04-28   Modified: 2020-03-30  

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