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Synthesis of pi-Extended Helical Aromatic Compounds and Investigation on Their Chiral Molecular Functions

Research Project

Project/Area Number 18K05077
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
Research InstitutionKyoto University

Principal Investigator

Hirose Takashi  京都大学, 化学研究所, 准教授 (30626867)

Project Period (FY) 2018-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2020: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2019: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2018: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywordsヘリセン / π拡張 / キラリティー / 円二色性 / 分子バネ / 単結晶構造解析 / 量子化学計算 / 単結晶構造 / 分子ワイヤー / 励起状態ダイナミクス / 中性ラジカル / エナンチオマー分離型 / カラムナー構造 / らせん反転 / 分子ばね定数 / 芳香族性 / 過渡吸収分光 / 芳香族化合物 / らせん構造 / π共役
Outline of Final Research Achievements

In this study, we have synthesized π-extended helical compounds and investigated their characteristic molecular functions derived from their chiral molecular structure.
The homogeneously π-extended helicenes, that is the helical analog of hexabenzocoronene, tend to have small HOMO-LUMO gap that is significantly decreases with increasing the helical length of the π-extended helicenes. We have also succeeded in the synthesis of π-expanded helical compounds with large helical diameter, which behave as a soft molecular spring with a small molecular spring constant that is ca. one-tenth of that of conventional helicenes.

Academic Significance and Societal Importance of the Research Achievements

本研究では、π拡張型およびπ伸長型らせん状化合物にユニークな物性の一般性を実験的に示すことができ、分子構造とキラルならせん構造に由来する物性との関係性についての新たな知見を得ることができた。具体的には、均一にπ拡張したらせん状分子は「世界最高レベルの優れた円偏光応答性」を示し、π伸長型らせん状分子は「高い柔軟性を持つナノスケールの分子ばね材料」としての応用が期待できることを明らかにした。

Report

(4 results)
  • 2020 Annual Research Report   Final Research Report ( PDF )
  • 2019 Research-status Report
  • 2018 Research-status Report
  • Research Products

    (30 results)

All 2021 2020 2019 2018 Other

All Journal Article (9 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 9 results,  Open Access: 2 results) Presentation (19 results) (of which Int'l Joint Research: 6 results,  Invited: 15 results) Remarks (2 results)

  • [Journal Article] Tuning Transition Electric and Magnetic Dipole Moments: [7]Helicenes Showing Intense Circularly Polarized Luminescence2021

    • Author(s)
      Kubo Hiromu、Hirose Takashi、Nakashima Takuya、Kawai Tsuyoshi、Hasegawa Jun-ya、Matsuda Kenji
    • Journal Title

      The Journal of Physical Chemistry Letters

      Volume: 12 Issue: 1 Pages: 686-695

    • DOI

      10.1021/acs.jpclett.0c03174

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Donor-Acceptor Type [5]Helicene Derivative with Strong Circularly Polarized Luminescence2021

    • Author(s)
      Kubo Hiromu、Hirose Takashi、Shimizu Daiki、Matsuda Kenji
    • Journal Title

      Chemistry Letters

      Volume: 50 Issue: 4 Pages: 804-807

    • DOI

      10.1246/cl.200913

    • NAID

      130008025830

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Circularly Polarized Luminescence Designed from Molecular Orbitals: A Figure-Eight-Shaped [5]Helicene Dimer with D2 Symmetry2020

    • Author(s)
      Kubo Hiromu、Shimizu Daiki、Hirose Takashi、Matsuda Kenji
    • Journal Title

      Organic Letters

      Volume: 22 Issue: 23 Pages: 9276-9281

    • DOI

      10.1021/acs.orglett.0c03506

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Self-assembly of photochromic diarylethene-peptide conjugates stabilized by β-sheet formation at the liquid/graphite interface2019

    • Author(s)
      Nobuhiko Nishitani, Takashi Hirose, Kenji Matsuda
    • Journal Title

      Chemical Communications

      Volume: 55 Issue: 35 Pages: 5099-5102

    • DOI

      10.1039/c9cc02093d

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Fabrication of Robust Spatially Resolved Photochromic Patterns on Cellulose Papers by Covalent Printing for Anticounterfeiting Applications2019

    • Author(s)
      Bretel Guillaume、Le Grognec Erwan、Jacquemin Denis、Hirose Takashi、Matsuda Kenji、Felpin Fran?ois-Xavier
    • Journal Title

      ACS Applied Polymer Materials

      Volume: 1 Issue: 5 Pages: 1240-1250

    • DOI

      10.1021/acsapm.9b00266

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] The polymorphism of porphyrin 2D assemblies at the liquid-graphite interface: the effect of a polar solvent additive and a flexible spacer on the face-on and edge-on type molecular arrangements2019

    • Author(s)
      Adachi Kenya、Hirose Takashi、Matsuda Kenji
    • Journal Title

      Chemical Communications

      Volume: 55 Issue: 60 Pages: 8836-8839

    • DOI

      10.1039/c9cc02579k

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] 2-D Self-assembly of Alkyl-substituted Oligophenylene Derivatives at the Liquid/Solid Interface: Influence of Core Size and Hydrogen Bonds on the Nucleation?Elongation Process2019

    • Author(s)
      Nishitani Nobuhiko、Hirose Takashi、Matsuda Kenji
    • Journal Title

      Chemistry Letters

      Volume: 48 Issue: 3 Pages: 253-256

    • DOI

      10.1246/cl.180944

    • NAID

      130007607631

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Self-assembly of metal-organic polyhedra into supramolecular polymers with intrinsic microporosity2018

    • Author(s)
      Carne-Sanchez Arnau、Craig Gavin A.、Larpent Patrick、Hirose Takashi、Higuchi Masakazu、Kitagawa Susumu、Matsuda Kenji、Urayama Kenji、Furukawa Shuhei
    • Journal Title

      Nature Communications

      Volume: 9 Issue: 1 Pages: 2506-2506

    • DOI

      10.1038/s41467-018-04834-0

    • NAID

      120006491831

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Synthesis of a Helical Analogue of Kekulene: A Flexible π-Expanded Helicene with Large Helical Diameter Acting as a Soft Molecular Spring2018

    • Author(s)
      Nakakuki Yusuke、Hirose Takashi、Matsuda Kenji
    • Journal Title

      Journal of the American Chemical Society

      Volume: 140 Issue: 45 Pages: 15461-15469

    • DOI

      10.1021/jacs.8b09825

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Presentation] Management of Chiroptical Properties using Helicene-based Molecules2020

    • Author(s)
      Takashi Hirose
    • Organizer
      Online Seminar at prof. Guido Clever's Research Group, Technische Universitat Dortmund (TU Dortmund)
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] π拡張型らせん状化合物の合成と物性開拓2020

    • Author(s)
      廣瀬崇至
    • Organizer
      第五回 "光"機到来! Qコロキウム
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Presentation] Tuning the Transition Electric and Magnetic Dipole Moments: [7]Helicenes Showing Intense Circularly Polarized Luminescence2020

    • Author(s)
      Takashi Hirose
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Annual Research Report
    • Invited
  • [Presentation] π拡張型らせん状芳香族化合物の合成と分子機能の評価2019

    • Author(s)
      廣瀬崇至
    • Organizer
      第7回慶應有機化学若手シンポジウム
    • Related Report
      2019 Research-status Report
    • Invited
  • [Presentation] らせん状π共役化合物のπ拡張と物性評価2019

    • Author(s)
      廣瀬崇至
    • Organizer
      第40回光化学若手の会
    • Related Report
      2019 Research-status Report
    • Invited
  • [Presentation] キラリティーを持つ分子集合体の光機能評価2019

    • Author(s)
      廣瀬崇至
    • Organizer
      第2回令和元年度化学研究所イブニングセミナー
    • Related Report
      2019 Research-status Report
    • Invited
  • [Presentation] Photophysical and Mechanical Properties of π-Extended Helicenes2019

    • Author(s)
      Takashi Hiorse
    • Organizer
      TU/e Meijer Symposium 2020
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] 分子間相互作用および分子軌道の制御に基づく高発光性分子の設計2019

    • Author(s)
      廣瀬崇至
    • Organizer
      日本化学会第100春季年会(講演予稿集)
    • Related Report
      2019 Research-status Report
    • Invited
  • [Presentation] Synthesis of Homogeneously π-Extended Helical Aromatic Compounds2019

    • Author(s)
      Takashi Hirose, Yusuke Nakakuki, Kenji Matsuda
    • Organizer
      The 18th International Symposium on Novel Aromatic Compounds (ISNA-18)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Development of Molecular Functions Based on Helically Twisted Polycyclic Aromatic Hydrocarbons2018

    • Author(s)
      Takashi Hirose
    • Organizer
      IRCCS The 2nd International Symposium "New Future by Chemical Synthesis and Energy Materials"
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] π拡張型らせん状分子のキラル分光特性と分子バネ特性2018

    • Author(s)
      廣瀬崇至
    • Organizer
      研究室講演会 (千葉大学グローバルプロミネント研究基幹 矢貝史樹研究室)
    • Related Report
      2018 Research-status Report
    • Invited
  • [Presentation] π拡張型らせん状芳香族化合物の合成と物性評価2018

    • Author(s)
      廣瀬崇至
    • Organizer
      物質科学セミナー (筑波大学数理物質系 山本洋平研究室)
    • Related Report
      2018 Research-status Report
    • Invited
  • [Presentation] キラリティーを持つ多環芳香族化合物の合成と分子機能2018

    • Author(s)
      廣瀬崇至
    • Organizer
      化学科講演会 (静岡大学理学部 山中正道研究室)
    • Related Report
      2018 Research-status Report
    • Invited
  • [Presentation] π-Extended Polycyclic Aromatic Hydrocarbons Having Axial or Helical Chirality2018

    • Author(s)
      Takashi Hirose
    • Organizer
      International Congress on Pure & Applied Chemistry Langkawi 2018 (ICPAC Langkawi)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] キラリティーを持つ大きなπ共役系分子の合成と分光特性評価2018

    • Author(s)
      廣瀬崇至
    • Organizer
      第5回π造形科学若手研究会
    • Related Report
      2018 Research-status Report
    • Invited
  • [Presentation] π拡張型キラル化合物の合成と分光特性2018

    • Author(s)
      廣瀬崇至
    • Organizer
      第7回化学フロンティア研究会
    • Related Report
      2018 Research-status Report
    • Invited
  • [Presentation] Development of the Basic Structures of Helically Twisted Polycyclic Aromatic Hydrocarbons2018

    • Author(s)
      T. Hirose, Y. Nakakuki, K. Matsuda
    • Organizer
      The 14th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-14)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] らせん状ケクレンの合成:大きならせん径を持つ拡張ヘリセン誘導体の構造と分光特性2018

    • Author(s)
      廣瀬崇至、中莖祐介、松田建児
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] フロンティア軌道の対称性に基づく強発光性ヘリセン誘導体の設計とCPL発光特性の評価2018

    • Author(s)
      廣瀬崇至、久保拓夢、松田建児
    • Organizer
      2018年光化学討論会
    • Related Report
      2018 Research-status Report
  • [Remarks] 京都大学化学研究所構造有機化学領域webページ

    • URL

      https://www.scl.kyoto-u.ac.jp/~kouzou/member/hirose.html

    • Related Report
      2020 Annual Research Report 2019 Research-status Report
  • [Remarks] 京都大学化学研究所村田研究室webページ

    • URL

      https://www.scl.kyoto-u.ac.jp/~kouzou/member/hirose.html

    • Related Report
      2018 Research-status Report

URL: 

Published: 2018-04-23   Modified: 2022-01-27  

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