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Development and application of supramolecular systems based on the assembly of synthetic helical polymers

Research Project

Project/Area Number 21H01984
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Review Section Basic Section 35010:Polymer chemistry-related
Research InstitutionNagoya University

Principal Investigator

Ikai Tomoyuki  名古屋大学, 工学研究科, 准教授 (90402495)

Co-Investigator(Kenkyū-buntansha) 田浦 大輔  名城大学, 理工学部, 准教授 (20622450)
Project Period (FY) 2021-04-01 – 2024-03-31
Project Status Completed (Fiscal Year 2023)
Budget Amount *help
¥17,420,000 (Direct Cost: ¥13,400,000、Indirect Cost: ¥4,020,000)
Fiscal Year 2023: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2022: ¥5,980,000 (Direct Cost: ¥4,600,000、Indirect Cost: ¥1,380,000)
Fiscal Year 2021: ¥7,020,000 (Direct Cost: ¥5,400,000、Indirect Cost: ¥1,620,000)
Keywordsらせん / 超分子ポリマー / キラリティ / 高次構造 / イソシアニド
Outline of Research at the Start

本研究では、DNAやタンパク質等の生体分子の構造から学び、ラセン二次構造の配列制御という新概念を着想し、「人工ラセン分子が様々な形態で規則配列した多彩な超分子構造体」を創成する新技術の確立およびラセンと超分子の構造特性・強みを掛け合わせることで初めて生み出されるラセン超分子系に固有の新物性・卓越機能を創出し、分離、認識、触媒、情報に関連する革新的材料の創製を目指す。さらに、一方向巻きラセン高分子を半永久的に生み出すことができる不斉増殖サイクルの実現にも挑戦する。

Outline of Final Research Achievements

In this project, we developed supramolecular assemblies of synthetic polymers with secondary structures, and investigated the exploration of new properties and outstanding functions by combining the structural features of secondary structures and supramolecules. Consequently, we were the first to succeed in the emergence of a high enantioseparation ability of the contracted one-handed helical tubular ladder polymers, defect-free synthesis of a fully π-conjugated optically-active helical ladder polymer, discovery of the coordination-driven homochiral self-sorting of triptycene-based metallomacrocycles, and synthesis of the multiple expanded helicene showing a very strong circularly polarized luminescence.

Academic Significance and Societal Importance of the Research Achievements

二次構造を有する高分子に関する研究は世界中で展開されているが、二次構造と超分子の強みを掛け合わせて機能発現を目指す研究は黎明期にある。本研究を通じて、これまで実現が困難であった合目的的な高次構造の構築に基づいたキラル認識能の発現、それを利用したキラル固定相への応用、極めて優れた円偏光発光性を示すホモヘリシティを有する一連の分子郡の開発は、学術的新規性・独創性はもとより、応用面においても重要な研究成果と位置づけられる。

Report

(4 results)
  • 2023 Annual Research Report   Final Research Report ( PDF )
  • 2022 Annual Research Report
  • 2021 Annual Research Report
  • Research Products

    (58 results)

All 2024 2023 2022 2021 Other

All Int'l Joint Research (3 results) Journal Article (16 results) (of which Int'l Joint Research: 4 results,  Peer Reviewed: 16 results,  Open Access: 8 results) Presentation (34 results) (of which Int'l Joint Research: 6 results,  Invited: 8 results) Remarks (3 results) Patent(Industrial Property Rights) (2 results) (of which Overseas: 2 results)

  • [Int'l Joint Research] 国立清華大学(その他の国・地域 台湾)

    • Related Report
      2023 Annual Research Report
  • [Int'l Joint Research] アンジェ大学(フランス)

    • Related Report
      2023 Annual Research Report
  • [Int'l Joint Research] 同済大学(中国)

    • Related Report
      2023 Annual Research Report
  • [Journal Article] 2,2′‐Tethered Binaphthyl‐Embedded One‐Handed Helical Ladder Polymers: Impact of the Tether Length on Helical Geometry and Chiroptical Property2024

    • Author(s)
      Ikai Tomoyuki、Mishima Namiki、Matsumoto Takehiro、Miyoshi Sayaka、Oki Kosuke、Yashima Eiji
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 63 Issue: 10

    • DOI

      10.1002/anie.202318712

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] One‐Handed Helical Polyacetylenes Bearing Axially‐Chiral 2‐Arylpyridyl‐N‐Oxide Units for Efficient Chromatographic Enantioseparation of Chiral Aromatic and Aliphatic Alcohols2023

    • Author(s)
      Ikai Tomoyuki、Ito Masaki、Oki Kosuke、Suzuki Nozomu、Yashima Eiji
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 62 Issue: 31

    • DOI

      10.1002/anie.202306252

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Control of One-Handed Helicity in Polyacetylenes: Impact of an Extremely Small Amount of Chiral Substituents2023

    • Author(s)
      Ikai Tomoyuki、Morita Yuki、Majima Tsuyoshi、Takeda Shoki、Ishidate Ryoma、Oki Kosuke、Suzuki Nozomu、Ohtani Hajime、Aoi Hiromi、Maeda Katsuhiro、Okoshi Kento、Yashima Eiji
    • Journal Title

      Journal of the American Chemical Society

      Volume: 145 Issue: 45 Pages: 24862-24876

    • DOI

      10.1021/jacs.3c09308

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Secondary Structure Modulation of Triptycene-Based One-Handed Helical Ladder Polymers through π-Extension of Achiral Segments2023

    • Author(s)
      Ikai Tomoyuki、Tanaka Atsuya、Shiotani Takumi、Oki Kosuke、Yashima Eiji
    • Journal Title

      Organic Materials

      Volume: 5 Issue: 04 Pages: 184-190

    • DOI

      10.1055/a-2208-4389

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Optically-Pure Triptycene-Based Metallomacrocycles and Homochiral Self-Sorting Assisted by Ladder Formation2023

    • Author(s)
      Oki Kosuke、Zheng Wei、Yashima Eiji、Ikai Tomoyuki
    • Journal Title

      Chemical Communications

      Volume: 59 Issue: 58 Pages: 8989-8992

    • DOI

      10.1039/d3cc02259e

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Amplification of macromolecular helicity of poly(biphenylylacetylene)s composed of a small amount of chiral [5]helicene units2023

    • Author(s)
      Ikai Tomoyuki、Anzai Shun、Oki Kosuke、Yashima Eiji
    • Journal Title

      Journal of Polymer Science

      Volume: 61 Issue: 10 Pages: 912-919

    • DOI

      10.1002/pol.20220658

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Defect‐Free Synthesis of a Fully π‐Conjugated Helical Ladder Polymer and Resolution into a Pair of Enantiomeric Helical Ladders**2023

    • Author(s)
      Ikai Tomoyuki、Miyoshi Sayaka、Oki Kosuke、Saha Ranajit、Hijikata Yuh、Yashima Eiji
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 62 Issue: 20

    • DOI

      10.1002/anie.202301962

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Remote Control of One‐Handed Helicity in Polyacetylenes through Flexible Spacers in Water: Impact of the Spacer Length2023

    • Author(s)
      Ikai Tomoyuki、Nakamura Koshi、Mizumoto Kosuke、Oki Kosuke、Yashima Eiji
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 62 Issue: 20

    • DOI

      10.1002/anie.202301127

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereospecific Synthesis of Enantiopure [6]Helicene Containing a Seven‐Membered Ring and [7]Helicene by Acid‐Promoted Stepwise Alkyne Annulations of Doubly Axial‐Chiral Precursors**2023

    • Author(s)
      Ikai Tomoyuki、Oki Kosuke、Yamakawa Shoya、Yashima Eiji
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 62 Issue: 18

    • DOI

      10.1002/anie.202301836

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] One‐Handed Helical Tubular Ladder Polymers for Chromatographic Enantioseparation**2023

    • Author(s)
      Zheng Wei、Oki Kosuke、Saha Ranajit、Hijikata Yuh、Yashima Eiji、Ikai Tomoyuki
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 62 Issue: 11

    • DOI

      10.1002/anie.202218297

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Chiral and Achiral Pendant-Bound Poly(biphenylylacetylene)s Bearing Amide and/or Carbamate Groups: One-Handed Helix Formations and Chiral Recognition Abilities2022

    • Author(s)
      Ikai Tomoyuki、Okuda Shogo、Aizawa Motoki、Yashima Eiji
    • Journal Title

      Macromolecules

      Volume: 55 Issue: 16 Pages: 7023-7031

    • DOI

      10.1021/acs.macromol.2c01362

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic One-Handed Helix Induction and Subsequent Static Memory of Poly(biphenylylacetylene)s Assisted by a Small Amount of Carboxy Groups Introduced at the Pendants2022

    • Author(s)
      Ikai Tomoyuki、Takeda Shoki、Yashima Eiji
    • Journal Title

      ACS Macro Letters

      Volume: 11 Issue: 4 Pages: 525-531

    • DOI

      10.1021/acsmacrolett.2c00136

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Consecutively fused single‐, double‐, and triple‐expanded helicenes2022

    • Author(s)
      Zheng Wei、Ikai Tomoyuki、Oki Kosuke、Yashima Eiji
    • Journal Title

      Natural Sciences

      Volume: 2 Issue: 2

    • DOI

      10.1002/ntls.20210047

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Macromolecular helicity induction and static helicity memory of poly(biphenylylacetylene)s bearing aromatic pendant groups and their use as chiral stationary phases for high‐performance liquid chromatography2021

    • Author(s)
      Ikai Tomoyuki、Okuda Shogo、Yashima Eiji
    • Journal Title

      Chirality

      Volume: 34 Issue: 2 Pages: 306-316

    • DOI

      10.1002/chir.23399

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chiral amplification of supramolecular coassemblies of chiral and achiral acylhydrazine-functionalized biphenyls and their copolymers2021

    • Author(s)
      Ikai Tomoyuki、Kawabata Satoshi、Okuda Shogo、Ousaka Naoki、Yashima Eiji
    • Journal Title

      Polymer Journal

      Volume: 53 Issue: 12 Pages: 1475-1480

    • DOI

      10.1038/s41428-021-00550-7

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Emergence of Highly Enantioselective Catalytic Activity in a Helical Polymer Mediated by Deracemization of Racemic Pendants2021

    • Author(s)
      Ikai Tomoyuki、Ando Mitsuka、Ito Masaki、Ishidate Ryoma、Suzuki Nozomu、Maeda Katsuhiro、Yashima Eiji
    • Journal Title

      Journal of the American Chemical Society

      Volume: 143 Issue: 32 Pages: 12725-12735

    • DOI

      10.1021/jacs.1c05620

    • NAID

      120007190671

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Presentation] Synthesis and application of one-handed helical ladder polymers2024

    • Author(s)
      Tomoyuki Ikai
    • Organizer
      National Tsing Hua University Seminar
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Defect-free synthesis and function of helical ladder polymers2024

    • Author(s)
      Tomoyuki Ikai
    • Organizer
      2024 Trilateral Conference on Modern Challenges in Polymer Science and Technology
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] ラダー化が導く二次構造制御の幕開け2024

    • Author(s)
      井改知幸
    • Organizer
      2023年度 化学生命工学講演会「化学生命の最前線1」
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Defect-Free Ladder Polymers with a One-Handed Helical Geometry: Synthesis and Application2024

    • Author(s)
      井改知幸
    • Organizer
      日本化学会第 104 春季年会
    • Related Report
      2023 Annual Research Report
    • Invited
  • [Presentation] Helical ladderization: らせん二次構造の自在構築2023

    • Author(s)
      井改知幸
    • Organizer
      第49回中国四国地区高分子講座
    • Related Report
      2023 Annual Research Report
    • Invited
  • [Presentation] Synthesis of single-handed helical spiro-conjugated ladder polymers with or without a helical cavity2023

    • Author(s)
      Tomoyuki Ikai
    • Organizer
      14th Japan-China Joint Symposium on Conduction and Photoconduction in Organic Solids and Related Phenomena
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Defect Free Synthesis of Fully pi-Conjugated Optically-Active Helical Ladder Polymers Consisting of Totally Achiral Monomer Units2023

    • Author(s)
      Tomoyuki Ikai, Sayaka Miyoshi, Kosuke Oki, Ranajit Saha, Yuh Hijikata, Eiji Yashima
    • Organizer
      MRM2023/IUMRS-ICA2023
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of a Fully pi-Conjugated Helical Ladder Polymers and Resolution into a Pair of Enantiomeric Helices2023

    • Author(s)
      Tomoyuki Ikai, Sayaka Miyoshi, Kosuke Oki, Ranajit Saha, Yuh Hijikata, Eiji Yashima
    • Organizer
      Molecular Chirality 2023
    • Related Report
      2023 Annual Research Report
  • [Presentation] 様々な置換基を導入した2-アリールピリジル-N-オキシド部位を有する ポリアセチレン誘導体の合成とHPLC用キラル固定相への応用2023

    • Author(s)
      井改知幸、伊藤正樹、沖光脩、鈴木望、八島栄次
    • Organizer
      高分子討論会2023
    • Related Report
      2023 Annual Research Report
  • [Presentation] アキラルユニットのみからなる光学活性な全共役ヘリカルラダーポリマーの合成と光学特性2023

    • Author(s)
      井改知幸、三好沙也加、八島栄次
    • Organizer
      第72回高分子学会年次大会
    • Related Report
      2023 Annual Research Report
  • [Presentation] 不斉増幅を利用したポリ(ビフェニルイルアセチレン)誘導体のらせん構造制御とキラル固定相への応用2023

    • Author(s)
      井改知幸、森田祐己、間嶋剛、八島栄次
    • Organizer
      第72回高分子学会年次大会
    • Related Report
      2023 Annual Research Report
  • [Presentation] 光学活性なビナフチルユニットを含有する一方向巻きヘリカルラダーポリマーの合成とキロプティカル特性2023

    • Author(s)
      三島 波采・三好 沙也加・沖 光脩・井改 知幸・八島 栄次
    • Organizer
      日本化学会第103春季年会(2023)
    • Related Report
      2022 Annual Research Report
  • [Presentation] 側鎖に光学活性基を導入した全共役ラダーポリマーの合成とキロプティカル特性2023

    • Author(s)
      西野 巧起・井改 知幸・八島 栄次
    • Organizer
      日本化学会第103春季年会(2023)
    • Related Report
      2022 Annual Research Report
  • [Presentation] 側鎖に動的キラルな[5]ヘリセンユニットを有するポリ(ビフェニルイルアセチレン)誘導体の合成とらせん構造制御2023

    • Author(s)
      安齋 俊・井改 知幸・八島 栄次
    • Organizer
      日本化学会第103春季年会(2023)
    • Related Report
      2022 Annual Research Report
  • [Presentation] ラダー化を利用した二次構造制御2022

    • Author(s)
      井改知幸
    • Organizer
      22-1 高分子学会講演会
    • Related Report
      2022 Annual Research Report
    • Invited
  • [Presentation] ラセン構造を有するラダーポリマーの開発と機能2022

    • Author(s)
      井改知幸
    • Organizer
      持続社会発展のための機能化学研究委員会 第5回(R4-2)定期研究会
    • Related Report
      2022 Annual Research Report
  • [Presentation] Synthesis of Single-Handed Spiro-Conjugated Helical Ladder Polymers2022

    • Author(s)
      Tomoyuki Ikai, Wei Zheng, Eiji Yashima
    • Organizer
      The 6th Molecular Chirality Asia 2022
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research
  • [Presentation] フルオレン骨格を含有する構造欠陥のないπ共役ヘリカルラダーポリマーの合成と光学特性2022

    • Author(s)
      三好沙也加・井改知幸・八島栄次
    • Organizer
      第71回高分子年次大会
    • Related Report
      2022 Annual Research Report
  • [Presentation] 主鎖がヘリセン骨格のみからなる新規π共役ラダーポリマーの合成と光学特性2022

    • Author(s)
      稲垣隼人・井改知幸・八島栄次
    • Organizer
      第71回高分子年次大会
    • Related Report
      2022 Annual Research Report
  • [Presentation] アルキン芳香環化を利用した[6]-および[7]ヘリセンの同 時合成とそのキロプティカル特性2022

    • Author(s)
      沖 光脩・山川 翔也・井改 知幸・八島 栄次
    • Organizer
      第71回高分子年次大会
    • Related Report
      2022 Annual Research Report
  • [Presentation] フルオレン骨格を含有する構造欠陥のないπ共役ヘリカルラダーポリマーの合成とその光学分割2022

    • Author(s)
      三好沙也加・井改知幸・八島栄次
    • Organizer
      第71回高分子討論会
    • Related Report
      2022 Annual Research Report
  • [Presentation] アルキン芳香環化を利用した[7]ヘリセンおよび7員 環を含有する[6]ヘリセンの同時合成、光学分割及びキロプティカル特性2022

    • Author(s)
      沖 光脩・山川 翔也・井改 知幸・八島 栄次
    • Organizer
      第71回高分子討論会
    • Related Report
      2022 Annual Research Report
  • [Presentation] 側鎖にヘリセン部位を導入したポリ(ビフェニルイルアセチレン)誘導体の合成とらせん構造制御2022

    • Author(s)
      安齋俊・井改知幸・八島栄次
    • Organizer
      第71回高分子討論会
    • Related Report
      2022 Annual Research Report
  • [Presentation] 主鎖が動的キラルな[4]ヘリセン骨格のみからなる全共役ラダーポリマーの合成と光学特性2022

    • Author(s)
      稲垣隼人・井改知幸・八島栄次
    • Organizer
      第71回高分子討論会
    • Related Report
      2022 Annual Research Report
  • [Presentation] スピロビフルオレン骨格を含有するスピロ共役型ヘリカルラダーポリマーの合成とキラル固定相への応用2022

    • Author(s)
      松本武大・加藤義貴・沖 光脩・井改知幸・八島栄次
    • Organizer
      第71回高分子討論会
    • Related Report
      2022 Annual Research Report
  • [Presentation] 新規U字型π共役ラダー分子の合成と光学特性2022

    • Author(s)
      井崎宏一・井改知幸・八島栄次
    • Organizer
      第71回高分子討論会
    • Related Report
      2022 Annual Research Report
  • [Presentation] 光学活性なスピロビフルオレンユニットを主鎖に含有する一方向巻きスピロ共役型ヘリカルラダーポリマーの合成とキラル固定相への応用2022

    • Author(s)
      松本武大・加藤義貴・沖 光脩・井改知幸・八島栄次
    • Organizer
      第53回中部化学関係学協会支部連合秋季大会
    • Related Report
      2022 Annual Research Report
  • [Presentation] 側鎖に光学活性な[5]ヘリセンユニットを有するポリ(ビフェニルイルアセチレン)誘導体の合成とらせん構造制御2022

    • Author(s)
      安齋 俊・井改 知幸・八島 栄次
    • Organizer
      第53回中部化学関係学協会支部連合秋季大会
    • Related Report
      2022 Annual Research Report
  • [Presentation] [4]ヘリセン骨格のみからなる全共役ラダーポリマーの合成2022

    • Author(s)
      稲垣隼人・井改知幸・八島栄次
    • Organizer
      第53回中部化学関係学協会支部連合秋季大会
    • Related Report
      2022 Annual Research Report
  • [Presentation] 9,9’-スピロビフルオレンユニットを含有する一方向巻きスピロ共役型ヘリカルラダーポリマーの合成2022

    • Author(s)
      松本武大, 加藤 義貴, 沖 光脩, 井改 知幸, 八島 栄次
    • Organizer
      日本化学会 第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] ラダー化によるラセン秩序の創出とキラル機能2021

    • Author(s)
      井改知幸
    • Organizer
      第25回VBLシンポジウム
    • Related Report
      2021 Annual Research Report
    • Invited
  • [Presentation] 構造欠陥のない一方向巻きスピロ共役型ヘリカルラダーポリマーの合成2021

    • Author(s)
      井改知幸, Wei Zheng,八島栄次
    • Organizer
      Molecular Chirality 2021
    • Related Report
      2021 Annual Research Report
  • [Presentation] 新規π共役ヘリカルラダーポリマーの合成と光学特性2021

    • Author(s)
      三好沙也加, 井改知幸, 八島栄次
    • Organizer
      第70回高分子討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] フルオレン骨格を含有する光学活性π共役ヘリカルラダーポリマーの合成2021

    • Author(s)
      三好沙也加, 井改知幸, 八島栄次
    • Organizer
      第52回中部化学関係学協会支部連合秋季大会
    • Related Report
      2021 Annual Research Report
  • [Remarks] 名古屋大学大学院工学研究科 有機・高分子化学専攻 井改グループ

    • URL

      https://www.chembio.nagoya-u.ac.jp/labhp/polymer4/TIG/j/TOP.html

    • Related Report
      2023 Annual Research Report
  • [Remarks] 名古屋大学大学院工学研究科 有機・高分子化学専攻 八島研究室

    • URL

      https://www.chembio.nagoya-u.ac.jp/labhp/polymer4/j/profile/ikai.html

    • Related Report
      2022 Annual Research Report
  • [Remarks] 名古屋大学大学院工学研究科 有機・高分子化学専攻 八島研究室

    • URL

      http://www.helix.chembio.nagoya-u.ac.jp/j/profile/ikai.html

    • Related Report
      2021 Annual Research Report
  • [Patent(Industrial Property Rights)] 分離剤2024

    • Inventor(s)
      井改 知幸、八島 栄次
    • Industrial Property Rights Holder
      株式会社ダイセル、国立大学法人東海国立大学機構
    • Industrial Property Rights Type
      特許
    • Filing Date
      2024
    • Related Report
      2023 Annual Research Report
    • Overseas
  • [Patent(Industrial Property Rights)] 分離剤2023

    • Inventor(s)
      井改知幸・八島栄次
    • Industrial Property Rights Holder
      井改知幸・八島栄次
    • Industrial Property Rights Type
      特許
    • Filing Date
      2023
    • Related Report
      2022 Annual Research Report
    • Overseas

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Published: 2021-04-28   Modified: 2025-01-30  

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