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Chemistry of strained contracted porphyrins based on polyketones

Research Project

Project/Area Number 23K23326
Project/Area Number (Other) 22H02058 (2022-2023)
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeMulti-year Fund (2024)
Single-year Grants (2022-2023)
Section一般
Review Section Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
Research InstitutionHokkaido University

Principal Investigator

Inokuma Yasuhide  北海道大学, 工学研究院, 教授 (80555566)

Project Period (FY) 2024-04-01 – 2025-03-31
Project Status Completed (Fiscal Year 2024)
Budget Amount *help
¥17,420,000 (Direct Cost: ¥13,400,000、Indirect Cost: ¥4,020,000)
Fiscal Year 2024: ¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2023: ¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2022: ¥6,760,000 (Direct Cost: ¥5,200,000、Indirect Cost: ¥1,560,000)
Keywordsポルフィリン / ポリケトン / 歪み / π共役 / 大環状化合物 / マクロサイクル / 色素 / 構造有機化学 / 歪み化合物 / キラル / ポルフィリノイド
Outline of Research at the Start

単分散ポリケトンを基盤原料として、そこから分子内環化反応とPaal-Knorr反応を駆使して作り出される歪んだ環縮小ポルフィリン類縁体、特にCalix[3]pyrrole類の合成法開拓と物性解明、機能性材料への応用を行う。
環歪みが誘起する特徴的な環縮小ポルフィリン類の性質として、歪み誘起環拡大反応や吸収・発光特性の変化に着目し、それらを環境応答性色素などの材料創出へと繋げる。

Outline of Final Research Achievements

We have succeeded in synthesizing a series of new porphyrin analogues, such as calixpyrrole and cyclo[4]pyrrole, which have high macrocyclic ring strain by developing novel synthetic routes using polyketone precursors. These new porphyrinoids were used for super acid-resistant fluorescent dyes and anion receptors that undergo ring-expansion reactions upon strain. These results have made significant contributions to the elucidation of novel properties of porphyrinoids induced by ring contraction and strain and their application to materials.

Translated with www.DeepL.com/Translator (free version)

Academic Significance and Societal Importance of the Research Achievements

ポルフィリノイドの多くは、平面性の高い構造と環全体にわたるπ共役電子系に由来する物性が注目を集めてきたが、本研究では高い環歪みエネルギーを持つポルフィリン類縁体をポリケトン前駆体から初めて作りだしたことで、歪みや環縮小効果がもたらす新しい物性変化を解明することができた。主として、特異な反応性や酸耐性に現れた新物性は、今後のポルフィリン類縁体の合成開発において新しい基軸を示したとともに、従来にない応用展開が拓けると考えられる。

Report

(4 results)
  • 2024 Annual Research Report   Final Research Report ( PDF )
  • 2023 Annual Research Report
  • 2022 Annual Research Report
  • Research Products

    (54 results)

All 2025 2024 2023 2022 Other

All Int'l Joint Research (2 results) Journal Article (17 results) (of which Int'l Joint Research: 5 results,  Peer Reviewed: 17 results,  Open Access: 6 results) Presentation (33 results) (of which Int'l Joint Research: 12 results,  Invited: 14 results) Remarks (2 results)

  • [Int'l Joint Research] テキサス大学オースティン校(米国)

    • Related Report
      2022 Annual Research Report
  • [Int'l Joint Research] ウプサラ大学(スウェーデン)

    • Related Report
      2022 Annual Research Report
  • [Journal Article] Size-selective synthesis of calix[n]furan[2n]thiazoles bearing meso-CH2 bridges2025

    • Author(s)
      Shibata Kotaro、Nakabayashi Takuma、Watanabe Keita、Ide Yuki、Ichino Tomoya、Inokuma Yasuhide
    • Journal Title

      Journal of Porphyrins and Phthalocyanines

      Volume: 印刷中 Issue: 01n02 Pages: 184-190

    • DOI

      10.1142/s1088424625500105

    • Related Report
      2024 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Contracted porphyrins and calixpyrroles: synthetic challenges and ring-contraction effects2024

    • Author(s)
      Watanabe Keita、Pati Narendra Nath、Inokuma Yasuhide
    • Journal Title

      Chemical Science

      Volume: 15 Issue: 19 Pages: 6994-7009

    • DOI

      10.1039/d4sc02028f

    • Related Report
      2024 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Discrete polyketones: synthesis, derivatization, and potential applications2024

    • Author(s)
      Inokuma Yasuhide
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 97 Issue: 7

    • DOI

      10.1093/bulcsj/uoae072

    • Related Report
      2024 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Strain-based design, direct macrocyclization, and metal complexation of thiazole-containing calix[3]pyrrole analogues2024

    • Author(s)
      Watanabe Keita、Shibata Kotaro、Ichino Tomoya、Ide Yuki、Yoneda Tomoki、Maeda Satoshi、Inokuma Yasuhide
    • Journal Title

      Inorganic Chemistry Frontiers

      Volume: 11 Issue: 12 Pages: 3548-3554

    • DOI

      10.1039/d4qi00684d

    • Related Report
      2024 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Molecular Dynamics‐Based Conformational Simulation Method for Analysis of Arrival Time Distributions in Ion Mobility Mass Spectrometry2024

    • Author(s)
      Tashiro Keisuke、Ide Yuki、Taketsugu Tetsuya、Ohara Kazuaki、Yamaguchi Kentaro、Kobayashi Masato、Inokuma Yasuhide
    • Journal Title

      Advanced Theory and Simulations

      Volume: 7 Issue: 11 Pages: 2400691-2400691

    • DOI

      10.1002/adts.202400691

    • Related Report
      2024 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cyclo[4]pyrrole with α-β direct linkages2024

    • Author(s)
      Sun Yuhua、Kitahara Riku、Ichino Tomoya、Ide Yuki、Senboku Hisanori、Shimizu Soji、Tanaka Takayuki、Inokuma Yasuhide
    • Journal Title

      Chemical Science

      Volume: 15 Issue: 46 Pages: 19571-19576

    • DOI

      10.1039/d4sc06670g

    • Related Report
      2024 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Drug-drug conjugates of MEK and Akt inhibitors for RAS-mutant cancers2024

    • Author(s)
      Fujita Hikaru、Arai Sachiko、Arakawa Hiroshi、Hamamoto Kana、Kato Toshiyuki、Arai Tsubasa、Nitta Nanaka、Hotta Kazuki、Hosokawa Natsuko、Ohbayashi Takako、Takahashi Chiaki、Inokuma Yasuhide、Tamai Ikumi、Yano Seiji、Kunishima Munetaka、Watanabe Yoshihiro
    • Journal Title

      Bioorganic & Medicinal Chemistry

      Volume: 102 Pages: 117674-117674

    • DOI

      10.1016/j.bmc.2024.117674

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] One‐pot, Gram‐Scale Synthesis of Calix[5]‐ and Calix[6]furan: Derivatization for Polyketone‐ and Isopyrazole‐based Macrocycles with Conformational Analysis2024

    • Author(s)
      Yoneda Tomoki、Sano Taichi、Pati Narendra Nath、Ide Yuki、Inokuma Yasuhide
    • Journal Title

      Asian Journal of Organic Chemistry

      Volume: 13 Issue: 5

    • DOI

      10.1002/ajoc.202400023

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] The Geometry of Calix[3]pyrrole and the Formation of the Calix[3]pyrrole・F- Complex in Solution2023

    • Author(s)
      Saha Ranajit、Prillo Jenny、Ide Yuki、Inokuma Yasuhide、Hijikata Yuh
    • Journal Title

      Theoretical Chemistry Accounts

      Volume: - Issue: 5 Pages: 50-50

    • DOI

      10.1007/s00214-023-02982-1

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Identifying high-grade serous ovarian carcinoma-specific extracellular vesicles by polyketone-coated nanowires2023

    • Author(s)
      Yokoi, A; Ukai, M; Yasui, T; Inokuma, Y; HD, Kim; Matsuzaki, J; Yoshida, K; Kitagawa, M; Chattrairat, K; Iida, M; Shimada, T; Manabe, Y; Chang, IY; Asano-Inami, E; Koya, Y; Nawa, A; Nakamura, K, (他9名)
    • Journal Title

      Sci Adv

      Volume: 9 Issue: 27

    • DOI

      10.1126/sciadv.ade6958

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Machine Learning-Based Analysis of Molar and Enantiomeric Ratios and Reaction Yields Using Images of Solid Mixtures2023

    • Author(s)
      Ide Yuki、Shirakura Hayato、Sano Taichi、Murugavel Muthuchamy、Inaba Yuya、Hu Sheng、Takigawa Ichigaku、Inokuma Yasuhide
    • Journal Title

      Industrial & Engineering Chemistry Research

      Volume: 62 Issue: 35 Pages: 13790-13798

    • DOI

      10.1021/acs.iecr.3c01882

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Toward calix[2]-type macrocycles: Synthesis and structural analysis of cyclic tetraketone and highly strained?furanophane2023

    • Author(s)
      Sano Taichi、Sun Yuhua、Mukai Taichi、Inaba Yuya、Yoneda Tomoki、Ide Yuki、Pirillo Jenny、Hijikata Yuh、Inokuma Yasuhide
    • Journal Title

      Journal of Porphyrins and Phthalocyanines

      Volume: - Issue: 07n10 Pages: 1067-1073

    • DOI

      10.1142/s1088424623500189

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chiral Calix[3]pyrrole Derivatives: Synthesis, Racemization Kinetics, and Ring Expansion to Calix[9]‐ and Calix[12]pyrrole Analogues2023

    • Author(s)
      Inaba Yuya、Yang Jian、Kakibayashi Yu、Yoneda Tomoki、Ide Yuki、Hijikata Yuh、Pirillo Jenny、Saha Ranajit、Sessler Jonathan L.、Inokuma Yasuhide
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 62 Issue: 15

    • DOI

      10.1002/anie.202301460

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Chain-Length-Dependent Hydrogen-Bonded Self-Assembly of Terminally Functionalized Discrete Polyketones2023

    • Author(s)
      Kilingaru I. Shivakumar、Yumehiro Manabe、Tomoki Yoneda、Yuki Ide、Yasuhide Inokuma
    • Journal Title

      Precision Chemistry

      Volume: 1 Issue: 1 Pages: 34-39

    • DOI

      10.1021/prechem.3c00025

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Determination of the critical chain length for macromolecular crystallization using structurally flexible polyketones2022

    • Author(s)
      Ide Yuki、Manabe Yumehiro、Inaba Yuya、Kinoshita Yusuke、Pirillo Jenny、Hijikata Yuh、Yoneda Tomoki、Shivakumar Kilingaru I.、Tanaka Saki、Asakawa Hitoshi、Inokuma Yasuhide
    • Journal Title

      Chemical Science

      Volume: 13 Issue: 34 Pages: 9848-9854

    • DOI

      10.1039/d2sc03083g

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Absorption spectra of calix[3]pyrrole analogs as probes for contracted macrocycles2022

    • Author(s)
      Watanabe Keita、Saha Ranajit、Inaba Yuya、Manabe Yumehiro、Yoneda Tomoki、Ide Yuki、Hijikata Yuh、Inokuma Yasuhide
    • Journal Title

      Journal of Porphyrins and Phthalocyanines

      Volume: - Issue: 01n04 Pages: 157-163

    • DOI

      10.1142/s1088424622500754

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Carbonyl-Containing Solid Polymer Electrolyte Host Materials: Conduction and Coordination in Polyketone, Polyester, and Polycarbonate Systems2022

    • Author(s)
      Therese Eriksson, Harish Gudla, Yumehiro Manabe, Tomoki Yoneda, Daniel Friesen, Chao Zhang, Yasuhide Inokuma, Daniel Brandell, Jonas Mindemark
    • Journal Title

      Macromolecules

      Volume: 55 Issue: 24 Pages: 10940-10949

    • DOI

      10.1021/acs.macromol.2c01683

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Presentation] ポリケトンを基盤とする機能性分子合成 -はじめたキッカケ、悩んだこと、思わぬ出会いと発見-2024

    • Author(s)
      猪熊 泰英
    • Organizer
      超分子創製化学セミナー(第95 回)
    • Related Report
      2024 Annual Research Report
    • Invited
  • [Presentation] ポリケトン分子ひもで 機能性分子の一筆書き合成2024

    • Author(s)
      猪熊 泰英
    • Organizer
      第17回 有機π電子系シンポジウム
    • Related Report
      2024 Annual Research Report
    • Invited
  • [Presentation] Coordination Chemistry of Calix[3]pyrrole-Related Macrocycles2024

    • Author(s)
      Yasuhide Inokuma
    • Organizer
      The 245th ECS Meeting
    • Related Report
      2024 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis and properties of calix[3]pyrrole related macrocycles2024

    • Author(s)
      Yasuhide Inokuma
    • Organizer
      The 13th International Conference on Porphyrins and Phthalocyanines (ICPP-13)
    • Related Report
      2024 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Discrete Polyketones as Shapable Molecular Ropes for Development of Functional Organic Materials2024

    • Author(s)
      Yasuhide Inokuma
    • Organizer
      5th International Conference on Emerging Advanced Nanomaterials ICEAN 2024
    • Related Report
      2024 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Calix[3]pyrrole類縁体の高効率合成と金属錯化2024

    • Author(s)
      渡辺 敬太、猪熊 泰英
    • Organizer
      第34回基礎有機化学討論会
    • Related Report
      2024 Annual Research Report
  • [Presentation] π共役拡張型トリピロールマクロサイクルの合成2024

    • Author(s)
      間宮俊介、柴田昂太郎、渡辺敬太、井手雄紀、猪熊泰英
    • Organizer
      第34回基礎有機化学討論会
    • Related Report
      2024 Annual Research Report
  • [Presentation] 単分散ポリケトンに立脚した 機能性有機分子の創出2024

    • Author(s)
      猪熊 泰英
    • Organizer
      日本化学会 第104春季年会
    • Related Report
      2023 Annual Research Report
    • Invited
  • [Presentation] Calix[3]Pyrrole and Related Macrocycles: Synthesis and Properties2023

    • Author(s)
      Yasuhide Inokuma
    • Organizer
      The 243rd ECS Meeting
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] From Polyketone to Calix[3]pyrrole-type Macrocycles2023

    • Author(s)
      Yasuhide Inokuma
    • Organizer
      The 17th International Symposium on Macrocyclic and Supramolecular Chemistry (ISMSC)
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] ICReDD Collaboration Research Frontier: Calix[3]Pyrrole Chemistry & Image-Based Machine Learning for Mixing Ratio Prediction2023

    • Author(s)
      Yasuhide Inokuma
    • Organizer
      The 6th ICReDD International Symposium
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Polyketones as Rope-like HUB compounds for functional organic materials2023

    • Author(s)
      Yasuhide Inokuma
    • Organizer
      MIRAI 2.0 R&I Week 2023, Material Science Workshop: Advanced electrolyte materials for energy and conversion
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Polyketones as shapable molecular ropes2023

    • Author(s)
      猪熊泰英
    • Organizer
      北海道大学 農学研究院-ICReDD合同シンポジウム
    • Related Report
      2022 Annual Research Report
    • Invited
  • [Presentation] Visual Reaction Yield Analysis Using Image-based Machine Learning2023

    • Author(s)
      Hayato Shirakura, Yuki Ide, Sheng Hu, Ichigaku Takigawa, Yasuhide Inokuma
    • Organizer
      5th ICReDD International Symposium
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Hydrogen Bonded Self-Assembly of Pyridine Terminated Oligoketones2023

    • Author(s)
      Kilingaru I. Shivakumar, Yasuhide Inokuma
    • Organizer
      5th ICReDD International Symposium
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research
  • [Presentation] トリピロールマクロサイクルにおけるホウ素の安定化効果2023

    • Author(s)
      稲葉 佑哉・猪熊 泰英
    • Organizer
      日本化学会第103春季年会
    • Related Report
      2022 Annual Research Report
  • [Presentation] 画像を用いた機械学習による結晶性化合物の混合比予測2023

    • Author(s)
      白倉 逸人・佐野太一・井_ 雄紀・Sheng Hu ・瀧川 一学・猪熊 泰英
    • Organizer
      日本化学会第103春季年会
    • Related Report
      2022 Annual Research Report
  • [Presentation] Hydrogen Bonded Self-Assembly of Pyridine Terminated Oligoketones2023

    • Author(s)
      Kilingaru I. Shivakumar,Yuki Ide,Yasuhide Inokuma
    • Organizer
      日本化学会第103春季年会
    • Related Report
      2022 Annual Research Report
  • [Presentation] calix[3]pyrrole類縁体の紫外可視吸収スペクトルと構造的解釈2023

    • Author(s)
      渡辺 敬太・稲葉 佑哉・米田 友貴・井手 雄紀・Ranajit Saha・土方 優・猪熊 泰英
    • Organizer
      日本化学会第103春季年会
    • Related Report
      2022 Annual Research Report
  • [Presentation] 固体混合物画像を利用した機械学習によるエナンチオマー割合診断2023

    • Author(s)
      佐野 太一・白倉 逸人・井手 雄紀・Sheng Hu・瀧川 一学・猪熊 泰英
    • Organizer
      日本化学会第103春季年会
    • Related Report
      2022 Annual Research Report
  • [Presentation] Synthesis of Cyclic Tetraketone and Furanophane Toward Calix[2]pyrrole2023

    • Author(s)
      Yuhua Sun・Taichi Sano・Yuya Inaba・Tomoki Yoneda・ Yusuke Kinoshita・Yuki Ide・Jenny Pirillo・Yuh Hijikata・Yasuhide Inokuma
    • Organizer
      日本化学会第103春季年会
    • Related Report
      2022 Annual Research Report
  • [Presentation] 「カルボニルひも」で作り出す夢の分子2022

    • Author(s)
      猪熊泰英
    • Organizer
      第53回構造有機化学若手の会夏の学校
    • Related Report
      2022 Annual Research Report
    • Invited
  • [Presentation] Calix[3]pyrrole: Synthesis and Strain Induced Reactions2022

    • Author(s)
      Yasuhide Inokuma
    • Organizer
      International Conference on Porphyrins and Phthalocyanines (ICPP)-12
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 分_ひもで切り拓く構造有機化学 ~_由な発想で新しい分_を創る~2022

    • Author(s)
      猪熊泰英
    • Organizer
      令和4年度京都大学化学研究所 客員准教授 講演会
    • Related Report
      2022 Annual Research Report
    • Invited
  • [Presentation] Synthesis and Strain-induced Reactions of Calix[3]pyrrole and Related Macrocycles2022

    • Author(s)
      Yuya Inaba,Yasuhide Inokuma
    • Organizer
      International Conference on Porphyrins and Phthalocyanines (ICPP)-12
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis and Functionalization of Isopyrazole-masked Tetraketone for Fluorescent Metal Ligands2022

    • Author(s)
      Narito Ozawa,Shivakumar Kilingaru Ishwara,Muthuchamy Murugavel,Yuya Inaba,Yuki Ide,Yasuhide Inokuma
    • Organizer
      International Conference on Porphyrins and Phthalocyanines (ICPP)-12
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 構造柔軟な脂肪族ポリケトンの単分散合成と鎖長に依存した結晶性変化2022

    • Author(s)
      眞部 夢大・井手 雄紀・稲葉 佑哉・木下 雄介・米田 友貴・猪熊 泰英
    • Organizer
      第71回高分子化学討論会
    • Related Report
      2022 Annual Research Report
  • [Presentation] 単分散ポリケトンの分子鎖長に応じた結晶性の変化2022

    • Author(s)
      眞部 夢大・井手 雄紀・稲葉 佑哉・木下 雄介・米田 友貴・猪熊 泰英
    • Organizer
      第32回基礎有機化学討論会
    • Related Report
      2022 Annual Research Report
  • [Presentation] トリピロールマクロサイクルにおけるホウ素の安定化効果2022

    • Author(s)
      稲葉 佑哉・猪熊 泰英
    • Organizer
      第32回基礎有機化学討論会
    • Related Report
      2022 Annual Research Report
  • [Presentation] π共役イミン類縁体を利用した金属イオン検出2022

    • Author(s)
      白倉逸人・眞部夢大・稲葉佑哉・井_雄紀・米田友貴・猪熊泰英
    • Organizer
      第32回基礎有機化学討論会
    • Related Report
      2022 Annual Research Report
  • [Presentation] 環状ポリケトンによるアルカリ金属イオン認識2022

    • Author(s)
      小澤 成達・Shivakumar Kilingaru Ishwara・木下 雄介・井手 雄紀・米田 友貴・猪熊 泰英
    • Organizer
      第32回基礎有機化学討論会
    • Related Report
      2022 Annual Research Report
  • [Presentation] Calix[3]pyrrole類縁体の歪み誘起環拡大反応2022

    • Author(s)
      渡辺 敬太・稲葉 佑哉・猪熊 泰英
    • Organizer
      第32回基礎有機化学討論会
    • Related Report
      2022 Annual Research Report
  • [Presentation] オリゴアセチルアセトンの選択的シリル化による合成2022

    • Author(s)
      佐野 太一・稲葉 佑哉・白倉 逸人・猪熊 泰英
    • Organizer
      第32回基礎有機化学討論会
    • Related Report
      2022 Annual Research Report
  • [Remarks] 北海道大学工学部応用化学部門 反応有機化学研究室HP

    • URL

      https://www.eng.hokudai.ac.jp/labo/lor/HP/index.html

    • Related Report
      2023 Annual Research Report
  • [Remarks] 反応有機化学研究室猪熊グループHP(業績リスト)

    • URL

      https://www.eng.hokudai.ac.jp/labo/lor/HP/publication.html

    • Related Report
      2022 Annual Research Report

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Published: 2022-04-19   Modified: 2026-01-16  

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