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Functionalizations of Nitrogen-doped Polycyclic Aromatic Compounds

Research Project

Project/Area Number 18K14199
Research Category

Grant-in-Aid for Early-Career Scientists

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

Principal Investigator

Tanaka Takayuki  京都大学, 理学研究科, 助教 (20705446)

Project Period (FY) 2018-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2019: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2018: ¥3,120,000 (Direct Cost: ¥2,400,000、Indirect Cost: ¥720,000)
Keywordsサーキュレン / 求核置換反応 / 蛍光 / 非平面構造 / 溶解性 / ラジカルカチオン / コロール / 反芳香族性 / X線結晶構造解析 / 近赤外光吸収 / ジラジカル / 二重らせん / 多環芳香族炭化水素 / コラニュレン / 水溶性 / ヘリセン / 光学分割
Outline of Final Research Achievements

I have explored novel polycyclic aromatic hydrocarbons containing nitrogen atoms in the core. Particular focus has been provided to their distorted structures induced by peripheral functionalization, and molecular assembly. For this purpose, I developed new reactions such as nucleophilic aromatic substitution reaction to form diazadithia[8]circulene and palladium-catalyzed amination reaction on corannulene. The structures of new products were revealed by X-ray diffraction analysis. Studies on their solubility in organic solvents and photophysical properties have been also conducted.

Academic Significance and Societal Importance of the Research Achievements

湾曲した構造をもつ分子の合成は一般に難しく、自らが開発したオリジナル分子を非平面構造に展開した意義は大きい。さらに、そうした非平面構造の含窒素多環芳香族炭化水素化合物に特有の物性の解明にも挑み、ラジカルカチオンの安定化や溶解性の高さなど、有機電子材料や有機磁性材料として有用な性質を見出した。

Report

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

    (47 results)

All 2020 2019 2018 Other

All Int'l Joint Research (3 results) Journal Article (17 results) (of which Int'l Joint Research: 8 results,  Peer Reviewed: 17 results,  Open Access: 4 results) Presentation (27 results) (of which Int'l Joint Research: 8 results,  Invited: 4 results)

  • [Int'l Joint Research] Yonsei University(韓国)

    • Related Report
      2019 Annual Research Report
  • [Int'l Joint Research] National University of Singapore(シンガポール)

    • Related Report
      2019 Annual Research Report
  • [Int'l Joint Research] 延世大学(韓国)

    • Related Report
      2018 Research-status Report
  • [Journal Article] Stable meso-meso Linked 2NH-Corrole Radical Dimers as a Key Intermediate to Corrole Tape2020

    • Author(s)
      S. Ooi, B. Adinarayana, D. Shimizu, T. Tanaka, A. Osuka
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 59 Issue: 24 Pages: 9423-9427

    • DOI

      10.1002/anie.202002976

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Figure‐eight Octaphyrin Bis‐Ge(IV) Complexes: Synthesis, Structures, Aromaticity, and Chiroptical Properties2020

    • Author(s)
      M. Izawa, T. Suito, S.-i. Ishida, D. Shimizu, T. Tanaka, T. Mori, A. Osuka
    • Journal Title

      Chem. Asian J.

      Volume: N/A Issue: 9 Pages: 1440-1448

    • DOI

      10.1002/asia.202000159

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rational Synthesis of 5,10-Diazaporphyrins via Nucleophilic Substitution Reactions of α,α’-Dibromotripyrrin and Dihydrogenation to Give 5,10-Diazachlorins2020

    • Author(s)
      M. Umetani, G. Kim, T. Tanaka, D. Kim, A. Osuka
    • Journal Title

      J. Org. Chem.

      Volume: 85 Issue: 5 Pages: 3849-3857

    • DOI

      10.1021/acs.joc.9b03467

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Cyclophane‐type Chlorin Dimers from Dynamic Covalent Chemistry of 2,18‐Porphyrinyl Dicyanomethyl Diradicals2020

    • Author(s)
      B. Adinarayana, K. Kato, D. Shimizu, T. Tanaka, K. Furukawa, A. Osuka
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 49 Issue: 11 Pages: 4320-4323

    • DOI

      10.1002/anie.201914480

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Synthesis of azabenziporphyrinoids by SN Ar reactions2019

    • Author(s)
      Umetani Masataka、Tanaka Takayuki、Osuka Atsuhiro
    • Journal Title

      Journal of Porphyrins and Phthalocyanines

      Volume: 23 Issue: 05n07 Pages: 1-8

    • DOI

      10.1142/s1088424619501827

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Facile synthesis of fluorescent hetero[8]circulene analogues with tunable solubilities and optical properties2019

    • Author(s)
      Yusuke Matsuo, Fengkun Chen, Koki Kise, Takayuki Tanaka, Atsuhiro Osuka
    • Journal Title

      Chemical Science

      Volume: 10 Issue: 48 Pages: 11006-11012

    • DOI

      10.1039/c9sc05087f

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Singly and Doubly Neo-confused Smaragdyrins2019

    • Author(s)
      Y. Rao, W. Zhou, L. Xu, M. Zhou, B. Yin, T. Tanaka, A. Osuka, J. Song
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 141 Issue: 47 Pages: 18836-18844

    • DOI

      10.1021/jacs.9b10270

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Phenylene‐bridged Porphyrin meso‐Oxy Radical Dimers2019

    • Author(s)
      T. Yamamoto, K. Kato, D. Shimizu, T. Tanaka, A. Osuka
    • Journal Title

      Chem. Asian J.

      Volume: 14 Issue: 22 Pages: 4031-4034

    • DOI

      10.1002/asia.201901033

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 5,20-Diheterohexaphyrins: metal-template-free synthesis and aromaticity switching2019

    • Author(s)
      M. Umetani, J. Kim, T. Tanaka, D. Kim, A. Osuka
    • Journal Title

      Chem. Commun.

      Volume: 55 Issue: 71 Pages: 10547-10550

    • DOI

      10.1039/c9cc05580k

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] ortho-Phenylene Bridged Hybrid Nanorings of 2,5-Pyrrolylenes and 2,5-Thienylenes2019

    • Author(s)
      Fengkun Chen, Yongseok Hong, Yusuke Matsuo, Dongho Kim, Takayuki Tanaka, and Atsuhiro Osuka
    • Journal Title

      Asian Journal of Organic Chemistry

      Volume: N/A Issue: 7 Pages: 994-1000

    • DOI

      10.1002/ajoc.201900168

    • Related Report
      2019 Annual Research Report 2018 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Synthesis, Structures, and Near‐IR Absorption of Heterole‐fused Earring Porphyrins2019

    • Author(s)
      L. Wu, F. Li, Y. Rao, B. Wen, L. Xu, M. Zhou, T. Tanaka, A. Osuka, J. Song
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 58 Issue: 24 Pages: 8124-8128

    • DOI

      10.1002/anie.201903446

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Bis‐copper(II) Complex of Triply‐linked Corrole Dimer and Its Dication2019

    • Author(s)
      大井翔太、田中隆行、池上崇久、山角和久、植田賢人、清水大貴、石田真敏、古田弘幸、大須賀篤弘
    • Journal Title

      Chemistry-An Asian Journal

      Volume: 印刷中 Issue: 10 Pages: 1771-1776

    • DOI

      10.1002/asia.201801467

    • Related Report
      2019 Annual Research Report 2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of meso-Diarylaminocorroles via SNAr Reactions2019

    • Author(s)
      Kento Ueta, Takayuki Tanaka, and Atsuhiro Osuka
    • Journal Title

      Molecules

      Volume: 24 Issue: 3 Pages: 642-642

    • DOI

      10.3390/molecules24030642

    • NAID

      120006578939

    • Related Report
      2019 Annual Research Report 2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] [n]Cyclo-para-biphenylmethine Polyradicaloids: [n]Annulene Analogs and Unusual Valence Tautomerization2019

    • Author(s)
      Y. Ni, M. E. Sandoval-Salinas, T. Tanaka, H. Phan, T. S .Herng, T. Y. Gopalakrishna, J. Ding, A. Osuka, D. Casanova, and J. Wu
    • Journal Title

      Chem

      Volume: 5 Issue: 1 Pages: 108-121

    • DOI

      10.1016/j.chempr.2018.09.025

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] “Synthesis and Characterizations of meso-Nitrocorroles”2018

    • Author(s)
      K. Ueta, T. Tanaka, and A. Osuka
    • Journal Title

      Chem. Lett.

      Volume: 47 Issue: 7 Pages: 916-919

    • DOI

      10.1246/cl.180309

    • NAID

      130007402805

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] “Conjugated double helices via self-dimerization of α,α’-Dianilinotripyrrins”2018

    • Author(s)
      M. Umetani, T. Tanaka, and A. Osuka
    • Journal Title

      J. Phys. Chem. Lett.

      Volume: 9 Issue: 33 Pages: 6853-6859

    • DOI

      10.1039/c8sc02739k

    • NAID

      120006534587

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] “Stable Face-to-Face Singlet Diradicaloids: Doubly u-Hydroxo-Bridged Triply-Linked Corrole Dimer Ga(III) Complexes”2018

    • Author(s)
      S. Ooi, D. Shimizu, K. Furukawa, T. Tanaka, and A. Osuka
    • Journal Title

      Angew. Chem. Int. Ed

      Volume: 57 Issue: 45 Pages: 14916-14920

    • DOI

      10.1002/anie.201810200

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Presentation] 新規ポルフィリノイドおよび含窒素ナノグラフェンの合成化学2020

    • Author(s)
      田中隆行
    • Organizer
      純正・応用化学シンポジウム
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] メゾアリールコロールの酸化的カップリングに関する研究と考察2020

    • Author(s)
      田中隆行・大井翔太・大須賀篤弘
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] meso-Oxoisocorrole Metal Complexes and their Antiaromaticity2020

    • Author(s)
      Kento Ueta・Takayuki Tanaka・Atsuhiro Osuka
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] ピロールとチオフェンから成る環状混成体の酸化的縮環反応2020

    • Author(s)
      松尾悠佑・田中隆行・大須賀篤弘
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 構造的・電子的に柔軟なポルフィリノイド金属錯体の開拓2019

    • Author(s)
      田中隆行
    • Organizer
      錯体化学若手の会第60回近畿支部勉強会
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] Aza[8]circulenes: novel fluorescent hetero-PAHs2019

    • Author(s)
      Takayuki Tanaka, Fengkun Chen, Yusuke Matsuo, Koki Kise, Atsuhiro Osuka
    • Organizer
      ISNA-18
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of 5,10-diazaporphyrins via nucleophilic substitution reactions2019

    • Author(s)
      Masataka Umetani, Takayuki Tanaka, Atsuhiro Osuka
    • Organizer
      ISNA-18
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] meso-Oxoisocorroles: An Antiaromatic Porphyrinoid2019

    • Author(s)
      Kento Ueta,Takayuki Tanaka, Atsuhiro Osuka
    • Organizer
      ISNA-18
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis and Properties of Novel Hetero[8]circulenes2019

    • Author(s)
      Yusuke Matsuo, Takayuki Tanaka, Atsuhiro Osuka
    • Organizer
      ISNA-18
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 求核置換反応を用いた5,10-ジアザポルフィリンの合成2019

    • Author(s)
      梅谷将隆・田中隆行・大須賀篤弘
    • Organizer
      第30回基礎有機化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 酸化的縮環反応によるヘテロ[8]サーキュレンの合成とN上修飾2019

    • Author(s)
      松尾悠佑・黄瀬光稀・田中隆行・大須賀篤弘
    • Organizer
      第30回基礎有機化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] meso-Oxoisocorrole Metal Complexes and their Antiaromaticity2019

    • Author(s)
      Kento Ueta・Takayuki Tanaka・Atsuhiro Osuka
    • Organizer
      錯体化学会第69討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] 8の字型オクタフィリンGe二核錯体の合成とそのキラル特性2019

    • Author(s)
      水藤泰介・井澤主水・清水大貴・ 田中隆行・ 大須賀篤弘
    • Organizer
      錯体化学会第69討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] ピロールとチオフェンから成る環状混成体の酸化的縮環反応2019

    • Author(s)
      松尾悠佑・黄瀬光稀・田中隆行・大須賀篤弘
    • Organizer
      第46回有機典型元素化学討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] ジアミノトリピリンの自己二量化による共役二重らせん形成2019

    • Author(s)
      田中隆行・植田賢人・梅谷将隆・大須賀篤弘
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] 求核置換反応を用いた5,10-ジアザポルフィリンの合成2019

    • Author(s)
      梅谷将隆・田中隆行・大須賀篤弘
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] メゾ位にジフェニルアミノ基を有するコロール誘導体の合成2019

    • Author(s)
      植田賢人・田中隆行・大須賀篤弘
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] 新規ヘテロ[8]サーキュレン分子の合成とその物性2019

    • Author(s)
      松尾悠佑・黄瀬光稀・田中隆行・大須賀篤弘
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] 8の字型オクタフィリンGe二核錯体の合成とそのキラル特性2019

    • Author(s)
      水藤泰介・井澤主水・清水大貴・田中隆行・大須賀篤弘
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] Aza[8]circulenes: Novel Fluorescent Hetero-PAHs2018

    • Author(s)
      Takayuki Tanaka
    • Organizer
      10th Singapore International Chemistry Conference (SICC10)
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] u-Oxo-Bridged Dimers of Metallocorroles2018

    • Author(s)
      Takayuki Tanaka,Kento Ueta,Shota Ooi,Atsuhiro Osuka
    • Organizer
      ICPP10
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] コロール典型元素錯体20182018

    • Author(s)
      田中隆行・植田賢人・大井翔太・大須賀篤弘
    • Organizer
      第45回有機典型元素化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] Synthesis of Novel Heteroporphyrinoids Using Dibromotripyrrin as a Precursor2018

    • Author(s)
      Masataka Umetani,Takayuki Tanaka,AtsuhiroOsuka
    • Organizer
      ICPP10
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] meso-Aryl Corrole Silicon(Ⅳ)Complexes2018

    • Author(s)
      Kento Ueta,Masaya Fukuda,Gakhyun Kim,Soji Shimizu,Takayuki Tanaka,Dongho Kim, Atsuhiro Osuka
    • Organizer
      ICPP10
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] メゾーメゾ結合コロール二量体の酸化反応機構2018

    • Author(s)
      大井翔太・田中隆行・大須賀篤弘
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] ジブロモトリピリンを前駆体に用いた新しいヘテロポルフィリノイド合成2018

    • Author(s)
      梅谷将隆・田中隆行・大須賀篤弘
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Research-status Report
  • [Presentation] メゾ-ニトロコロールの合成と物性2018

    • Author(s)
      植田賢人・田中隆行・大須賀篤弘
    • Organizer
      第29回基礎有機化学討論会
    • Related Report
      2018 Research-status Report

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Published: 2018-04-23   Modified: 2021-02-19  

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