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Development of Azaporphyrin Main-Group Element complexes

Research Project

Project/Area Number 15K05409
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Organic chemistry
Research InstitutionKanazawa University

Principal Investigator

Furuyama Taniyuki  金沢大学, 物質化学系, 准教授 (30584528)

Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2017: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2015: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywordsアザポルフィリン / 機能性色素 / 典型元素化学 / 一重項酸素 / 光安定性 / ソルバトクロミズム / 五価リン / 還元特性 / ラジカル
Outline of Final Research Achievements

The effects of main-group elements in the synthesis and properties of azaporphyrins have been investigated. The tetraazaporphyrin phosphorus(V) complex was reduced by addition of base, and extremely air-stable neutral radical (formally 19π electrons) could be isolated. Two novel synthetic reactions mediated sulfur have been developed. 1. A diamino-beta-isoindigo skeleton was obtained directly from phthalonitriles, and a new antiaromatic expanded phthalocyanine skeleton (pentabenzotriazasmaragdyrin, PBTAS) was obtained by the condensation with such isoindigo and other phthalonitrile. 2. Three-component coupling reaction of element sulfur, organometallic reagents, and phthalonitrile was developed, and functionalized phthalocyanines that have an intense absorption band in the near-IR region have been synthesized. Electron-withdrawing phthalocyanines were synthesized by lead-mediated reactions. Some metal complexes have high efficiency of singlet oxygen generation.

Report

(4 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • Research Products

    (35 results)

All 2017 2016 2015 Other

All Int'l Joint Research (3 results) Journal Article (21 results) (of which Int'l Joint Research: 9 results,  Peer Reviewed: 20 results,  Acknowledgement Compliant: 16 results,  Open Access: 1 results) Presentation (8 results) (of which Int'l Joint Research: 3 results,  Invited: 3 results) Remarks (3 results)

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

    • Related Report
      2017 Annual Research Report
  • [Int'l Joint Research] Simon Fraser University(カナダ)

    • Related Report
      2016 Research-status Report
  • [Int'l Joint Research] Simon Fraser University(カナダ)

    • Related Report
      2015 Research-status Report
  • [Journal Article] Structural, Photophysical, and Magnetic Circular Dichroism Studies of Three Rigidified meso-Pentafluorophenyl-Substituted Hexaphyrin Analogues2017

    • Author(s)
      Ishida Masatoshi、Furuyama Taniyuki、Lim Jong Min、Lee Sangsu、Zhang Zhan、Ghosh Sudip K.、Lynch Vincent M.、Lee Chang-Hee、Kobayashi Nagao、Kim Dongho、Sessler Jonathan L.
    • Journal Title

      Chemistry - A European Journal

      Volume: 23 Issue: 27 Pages: 6682-6692

    • DOI

      10.1002/chem.201700759

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] D-A-D type dinitriles with vapor-dependent luminescence in the solid state2017

    • Author(s)
      Furuyama Taniyuki、Shinozaki Junichi、Tasso Thiago Teixeira、Maeda Hajime、Segi Masahito、Kobayashi Nagao
    • Journal Title

      Tetrahedron Letters

      Volume: 58 Issue: 45 Pages: 4243-4247

    • DOI

      10.1016/j.tetlet.2017.09.068

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Azaporphyrin phosphorus(v) complexes: synthesis, structure, and modification of optical properties2017

    • Author(s)
      Furuyama Taniyuki、Kobayashi Nagao
    • Journal Title

      Physical Chemistry Chemical Physics

      Volume: 19 Issue: 24 Pages: 15596-15612

    • DOI

      10.1039/c7cp02155k

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Preparation, Optical and Electrochemical Properties, and Molecular Orbital Calculations of Tetraazaporphyrinato Ruthenium (II) Bis(4-methylpyridine) Fused with One to Four Diphenylthiophene Units2016

    • Author(s)
      T. Kimura, N. Murakami, E. Suzuki, T. Furuyama, T. Nakahodo, H. Fujihara, and N. Kobayashi
    • Journal Title

      Journal of Inorganic Biochemistry

      Volume: 158 Pages: 35-44

    • DOI

      10.1016/j.jinorgbio.2016.01.010

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis, Optical Properties, and Electronic Structures of Tetrakis(pentafluorophenyl)tetrathiaisophlorin Dioxide2016

    • Author(s)
      Mishra, V. L.; Furuyama, T.; Kobayashi, N.; Goto, K.; Miyazaki, T.; Yang, J.-S.; Shinmyozu, T.
    • Journal Title

      Chem. Eur. J.

      Volume: 22 Issue: 27 Pages: 9190-9197

    • DOI

      10.1002/chem.201505079

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Double-decker Bis(tetradiazepinoporphyrazinato) Rare Earth Complexes: Crucial Role of Intramolecular Hydrogen Bonding2016

    • Author(s)
      Tarakanova, E. N.; Trashin, S.; Simakov, A. O.; Furuyama, T.; Dzuban, A. V.; Inasaridze, L. N.; Tarakanov, P. A.; Troshin, P.; Pushkarev, V.; Kobayashi, N.; Tomilova, L. B.
    • Journal Title

      Dalton Trans.

      Volume: 45 Issue: 30 Pages: 12041-12052

    • DOI

      10.1039/c6dt01779g

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Formation of a Trithia[5]helicene in an Unexpected Photoreaction of a Methyl-substituted Bis(dithienylethenyl)thiophene through a Double Sequence of 6π-Electrocyclization/Aromatization (Dehydrogenation/Demethylation)2016

    • Author(s)
      A. Yamamoto, Y. Matsui, E. Ohta, T. Ogaki, H. Sato, T. Furuyama, N. Kobayashi, K. Mizuno, H. Ikeda
    • Journal Title

      J. Photochem. Photobiol. A. Chem.

      Volume: in press Pages: 48-55

    • DOI

      10.1016/j.jphotochem.2015.10.012

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Simple primary β-amino alcohol catalyzed enantioselective Diels-Alder reaction of 3-hydroxy-2-pyridones2016

    • Author(s)
      Takahashi, T., Reddy, U.V.S., Kohari, Y., Seki, C., Furuyama, T., Kobayashi, N., Okuyama, Y., Kwon, E., Uwai, U., Tokiwa, M., Takeshita, M., Nakano, H.
    • Journal Title

      Tetrahedron Letters

      Volume: 57 Issue: 51 Pages: 5771-5776

    • DOI

      10.1016/j.tetlet.2016.11.030

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of meta-methoxyphenyl substituted tetraazaporphyrin and corrolazine phosphorus(V) complexes2016

    • Author(s)
      Furuyama, T.; Sugiya, Y.; Yoshida, T.; Kobayashi, N.
    • Journal Title

      J. Porphyrins Phthalocyanines

      Volume: 20 Issue: 08n11 Pages: 1075-1081

    • DOI

      10.1142/s1088424616500619

    • NAID

      120005973604

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Metallophthalocyanin-ocenes: Scandium Phthalocyanines with an η5-bound Cp Ring2015

    • Author(s)
      Platel, R. H.; Tasso, T. T.; Zhou, W.; Furuyama, T.; Kobayashi, N.: Leznoff, D. B.
    • Journal Title

      Chem. Commun.

      Volume: 51 Issue: 27 Pages: 5986-5989

    • DOI

      10.1039/c5cc00237k

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Optical, Electrochemical, and Magnetic Properties of Pyrrole- and Thiophene-Bridged 5,15-Diazaporphyrin Dimers2015

    • Author(s)
      Omomo, S.; Maruyama, Y.; Furukawa, K.; Furuyama, T., Nakano, H.; Kobayashi, N.; Matano, Y.
    • Journal Title

      Chem. Eur. J.

      Volume: 21 Issue: 5 Pages: 2003-2010

    • DOI

      10.1002/chem.201405482

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis, Spectral Properties and TD-DFT Calculations of Nonclassical Binuclear Thienoporphyrazines.2015

    • Author(s)
      T. V. Dubinina, N. E. Borisova, L. G. Tomilova, T. Furuyama, and N. Kobayashi
    • Journal Title

      Dyes & Pigm.

      Volume: 51 Pages: 1-6

    • DOI

      10.1016/j.dyepig.2015.01.023

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] A Stable iso-Bacteriochlorin Mimics from Porpholactone: Effect of β-oxazolone Moiety on the Frontier π-Molecular Orbitals2015

    • Author(s)
      Yu, Y.; Furuyama, T.; Tang, J.; Wu, Z.-Y.; Chen, J.-Z.; Kobayashi, N.; Zhang, J.-L.
    • Journal Title

      Inorg. Chem. Front.

      Volume: 2 Issue: 7 Pages: 671-677

    • DOI

      10.1039/c5qi00054h

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Reducing Zirconium(IV) Phthalocyanines and the Structure of a Pc4–Zr Complex2015

    • Author(s)
      Zhou, W.; Platel, R. H.; Tasso, T. T.; Furuyama, T.; Kobayashi, N.; Leznoff, D. B.
    • Journal Title

      Dalton Trans.

      Volume: 44 Issue: 31 Pages: 13955-13961

    • DOI

      10.1039/c5dt01778e

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] An Extremely Air-Stable 19π Porphyrinoid2015

    • Author(s)
      Yoshida, T.; Zhou, W.; Furuyama, T.*; Leznoff, D. B.; Kobayashi, N.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 137 Issue: 29 Pages: 9258-9261

    • DOI

      10.1021/jacs.5b05781

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Fluorescence Enhancement of Tetraazaporphyrins by Use of Bulky Substituent Effects2015

    • Author(s)
      Yoshida, T.; Furuyama, T.; Asai, M.; Kobayashi, N.
    • Journal Title

      Chem. Lett.

      Volume: 44 Issue: 8 Pages: 1056-1058

    • DOI

      10.1246/cl.150304

    • NAID

      130005092598

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Solution-Cast Monolayers of Cobalt Crown Ether Phthalocyanine on Highly Ordered Pyrolytic Graphite2015

    • Author(s)
      Lu, H.; Kwak, I.; Park, J. H.; O’Neill, K.; Furuyama, T.; Kobayashi, N.; Seabaugh, A.; Kummel, A.; Fullerton-Shirey, S. K.
    • Journal Title

      J. Phys. Chem. C

      Volume: 119 Issue: 38 Pages: 21992-22000

    • DOI

      10.1021/acs.jpcc.5b05233

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] A Bottom-up Synthesis of Antiaromatic Expanded Phthalocyanines: Pentabenzotriazasmaragdyrins, i.e. Norcorroles of Superphthalocyanines2015

    • Author(s)
      Furuyama, T.; Sato, T.; Kobayashi, N.
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 137 Issue: 43 Pages: 13788-13791

    • DOI

      10.1021/jacs.5b09853

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis and Photophysical Investigation of Tetraazaporphyrin Substituted with Aggregation-Induced Emission (AIE) Active Moieties2015

    • Author(s)
      Thiago, T. T.; Furuyama, T.; Mack, J.; Nyokong, T.; Kobayashi, N.
    • Journal Title

      Eur. J. Inorg. Chem.

      Volume: 2015 Issue: 33 Pages: 5516-5522

    • DOI

      10.1002/ejic.201500726

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] 高原子価リンを活用したアザポルフィリン類の光物性制御2015

    • Author(s)
      古山 渓行
    • Journal Title

      化学と工業

      Volume: 68 Pages: 644-645

    • Related Report
      2015 Research-status Report
    • Acknowledgement Compliant
  • [Journal Article] Design, Synthesis, and Properties of Azaporphyrin Phosphorus Complexes2015

    • Author(s)
      古山 渓行、小林 長夫
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 73 Issue: 8 Pages: 833-843

    • DOI

      10.5059/yukigoseikyokaishi.73.833

    • NAID

      130005098866

    • ISSN
      0037-9980, 1883-6526
    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 機能性π共役化合物の設計・合成と近赤外光利活用への挑戦2017

    • Author(s)
      古山渓行
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      宮城県仙台市
    • Year and Date
      2017-03-24
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] アザポルフィリンを活用する近赤外光材料の開発2017

    • Author(s)
      古山渓行
    • Organizer
      第38回光化学若手の会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Optical Properties of Near-IR Absorbing Phthalocyanine Sensitizers2017

    • Author(s)
      Takayuki Iwamoto, Mashiro Hata, Maria Sugimori, Daichi Tamura, Ryo Yanagisawa, and Taniyuki Furuyama
    • Organizer
      第3回超分子による革新的マテリアル開発の拠点形成国際シンポジウム
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] An Air-stable 19π Azaporphyrinoid Radical2016

    • Author(s)
      Taniyuki Furuyama, Takuya Yoshida, Wen Zhou, Daniel B. Leznoff, Nagao Kobayashi
    • Organizer
      9th International Conference on Porphyrins and Phthalocyanines (ICPP-9)
    • Place of Presentation
      Nanjing, China
    • Year and Date
      2016-07-03
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] 異常π電子価化合物の設計・機能2016

    • Author(s)
      古山渓行・吉田拓矢・佐藤岳仁・小林長夫
    • Organizer
      第14回次世代を担う有機化学シンポジウム
    • Place of Presentation
      東京都渋谷区
    • Year and Date
      2016-05-27
    • Related Report
      2016 Research-status Report
  • [Presentation] Chalcogenide-Substituted Phthalocyanines: The Most Distorted Phthalocyanines2016

    • Author(s)
      Taniyuki Furuyama, Koh Satoh, Nagao Kobayashi
    • Organizer
      13th International Conference on the Chemistry of Selenium and Tellurium (ICCST-13)
    • Place of Presentation
      Gifu, Japan
    • Year and Date
      2016-05-23
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] 中心元素・周辺置換基効果を活用したテトラアザポルフィリンの機能創出2015

    • Author(s)
      古山渓行・吉田拓矢・浅井光夫・下岡千尋・小林長夫
    • Organizer
      第42回有機典型元素化学討論会
    • Place of Presentation
      愛知県名古屋市
    • Year and Date
      2015-12-03
    • Related Report
      2015 Research-status Report
  • [Presentation] 環拡張フタロシアニン類の開発および物性制御2015

    • Author(s)
      古山渓行・小倉陽祐・佐藤岳仁・小林長夫
    • Organizer
      第26回基礎有機化学討論会
    • Place of Presentation
      愛媛県松山市
    • Year and Date
      2015-09-24
    • Related Report
      2015 Research-status Report
  • [Remarks] 金沢大学研究者情報

    • URL

      http://ridb.kanazawa-u.ac.jp/public/detail.php?id=4466&page=3&org2_cd=340400

    • Related Report
      2017 Annual Research Report 2016 Research-status Report 2015 Research-status Report
  • [Remarks] 金沢大学理工研究域物質化学系 精密有機合成化学研究室

    • URL

      http://kohka.ch.t.kanazawa-u.ac.jp/lab4/TFProfile.html

    • Related Report
      2017 Annual Research Report
  • [Remarks] 金沢大学理工研究域物質化学系 精密有機合成化学研究室

    • URL

      http://kohka.ch.t.kanazawa-u.ac.jp/lab4/TFProfile.html

    • Related Report
      2016 Research-status Report 2015 Research-status Report

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Published: 2015-04-16   Modified: 2019-03-29  

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