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Synthesis and Characterization of Bent Porphyrins

Research Project

Project/Area Number 16K17950
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Organic and hybrid materials
Research InstitutionIwate University

Principal Investigator

KUZUHARA Daiki  岩手大学, 理工学部, 助教 (00583717)

Project Period (FY) 2016-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2017: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywords有機化学 / ポルフィリン / 湾曲構造 / 超分子 / 環状化合物 / 金属錯体 / 有機半導体 / 超分子化学 / 太陽電池
Outline of Final Research Achievements

We have established the method of synthesis of porphyrins(2.1.2.1) from 1,2-di(pyrro-2-yl)benzene and benzaldehydes under condensation reaction. X-ray crystallography reveals that porphyrins(2.1.2.1) form highly saddle-shaped bent structures. In addition, porphyrins(2.1.2.1) can be converted to various metal complexes as well as pristine porphyrin.
Bent structure of porphyrin(2.1.2.1) is a suitable platform for construction of cyclic structures. We have synthesized two type of porphyrin(2.1.2.1)-based cyclic trimers. In particular, cyclic porphyrins(2.1.2.1) trimer that is connected by benzene linkages can capture the two fullerenes in its cavity.

Report

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

    (24 results)

All 2018 2017 2016

All Journal Article (8 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 8 results,  Open Access: 3 results,  Acknowledgement Compliant: 1 results) Presentation (16 results) (of which Int'l Joint Research: 8 results,  Invited: 4 results)

  • [Journal Article] Engineering Thin Films of a Tetrabenzoporphyrin toward Efficient Charge-Carrier Transport: Selective Formation of a Brickwork Motif2017

    • Author(s)
      K. Takahashi, B. Shan, X. Xu, S. Yang, T. Koganezawa, D. Kuzuhara, N. Aratani, M. Suzuki, Q. Miao, H. Yamada
    • Journal Title

      ACS Appl. Mater. Interfaces

      Volume: 9 Issue: 9 Pages: 8211-8218

    • DOI

      10.1021/acsami.6b13988

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Synthesis, Characterization and Protonation Behavior of Quinoxaline-Fused Porphycenes2017

    • Author(s)
      Kuzuhara Daiki、Sakaguchi Mika、Furukawa Wataru、Okabe Takuya、Aratani Naoki、Yamada Hiroko
    • Journal Title

      Molecules

      Volume: 22 Issue: 6 Pages: 908-908

    • DOI

      10.3390/molecules22060908

    • NAID

      120006369663

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Improved performance of organic photovoltaic cells with PTB7-Th:PC71 BM by optimized solvent evaporation time in electrospray deposition2017

    • Author(s)
      T. Fukuda, A. Toda, K. Takahira, D. Kuzuhara, N. Yoshimoto
    • Journal Title

      Org. Electron.

      Volume: 48 Pages: 96-105

    • DOI

      10.1016/j.orgel.2017.05.049

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Side-chain engineering in a thermal precursor approach for efficient photocurrent generation2017

    • Author(s)
      Takahashi Kohtaro、Kumagai Daichi、Yamada Naoya、Kuzuhara Daiki、Yamaguchi Yuji、Aratani Naoki、Koganezawa Tomoyuki、Koshika Sota、Yoshimoto Noriyuki、Masuo Sadahiro、Suzuki Mitsuharu、Nakayama Ken-ichi、Yamada Hiroko
    • Journal Title

      J. Mater. Chem. A

      Volume: 5 Issue: 27 Pages: 14003-14011

    • DOI

      10.1039/c7ta04162d

    • NAID

      120006369665

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Studies on Pyrene and Perylene Derivatives upon Oxidation and Application to a Higher Analogue2017

    • Author(s)
      A. Matsumoto, M. Suzuki, H. Hayashi, D. Kuzuhara, J. Yuasa, T. Kawai, N. Aratani, H. Yamada
    • Journal Title

      Bull. Chem. Soc. Jpn

      Volume: 90 Issue: 6 Pages: 667-677

    • DOI

      10.1246/bcsj.20160337

    • NAID

      130006770647

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis and Metalation of Doubly o-Phenylene-Bridged Cyclic Bis(dipyrrin)s with Highly Bent Skeleton of Dibenzoporphyrin(2.1.2.1)2016

    • Author(s)
      D. Kuzuhara, W. Furukawa, A. Kitashiro, N. Aratani, H. Yamada
    • Journal Title

      Chem. Eur. J.

      Volume: 22 Issue: 30 Pages: 10671-10678

    • DOI

      10.1002/chem.201601083

    • NAID

      120006334984

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis and Characterization of an Iridium Triphyrin Complex2016

    • Author(s)
      S. Xue, D. Kuzuhara, N. Aratani, H. Yamada
    • Journal Title

      Inorg. Chem.

      Volume: 55 Issue: 20 Pages: 10106-10109

    • DOI

      10.1021/acs.inorgchem.6b01841

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Porphycene Dimer Based Non-Fullerene Acceptor for Organic Solar Cell2016

    • Author(s)
      T. Okabe, D. Kuzuhara, M. Suzuki, N. Aratani, H. Yamada
    • Journal Title

      J. Porphyrins Phthalocyanines

      Volume: 20 Issue: 08n11 Pages: 1350-1360

    • DOI

      10.1142/s1088424616501108

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Presentation] Synthesis of Porphyrin(2.1.2.1) Nanobelt2018

    • Author(s)
      Songlin Xue, Daiki Kuzuhara, Naoki Aratani, Hiroko Yamada
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ヘキサフィリン(2.1.2.1.2.1)金属錯体の合成2018

    • Author(s)
      葛原大軌、薛松林、荒谷直樹、山田容子
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] エチレン架橋拡張ポルフィリン類の合成2017

    • Author(s)
      葛原大軌・薛松林・古川渉・荒谷直樹・吉本則之・山田 容子
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学 (神奈川県横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Research-status Report
  • [Presentation] 湾曲したポルフィリン(2.1.2.1)を用いた大環状化合物の合成2017

    • Author(s)
      古川渉・葛原大軌・荒谷直樹・山田容子
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学 (神奈川県横浜市)
    • Year and Date
      2017-03-16
    • Related Report
      2016 Research-status Report
  • [Presentation] ポルフィリン誘導体の合成とデバイス応用2017

    • Author(s)
      葛原大軌
    • Organizer
      化学系学協会東北大会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] ポルフィリン誘導体を用いた機能性材料の開発2017

    • Author(s)
      葛原大軌
    • Organizer
      第1回 産総研化学研究シンポジウム
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Synthesis of Bent and Distorted Expanded Porphyrins2017

    • Author(s)
      Kuzuhara, D.; Xue, S.; Furukawa, W.; Aratani, N.; Yoshimoto, N.; Yamada, H.
    • Organizer
      ECS meeting
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of [30]Hexaphyrins(2.1.2.1.2.1) with Different Conformations on Ethylene Bridges2017

    • Author(s)
      Songlin Xue, Daiki Kuzuhara, Naoki Aratani, Hiroko Yamada
    • Organizer
      17th International Symposium on Novel Aromatics
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ジフェニル-ジピロリルエテンを用いたπ共役拡張ポルフィリンの合成2016

    • Author(s)
      葛原大軌・薛松林・荒谷直樹・山田容子
    • Organizer
      π電子系シンポジウム
    • Place of Presentation
      あるう京北 (京都府京都市)
    • Year and Date
      2016-12-16
    • Related Report
      2016 Research-status Report
  • [Presentation] Synthesis and Metalation of Highly Bent Skeletons of Hexaphyrin(2.1.2.1.2.1) and Porphyrin(2.1.2.1)2016

    • Author(s)
      Songlin Xue, Daiki Kuzuhara, Naoki Aratani, Hiroko Yamada
    • Organizer
      第27回基礎有機化学討論会
    • Place of Presentation
      広島国際会議場 (広島県広島市)
    • Year and Date
      2016-09-01
    • Related Report
      2016 Research-status Report
  • [Presentation] Dibenzoporphyrin(2.1.2.1): Highly Bent o-Phenylene Bridged Bisdipyrrin2016

    • Author(s)
      Daiki Kuzuhara, Wataru Furukawa, Naoki Aratani, Hiroko Yamada
    • Organizer
      International Conference on. Porphyrins and Phthalocyanines
    • Place of Presentation
      Nanjing, China
    • Year and Date
      2016-07-03
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthesis of Non-planar Porphycene Dimers for New n-type Organic Semiconductors2016

    • Author(s)
      Takuya Okabe, Daiki Kuzuhara, Naoki Aratani, Hiroko Yamada
    • Organizer
      International Conference on. Porphyrins and Phthalocyanines
    • Place of Presentation
      Nanjing, China
    • Year and Date
      2016-07-03
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] Fullerene Linked Benzoporphyrins for Solution-Processed Organic Photovoltaic Material2016

    • Author(s)
      Yuto Tamura, Daiki Kuzuhara, Mitsuharu Suzuki, Hiroko Yamada, H.
    • Organizer
      International Conference on. Porphyrins and Phthalocyanines
    • Place of Presentation
      Nanjing, China
    • Year and Date
      2016-07-03
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] Functionalized Porphycenes for Organic Electronics2016

    • Author(s)
      Daiki Kuzuhara, Takuya Okabe, Mika Sakaguchi, Naoki Aratani, Hiroko Yamada
    • Organizer
      International Conference on. Porphyrins and Phthalocyanines
    • Place of Presentation
      Nanjing, China
    • Year and Date
      2016-07-03
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis of Oxatriphyrin(2.1.1) and its Boron Complex2016

    • Author(s)
      Hiroko Yamada, Daiki Kuzuhara, Shinsuke Kawatsu, Songlin Xue, Naoki Aratani
    • Organizer
      International Conference on. Porphyrins and Phthalocyanines
    • Place of Presentation
      Nanjing, China
    • Year and Date
      2016-07-03
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis of Highly Bent Porphyrins(2.1.2.1) and Their Metal Complexes2016

    • Author(s)
      Wataru Furukawa, Daiki Kuzuhara, Naoki Aratani, Hiroko Yamada
    • Organizer
      The 26th IUPAC Symposium on Photochemistry
    • Place of Presentation
      Osaka, Japan
    • Year and Date
      2016-04-03
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research

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Published: 2016-04-21   Modified: 2019-03-29  

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