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2016 Fiscal Year Annual Research Report

電荷非局在型色素に基づく光捕集システムの構築

Publicly Offered Research

Project AreaChemical conversion of solar energy by artificial photosynthesis: a breakthrough by fusion of related fields toward realization of practical processes
Project/Area Number 15H00876
Research InstitutionNara Institute of Science and Technology

Principal Investigator

荒谷 直樹  奈良先端科学技術大学院大学, 物質創成科学研究科, 准教授 (60372562)

Project Period (FY) 2015-04-01 – 2017-03-31
Keywords人工光合成 / 近赤外発光 / 近赤外吸収 / 有機半導体
Outline of Annual Research Achievements

本研究課題では、通常の有機分子では獲得することのできない低エネルギー光捕集するために、近赤外吸収をもつ炭化水素の分子設計を探求している。これまで化学的安定性を十分に有する、分子内に電荷をもつπ共役系を高いアスペクト比を保ったままで拡張し、比較的少ない芳香環ユニット数で吸収波長の長波長化を目指してきた。このような色素の特長を活かして高効率の光捕集の達成を目指している。さらにその集積体を利用して、励起子伝達・エネルギー移動が可能な人工光合成アンテナ系を創製し、化学エネルギーへの変換系との有機的な結合法の開発も目的としている。これまでにフルオロンの共役系をベンゼン環2つ分拡張したDBXの開発に成功し、近赤外領域の817 nmを極大とする吸収および853 nmを極大とする蛍光発光を明らかにした。さらに蛍光量子収率は6.4%と近赤外発光分子としては非常に大きな値を示した。
研究後半では閉殻系の分子として1000 nmを超える近赤外吸収分子の創製を目指し、さらなるπ共役系拡張による吸収スペクトルの長波長化をするために様々な合成ルートを検討した結果、現在π拡張フルオロン(DNX)の合成に挑戦している。分子サイズの拡張に伴って反応性が変化したため、π共役系拡張にともなう酸化電位の低下を抑制しつつ溶解性を確保する目的で、電子求引性の置換基を立体的に導入している。すでに炭素骨格はできあがっている。計算と合成の両面のアプローチからDNXアニオンの物性について議論している。

Research Progress Status

28年度が最終年度であるため、記入しない。

Strategy for Future Research Activity

28年度が最終年度であるため、記入しない。

  • Research Products

    (39 results)

All 2017 2016 Other

All Int'l Joint Research (3 results) Journal Article (15 results) (of which Int'l Joint Research: 5 results,  Peer Reviewed: 15 results,  Acknowledgement Compliant: 6 results,  Open Access: 1 results) Presentation (20 results) (of which Int'l Joint Research: 8 results,  Invited: 4 results) Remarks (1 results)

  • [Int'l Joint Research] National Unversity of Singapore/Nanyang Technplogical University(Singapore)

    • Country Name
      Singapore
    • Counterpart Institution
      National Unversity of Singapore/Nanyang Technplogical University
  • [Int'l Joint Research] Yonsei University(韓国vvvv)

    • Country Name
      KOREA (REP. OF KOREA)
    • Counterpart Institution
      Yonsei University
  • [Int'l Joint Research] Autanoma University of Madrid(Spain)

    • Country Name
      Spain
    • Counterpart Institution
      Autanoma University of Madrid
  • [Journal Article] Rylene Ribbons with Unusual Diradical Character2017

    • Author(s)
      W. Zeng, H. Phan, T. S. Herng, T. Y. Gopalakrishna, N. Aratani, Z. Zeng, H. Yamada, J. Ding, J. Wu
    • Journal Title

      Chem

      Volume: 2 Pages: 81-92

    • DOI

      10.1016/j.chempr.2016.12.001

    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Fullerene-Based n-Type Materials That Can Be Processed by a Photoprecursor Approach for Photovoltaic Applications2017

    • Author(s)
      K. Kawajiri, T. Kawanoue, M. Yamato, K. Terai, M. Yamashita, M. Furukawa, N. Aratani, M. Suzuki, K.-i. Nakayama, H. Yamada
    • Journal Title

      ECS J. Solid State Sci. Technol.

      Volume: 6 Pages: M3068-M3074

    • DOI

      10.1149/2.0141706jss

    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [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 Pages: 8211-8218

    • DOI

      10.1021/acsami.6b13988

    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Semiconducting Self-assembled Nanofibers Prepared from Photostable Octafluorinated Bisanthene Derivatives2017

    • Author(s)
      H. Hayashi, N. Aratani, H. Yamada
    • Journal Title

      Chem. Eur. J.

      Volume: 23 Pages: in press

    • DOI

      10.1002/chem.201700080

    • Peer Reviewed / Acknowledgement Compliant
  • [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 Pages: in press

    • DOI

      10.1246/bcsj.20160337

    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Rearrangement of an aniline linked perylene bisimide under acidic conditions and visible to near-infrared emission from intramolecular charge-transfer state of its fused derivatives2017

    • Author(s)
      M. Kojima, A. Tamoto, N. Aratani, H. Yamada
    • Journal Title

      Chem. Commun.

      Volume: 53 Pages: in press

    • DOI

      10.1039/C7CC01520H

    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] β-to-β 2,5-Pyrrolylene-Linked Cyclic Porphyrin Oligomers2016

    • Author(s)
      Y. Rao, J. O. Kim, W. Kim, G. Zhong, B. Yin, M. Zhou, H. Shinokubo, N. Aratani, T. Tanaka, S. Liu, A. Osuka, D. Kim, J. Song
    • Journal Title

      Chem. Eur. J.

      Volume: 52 Pages: 8801-8804

    • DOI

      10.1002/chem.201601306

    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Switching charge-transfer characteristics from p-type to n-type through molecular “doping” (cocrystallization)2016

    • Author(s)
      J. Zhang, P. Gu, G. Long, R. Ganguly, Y. Li, N. Aratani, H. Yamada, Q. Zhang
    • Journal Title

      Chem. Sci.

      Volume: 7 Pages: 3851-3856

    • DOI

      10.1039/c5sc04954g

    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Bisanthra-thianthrene: synthesis, structure and oxidation properties2016

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

      RSC Adv.

      Volume: 6 Pages: 70700-70703

    • DOI

      10.1039/c6ra13036d

    • 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 Pages: 10671-10678

    • DOI

      10.1002/chem.201601083

    • Peer Reviewed
  • [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 Pages: 1350-1360

    • DOI

      10.1142/S1088424616501108

    • Peer Reviewed
  • [Journal Article] Benzo[4,5]cyclohepta[1,2-b]fluorene: an isomeric motif for pentacene containing linearly fused five-, six- and seven-membered rings2016

    • Author(s)
      X. Yang, X. Shi, N. Aratani, T. P. Gonalves, K.-W. Huang, H. Yamada, C. Chi, Q. Miao
    • Journal Title

      Chem. Sci.

      Volume: 7 Pages: 6176-6181

    • DOI

      10.1039/c6sc01795a

    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Aromaticity Relocation in Perylene Derivatives upon Two-electron Oxidation to Form Anthracene and Phenanthrene2016

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

      Chem. Eur. J.

      Volume: 22 Pages: 14462-14466

    • DOI

      10.1002/chem.201602188

    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Fullerene-linked tetrabenzoporphyrins for solution-processed organic photovoltaics: flexible vs. rigid linkers2016

    • Author(s)
      Y. Tamura, D. Kuzuhara, M. Suzuki, H. Hayashi, N. Aratani, H. Yamada
    • Journal Title

      J. Mater. Chem. A

      Volume: 4 Pages: 15333-15342

    • DOI

      10.1039/c6ta06599f

    • Peer Reviewed
  • [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 Pages: 10106-10109

    • DOI

      10.1021/acs.inorgchem.6b01841

    • Peer Reviewed
  • [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、荒谷 直樹、山田 容子
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学理工学部(神奈川県横浜市)
    • Year and Date
      2017-03-16 – 2017-03-19
  • [Presentation] 二重1,8-ナフチレン架橋対面型ペリレン2量体の合成2017

    • Author(s)
      村山 智寿・荒谷 直樹・山田 容子
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学理工学部(神奈川県横浜市)
    • Year and Date
      2017-03-16 – 2017-03-19
  • [Presentation] Synthesis of an N-doped nanographene2017

    • Author(s)
      IKEDA, Erika; ARATANI, Naoki; YAMADA, Hirorko
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学理工学部(神奈川県横浜市)
    • Year and Date
      2017-03-16 – 2017-03-19
  • [Presentation] ベンゾジサルチンを利用した高次アセンの合成法の開拓2017

    • Author(s)
      田中 智士・荒谷 直樹・山田 容子
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学理工学部(神奈川県横浜市)
    • Year and Date
      2017-03-16 – 2017-03-19
  • [Presentation] Synthesis of Macrocyclic Molecules with Twisted Porphyrins(2.1.2.1)2017

    • Author(s)
      FURUKAWA, Wataru; KUZUHARA, Daiki; ARATANI, Naoki; YAMADA, Hiroko
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学理工学部(神奈川県横浜市)
    • Year and Date
      2017-03-16 – 2017-03-19
  • [Presentation] Substituent Impact on the Open-Circuit Voltage in Organic Solar Cells Prepared through a Photoprecursor Approach2017

    • Author(s)
      Mitsuharu Suzuki, Kengo Terai, Naoki Aratani, Hiroko Yamada
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学理工学部(神奈川県横浜市)
    • Year and Date
      2017-03-16 – 2017-03-19
  • [Presentation] From Nanographene to Molecular Graphite;Development of Pyrene and Perylene-based Large π-Conjugated Systems2016

    • Author(s)
      Naoki Aratani, Akinobu Matsumoto, Akira Tamoto, Tomohisa Murayama, and Hiroko Yamada
    • Organizer
      9th Singapore International Chemistry Conference
    • Place of Presentation
      NUS University Town, Singapore
    • Year and Date
      2016-12-11 – 2016-12-14
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis of a 56 All-Carbon Conjugated Tetrabenzoperipentacene2016

    • Author(s)
      Akinobu Matsumoto, Mitsuharu Suzuki, Daiki Kuzuhara, Hironobu Hayashi, Naoki Aratani, and Hiroko Yamada
    • Organizer
      9th Singapore International Chemistry Conference
    • Place of Presentation
      NUS University Town, Singapore
    • Year and Date
      2016-12-11 – 2016-12-14
    • Int'l Joint Research
  • [Presentation] The structure and property of nonabenzocoronene for organic electronics2016

    • Author(s)
      A. Tamoto, N. Aratani, A. Briseno, H. Yamada
    • Organizer
      9th Singapore International Chemistry Conference
    • Place of Presentation
      NUS University Town, Singapore
    • Year and Date
      2016-12-11 – 2016-12-14
    • Int'l Joint Research
  • [Presentation] Photophysical Properties of Face-to-face Perylene Dimer and Trimer2016

    • Author(s)
      Murayama Tomohisa, Naoki Aratani, Hiroko Yamada
    • Organizer
      2016年光化学討論会
    • Place of Presentation
      東京大学駒場第一キャンパス(東京都目黒区)
    • Year and Date
      2016-09-06 – 2016-09-08
  • [Presentation] π拡張したペリレンビスイミド誘導体の合成と物性2016

    • Author(s)
      松本彬伸、荒谷直樹、山田容子
    • 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 – 2016-09-03
  • [Presentation] ナフタレン縮環TTF bisimideの合成とそのラジカルカチオンの性質2016

    • Author(s)
      山下正貴、荒谷直樹、山田容子
    • 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 – 2016-09-03
  • [Presentation] ノナベンゾコロネンの結晶構造とデバイス性能2016

    • Author(s)
      田本彬、荒谷直樹、Briseno Alejandro、山田容子
    • 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 – 2016-09-03
  • [Presentation] 湾曲構造を有するヘキサフィリン(2.1.2.1.2.1)とポルフィリン(2.1.2.1)とその金属錯体の合成2016

    • Author(s)
      薛 松林・葛原・大軌・荒谷直樹・山田容子
    • 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 – 2016-09-03
  • [Presentation] 分子性グラファイトを志向した対面型ペリレン多量体の構築2016

    • Author(s)
      荒谷直樹、村山智寿、松本彬伸、田本彬、山田容子
    • 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 – 2016-09-03
  • [Presentation] Synthesis of Oxatriphyrin(2.1.1) and its Boron Complex2016

    • Author(s)
      Hiroko Yamada, Daiki Kuzuhara, Shinsuke Kawatsu, Songlin Xue, Naoki Aratani
    • Organizer
      Ninth international conference on porphyrins and phthalicyanines (ICPP-9)
    • Place of Presentation
      Nanjing, China
    • Year and Date
      2016-07-03 – 2016-07-08
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis of Non-planar Dimers for New n-type Organic Semiconductors2016

    • Author(s)
      Takuya Okabe, Daiki Kuzuhara, Naoki Aratani, Hiroko Yamada
    • Organizer
      Ninth international conference on porphyrins and phthalicyanines (ICPP-9)
    • Place of Presentation
      Nanjing, China
    • Year and Date
      2016-07-03 – 2016-07-08
    • Int'l Joint Research
  • [Presentation] Dibenzoporphyrin(2.1.2.1):Highly Bent o-Phenylene Bridged Bisdipyrrin2016

    • Author(s)
      Daiki Kuzuhara, Wataru Furukawa, Naoki Aratani, Hiroko Yamada
    • Organizer
      Ninth international conference on porphyrins and phthalicyanines (ICPP-9)
    • Place of Presentation
      Nanjing, China
    • Year and Date
      2016-07-03 – 2016-07-08
    • Int'l Joint Research / Invited
  • [Presentation] Functionalized Porphycenes for Organic Electronics2016

    • Author(s)
      Daiki Kuzuhara, Takuya Okabe, Mika Sakaguchi, Naoki Aratani, Hiroko Yamada
    • Organizer
      Ninth international conference on porphyrins and phthalicyanines (ICPP-9)
    • Place of Presentation
      Nanjing, China
    • Year and Date
      2016-07-03 – 2016-07-08
    • 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
      26th IUPAC International Symposium on Photochemistry
    • Place of Presentation
      Osaka, Japan
    • Year and Date
      2016-04-03 – 2016-04-08
    • Int'l Joint Research
  • [Remarks] 奈良先端科学技術大学院大学 有機光分子科学研究室

    • URL

      http://mswebs.naist.jp/LABs/env_photo_greenmat/

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Published: 2018-01-16   Modified: 2022-02-01  

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