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2010 Fiscal Year Final Research Report

Construction of Highly Conjugated Compounds Based on the Pericyclic Cycloreversion

Research Project

  • PDF
Project/Area Number 20550047
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionEhime University

Principal Investigator

UNO Hidemitsu  Ehime University, 大学院・理工学研究科, 教授 (20168735)

Research Collaborator YAMADA Hiroko  奈良先端科学技術大学院, 准教授 (20372724)
OKUJIMA Tetsuo  愛媛大学, 大学院・理工学研究科, 准教授 (60359924)
KOBAYASHI Nagao  東北大学, 大学院・理学研究科, 教授 (60124575)
MORI Shigeki  愛媛大学, 総合科学研究支援センター, 助教 (30572028)
KIM DongHo  Yonsei University, Korea, Professor
Project Period (FY) 2008 – 2010
Keywords構造有機化学 / 有機電子材料
Research Abstract

I have explored the methodology for synthesis of highly conjugated compounds applying the pericyclic cycloreversion of the precursors in the final step such as thermal retro-Diels-Alder reaction and photo de-thiocarbonylation. These precursors are easily purified due to high solubility toward common solvents and high stability toward oxidation. The targeted highly conjugated compounds can be obtained in a highly pure form by the thorough purification of the precursors. I have developed this methodology, prepared the π-fused compounds, and then clarified their intrinsic properties.

  • Research Products

    (60 results)

All 2011 2010 2009 2008 Other

All Journal Article (32 results) Presentation (20 results) Remarks (1 results) Patent(Industrial Property Rights) (7 results) (of which Overseas: 2 results)

  • [Journal Article] Cyclo[8]isoindoles : Ring-Expanded and Annelated Porphyrinoids2011

    • Author(s)
      T.Okujima, G.Jin, N.Matsumoto, J.Mack, S.Mori, K.Ohara, D.Kuzuhara, C.Ando, N.Ono, H.Yamada, H.Uno, N.Kobayashi
    • Journal Title

      Angew.Chem.Int.Ed. in press

      Pages: DOI:10.1002/anie.201007510.

  • [Journal Article] Synthesis of π-Expanded O-Chelated Boron-Dipyrromethene As an NIR Dye2011

    • Author(s)
      Y.Tomimori, T.Okujima, T.Yano, S.Mori, N.Ono, H.Yamada, H.Uno
    • Journal Title

      Tetrahedron 67

      Pages: 3187-3193

  • [Journal Article] Ultrafast Intramolecular Energy Relaxation Dynamics of Benzoporphyrins : Influence of Fused Benzo Rings on Singlet Exited States2011

    • Author(s)
      P.Kim, J.Sung, H.Uoyama, T.Okujima, H.Uno, D.Kim
    • Journal Title

      J.Phys.Chem.B 115

      Pages: 3784-3792

  • [Journal Article] Synthesis, Properties, and Ambipolar Organic Field-Effect Transistor Performances of Symmetrically Cyanated Pentacene and Naphthacene as Air-Stable Acene Derivatives2011

    • Author(s)
      S.Katsuta, D.Miyagi, H.Yamada, T.Okujima, S.Mori, K.Nakayama, H.Uno
    • Journal Title

      Org.Lett. 13

      Pages: 1454-1457

  • [Journal Article] First Synthesis of Dodecasubstituted Porphycenes2011

    • Author(s)
      D.Kuzuhara, H.Yamada, K.Yano, T.Okujima, S.Mori, H.Uno
    • Journal Title

      Chem.Eur.J. 17

      Pages: 3376-3383

  • [Journal Article] Photophysical insights into supramolecular interaction of a designed bisporphyrin with fullerenes C_<60> and C_<70>2011

    • Author(s)
      D.Pal, M.Furukawa, N.Komatsu, H.Uno, S.Bhattacharya
    • Journal Title

      Spectrochim.Acta A 78

      Pages: 185-190

  • [Journal Article] New synthesis of meso-free-[14]triphyrin (2.1.1) by McMurry coupling and its derivatization to Mn (I) and Re (I) complexes2011

    • Author(s)
      D.Kuzuhara, H.Yamada, Z.-L.Xue, T.Okujima, S.Mori, Z.Shen, H.Uno
    • Journal Title

      Chem.Commun. 47

      Pages: 722-724

  • [Journal Article] Synthesis and properties of BCOD-fused trithiasapphyrin and trithiabenzosapphyrins2010

    • Author(s)
      T.Okujima, T.Kikkawa, S.Kawakami, Y.Shimizu, H.Yamada, N.Ono, H.Uno
    • Journal Title

      Tetrahedron 66

      Pages: 7213-7218

  • [Journal Article] Synthesis of π-expanded BODIPYs and their fluorescent properties in the visible-near-infrared region2010

    • Author(s)
      T.Okujima, Y.Tomimori, J.Nakamura, H.Yamada, H.Uno, N.Ono
    • Journal Title

      Tetrahedron 66

      Pages: 6895-6900

  • [Journal Article] Pentacene precursors for solutionprocessed OFETs2010

    • Author(s)
      H.Uoyama, H.Yamada, T.Okujima, H.Uno
    • Journal Title

      Tetrahedron 66

      Pages: 6889-6894

  • [Journal Article] Synthesis, Crystal Structure, and Photodynamics of π-Expanded Porphyrin-Fullerene Dyads Synthesized by Diels-Alder Reaction2010

    • Author(s)
      H.Yamada, K.Ohkubo, D.Kuzuhara, T.Takahashi, A.S.D.Sandanayaka, T.Okujima, K.Ohara, O.Ito, H.Uno, N.Ono, S.Fukuzumi, J.Phys.
    • Journal Title

      Chem.B 114

      Pages: 14717-14728

  • [Journal Article] Synthesis of 2,3-dihydrobenzo[1,4]dithiinfused porphyrins2010

    • Author(s)
      G.Jin, T.Okujima, Y.Hashimoto, H.Yamada, H.Uno, N.Ono
    • Journal Title

      Phosphorus, Sulfur Silicon Relat.Elem. 185

      Pages: 1108-1116

  • [Journal Article] Highly Pure Synthesis, Spectral Assignments, and Two-Photon Properties of Cruciform Porphyrin Pentamers Fused with Benzene Units2010

    • Author(s)
      H.Uoyama, K.S.Kim, K.Kuroki, J.-Y.Shin, T.Nagata, T.Okujima, H.Yamada, N.Ono, D.Kim, H.Uno
    • Journal Title

      Chem.Eur.J. 16

      Pages: 4063-4074

  • [Journal Article] Synthesis and photochemical properties of π-diks precursors for π-expanded porphyrins etoporphyrins as precursors for π-expanded porphyrins2010

    • Author(s)
      H.Yamada, D.Kuzuhara, K.Ohkubo, T.Takahashi, T.Okujima, H.Uno, N.Ono, S.Fukuzumi
    • Journal Title

      J.Mater.Chem. 20

      Pages: 3011-3024

  • [Journal Article] Preparation of highly conjugated oligoaza-PAHs based on the oxidative intramolecular coupling of bicyclo[2.2.2]-octadiene-fused pyrrole2010

    • Author(s)
      H.Uno, T.Takiue, H.Uoyama, T.Okujima, H.Yamada, G.Masuda
    • Journal Title

      Heterocycles 82

      Pages: 791-802

  • [Journal Article] Synthesis of Tetrabenzoporphyrins Fused with Fluoranthenes2010

    • Author(s)
      J.Nakamura, T.Okujima, Y.Tomimori, N.Komobuchi, H.Yamada, H.Uno, N.Ono
    • Journal Title

      Heterocycles 80

      Pages: 1165-1175

  • [Journal Article] Thermal Behabior of Bicyclo[2.2.2]-octadiene-Installed Precursors for 2H-Anthra[2,3-c]pyrroles and Anthra-[2,3-c]thiophene2010

    • Author(s)
      H.Uoyama, C.Chenxin, H.Tahara, Y.Shimizu, H.Hagiwara, Y.Hanasaki, H.Yamada, T.Okujima, H.Uno
    • Journal Title

      Heterocycles 80

      Pages: 1187-1196

  • [Journal Article] Photochemical Synthesis of Tetraarylsubstituted Pentacenes2010

    • Author(s)
      S.Katsuta, H.Yamada, T.Okujima, H.Uno
    • Journal Title

      Tetrahedron Lett. 51

      Pages: 1397-1400

  • [Journal Article] First Synthesis of meso-Chlorinated Tetrabenzoporphyrins2009

    • Author(s)
      S.Ito, L.T.Phong, T.Komatsu, N.Igarashi, S.Otsubo, Y.Sakai, A.Ohno, S.Aramaki, Y.Tanaka, H.Uno, T.Oba, K.Hiratani
    • Journal Title

      Eur.J.Org.Chem.

      Pages: 5373-5382

  • [Journal Article] First Synthesis of Porphyrin-Fused 1,10-Phenanthroline-Ruthenium (II) Complexes2009

    • Author(s)
      T.Okujima, A.Mifuji, J.Nakamura, H.Yamada, H.Uno, N.Ono
    • Journal Title

      Org.Lett. 11

      Pages: 4088-4091

  • [Journal Article] 1-Aminoisoindole as a useful π-system elongation unit2009

    • Author(s)
      T.Akiyama, H.Uoyama, T.Okujima, H.Yamada, N.Ono, H.Uno
    • Journal Title

      Tetrahedron 65

      Pages: 4345-4350

  • [Journal Article] Organic Thin-Film Transistor from a Pentacene Photo Precursor2009

    • Author(s)
      A.Masumoto, Y.Yamashita, S.Go, T.Kikuchi, H.Yamada, T.Okujima, N.Ono, H.Uno
    • Journal Title

      Jpn.J.Appl.Phys.

      Pages: 051505/1-5

  • [Journal Article] Synthesis, structures, and properties of BCOD-fused porphyrins and benzoporphyrins2009

    • Author(s)
      H.Uoyama, T.Takiue, K.Tominaga, N.Ono, H.Uno
    • Journal Title

      J.Porphyrins Phthalocyanines 13

      Pages: 122-135

  • [Journal Article] Synthesis and properties of benzene-fused diporphyrins with various metals2009

    • Author(s)
      H.Uno, M.Hashimoto, A.Fujimoto
    • Journal Title

      Heterocycles 77

      Pages: 887-898

  • [Journal Article] Soluble precursors of 2,3-naphthalocyanine and phthalocyanine for use in thin film transistors2008

    • Author(s)
      A.Hirao, T.Akiyama, T.Okujima, H.Yamada, H.Uno, Y.Sakai, S.Aramaki, N.Ono
    • Journal Title

      Chem.Commun.

      Pages: 4714-4716

  • [Journal Article] Preparation of 1,3,3a,7a-tetrahydroisothia-naphthene and its application to tetrahydrothiophene-fused porphyrin2008

    • Author(s)
      Y.Katsuyama, E.Yoshida, H.Uoyama, N.Ono, H.Uno
    • Journal Title

      Heterocycles 76

      Pages: 667-678

  • [Journal Article] Synthesis and Characterization of Tetraanthroporphyrins2008

    • Author(s)
      H.Yamada, D.Kuzuhara, T.Takahashi, Y.Shimizu, K.Uota, T.Okujima, H.Uno, N.Ono
    • Journal Title

      Org.Lett. 10

      Pages: 2947-2950

  • [Journal Article] Selective synthesis of 5-alkenyl-15-alkynyl-porphyrin and 5,15-dialkynylporphyrin by 2+2 acid-catalyzed condensation of dipyrrylmethane and TMS propynal2008

    • Author(s)
      H.Yamada, K.Kushibe, S.Mitsuogi, T.Okujima, H.Uno, N.Ono
    • Journal Title

      Tetrahedron Lett. 49

      Pages: 4731-4733

  • [Journal Article] Application of MCD Spectroscopy and TD-DFT to Nonplanar Core-Modified Tetrabenzoporphyrins : Effect of ReducedSymmetry on Nonplanar Porphyrinoids2008

    • Author(s)
      J.Mack, M.Bunya, Y.Shimizu, H.Uoyama, N.Komobuchi, T.Okujima, H.Uno, S.Ito, M.J.Stillman, N.Ono, N.Kobayashi
    • Journal Title

      Chem.Eur.J. 14

      Pages: 5001-5020

  • [Journal Article] Photophysical properties of a novel Ni(II)-diporphyrin in presence of fullerenes : Insights from experimental and theoretical studies2008

    • Author(s)
      S.Bhattacharya, M.Hashimoto, A.Fujimoto, T.Kimura, H.Uno, N.Komatsu
    • Journal Title

      Spectrochim.Acta, Part A 70A

      Pages: 416-424

  • [Journal Article] Synthesis of extremely soluble precursors of tetrabenzoporphyrins2008

    • Author(s)
      T.Okujima, Y.Hashimoto, G.Jin, H.Yamada, H.Uno, N.Ono
    • Journal Title

      Tetrahedron 64

      Pages: 2405-2411

  • [Journal Article] Thermal behavior of free-base and core-modified bicyclo [2.2.2] octadienefused porphyrins2008

    • Author(s)
      H.Uno, Y.Shimizu, H.Uoyama, Y.Tanaka, T.Okujima, N.Ono
    • Journal Title

      Eur.J.Org.Chem.

      Pages: 87-98

  • [Presentation] ベンゾ[1,2-c;4,5-c']ジピロール前駆体の合成とその反応2011

    • Author(s)
      田原寛之、山上薫、桑島未紀、奥島鉄雄、森重樹、山田容子、宇野英満
    • Organizer
      日本化学会第91春季年会(震災により講演中止)
    • Year and Date
      20110300
  • [Presentation] ベンゼン架橋オリゴポルフィリンの合成と物性2011

    • Author(s)
      魚山大樹、奥島鉄雄、山田容子、宇野英満
    • Organizer
      日本化学会第91春季年会(震災により講演中止)
    • Year and Date
      20110300
  • [Presentation] β位で縮環したbisBODIPYの合成と物性2011

    • Author(s)
      中村光則、田原寛之、魚山大樹、奥島鉄雄、山田容子、森重樹、宇野英満
    • Organizer
      日本化学会第91春季年会(震災により講演中止)
    • Year and Date
      20110300
  • [Presentation] Synthesis and properties of π-fused core-modified porphyrin oligomers2010

    • Author(s)
      H.Watanabe, H.Uoyama, S.Mori, T.Okujima, H.Yamada, H.Uno
    • Place of Presentation
      Honolulu, USA.
    • Year and Date
      2010-12-17
  • [Presentation] Synthesis and properties of bicyclo[2.2.2]-octadiene-connected hexaphyrin2010

    • Author(s)
      S.Mori, H.Uoyama, T.Takiue, H.Uno
    • Place of Presentation
      Honolulu, USA.
    • Year and Date
      2010-12-17
  • [Presentation] ビシクロ[2.2.2]オクタジエン架橋ジピロールを用いた新規ポルフィリノイドの探索2010

    • Author(s)
      田原寛之・魚山大樹、奥島鉄雄、森重樹、山田容子、宇野英満
    • Organizer
      第40回複素環化学討論会
    • Place of Presentation
      仙台
    • Year and Date
      2010-10-19
  • [Presentation] Synthesis of Porphyrinoids with Novel π-System from BCOD-connected Dipyrrole2010

    • Author(s)
      宇野英満
    • Place of Presentation
      New Mexico, USA.
    • Year and Date
      2010-07-08
  • [Presentation] ビシクロ[2.2.2]オクタジエン環を組み込んだポルフィリノイドの合成と物性2010

    • Author(s)
      田原寛之、魚山大樹、山田容子、奥島鉄雄、森重樹、宇野英満
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      東大阪
    • Year and Date
      2010-03-27
  • [Presentation] Synthesis of Diethanoacene-fused Diporphyrins and their Complex Formation with Fullerenes2009

    • Author(s)
      M.Furukawa, S.Bhattacharya, N.Komatsu, H.Uno
    • Organizer
      IKCOC-11
    • Place of Presentation
      Kyoto
    • Year and Date
      2009-11-12
  • [Presentation] テトラブロモ-o-キシレンを用いたアンスラ[2,3-c]ヘテロ五員環前駆体の合成2009

    • Author(s)
      田原寛之、魚山大樹、小野昇、奥島鉄雄、山田容子、宇野英満
    • Organizer
      日本化学会西日本大会
    • Place of Presentation
      松山
    • Year and Date
      2009-11-08
  • [Presentation] ビシクロ[2.2.1]ヘプタジエン-7-オンのキレトロピー反応を用いた新規π電子系化合物の合成2009

    • Author(s)
      桑島未紀、垣谷兆政、山田容子、奥島鉄雄、宇野英満
    • Organizer
      日本化学会西日本大会
    • Place of Presentation
      松山
    • Year and Date
      2009-11-08
  • [Presentation] 溶液法を用いた有機薄膜トランジスタ作成のためのペンタセン前駆体の熱及び光変換の研究2009

    • Author(s)
      魚山大樹、永田央、奥島鉄雄、山田容子、宇野英満
    • Organizer
      日本化学会西日本大会
    • Place of Presentation
      松山
    • Year and Date
      2009-11-08
  • [Presentation] ベンゼン架橋十字型ポルフィリン5量体の合成と物性2009

    • Author(s)
      魚山大樹、永田央、奥島鉄雄、山田容子、宇野英満
    • Organizer
      日本化学会西日本大会
    • Place of Presentation
      松山
    • Year and Date
      2009-11-07
  • [Presentation] Complex Formation of Diethanoacenebridged Diporphyrins with Fullerenes2009

    • Author(s)
      M.Furukawa, M.Hashimoto, S.Bhattacharya, N.Komatsu, H.Uno
    • Place of Presentation
      Luxembourg.
    • Year and Date
      2009-07-11
  • [Presentation] ビシクロ[2.2.2]オクタジエンを内部に架橋したヘキサフィリンの合成2009

    • Author(s)
      魚山大樹、滝上貴大、宇野英満
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2009-03-29
  • [Presentation] 7-t-ブトキシビシクロ[2.2.1]オクタジエンが縮環したピロールの合成と反応2009

    • Author(s)
      宇野英満、魚山大樹、垣谷兆政
    • Place of Presentation
      船橋
    • Year and Date
      2009-03-28
  • [Presentation] ジエタノアセン融合ジポルフィリンとフラーレンとの錯形成2009

    • Author(s)
      古川美奈、橋本昌和、小松直樹、宇野英満
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      船橋
    • Year and Date
      2009-03-27
  • [Presentation] ビシクロ[2.2.2]オクタジエンおよびベンゼン縮合オリゴポルフィリンの構造と物性2008

    • Author(s)
      魚山大樹、宇野英満
    • Organizer
      第38回複素環化学討論会
    • Place of Presentation
      福山
    • Year and Date
      2008-11-21
  • [Presentation] 分子認識ツールを指向したジエタノアントラセン融合ジポルフィリンの合成研究2008

    • Author(s)
      橋本昌和、宇野英満
    • Organizer
      第38回複素環化学討論会
    • Place of Presentation
      福山
    • Year and Date
      2008-11-21
  • [Presentation] Bicyclo[2.2.2]octadiene-fused Porphyrins. Structures, Properties, and Reactivities2008

    • Author(s)
      宇野英満
    • Organizer
      5th Inernational Conference on Porphyrins and Phthalocyanines
    • Place of Presentation
      Moscow, Russia.
    • Year and Date
      2008-07-06
  • [Remarks] ホームページ等

    • URL

      http://chem.sci.ehime-u.ac.jp/~orgchem1/

  • [Patent(Industrial Property Rights)] アセンジイミド化合物の製造法2011

    • Inventor(s)
      宇野英満、山田容子、勝田修平、田中和樹
    • Industrial Property Rights Holder
      愛媛大学
    • Industrial Property Number
      特許,特願2011-48301
    • Filing Date
      20110000
  • [Patent(Industrial Property Rights)] 高共役化合物及びその前駆体、並びに高共役化合物の製造法2010

    • Inventor(s)
      宇野英満、増田豪
    • Industrial Property Rights Holder
      愛媛大学、日本触媒
    • Industrial Property Number
      特許,特願2010-28231
    • Filing Date
      20100000
  • [Patent(Industrial Property Rights)] 含ハロゲン-1,3-ジホルミル-2-ベンゾチオフェン、含ハロゲンチアポルフィリンおよびこれらの製造方法2009

    • Inventor(s)
      宇野英満、増田豪
    • Industrial Property Rights Holder
      愛媛大学、日本触媒
    • Patent Publication Number
      特許特開2009-023931
    • Filing Date
      20090000
  • [Patent(Industrial Property Rights)] 含ハロゲンベンゾポルフィリンおよびその錯体、並びに含ハロゲンベンゾポルフィリンの製造方法2009

    • Inventor(s)
      宇野英満、増田豪
    • Industrial Property Rights Holder
      愛媛大学、日本触媒
    • Patent Publication Number
      特許,特開2009-062356
    • Filing Date
      20090000
  • [Patent(Industrial Property Rights)] 新規化合物および有機半導体素子の製造方法2009

    • Inventor(s)
      桝本茜、菊池憲裕、小野昇、宇野英満、中島容子
    • Industrial Property Rights Holder
      キヤノン
    • Patent Publication Number
      特許,特開2009-081408
    • Filing Date
      20090000
  • [Patent(Industrial Property Rights)] Isoindoles, compounds prepared from the same, and processes for production of both2008

    • Inventor(s)
      宇野英満, 増田豪, T.Iida
    • Industrial Property Rights Holder
      愛媛大学、日本触媒
    • Industrial Property Number
      特許,WO 2008016085
    • Filing Date
      20080000
    • Overseas
  • [Patent(Industrial Property Rights)] Novel organic precursor compound and method of producing organic semiconductor device2008

    • Inventor(s)
      A.Masumoto, 中島容子 菊池憲, 宇野英満, 小野昇
    • Industrial Property Rights Holder
      キヤノン
    • Industrial Property Number
      特許,US 2008171403
    • Filing Date
      20080000
    • Overseas

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Published: 2012-01-26   Modified: 2016-04-21  

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