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Photochemical Synthesis of Novel Heterocyclic Compounds Using Flow Micro Reactor

Research Project

Project/Area Number 26410049
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Organic chemistry
Research InstitutionNara Institute of Science and Technology

Principal Investigator

Mizuno Kazuhiko  奈良先端科学技術大学院大学, 物質創成科学研究科, 客員教授 (10109879)

Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywordsフロー系マイクロリアクター / エキシプレックス / 分子内光環化反応 / ヘテロ環化合物 / 光誘起電子移動反応 / [2+2]光環化付加反応 / FEPチューブ / 分子内環化付加反応 / 含窒素ヘテロ環化合物 / 含酸素ヘテロ環化合物
Outline of Final Research Achievements

Intramolecular photocyclization by use of flow micro reactor was examined for synthesis of novel heterocyclic compounds in highly efficient and selective photoreaction. Irradiation of benzene solution containing 1-cyanonaphthalene derivatives tethered by prenyl or vinyloxy group at 2- or 4-position afforded intramolecular [2+2] photocycloadduct as heterocyclic compound. The photoreaction using flow micro reactor (1 mm diameter, 2-5 m length FEP tubing) was much faster than that in the batch system (10 mm diameter, 20 cm length, Pyrex glass tubing). Similar photoreaction of phenanthrene and aniline tethered by methylene chain (n=2~5) afforded spiro-compounds (n=3, 5) and 9-methylene-9,10-dihydrophenanthrene (n=2) in high yields when flow micro reactor system was used.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (43 results)

All 2017 2016 2015 2014

All Journal Article (16 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 16 results,  Open Access: 10 results,  Acknowledgement Compliant: 8 results) Presentation (20 results) (of which Int'l Joint Research: 4 results,  Invited: 2 results) Book (7 results)

  • [Journal Article] Electron-Transfer Reactions Triggered by Neutral or Cationic Photosensitizer: Methodology for Generation of o-Quinodimethane and Analysis of Back Electron-Transfer Process.2017

    • Author(s)
      Matsui, Y.; Ikeda, T.; Takahashi, Y.; Kamata, M.; Akagi, M.; Ohya, Y.; Fujino, R.; Namai, H.; Ohta, E.; Ogaki, T.; Miyashi, T.; Tero-Kubota, S.; Mizuno, K.; Ikeda, H
    • Journal Title

      Asian J. Org. Chem.

      Volume: 2017

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Synthesis and fluorescence properties of dioxa-, dithia-, and diselena[3.3](1,3)pyrenophanes.2017

    • Author(s)
      Hajime Maeda, Masato Hironishi, Rikiya Ishibashi, Kazuhiko Mizuno, Masahito Segi,
    • Journal Title

      Photochem. Photobiol. Sci.

      Volume: 2017

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Synthesis of Pentacyclic Compounds via Intramolecular [3+2] Photocycloaddition of Cycloalkene Linked Naphthalenes2017

    • Author(s)
      Hajime Maeda, Tomoya Uesugi, Yasufumi Fujimoto, Hirofumi Mukae, Kazuhiko Mizuno
    • Journal Title

      J. Photochem. Photobiol. A: Chem.

      Volume: 2017

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Effects of substituents on the fluorescence properties of silylethynylnaphthalenes in solutions, thin films and solid states.2017

    • Author(s)
      Hajime Maeda, Takayuki Fujii, Keita Minamida, Kazuhiko Mizuno
    • Journal Title

      J. Photochem. Photobiol. A: Chem.

      Volume: 2017

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Preparation of Polycyclic Compounds by Intramolecular Photospirocyclization and Photocycloaddition Reactions of 4-Alkenyl-1-cyanonaphthalene Derivatives2016

    • Author(s)
      Maeda, H.; Wada, H.; Mukae, H.; Mizuno, K.
    • Journal Title

      Journal of Photochemistry and Photobiology A: Chemistry

      Volume: 未定 Pages: 29-41

    • DOI

      10.1016/j.jphotochem.2016.01.005

    • Related Report
      2016 Annual Research Report 2015 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Intramolecular Photocycloaddition Reactions of Arylcyclopropane Tethered 1-Cyanonaphthalenes.2016

    • Author(s)
      Hajime Maeda, Shoji Matsuda, Kazuhiko Mizuno
    • Journal Title

      J. Org. Chem.

      Volume: 81 Pages: 8544-8551

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Synthesis and Conformational Analysis of 2,11-Disila[3.3]metacyclophanes.2016

    • Author(s)
      Tomoo Hayamizu, Hajime Maeda, Takashi Ouchi, Naoki Kakiuchi, Kazuhiko Mizuno
    • Journal Title

      Eur J. Org. Chem.

      Volume: 2016 Pages: 3934-3938

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Intermolecular Hydrogen Bonding Controlled Stereoselective Photocycloaddition of Vinyl Ethers to 1-Cyanonaphthalenes.2016

    • Author(s)
      Hajime Maeda, Hiroki Takenaka, Kazuhiko Mizuno
    • Journal Title

      Photochem. Photobiol. Sci.

      Volume: 15 Pages: 1385-1392

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / 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
      2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Intramolecular [2+2] Photocycloaddition and Cycloreversion of Ferulic Acid Derivatives2015

    • Author(s)
      Maeda, H.; Nishimura, K.; Yokoyama, A.; Sugimoto, A.; Mizuno, K.; Hosoda, A.; Nomura, E.; Taniguchi, H.
    • Journal Title

      Rapid Communication in Photoscience

      Volume: 4 Issue: 1 Pages: 12-15

    • DOI

      10.5857/rcp.2015.4.1.12

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Novel Fluorescence Domain "Excited Multimer" Formed upon Photoexcitation of Continuously-stacked Diaroylmethanatoboron Difluoride Molecules with Fused π-Orbital in Crystals2015

    • Author(s)
      A. Sakai, E. Ohta, Y. Yoshimoto, M. Tanaka, Y. Matsui, K. Mizuno, H. Ikeda
    • Journal Title

      Chem. Eur. J.

      Volume: 21 Issue: 50 Pages: 18128-18137

    • DOI

      10.1002/chem.201503132

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] フローマイクロリアクターを利用した高効率·高選択的なジアステレオ区別有機光反応2015

    • Author(s)
      西山靖浩,水野一彦
    • Journal Title

      有機合成化学協会誌

      Volume: 73 Pages: 460-468

    • NAID

      130005077686

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Intramolecular [2+2] Photocycloaddition and Cycloreversion of Ferulic Acid Derivatives2015

    • Author(s)
      H. Maeda, K. Nishimura, A. Yokoyama, A. Sugimoto, K. Mizuno, A. Hosoda, E. Nomura, and H. Taniguchi
    • Journal Title

      Rapid Commun. Photosci.

      Volume: 4

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] フローマイクロリアクターを利用した高効率・高選択的ジアステレオ選択的有機光反応2015

    • Author(s)
      西山靖浩,水野一彦
    • Journal Title

      有機合成化学協会誌

      Volume: 73

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Formation of a New Benzotriquinane Skeleton via Intramolecular Photocycloaddition Reactions of a Phenylethynes Moiety to a 1-Cyanonaphthalene Ring System2014

    • Author(s)
      Mizuno, K.; Negoro, N.; Nagayama, Y.; Maeda, H.; Ikeda, H.
    • Journal Title

      Photochem. Photobiol. Sci.

      Volume: 13 Issue: 2 Pages: 145-148

    • DOI

      10.1039/c3pp50243k

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] One-pot Photochemical Synthesis of Novel Thienobis[1]benzothiophene with an Angularly-fused Structure that Promotes Unique Intermolecular S---S Contacts in the Crystalline State2014

    • Author(s)
      Ogaki, T.; Ohta, E.; Yamamoto, A.; Sato, H.; Mizuno, K.; Ikeda, H.
    • Journal Title

      Tetrahedron Lett.

      Volume: 55 Issue: 30 Pages: 4269-4273

    • DOI

      10.1016/j.tetlet.2014.05.096

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 光誘起電子移動を経由するケイ皮酸ニトリルの二量化反応2016

    • Author(s)
      森下直哉,小西玄一,水野一彦
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス( 京田辺市,京都府)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] LEDを用いたレドックス光増感反応:増感剤の設計と反応2016

    • Author(s)
      小西玄一,亀井康平,水野一彦
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス( 京田辺市,京都府)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] 結晶中で連続的に積層した有機ホウ素錯体の光励起で生じる新規発光種”励起マルチマー”2016

    • Author(s)
      太田英輔,酒井敦史,吉本裕一,田中未来,松井康哲,水野一彦,池田浩
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス( 京田辺市,京都府)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] Emission properties of diaroylmethanatoboron difluorides controlled by the steric bulkiness of substituents2015

    • Author(s)
      M. Tanaka, A. Sakai, Y. Yoshimoto, Y. Matsui, E. Ohta, K. Mizuno, H. Ikeda
    • Organizer
      International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Unique cyclization-aromatization reactions of bis(dimethylethenyl)thiophene derivatives promoted by photoinduced electron transfer2015

    • Author(s)
      A. Yamamoto, T. Ogaki, E. Ohta, Y. Matsui, K. Mizuno, H. Ikeda
    • Organizer
      International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthesis and basic properties of tetrathienonaphthalene: Photoinduced electron-transfer cyclization-dehydrogenation reactions of tetra(3-thienyl)ethane2015

    • Author(s)
      A. Yamamoto, E. Ohta, Y. Matsui, K. Mizuno, H. Ikeda
    • Organizer
      International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthesis and crystallographic studies of an angularly-fused thienobis[1]benzothiophene and its CT cocrystal with TCNQ2015

    • Author(s)
      T. Ogaki, A. Yamamoto, E. Ohta, Y. Matsui, K. Mizuno, H. Ikeda
    • Organizer
      International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, Hawaii, USA
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] ケイ皮酸ニトリルとケテンシリルアセタールの増感剤テトラブチルピレンによる光誘起電子移動反応2015

    • Author(s)
      森下直哉,小西玄一,水野一彦
    • Organizer
      基礎有機化学討論会
    • Place of Presentation
      愛媛大学( 松山市,愛媛県)
    • Year and Date
      2015-09-24
    • Related Report
      2015 Research-status Report
  • [Presentation] [2.2]パラシクロファン骨格を有するホウ素二フッ化物 β-ジケトナート錯体の結晶構造と発光特性2015

    • Author(s)
      田中未來,村岡峻祐,酒井敦史,松井 康哲,太田英輔,水野一彦,池田 浩
    • Organizer
      基礎有機化学討論会
    • Place of Presentation
      愛媛大学( 松山市,愛媛県)
    • Year and Date
      2015-09-24
    • Related Report
      2015 Research-status Report
  • [Presentation] テトラブチルピレンを増感剤に用いたケイ皮酸ニトリルとケテンシリルアセタールとの光誘起電子移動反応2015

    • Author(s)
      森下直哉,小西玄一,水野一彦
    • Organizer
      光化学討論会
    • Place of Presentation
      大阪市立大学杉本キャンパス( 大阪市,大阪府)
    • Year and Date
      2015-09-09
    • Related Report
      2015 Research-status Report
  • [Presentation] Photophysical properties of difluoroboron β-diketonate complex processing the [2.2]paracyclophane moiety2015

    • Author(s)
      M. Tanaka, S. Muraoka, A. Sakai, Y. Matsui, E. Ohta, K. Mizuno, H. Ikeda
    • Organizer
      光化学討論会
    • Place of Presentation
      大阪市立大学杉本キャンパス( 大阪市,大阪府)
    • Year and Date
      2015-09-09
    • Related Report
      2015 Research-status Report
  • [Presentation] [2.2]パラシクロファン骨格を導入したジアロイルメタナートホウ素二フッ化物の結晶構造と発光特性2014

    • Author(s)
      田中未来,村岡峻祐,酒井敦史,太田英輔,水野一彦,池田 浩
    • Organizer
      2014光化学討論会
    • Place of Presentation
      北海道大学札幌キャンパス ( 北海道札幌市 )
    • Year and Date
      2014-10-11 – 2014-10-13
    • Related Report
      2014 Research-status Report
  • [Presentation] ハロゲン原子を有するジアロイルメタナートボロンジフロリドの常温燐光2014

    • Author(s)
      酒井敦史,太田英輔,水野一彦,池田 浩
    • Organizer
      2014光化学討論会
    • Place of Presentation
      北海道大学札幌キャンパス ( 北海道札幌市 )
    • Year and Date
      2014-10-11 – 2014-10-13
    • Related Report
      2014 Research-status Report
  • [Presentation] 光誘起電子移動環化反応によるチエノビス[1]ベンゾチオフェン誘導体の一段階合成2014

    • Author(s)
      山本惇司,大垣拓也,太田英輔,松井康哲,水野一彦,池田 浩
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      東北大学川内キャンパス ( 宮城県仙台市 )
    • Year and Date
      2014-09-07 – 2014-09-09
    • Related Report
      2014 Research-status Report
  • [Presentation] [2.2]パラシクロファン骨格を有するジアロイルメタナートホウ素二フッ化物の結晶構造と光学特性2014

    • Author(s)
      田中未来,村岡峻祐,酒井敦史,太田英輔,水野一彦,池田 浩
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      東北大学川内キャンパス ( 宮城県仙台市 )
    • Year and Date
      2014-09-07 – 2014-09-09
    • Related Report
      2014 Research-status Report
  • [Presentation] ハロゲン原子を有するジアロイルメタナートホウ素二フッ化物の常温燐光2014

    • Author(s)
      酒井敦史,太田英輔,松井康哲,水野一彦,池田 浩
    • Organizer
      第25回基礎有機化学討論会
    • Place of Presentation
      東北大学川内キャンパス ( 宮城県仙台市 )
    • Year and Date
      2014-09-07 – 2014-09-09
    • Related Report
      2014 Research-status Report
  • [Presentation] 摩訶不思議な電子移動反応性中間体2014

    • Author(s)
      水野一彦
    • Organizer
      第10回有機電子移動化学若手の会
    • Place of Presentation
      羽島温泉かんぽの宿 ( 岐阜県羽島市 )
    • Year and Date
      2014-06-27 – 2014-06-28
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] 光誘起電子環状反応―脱水素反応によるテトラチエノナフタレンの合成と性質2014

    • Author(s)
      太田英輔,山本惇司,塚原典宏,冨依勇佑,佐藤寛泰,狩野佑介,松井康哲,水野一彦,池田 浩
    • Organizer
      第38回有機電子移動化学討論会
    • Place of Presentation
      長良川国際会議場 ( 岐阜県岐阜市 )
    • Year and Date
      2014-06-26 – 2014-06-27
    • Related Report
      2014 Research-status Report
  • [Presentation] 電子移動反応により発生したフェノニウムイオン型中間体の単離とその構造解析2014

    • Author(s)
      倉本悠太郎,浅田直哉,松井康哲,太田英輔,水野一彦,池田 浩
    • Organizer
      第38回有機電子移動化学討論会
    • Place of Presentation
      長良川国際会議場 ( 岐阜県岐阜市 )
    • Year and Date
      2014-06-26 – 2014-06-27
    • Related Report
      2014 Research-status Report
  • [Presentation] 有機光化学を学んで2014

    • Author(s)
      水野一彦
    • Organizer
      丸山記念研究奨励賞講演会
    • Place of Presentation
      京都大学理学研究科化学科セミナー室 ( 京都府京都市 )
    • Year and Date
      2014-04-12
    • Related Report
      2014 Research-status Report
    • Invited
  • [Book] Photochemistry Vol. 422016

    • Author(s)
      Kazuhiko Mizuno
    • Total Pages
      278
    • Publisher
      The Royal Society of Chemistry
    • Related Report
      2016 Annual Research Report
  • [Book] 有機合成実験法ハンドブック第2版2015

    • Author(s)
      水野一彦
    • Total Pages
      3
    • Publisher
      丸善出版
    • Related Report
      2015 Research-status Report
  • [Book] Photochemistry Vol. 422015

    • Author(s)
      Kazuhiko Mizuno
    • Total Pages
      53
    • Publisher
      Royal Society of Chemistry
    • Related Report
      2015 Research-status Report
  • [Book] Photochemistry2015

    • Author(s)
      Kazuhiko Mizuno
    • Total Pages
      53
    • Publisher
      Royal Society of Chemistry
    • Related Report
      2014 Research-status Report
  • [Book] 有機合成実験法ハンドブック2015

    • Author(s)
      水野一彦
    • Total Pages
      3
    • Publisher
      丸善出版
    • Related Report
      2014 Research-status Report
  • [Book] 光化学の事典2014

    • Author(s)
      水野一彦
    • Total Pages
      1
    • Publisher
      朝倉書店
    • Related Report
      2014 Research-status Report
  • [Book] フロー・マイクロ合成2014

    • Author(s)
      水野一彦
    • Total Pages
      22
    • Publisher
      化学同人
    • Related Report
      2014 Research-status Report

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Published: 2014-04-04   Modified: 2018-03-22  

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