Development of functional organic materials showing adhesive or coating ability with gelation.

• Project/Area Number: 15K05480
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Functional solid state chemistry
• Research Institution: Kyushu Institute of Technology
• Principal Investigator: Tsuge Akihiko 九州工業大学, 大学院工学研究院, 教授 (80179986)
• Co-Investigator(Kenkyū-buntansha): 北村 充 九州工業大学, 大学院工学研究院, 教授 (10313199)
• Project Period (FY): 2015-04-01 – 2018-03-31
• Project Status: Completed (Fiscal Year 2017)
• Budget Amount: ¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000); Fiscal Year 2017: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000); Fiscal Year 2016: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000); Fiscal Year 2015: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
• Keywords: ゲル / 酸化還元 / 水素結合 / オルガノゲル / シクロファン / フェロセン / 分子認識 / 蛍光発光

Outline of Final Research Achievements

In this research organogelator candidates which consist of the ferrocene unit have been prepared. It has been suggested that two amino acid residues in the structure are necessary to form a stable organogel. Addition of an oxidizing agent such as NaClO induces the collapse of the gel, and reproduction of the gel was observed by addition of a reducing agent such as glutathione. It has been found out that the on-off switching of gel formation can be achieved by red-ox reaction. Two kinds of glutamaic acid-based coumarin derivatives show a quite different trend against gelation in organic solvents in terms of inter- or intramolecular hydrogen bonds involved. It has been found out that addition of the valinate structure into the coumarine derivative could improve its gelation ability.

Research Products

• [Journal Article] On-off switching of gel formation by red-ox reaction. (2018)
  • Author(s): Daisuke Yakeya, Tetsuji Moriguchi, Akihiko Tsuge
  • Journal Title: Tetrahedron Letters Volume: 59 Issue: 8 Pages: 712-714
  • DOI: 10.1016/j.tetlet.2018.01.013
  • Peer Reviewed
• [Journal Article] Design and properties of glutamic acid-based coumarin derivatives as organogelators (2017)
  • Author(s): Daisuke Yakeya, Naoya Kitou, Shougo Kinugawa, Tetsuji Moriguchi, Akihiko Tsuge
  • Journal Title: Tetrahedron Volume: 73 Issue: 27-28 Pages: 3973-3978
  • DOI: 10.1016/j.tet.2017.05.074
  • Peer Reviewed
• [Journal Article] Efficient synthesis of novel pyrrolo[2,3-c]pyridone derivatives using Ugi four-componeny reaction followed by condensation reaction (2017)
  • Author(s): Jalli Venkataprasado Jalli, Suvratha Krishnamurthy, Tetsuji Moriguchi, Akihiko Tsuge
  • Journal Title: New Journal of Chemistry Volume: 41 Issue: 1 Pages: 97-107
  • DOI: 10.1039/c6nj02569b
  • Peer Reviewed
• [Journal Article] Synthesis and Molecular Structures of Two Novel p-Conjugated Extended Dithia[3.3]metacyclophanes (2017)
  • Author(s): Tetsuji Moriguchi, Daisuke Yakeya, Venkataprasad Jalli, Akihiko Tsuge, Kenji Yoza
  • Journal Title: Cryst Struct Theor Appl Volume: 6 Issue: 01 Pages: 1-10
  • DOI: 10.4236/csta.2017.61001
  • Peer Reviewed / Open Access
• [Journal Article] The Syntheses, Crystal Structure and Luminescence Properties of Cone-Like Octadentate Europium (III) Complexes with Four Short Alkoxy Substituents (2017)
  • Author(s): Tetsuji Moriguchi, Satoshi Hirosaki, Venkataprasad Jalli, Akihiko Tsuge, Kenji Yoza
  • Journal Title: Crystals Volume: 7 Pages: 85-94
  • Peer Reviewed
• [Journal Article] One-pot four component synthesis of novel 3-furyl coumarin derivatives (2016)
  • Author(s): Venkataprasad Jalli, Suvratha Krishna Murthy, Tetsuji Moriguchi, Akihiko Tsuge
  • Journal Title: J.Chem.Sci. Volume: 128 Issue: 2 Pages: 217-226
  • DOI: 10.1007/s12039-015-1014-8
  • Peer Reviewed
• [Journal Article] Syntheses, Characterization and DFT Analysis of Two Novel Thiaheterohelicene Derivatives (2016)
  • Author(s): Tetsuji Moriguchi, Keiichi Mitsumoto, Yuki Nishizawa, Daisuke Yakeya, Venkataprasad Jalli, Akihiko Tsuge
  • Journal Title: Cryst Struct Theor Appl Volume: 5 Issue: 04 Pages: 63-73
  • DOI: 10.4236/csta.2016.54006
  • Peer Reviewed / Open Access
• [Journal Article] Organogelators based on metacyclophane skeleton having urea units in the bridge (2015)
  • Author(s): Akihiko Tsuge, Tsugumichi Fujiwara, Daisuke Yakeya, Hiroyoshi Kawasaki, Tetsuji Moriguchi, Koji Araki
  • Journal Title: Tetrahedron Volume: 71 Issue: 50 Pages: 9429-9432
  • DOI: 10.1016/j.tet.2015.10.056
  • Peer Reviewed
• [Journal Article] a-Chymotrypsin and L-acylase aided synthesis of 5-hydroxypipecolic acid via Jacobsen's hydrolytic kinetic resolution of epoxy amino acids (2015)
  • Author(s): Suvratha Krishnamurthy, Venkataprasad Jalli, Tarun Chand Vagvala, Tetsuji Moriguch, Akihiko Tsuge
  • Journal Title: RSC Advances Volume: 5 Issue: 64 Pages: 52154-52160
  • DOI: 10.1039/c5ra09207h
  • Peer Reviewed
• [Journal Article] SYNTHESIS OF NOVEL SPIRO[INDOL-2,20-PYRROLES] USING ISOCYANIDE-BASED MULTICOMPONENT REACTION (2015)
  • Author(s): Venkataprasad Jalli, Suvratha Krishnamurthy, Hiroyoshi Kawasaki, Tetsuji Moriguch, Akihiko Tsuge
  • Journal Title: Synthetic Communications Volume: 45 Issue: 19 Pages: 2216-2226
  • DOI: 10.1080/00397911.2015.1071396
  • Peer Reviewed
• [Presentation] 新規ピンセット型有機ゲル化剤の合成とその特性 (2018)
  • Author(s): 濱松 千明, 森口 哲次, 荒木 孝司, 柘植 顕彦
  • Organizer: 日本化学会第９８春季年会
• [Presentation] シクロファン骨格を基盤とした有機ゲル化剤の合成とその特性 (2018)
  • Author(s): 駄場 勇貴, 森口 哲次, 荒木 孝司, 柘植 顕彦
  • Organizer: 日本化学会第９８春季年会
• [Presentation] カテコール部位を基本骨格とするゲル化剤の合成とその特性 (2017)
  • Author(s): ：嘉本崚汰，森口哲次、柘植顕彦
  • Organizer: 日本化学会第９７春季年会
  • Place of Presentation: 慶応大学
  • Year and Date: 2017-03-16
• [Presentation] スチルベン骨格を有するメタシクロファン類の合成とその渡環相互作用 (2017)
  • Author(s): 宮本大輔，森口哲次、柘植顕彦
  • Organizer: 日本化学会第９７春季年会
  • Place of Presentation: 慶応大学
  • Year and Date: 2017-03-16
• [Presentation] ピンセット型ゲル化剤の合成とその特性 (2017)
  • Author(s): 濱松千明、森口哲次、柘植顕彦
  • Organizer: 日本化学会第９７春季年会
  • Place of Presentation: 慶応大学
  • Year and Date: 2017-03-16
• [Presentation] カテコール部位の特性を活用した有機ゲル化剤の合成とその評価 (2017)
  • Author(s): 嘉本崚汰、森口哲次、柘植顕彦
  • Organizer: 第２８回基礎有機化学討論会
• [Presentation] Organogelators Consisting of Some Unique Moieties (2017)
  • Author(s): Akihiko Tsuge
  • Organizer: Symposium on Applied Engineering and Sciences (SAES2017)
  • Int'l Joint Research / Invited
• [Presentation] フェロセン部位を有するゲル化剤の合成とその特性 (2017)
  • Author(s): 焼谷大輔，森口哲次、柘植顕彦
  • Organizer: 日本化学会第９７春季年会
• [Presentation] 配位子型ゲル化剤の合成とその特性評価 (2016)
  • Author(s): 末原俊平、森口哲次、柘植顕彦
  • Organizer: 第１０回有機π電子シンポジウム
  • Place of Presentation: 京都
  • Year and Date: 2016-12-16
• [Presentation] クマリン及びフェロセン部位を有するゲル化剤の合成とその特性 (2016)
  • Author(s): 焼谷大輔，森口哲次、柘植顕彦
  • Organizer: 第２７回基礎有機化学討論会
  • Place of Presentation: 広島
  • Year and Date: 2016-09-01
• [Presentation] フェロセン部位を有するゲル化剤の合成とその酸化還元応答ゲル化特性 (2016)
  • Author(s): 焼谷大輔，森口哲次、荒木孝司、柘植顕彦
  • Organizer: 日本化学会第９６春季年会
  • Place of Presentation: 同志社大学
  • Year and Date: 2016-03-24
• [Presentation] 配位Eu錯体の合成とその構造特性評価 (2016)
  • Author(s): 廣﨑聖，森口哲次、荒木孝司、柘植顕彦
  • Organizer: 日本化学会第９６春季年会
  • Place of Presentation: 同志社大学
  • Year and Date: 2016-03-24
• [Presentation] 配位子型ゲル化剤の合成とそのゲル化特性 (2016)
  • Author(s): 末原俊兵，森口哲次、荒木孝司、柘植顕彦
  • Organizer: 日本化学会第９６春季年会
  • Place of Presentation: 同志社大学
  • Year and Date: 2016-03-24
• [Presentation] カテコール部位を有するゲル化剤の合成とその特性 (2016)
  • Author(s): 嘉本崚汰，森口哲次、荒木孝司、柘植顕彦
  • Organizer: 日本化学会第９６春季年会
  • Place of Presentation: 同志社大学
  • Year and Date: 2016-03-24