Development of electron-accepting conjugated molecules densely-substituted with boron atoms

• Project/Area Number: 21750037
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Organic chemistry
• Research Institution: Kyoto University
• Principal Investigator: AGOU Tomohiro Kyoto University, 次世代開拓研究ユニット, 助教 (90466798)
• Project Period (FY): 2009 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000); Fiscal Year 2010: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000); Fiscal Year 2009: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
• Keywords: 有機ホウ素化合物 / ボラアセン / 電子受容体 / アニオンセンシング / ポリボラアセン / 反芳香族分子 / ディスク状共役系

Research Abstract

Synthesis of functional hetero-π-conjugated molecules by taking advantage of electron-withdrawing property and Lewis acidity of boron was investigated for the development of electron-transporting material and anion sensors. Fluorescence molecular sensors for biologically active anions, such as fluoride and cyanide ions, were developed using a dibenzoazaborine framework. The synthesis of electron-accepting conjugated molecules based on oligoacene-like frameworks substituted with boron atoms was investigated. The electron-accepting and anion-complexation abilities of a 9,10-dihydro-9,10-diboraanthracene were elucidated.

Research Products

• [Journal Article] Folding of a coordination polymer framework incorporating swiveling pins driven by π-π interactions (2011)
  • Author(s): Tomohiro Agou, Christophe Lescop, Regis Reau
  • Journal Title: Inorganic Chemistry 50 Pages: 3183-3185
  • Peer Reviewed
• [Journal Article] Assembling N,P,N Pincers for Coordination-Driven Synthesis of Supramolecular [2,2]Paracyclophane (2011)
  • Author(s): Ana Isabel Aranda Perez, Thomas Biet, Sebastien Graule, Tomohiro Agou, Christophe Lescop, Neil R. Branda, Jeanne Crassous, Regis Reau
  • Journal Title: Chemistry A European Journal 17 Pages: 1337-1351
  • Peer Reviewed
• [Journal Article] Assembling N, P, N Pincers for Coordination-Driven Synthesis of Supramolecular [2,2]Paracyclophane (2011)
  • Author(s): Ana Isabel Aranda Perez, Thomas Biet, Sebastien Graule, Tomehiro Agou, Christophe Lescop, Neil R.Branda, Jeanne Crassous, Regis Beau
  • Journal Title: Chemistry A European Journal Volume: 17 Pages: 1337-1351
  • Peer Reviewed
• [Journal Article] Folding of a coordination polymer framework incorporating swiveling pins driven by π-π interactions (2011)
  • Author(s): Tomohiro Agou, Manuel Sebastian, Christophe Lescop, Regis Reau
  • Journal Title: Inroganic Chemistry Volume: 50 Pages: 3183-3185
  • Peer Reviewed
• [Journal Article] Synthesis and Optical Properties of a Bis(benzothiaborino)carbazole, a Thiaborin-Carbazole Mixed Ladder-Type.-Conjugated Molecule (2010)
  • Author(s): Tomohiro Agou, Junji Kobayashi, Takayuki Kawashima
  • Journal Title: Phosphorus, Sulfur, Silicon and Related Elements 185 Pages: 6762-6764
  • Peer Reviewed
• [Journal Article] Stepwise synthesis and properties of a 9,10-dihydro-9,10-diboraanthracene (2010)
  • Author(s): Tomohiro Agou,Masaki Sekine, Takayuki Kawashima
  • Journal Title: Tetrahedron Letters 51 Pages: 5013-5015
  • Peer Reviewed
• [Journal Article] Structure, and Properties of a Dinaphthoazaborine (2010)
  • Author(s): Tomohiro Agou, Hiroki Arai, Takayuki Kawashima, Synthesis
  • Journal Title: Chemistry Letters 39 Pages: 612-613
  • Peer Reviewed
• [Journal Article] Detection of Biologically Important Anions in Aqueous Media by Dicationic Azaborines Bearing Ammonio or Phosphonio Groups (2010)
  • Author(s): Tomohiro Agou, Masaki Sekine, Junji Kobayashi, Takayuki Kawashima
  • Journal Title: Chemistry A European Journal 15 Pages: 5056-5062
  • Peer Reviewed
• [Journal Article] Synthesis and Optical Properties of a Bis(benzothiaborino)carbazole, a Thiaborin-Carbazole Mixed Ladder-Type π-Conjugated Molecule (2010)
  • Author(s): Tomohiro Agou, Junji Kobayashi, Takayuki Kawashima
  • Journal Title: Phosphorus, Sulfur, Silicon and Related Elements Volume: 185 Pages: 6762-6764
  • Peer Reviewed
• [Journal Article] Stepwise synthesis and properties of a 9,10-dihydro-9,10-diboraanthracene (2010)
  • Author(s): Tomohiro Agou, Masaki Sekine, Takayuki Kawashima
  • Journal Title: Tetrahedron Letters Volume: 51 Pages: 5013-5015
  • Peer Reviewed
• [Journal Article] Synthesis, Structure, and Properties of a Dinaphthoazaborine (2010)
  • Author(s): Tomohiro Agou, Hiroki Arai, Takayuki Kawashima
  • Journal Title: Chemistry Letters 39
  • NAID: 10027181603
  • Peer Reviewed
• [Journal Article] Two-photon absorption properties of heterafluorenes and spirobiheterafluorenes bearing aminostyryl arms (2009)
  • Author(s): Tomohiro Agou, Md. Delwar Hossain, Takayuki Kawashima,Kenji Kamada, Koji Ohta
  • Journal Title: Chemical Communications Pages: 6762-6764
  • Peer Reviewed
• [Journal Article] Synthesis and Reactivity of a Bis(dimesitylboryl)azaborine and Its Fluoride Sensing Abilitiy (2009)
  • Author(s): Tomohiro Agou, Masaki Sekine, Junji Kobayashi, Takayuki Kawashima
  • Journal Title: Chemical Communications Pages: 1894-1896
  • Peer Reviewed
• [Journal Article] Synthesis of .-Conjugated Dendrimers Based on Azaborines (2009)
  • Author(s): Tomohiro Agou, Tatsuo Kojima, Junji Kobayashi, Takayuki Kawashima
  • Journal Title: Organic Letters 11 Pages: 3534-3537
  • Peer Reviewed
• [Journal Article] Multi-step Detection of Cyanide Ion by a Bis(dimesitylboryl)dibenzoazaborine (2009)
  • Author(s): Tomohiro Agou, Masaki Sekine, Junji Kobayashi, Takayuki Kawashima
  • Journal Title: Journal of Organometallic Chemistry 694 Pages: 3833-3836
  • Peer Reviewed
• [Journal Article] Synthesis, Optical Properties, and Theoretical Calculations of Silafluorenes and Spirobisilafluorene Bearing Electron-Donating Aminostyryl Arms around a Silafluorene Core (2009)
  • Author(s): Tomohiro Agou, Md. Delwar Hossain, Takayuki Kawashima
  • Journal Title: Chemistry A European Journal 16 Pages: 368-375
  • Peer Reviewed
• [Journal Article] Detection of Biologically Important Anions in Aqueous Media by Dicationic Azaborines Bearing Ammonio or (2009)
  • Author(s): Tomohiro Agou, Masaki Sekine, Junji Kobayashi, Takayuki
  • Journal Title: Chemistry A European Journal 15 Pages: 5056-5062
  • Peer Reviewed
• [Journal Article] Synthesis and Reactivity of a Bis(dimesitylboryl)azaborine and Its Fluoride Sensing (2009)
  • Author(s): Tomohiro Agou, Masaki Sekine, Junji Kobayashi, Takayuki
  • Journal Title: Chemical Communications 2009 Pages: 1894-1896
  • Peer Reviewed
• [Journal Article] Synthesis of pi-Conjugated Dendrimers Based on Azaborines (2009)
  • Author(s): Tomohiro Agou, Tatsuo Kojima, Junji Kobayashi, Takayuki
  • Journal Title: Organic Letters 11 Pages: 3534-3537
  • Peer Reviewed
• [Journal Article] Multi-step Detection of Cyanide Ion by a Bis(dimesitylboryl)dibenzoazaborine (2009)
  • Author(s): Tomohiro Agou, Masaki Sekine, Junji Kobayashi, Takayuki
  • Journal Title: Journal of Organometallic Chemistry 694 Pages: 3833-3836
  • Peer Reviewed
• [Journal Article] Two-photon absorption properties of heterafluorenes and spirobiheterafluorenes bearing aminostyryl arms (2009)
  • Author(s): Tomohiro Agou, Md.Delwar Hossain, Takayuki Kawashima, Kenji Kamada
  • Journal Title: Chemical Communications 2009 Pages: 6762-6764
  • Peer Reviewed
• [Journal Article] Syntheses, Optical Properties, and Theoretical Calculations of Silafluorenes and Spirobisilafluorenes (2009)
  • Author(s): Tomohiro Agou, Md.Delwar Hossain, Takayuki Kawashima
  • Journal Title: Chemistry A European Journal 16 Pages: 368-375
  • Peer Reviewed
• [Presentation] 安定な1,2-ジブロモジシレンの反応性 (2011)
  • Author(s): 吾郷友宏、韓準秀、笹森貴裕、時任宣博
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 横浜
• [Presentation] 安定な1,2-ジヒドロジメタレンの合成と性質 (2010)
  • Author(s): 吾郷友宏、杉山佑介、笹森貴裕、時任宣博
  • Organizer: 第37回有機典型元素化学討論会
  • Place of Presentation: 室蘭
• [Presentation] 安定な1,2-ジヒドロジシレンの合成と異性化反応 (2010)
  • Author(s): 吾郷友宏、杉山佑介、笹森貴裕、高木望、永瀬茂、酒井平祐、古川行夫、時任宣博
  • Organizer: 第14回ケイ素化学協会シンポジウム
  • Place of Presentation: 湯河原
• [Presentation] 第3世代アザボリンデンドリマーの合成と光物性 (2010)
  • Author(s): 小島達央、吾郷友宏、小林潤司、川島隆幸
  • Organizer: 日本化学会第90回春季年会
  • Place of Presentation: 大阪
• [Presentation] ナフタレン縮環型アザボリンの合成と光学的性質 (2010)
  • Author(s): 荒井博貴、吾郷友宏、川島隆幸
  • Organizer: 日本化学会第90回春季年会
  • Place of Presentation: 大阪
• [Presentation] Synthesis and Optical Properties of Dibenzoazaborine-Based Dendrimers (2009)
  • Author(s): Tomohiro Agou, Tatsuo Kojima, Junji Kobayashi, Takayuki Kawashima
  • Organizer: 12th Kyushu International Symposium on Physical Organic Chemistry
  • Place of Presentation: Fukuoka
• [Presentation] ラダー型縮環ジボリンの新規合成法の開発 (2009)
  • Author(s): 関根真樹、吾郷友宏、小林潤司、川島隆幸
  • Organizer: 第36回有機典型元素化学討論会
  • Place of Presentation: 鳥取
• [Presentation] 共役拡張スピロヘテラフルオレンの光物性 (2009)
  • Author(s): 小島達央、吾郷友宏、小林川島隆幸
  • Organizer: 第36回有機典型元素化学討論会
  • Place of Presentation: 鳥取
• [Presentation] アザボリンを基本骨格としたデンドリマーの光物性 (2009)
  • Author(s): 小島達央、吾郷友宏、小林潤司、川島隆幸
  • Organizer: 第20回基礎有機化学討論会
  • Place of Presentation: 桐生
• [Presentation] ラダー型縮環ジボリン類の新規合成法の開発 (2009)
  • Author(s): 関根真樹・吾郷友宏・川島隆幸
  • Organizer: 第36回有機典型元素化学討論会
  • Place of Presentation: 鳥取
• [Presentation] Synthesis and Optical Properties of Dibenzoazaborine-Based Dendrimers (2009)
  • Author(s): Tomohiro Agou, Tatsuo Kojima, Junji Kobayahshi, Takayuki
  • Organizer: 12th Kyushu International Symposium on Physical Organic Chemistry
  • Place of Presentation: 福岡