Syntheses of helicenes consisted of 2, 3, and 4 condensed benzene rings and their application to high-order structures

• Project/Area Number: 22790003
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Chemical pharmacy
• Research Institution: Tokyo Medical and Dental University
• Principal Investigator: AIKAWA Haruo 東京医科歯科大学, 生体材料工学研究所, 特任助教 (70547322)
• Project Period (FY): 2010 – 2011
• Project Status: Completed (Fiscal Year 2011)
• Budget Amount: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000); Fiscal Year 2011: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000); Fiscal Year 2010: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
• Keywords: 有機化学 / アダマルチル / キラルナフタレン / 分子間相互作用 / 不斉認識 / ラセミ化 / ヘリセン / オルト縮環 / キラル芳香族化合物 / アダマンチル / CD / ラセミ化障壁 / ペリ位 / ベンザイン / フェナントレン

Research Abstract

Single enantiomers of 1, 8-di(1-adamantyl) naphthalenes and their derivatives having various substituents at C3 and C6 were synthesized. Kinetic studies by CD revealed enantiomerization barriers of ca. 30 kcal/mol for these chiral naphthalenes. For the applications of helicenes to high-order structures, various helicene oligomer SAMswere constructed on the gold suface.

Research Products

• [Journal Article] Synthesis of 1, 8-di(1-adamantyl) naphthalenes as single enantiomers stable at ambient temperatures (2011)
  • Author(s): Haruo Aikawa, Yusuke Takahira, Masahiko Yamaguchi
  • Journal Title: Chemical Communications Volume: 47 Pages: 1479-1481
• [Journal Article] Formation of double helix self-assembled monolayers of ethynylhelicene oligomer disulfides on gold surfaces (2011)
  • Author(s): Koji Yamamoto, Hiroki Sugiura, Ryo Amemiya, Haruo Aikawa, Zengjian An, Masahiko Yamaguchi, Masashi Mizukami, Kazue Kurihara
  • Journal Title: Tetrahedron Volume: 67 Pages: 5972-5978
• [Journal Article] Synthesis of 1,8-Di (1-adamantyl) naphthalenes as Single Enantiomers Stable at Ambient Temperatures (2011)
  • Author(s): Haruo Aikawa
  • Journal Title: Chemical Communications Volume: 47 Pages: 1479-1481
  • Peer Reviewed
• [Presentation] Synthesis of optically active di(adamantly) phenanthrenes and di(adaman-tly)-benzophenanthrenes (2011)
  • Author(s): 盛夏、相川春夫、山口雅彦
  • Organizer: 第50回記念日本薬学会東北支部大会
  • Place of Presentation: 東北薬科大学(宮城県)
  • Year and Date: 2011-10-30
• [Presentation] Synthesis of optically active di(adamantly)phenanthrenes and di(adamantyl)benzophenanthrenes (2011)
  • Author(s): 盛夏、相川春夫、山口雅彦
  • Organizer: 第50回記念日本薬学会東北支部大会
  • Place of Presentation: 東北薬科大学
  • Year and Date: 2011-10-30
• [Presentation] 1-(1-アダマンチル)-8-(t-ブチル)ナフタレンの合成 (2011)
  • Author(s): 相川春夫
  • Organizer: 日本薬学会第131回年会
  • Place of Presentation: ツインメッセ静岡(静岡県)
  • Year and Date: 2011-03-31
• [Presentation] Synthesis of Novel Chiral Phenanthrenes (2011)
  • Author(s): Haruo Aikawa
  • Organizer: The 2011 WPI-AIMR Annual Workshop
  • Place of Presentation: 仙台国際センター(宮城県)
  • Year and Date: 2011-02-22
• [Presentation] Synthesis of Enantiopure 1, 8-Di(adamantly) naphthalenes Stable at Ambient Temperatures (2010)
  • Author(s): Haruo Aikawa, Yusuke Takahira, Masahiko Yamaguchi
  • Organizer: 10^<th> Tateshina Conference on Organic Chemistry
  • Place of Presentation: 蓼科フォーラム(長野県)
  • Year and Date: 2010-11-13
• [Presentation] Synthesis of Enantiopure 1,8-Di (adamantly) naphthalenes Stable at Ambient Temperature (2010)
  • Author(s): Haruo Aikawa
  • Organizer: 10^<th> Tateshina Conference on Organic Chemistry
  • Place of Presentation: 蓼科フォーラム(長野県)
  • Year and Date: 2010-11-13
• [Presentation] 室温で安定な不斉を有する1, 8-アダマンチルナフタレンの合成 (2010)
  • Author(s): 相川春夫、高平祐介、山口雅彦
  • Organizer: 第21回万有仙台シンポジウム
  • Place of Presentation: 仙台国際センター(宮城県)
  • Year and Date: 2010-06-05
• [Presentation] 室温で安定な不斉を有する1,8-アダマンチルナフタレンの合成 (2010)
  • Author(s): 相川春夫
  • Organizer: 第21回万有仙台シンポジウム
  • Place of Presentation: 仙台国際センター(宮城県)
  • Year and Date: 2010-06-05