Synthetic study on planar-chiral compounds and its dynamic behavior on their ratchet structures

• Project/Area Number: 15K13690
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Synthetic chemistry
• Research Institution: Tokyo Institute of Technology
• Principal Investigator: Ohmori Ken 東京工業大学, 理学院, 准教授 (50282819)
• Project Period (FY): 2015-04-01 – 2018-03-31
• Project Status: Completed (Fiscal Year 2017)
• Budget Amount: ¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000); Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2015: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
• Keywords: シクロファン / 面性不斉 / ポリフェニレン / ヘリシティー / パラシクロファン / ナフタレノファン / 面不斉 / 軸不斉 / ラチェット型分子

Outline of Final Research Achievements

Syntheses of planar planar-chiral cyclophane derivatives and their stereochemical property was studied by exploiting the orthogonal Suzuki-Miyaura coupling strategy by using a selectively-protected phenyldiboronic acid derivative and planar-chral carba-paracyclophane units. This method enabled efficient assembly of various heptaphenylene derivatives incorporating non-substituted phenylene spacers. circular dichroism (CD) spectra of these oligophenylenes show characteristic CD curve patterns, suggesting a helical conformation on their oligophenylene axis.

Research Products

• [Journal Article] Facile Synthesis of Stereodefined α-Iodovinyl Sulfoxides, Versatile Platform to Trisubstituted Olefins (2016)
  • Author(s): S. Jung, Y. Ueda, K, Suzuki, K. Ohmori
  • Journal Title: Synlett Volume: 27 Issue: 13 Pages: 2024-2028
  • DOI: 10.1055/s-0035-1561654
  • Peer Reviewed / Acknowledgement Compliant
• [Journal Article] Stereocontrolled Synthesis of Planar Chiral Carba-Paracyclophanes via Modular Assembly (2016)
  • Author(s): S. Jung, Y. Kitajima, Y. Ueda, K. Suzuki, K. Ohmori
  • Journal Title: Synlett Volume: 27 Issue: 10 Pages: 1521-1526
  • DOI: 10.1055/s-0035-1561937
  • Peer Reviewed / Acknowledgement Compliant
• [Presentation] 面不斉カルバパラシクロファン誘導体の合成とオリゴマー化に関する研究 (2017)
  • Author(s): 植田泰之、Suuna Jung、Vaidas Suvkynas、 鈴木啓介、大森建
  • Organizer: 第111回有機合成シンポジウム
• [Presentation] Synthetic studies on the cyclophane-derived polyphenylenes (2017)
  • Author(s): 植田泰之、Suuna Jung、Vaidas Suvkynas、 鈴木啓介、大森建
  • Organizer: Yasuyuki Ueda、Vaidas Suvkynus、Gaku Fukuhara、Keisuke Suzuki、Ken Ohmori
  • Int'l Joint Research
• [Presentation] 光学活性ナフタレノファンの合成と誘導体化に関する研究 (2017)
  • Author(s): 木崎拓也、植田泰之、鈴木啓介、大森建
  • Organizer: 日本化学会第98回春季年会
• [Presentation] シクロファンを基本単位とするポリフェニレン類の合成研究 (2017)
  • Author(s): 植田泰之、鈴木啓介、大森建
  • Organizer: 日本化学会第97春季年会
  • Place of Presentation: 慶應義塾大学日吉キャンパス（横浜）
• [Presentation] Synthetic Studies and Stereochemistry of Carba-paracyclophane (2016)
  • Author(s): Sunna Jung, Yasuyuki Ueda, Ken Ohmori, Keisuke Suzuki
  • 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
  • Year and Date: 2016-03-24
• [Presentation] 光学活性カルバパラシクロファンのオリゴマー化に関する研究 (2016)
  • Author(s): 植田泰之, 鄭善牙, 大森建, 鈴木啓介
  • 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
  • Year and Date: 2016-03-24
• [Presentation] 光学活性シクロファンのオリゴマー化に関する研究 (2016)
  • Author(s): 植田泰之、鈴木啓介、大森建
  • Organizer: 第51回天然物談話会
  • Place of Presentation: 湯沢東映ホテル
• [Presentation] Synthesis and Stereochemical Properties of Planar-Chiral Paracyclophanes (2015)
  • Author(s): Ken Ohmori
  • Organizer: The 6th Japanese-Sino Symposium on Organic Chemistry for Young Scientists
  • Place of Presentation: Akiu Resort Hotel Crescent, Sendai
  • Year and Date: 2015-09-06
  • Int'l Joint Research / Invited
• [Remarks] SUZUKI-OHMORI RESEARCH GROUP
  • URL: http://www.org-synth.chem.sci.titech.ac.jp/suzukilab/