Creation of supramolecular materials based on curved pi-conjugated molecules

2018 Fiscal Year Final Research Report

• Project/Area Number: 16H06031
• Research Category: Grant-in-Aid for Young Scientists (A)
• Allocation Type: Single-year Grants
• Research Field: Organic chemistry
• Research Institution: Kyoto University (2017-2018); Nagoya University (2016)
• Principal Investigator: Hiroto Satoru 京都大学, 人間・環境学研究科, 准教授 (30547427)
• Project Period (FY): 2016-04-01 – 2019-03-31
• Keywords: 曲面 / π共役分子 / ヘリセン / バッキーボウル / 外部刺激応答性

Outline of Final Research Achievements

The purpose of this research was to disclose effect of curved structures on molecular functionalities compared with planar pi-conjugated molecules. As a result, we discovered unique supramolecular assemblies based on curved pi-conjugated molecules. In particular, we have achieved a creation of novel two-photon absorption switching host-guest molecules based on azabuckybowl and C60. In addition, we found a formation of supramolecular polymer with azabuckybowl dimer in the presence of stoichiometric amount of C60. These phenomena have not been reported for planar pi-conjugated molecules.
Secondly, stimuli-responsibilities of three-dimentional molecules have been developed by dimerization of hexa-peri-hexabenzocoronene. The dicyanoethano-bridged dimer exhibited mechanochromic behaviors. Furthermore, fluoromechanochromism was also observed for the dicyanoetheno-bridged dimer. These results would lead to creation of novel molecular sensors based on curved pi-conjugated molecules.

Free Research Field

構造有機化学

Academic Significance and Societal Importance of the Research Achievements

本研究により、分子が曲面になることで平面より優れた、または平面分子にはない反応性を示すことを実験的に明らかにできた。これは、分子の曲面という構造的な要因の意義を実験的に初めて示した学術的に重要な結果である。さらに、三次元分子の柔軟性および集積による外部刺激応答性を発現したことは、分子センサーの新たな設計の指針を示す。また、曲面上の窒素元素の効果を示したことは、炭素材料におけるヘテロ元素導入の効果を実験的に解明する重要な手がかりとなり、今後の炭素材料の発展に貢献できる。以上のように、本研究は、曲面分子という新たな分子材料の創出とともに従来の炭素材料の発展の促進に繋がる意義深いものである。