New Organic Chemistry and Materials Science of Curved pi-Conjugated Molecules

2020 Fiscal Year Final Research Report

• Project/Area Number: 16H06352
• Research Category: Grant-in-Aid for Scientific Research (S)
• Allocation Type: Single-year Grants
• Research Field: Organic chemistry
• Research Institution: Kyoto University
• Principal Investigator: Yamago Shigeru 京都大学, 化学研究所, 教授 (30222368)
• Co-Investigator(Kenkyū-buntansha): 梶 弘典 京都大学, 化学研究所, 教授 (30263148) ; 藤塚 守 大阪大学, 産業科学研究所, 教授 (40282040)
• Project Period (FY): 2016-05-31 – 2021-03-31
• Keywords: 環状π共役分子 / シクロパラフェニレン / ナノカーボン / 有機デバイス材料 / 芳香族性

Outline of Final Research Achievements

Various cyclic pi-conjugated molecules, in particular, cycloparaphenylenes (CPPs), which is the smallest cyclic constituent of armchair carbon nanotubes, were synthesized, and their physical properties and applications to organic electronic materials were studied. A gram-scale synthetic method of CPPs and their derivatives, and a new synthetic method for Mobius molecules, in which CPP is twisted due to the insertion of an alkene group, were developed by extending the previous synthetic method developed by our group. CPP derivatives were also successfully synthesized based on the elucidation of the chemical reactivity of CPPs. Highly soluble CPP derivatives in organic solvents were used for fabricating a device consisting of CPP thin films. Physical properties of the synthesized CPPs and derivatives were also studied. The Mobius CPPs showed unique size dependence of the bandgap, which becomes smaller as the conjugation becomes smaller.

Free Research Field

合成化学

Academic Significance and Societal Importance of the Research Achievements

研究代表者が開発した白金錯体を用いるCPPの合成法は、環状π共役分子の有用な合成法として世界中の研究者により既に利用されている。これまでは、環化前駆体の分子設計に限られていたが、ごく最近では、金等の別の金属を用いる合成への発展も広がっており、モノづくりの基礎化学に重要な貢献を行っていると考えている。さらに、研究代表者が開発したCPP合成法を民間会社へ技術移転することで、CPPが試薬として販売されている。これにより、CPPを伸縮性有機トランジスター材料のフィラーに用いる等、実用化に近い分野でCPPの新たな利用法の開拓が広がっており、社会実装も期待される。