Creation of novel conjugated molecules with heavy phenyl anions as building blocks

2020 Fiscal Year Final Research Report

• Project/Area Number: 18H01963
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Review Section: Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
• Research Institution: Kyoto University
• Principal Investigator: MIZUHATA Yoshiyuki 京都大学, 化学研究所, 准教授 (30437264)
• Project Period (FY): 2018-04-01 – 2021-03-31
• Keywords: 有機元素化学 / 高周期14族元素 / 芳香族化合物 / フェニルアニオン / 共役形化合物

Outline of Final Research Achievements

The synthesis of silabenzenyl anion in which the anion carbon of the phenyl anion was replaced with silicon was investigated, and a cyclic polyanion was obtained, suggesting the formation of silabenzenyl anion. The silicon system was found to be extremely reactive unlike the previously reported germanium and tin systems.
In addition, we investigated the reactions of germabenzenyl anion with various electrophiles and found a unique reactivity of exchange of heavy elements in the aromatic ring with 1,2-dibromodimethalene. In the reactions with chalcogen donors, we succeeded in the synthesis of heavy analogues of phenoxide, and the concept of "charge repulsion" applied to the stabilization of "heavy phenyl anions" can stabilize other highly reactive species.

Free Research Field

典型元素化学

Academic Significance and Societal Importance of the Research Achievements

重いフェニルアニオンは、母体であるフェニルアニオンとは大きく異なる反応性を示し、それを活用することで種々の未踏分子の合成が可能になった。また安定化に利用可能な置換基が限定的であった「重いベンゼン」の化学をさらに拡張させる点で学術的にも意義が大きい。