Creation of Functionalized Cyclic Pi-Conjugated Molecules by Catalytic Aromatic Ring Construction

2017 Fiscal Year Final Research Report

• Project/Area Number: 15H03775
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Tokyo Institute of Technology
• Principal Investigator: Tanaka Ken 東京工業大学, 物質理工学院, 教授 (40359683)
• Project Period (FY): 2015-04-01 – 2018-03-31
• Keywords: 有機合成化学

Outline of Final Research Achievements

The synthesis of [8]cycloparaphenylene octacarboxylate and [6]cycloparaphenylene tetracarboxylate was achieved by the stepwise chemo- and regioselective [2+2+2] cycloaddition reactions of diynes with symmetrical electron deficient internal alkynes using a cationic rhodium (I)/H8-BINAP catalyst and subsequent reductive aromatization. The structures and packing modes of these compounds were clarified by X-ray crystal structure analyses. In addition, we successfully synthesized a precursor of a branched cycloparaphenylene by the complete intermolecular homo-[2+2+2] cycloaddition reaction. Furthermore, we succeeded in developing the new cycloaddition reactions, which would be employed as a key reaction in the synthesis of various cyclic pi-conjugated molecules.

Free Research Field

有機合成化学