Synthesis and Electronic Properties of Nitrogen-Containing pi-Systems Substituted by Two Radicals

2015 Fiscal Year Final Research Report

• Project/Area Number: 26810023
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Organic chemistry
• Research Institution: Kyoto University (2015); Osaka University (2014)
• Principal Investigator: Sakamaki Daisuke 京都大学, 工学(系)研究科(研究院), 研究員 (60722741)
• Project Period (FY): 2014-04-01 – 2016-03-31
• Keywords: 有機ラジカル / ビラジカル / 芳香族アミン / アザアセン

Outline of Final Research Achievements

In this study, we investigated the structures and the electronic properties of N-containing conjugated molecules having two radical groups. We prepared a novel triphenylamine derivative having two phenoxyradicals appended to the amino nitrogen atom. X-ray single crystal analysis and the NMR and ESR measurements demonstrates the unexpected closed-shell electronic structure and two unusual C―N bonds with multiple-bond character. The theoretical calculations support the experimental results and predicted a small HOMO-LUMO gap originating from the nonbonding character of the HOMO. This study presents a new strategy to construct molecules with a small singlet-triplet energy gap and HOMO-LUMO gap.

Free Research Field

物理有機化学