Topological Control of pi-Conjugated Networks for Keeping Antiaromatic Character with Degenerated Frontier Orbitals
| Project/Area Number |
18K14201
|
|---|
| Research Category |
Grant-in-Aid for Early-Career Scientists
|
| Allocation Type | Multi-year Fund |
|---|
| Review Section |
Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
|
|---|
| Research Institution | Osaka University |
|---|
Principal Investigator |
|
|---|
| Project Period (FY) |
2018-04-01 – 2020-03-31
|
| Project Status |
Completed (Fiscal Year 2019)
|
| Budget Amount *help |
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2019: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2018: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
|
|---|
| Keywords | 反芳香族 / 開殻性 / π共役系 / ペンタレン / 反芳香族性 |
|---|
| Outline of Final Research Achievements |
Antiaromaticity is one of the crucial concepts for understanding cyclic π-conjugated systems. The pseudo-degenerated frontier orbitals of antiaromatic molecules would evoke the association with open-shell character. However, the systematic control of these characters in a series of molecular framework, i.e. actualizing one character and diminishing another character or enhancing both characters, remains unexplored. Toward clarifying this intriguing question, we have designed and synthesized the non-alternant hydrocarbons with an 4nπ-conjugated scaffold. Our pentalene (8π)-based molecules serve as acceptable model molecules to control the balance between antiaromaticity and open-shell character. Experimental and theoretical studies clearly demonstrated the importance of topological design for the π-electron networks in non-alternant polycyclic hydrocarbons.
|
| Academic Significance and Societal Importance of the Research Achievements |
国内外で反芳香族性や開殻性に着目した実験的・理論的研究は幅広く行われている。しかし、一方の性質解明、応用的展開に特化したものに限られてきた。本研究課題の大切な点は、両者の両立した発現を目指した分子設計の提案にある。その観点で、新規化合物であるジベンゾ[a,f]ペンタレンを基軸として得られた、反芳香族性と開殻性の相関についての知見は、両性質の基礎的な理解の深化に大きく貢献したと考えられる。さらに、開殻性や反芳香族性は小さなHOMO-LUMOギャップに由来した有機機能性材料に資する重要な性状をしめす。本研究で得られた両性質の相関に関する知見は、機能性材料の新たな設計指針になると期待される。
|
Report
(3 results)
Research Products
(57 results)
