Development of pseudo-aromatic systems consisting of cyclic resonance and multiple hydrogen bonding
| Project/Area Number |
18K05082
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Review Section |
Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
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| Research Institution | Shimane University |
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Principal Investigator |
Suzuki Masaaki 島根大学, 学術研究院環境システム科学系, 講師 (90506891)
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| Project Period (FY) |
2018-04-01 – 2023-03-31
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| Project Status |
Completed (Fiscal Year 2022)
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| Budget Amount *help |
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2020: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2019: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2018: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
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| Keywords | 共鳴構造 / 水素結合 / 互変異性 / 芳香族性 / プロトン共役電子移動 / ポルフィリノイド / トリピリン / 環拡張ポルフィリン / オリゴピロール / 構造有機化学 |
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| Outline of Final Research Achievements |
Aiming to reproduce the two-dimensional π-conjugated system seen in polycyclic aromatic hydrocarbons by means of resonance and other interactions, we have created a pseudoaromatic framework based on intramolecular multi-hydrogen bonding interactions and resonance structures.
Tripyrine, an acyclic ligand consisting of three pyrrole rings and a three-quarter substructure of porphyrin, was also recognized as a framework including intramolecular multi-hydrogen bonding interactions. The differences in various properties pf tripyrrin derivatives were evaluated by exchanging their terminal halogen substituents.
By tuning the electron-withdrawing properties of the 5,20-substituents of meso-aryl substituted hexaphyrin, we found that some of its conformations exhibit only type-II, an equilibrium mixture of type-I and type-II, and only type-I.
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| Academic Significance and Societal Importance of the Research Achievements |
次世代炭素材料として有望であるが合成戦略が限られる多環芳香族炭化水素に対し、それらと同等の電子系にいたる合成法の易化・多様化を狙うことで、軽量・柔軟・レアメタルフリーな機能分子開発が可能になる。本研究は、こうした材料開発によって輸送や原材料の入手、そして成形性の問題を高度に解決でき、経済や環境の負荷を低減するための礎を築くことができた。また、芳香族性という有機化学の根幹をなす概念に迫ることで、基礎学術的な観点からも興味深い成果となった。
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Report
(6 results)
Research Products
(30 results)
