2019 Fiscal Year Final Research Report
Development of new functions based on connection of biomolecular with planar polycyclic aromatic molecules
| Project Area | Middle molecular strategy: Creation of higher bio-functional molecules by integrated synthesis. |
|---|
| Project/Area Number |
15H05839
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)
|
| Allocation Type | Single-year Grants |
|---|
| Review Section |
Science and Engineering
|
|---|
| Research Institution | Keio University |
|---|
Principal Investigator |
|
|---|
| Project Period (FY) |
2015-06-29 – 2020-03-31
|
| Keywords | ルテニウム触媒 / 炭素－水素結合切断 / 炭素－酸素結合切断 / アリールボロン酸エステル / 芳香族ケトン / 多環芳香族炭化水素 / アリール化反応 / クロスカップリング |
|---|
| Outline of Final Research Achievements |
Various polycyclic aromatic hydrocarbons (PAHs) have been synthesized for utilization as functionalized organic materials and a large number of efforts have been paid for development of their efficient synthetic methods. Our group has been working on the efficient synthesis of polycyclic aromatic hydrocarbons (PAHs) based on our ruthenium-catalyzed C-H and C-O arylations of aromatic ketones. In this study we have applied this strategy to efficient synthesis of tetrabenzo[a,d,j,m]coronene (TBC) derivatives having a readily transformable formyl group.
The chemoselective C-O arylation of 1-methoxyanthraquinone with an arylboronate having an acetal group at a para position proceeded using RuH2(CO)(PPh3)3 as a catalyst to give a 1-arylanthraquinone. Subsequent C-H triarylation with another arylboronate provided tetraarylanthraquinone with one acetal group. Conversion of carbonyl oxygens to methylidenes, followed by Scholl reaction, afforded the TBC derivative bearing a formyl group.
|
| Free Research Field |
有希合成化学
|
| Academic Significance and Societal Importance of the Research Achievements |
多環芳香族炭化水素（PAH）は有機機能材料への応用を目指した研究が多く行われており、様々な合成法の開発が行われてきた。PAHが持つ光・電子特性ではなく、分子同士がπ-π相互作用で集積化しやすい性質を積極的に使い、薬剤などの有用化合物を目的場所に効果的に集める方法へと展開させる研究は、ほとんど行われていない。この研究により、溶液中で分子間相互作用で自己集積化する性質を持つPAHの効率的合成法の開発、またそれら分子に機能性物質を結合させることが可能な部位を導入する方法の開発は、PAHの新機能を創成することを示している。このように、新規合成手法の開発が機能性分子創成にとっても有用である。
|
