2021 Fiscal Year Annual Research Report
Enantio-selective transportation of natural small chiral molecules via discrete access-controllable nanotubes based on pillararene
| Project/Area Number |
21K14612
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| Research Institution | Kyoto University |
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Principal Investigator |
FA SHIXIN 京都大学, 工学研究科, 特定助教 (40835922)
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| Project Period (FY) |
2021-04-01 – 2022-03-31
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| Keywords | Pillar[5]arene / Chirality / Molecular Tube / Ionic Interaction / Assembly |
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| Outline of Annual Research Achievements |
Selectively transporting hydrophilic natural molecules with chirality through artificial channels is of crucial importance. However, this work is challenging due to the sophisticated molecular design and standing low efficiency. To achieve this goal, the construction of channels with chiral information is the primary task.
Taking advantage of the controllable planar-chiral properties of pillar[n]arenes, we started the project with a rim-differentiated pillar[5]arene bearing stereogenic centers on one rim and benzoic acids on the other rim. An diastereomeric excess of the pillar[5]arene was produced through the host-guest interaction with achiral linear guests. The trimeric nanotubes with specific helicity and stability were synthesized through the ionic interaction of the pre-regulated rim-differentiated pillar[5]arene with an amino pillar[5]arene.
Another strategy on construction of helical trimeric nanochannels was also practiced. An acidic rim-differentiated pillar[5]arene without stereogenic centers was isolated into two enantiomers firstly, and interacted with the amino pillar[5]arene to produce enantiomeric nanochannels. The constructed channels possessed pure left- and right-handed helicity.
These trimeric nanotubes were expected to work as artificial channels enabling enantio-selective transportation of natural small chiral molecules, because previous work has revealed the enantio-selective recognition of pillar[5]arenes.
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