2022 Fiscal Year Research-status Report
Development of Indigo Derivatives as Functional Molecules with Novel Photochemical Properties
| Project/Area Number |
22K20522
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| Research Institution | Hokkaido University |
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Principal Investigator |
HUANG CHUNG・YANG 北海道大学, 化学反応創成研究拠点, 准教授 (90956153)
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| Project Period (FY) |
2022-08-31 – 2024-03-31
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| Keywords | indigo / photochemistry / organic synthesis / metal catalysis |
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| Outline of Annual Research Achievements |
During the first year, we completed the optimization of indigo mono-N-arylation. By using copper catalyst and inexpensive reagents, we were able to achieve selective and efficient transformation under mild reaction conditions. The examination of substrate scope revealed that various useful functional groups can be included, which is crucial for future applications of indigos in multiple scientific fields. With these compounds in hand, we built a series of photoswitches and studied their photochemical properties under red-light irradiation. In particular, by using data science approaches, the thermal stabilities were correlated with structural descriptors obtained by computations, which serves as a useful tool for predicting the properties of novel compounds. On the other hand, in an international collaborative project, we successfully identified the key parameters for red-light-enabled photoswitching of indigos in polymer thin films. This study is critical in understanding their different behaviors between solution and solid-state environment. Overall, these works have moved forward the understanding and utility of indigos as functional molecules and laid the important foundation for future studies.
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| Current Status of Research Progress |
Current Status of Research Progress
2: Research has progressed on the whole more than it was originally planned.
Reason
For the indigo mono-N-arylation project, we are currently finishing up the collection of experimental data and will soon start the manuscript preparation. We plan to submit the manuscript in summer and present this work widely in various international conferences this year. The collaborative work on indigo photoswitching in polymer thin films was recently published in an international journal. We have also submitted a review manuscript on the topic of developing indigos as photo-responsive molecular tools. Moreover, by combining computation, data science, and synthetic organic chemistry, we have initiated another project to study the molecular interactions by indigo photoswitches. As such, we have made significant progress in various directions within this year.
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| Strategy for Future Research Activity |
In this year, we will focus on the following three goals. First, we will finish up the current project of indigo mono-N-arylation for publication and result dissemination in international conferences. Second, we will continue the study of utilizing indigo photoswitches for measuring the molecular interactions. Third, in collaborations with material scientists and medicinal chemists, we will explore the applications of indigos in various scientific disciplines. By combining all these efforts, we hope to push forward the synthetic availability, mechanistic understanding, and practical utility of indigo molecules as functional molecules.
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| Causes of Carryover |
Due to the necessity to utilize the financial support from Hokkaido University and WPI-ICReDD first, the consumption of funds from this project was diminished. Furthermore, many chemicals and instruments are for shared-use at WPI-ICReDD so we could take advantage of these resources. However, these financial supports for my group will decrease beginning from this fiscal year. Thus, we will start using the KAKENHI more.
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