2017 Fiscal Year Research-status Report
Irradiation-Responsive Ligands for Efficient Iron-Catalysis
| Project/Area Number |
17K14480
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| Research Institution | The University of Tokyo |
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Principal Investigator |
シャン ルイ 東京大学, 大学院理学系研究科(理学部), 特任講師 (50793212)
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| Project Period (FY) |
2017-04-01 – 2019-03-31
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| Keywords | iron-catalyzed / C-H activation / cyclization / conjugated pi-molecule / thiophene |
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| Outline of Annual Research Achievements |
In the past fiscal year, we explored various types of iron-catalyzed C-H functionalization reactions under irradiation of different wavelength. At the meanwhile, we designed and tried to make new phosphine and nitrogen ligands for iron and studied the irradiation-responsiveness of these iron complexs. The research achievement last year includes the following,
1.We discovered Fe-carbazole compelx is reactive to promote aliphatic C-H bond activation to form a C(sp3)-N bond under irradiation of blue LEDs. Iron-carbazole complex can be used as a catalyst to catalyzed C-C bond formation of aryl halides and heteroarenes. This novel reactivity is currently under intense exploration in our lab.
2.We discovered that Fe-catalysis can be used as a key cyclization step for synthesis of photoresponsive organic semiconductors . Fe-catalyst is used to synthesize oligophenylenevinylene compounds, which are known as promising organic semiconductor for laser and solar cell applications.
3.We explored iron-catalyzed two-fold C-H activation to synthesize bi(hetero)aryl compounds, and oligo thiophene compounds under irradiation and thermal conditions. It is proved that Fe-catalyst is competent for the two-fold C-H activation reactions to make biaryls, which were achieved with precious rare metal catalyst before. We are studying the property of fused thiophene compounds we synthesized and exploring their functions in organic photovoltaics.
The projects regarding to the above-mentioned results are currently proceeding in our lab, and these results are expected to be published in this fiscal year.
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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
We have discovered the novel reactivity of iron complex under irradiation for aliphatic C-H bond functionalization. Also, iron-catalyst is discovered to be a competent catalyst for two-fold C-H activation to synthesize oligothiophene and biaryls, which are of high interest in materials science.
We discovered both the novelty photo reactivity of iron complex and also the potential application of iron catalyst in synthesizing organic semiconductor materials. We are confident these results will be published in high level journals and will receive broad attention from both the synthesis and materials science communities.
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| Strategy for Future Research Activity |
In the new fiscal year, our research will continuously focus on iron-catalyzed C-H functionalization reaction under irradiation conditions, to discover various novelty reactivity of organo iron species and to explore their synthetic application in materials science. We believe the photo scission effect of certain iron-carbon bond in low valent iron complexes will induce unprecedent reactivity of iron-catalyst to make sustainable iron as an ideal catalyst for C-H borylarion, Murai reaction and hydroformylation reactions. Our research efforts will focus on the above-mentioned topics.
Meawhile, the utilization of iron-catalyst to make compounds promising as organic semiconductors will also be continuously explored in our lab. With the discovered several synthetic methods and the understanding of properties of several conjugated pi-materials we have synthesized, we will expand the library of our materials and further design to make materials of optimized structure. These materials will be explored as charge transporting materials and conducting organic molecules for solar cell application in the near future.
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