The preparation of β, β-fused-porphyrin oligomers by use of the building blocks.
| Project/Area Number |
16550047
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Organic chemistry
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| Research Institution | Ibaraki National College of Technology |
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Principal Investigator |
TANIGUCHI Shozo Ibaraki College of Technology, Department of Chemistry and Material Engineering, Professor, 物質工学科, 教授 (50042487)
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| Project Period (FY) |
2004 – 2005
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| Project Status |
Completed (Fiscal Year 2005)
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| Budget Amount *help |
¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 2005: ¥200,000 (Direct Cost: ¥200,000)
Fiscal Year 2004: ¥500,000 (Direct Cost: ¥500,000)
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| Keywords | building blocks / tripyrrane / 2,3-dimethylporphyrin / oxidation / porphyrin anhydride |
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| Research Abstract |
The π-conjugated porphyrin oligomers are very interesting in various fields of science and technology, because they may be used as organic conductive materials, molecular devices or light-harvesting substances. Numerous approaches have been adopted to the p -electron systems of porphyrins. The synthetic route for the designed porphyrin polymer was examined by the process of retro-synthesis. The result of searching route was very much similar to one of the anthracene synthetic method. We adopted new 2,3-dimethylporphyrin to be target compound as stating materials for the porphyrin oligomers. The porphyrin was synthesized from nitroethane via 8 steps. As the last step, the condensation of 2,5-bis(hydroxymethyl)-3,4-dimethylpyrrole with tripyrrane provided 2,3dimethylporphyrin in 27% yield. This ‘3+1' condensation is a typical "building blocks" technique. The structure of 2,3-dimethylporphyrin was determined by UV, NMR and MS techniques. The X-ray crystallography of 2,3-dimethylporphyrin shows that the structure has a plane one and the dimethylpyrrole core and its opposite core have the inner protons of porphyrin ring. Oxidation reaction of the methyl group on the dimethylporphyrin was investigated the following four ways ; potassium permanganate, potassium dichromate, nitric acid and N-hydroxyphthalimide in the presence of cobalt and manganese acetate. The three oxidation processes except the last N-hydroxyphthalimide (NHI) one did not provide the corresponding oxidative compounds. The LC-MS measurement of the products obtained by the catalytic NHI oxidation process showed the produce of the target molecule ‘porphyrin anhydride' and the porphyrin carboxylic acids.
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Report
(3 results)
Research Products
(11 results)
