1995 Fiscal Year Final Research Report Summary
Construction of Metalloporphyrins Blocked by Fluorine Groups and Evaluation of Their Oxygen-carrying and -activating Ability
| Project/Area Number |
06650991
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
有機工業化学
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| Research Institution | Seikei University |
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Principal Investigator |
TANAKA Kiyoshi Seikei University・Faculty of Engineering Professor, 工学部, 教授 (40138540)
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| Co-Investigator(Kenkyū-buntansha) |
IWATA Satoru Seikei University・Faculty of Engineering Research Assistant, 工学部, 助手 (10223398)
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| Project Period (FY) |
1994 – 1995
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| Keywords | Perfluoroalkylporphyrin / Hemin / Oxygen-carrying / Photochromism |
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| Research Abstract |
Linear and Cyclic perfluoroalkylated porphyrins were synthesized by the reactions of o-aminophenyl substituted porphyrins and the corresponding perfluoroalkylated carboxylic acid halides. It is of interest that the reaction with hexafluoroglutaryl chloride, bifunctional carboxylic acid chloride, produced imide-cyclic porphyrin. Atropisomers (cis and trans) were respectively isolated and characterized by spectroscopic data. Introduction of iron (III) chloride into trans-perfluoroalkylated porphyrins was easily performed by one pot reaction with iron (II) chloride and the similar introduction into cis-ones was so sluggish that other synthetic route via mu-oxodimer was developed.
Reduction of thus-obtained porphyrin iron (III) chloride to the corresponding porphyrin iron (II), which is expected to be large oxygen affinity, was attempted but full conversion was not recognized. That is still remaining problem to be resolved.
In a continuing investigation of spectroscopic characterization of the obtained porphyrins, an interesting photochromism of the porphyrins was noticed. It was found that the photochromism was caused by putting on and off hydrogen chloride, which is generated by photodegradation of solvent. The effects of solvent, porphyrin substituent, and wavelength of photoirradiation on the photochromism were made clear.
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