1998 Fiscal Year Final Research Report Summary
Development of Novel Synthetic Methods of (Polyfluoro) silanes and Their Application to Creation of Functional Materials
| Project/Area Number |
09450331
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
有機工業化学
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| Research Institution | Osaka University |
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Principal Investigator |
KOMATSU Mitsuo Osaka Univ., Graduate School of Engineering, Professor, 大学院・工学研究科, 教授 (60029197)
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| Co-Investigator(Kenkyū-buntansha) |
RYU Ilhyong Osaka Univ., Graduate School of Engineering, Associate Professor, 大学院・工学研究科, 助教授 (80210821)
KUNAI Atsutaka Hiroshima Univ., Faculty of Engineering, Professor, 工学部, 教授 (90029190)
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| Project Period (FY) |
1997 – 1998
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| Keywords | halosilanes / fluorine-containing silanes / generation of 1,3-dipoles / heterocyclic compounds / silicon-containing polymers / functional materials / electron-transporting materials / heat-resistant materials |
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| Research Abstract |
In this project are investigated development of new methods for synthesis of (polyfluoro)silanes, which bear more than two different functional groups, and their application to creation of functional materials such as heterocycles and organic silicon polymers. Major results obtained are summarized below.
1) Selective and efficient synthesis of a variety of hydrobromosilanes with high yields were achieved by treatment of hydrosilanes with copper bromide(II)/ copper iodide(I). Selective bromination of (polyhydro)silanes and (polyhydro)-
disilanes were also successful.
2) Highly efficient novel methodology for generation of azomethine ylides, typical 1,3-dipolar intermediates, utilizing di- or trifluorosilanes was found. Thus azaallyl anions or alpha-silylimines were treated with the fluorosilanes at room temperature to give azomethine ylides, which readily cycloadded to dipolaro-philes to afford various heterocycles.
3) Treatment of alpha-silylimidates, or in-situ generated imidates from alpha-silylamides, with trifluorosilanes caused generation of azomethine ylide intermediates even at room temperature and their cycloadditions afforded a variety of heterocycles.
4) To develop silicon-containing polymeric materials, synthetic methods of poly(silylenephenylene)s bearing Si-Cl and Si-F bonds were established. Various functional groups were introduced onto silicon atoms by nucleophilic displacement of the halogen moieties. Among them, a polymer containing ethynylphenyl functionality showed excellent heat-resistant ability.
5) Several silicon-bridged bithiophenes were unprecedently synthesized via difluorosilane derivatives and this class of compounds are good candidates for electron-transportaing materials.
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