2005 Fiscal Year Final Research Report Summary
Synthesis and Properties of Novel Non-planar Extended Quinonoid Molecules Having o-Quinonoid Structure
| Project/Area Number |
16550036
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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 | Osaka University |
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Principal Investigator |
KURATA Hiroyuki Osaka University, Graduate School of Science, Assistant Professor, 大学院・理学研究科, 助手 (40263199)
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| Project Period (FY) |
2004 – 2005
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| Keywords | quinone / non-planar / spiro-compound / photo-responce / Suzuki-Miyaura coupling / thiophene / redox behavior / diradical |
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| Research Abstract |
Our research results are summarized as follows.
1.Synthesis and properties of the extended pyracyloquinone derivative
The extended-quinone derivativeof cyclopenta[fg]acenaphthylene-1, 2-dione (pyracyloquinone) was first synthesized and characterized. The molecular structure determined by X-ray analysis and redox behavior reflect the antiaromatic characted of the pyracylene moiety.
2.Synthesis and properties of novel redox system having dithieno snnelsted bis(spirodienone) skeleton
In the course of the synthetic study on thioindigo-extended quinones, we prepared bis(benzo[b]thiophene)-annelated dispiro[5.4.5.0]hexadeca-1,4,7,9,12,15-hexaene-3,14-dione, a new skeleton molecule. This compound showed a ring-opening trasformation by two-electron reduction, and a photo-responsive property detected by ESR spectroscopy. Furthermore, a novel quaterquinone derivative based on dithieno-annelated dispiro[5.4.5.0]hexadeca-1,4,7,9,12,15-hexaene-3,14-dione was synthesized, which is a dark-green crystalline substance with metallic luster, shows a srtong absorption at 675nm. The temperature dependency of the redox process was elucidated by cyclic voltammetry.
3.Synthesis of dithieno annelated o-terphenoquinone derivatives
Novel o-terphenoquinone derivatives having benzo[2,1-b : 3,4-b']dithiophene and benzo[1,2-b : 4,3-b']dithiophene skeletons were synthesized from the correspondig bisphenols, prepared by McMurry coupling of the diketone derivatives. These quinones exist as the equiblibium mixture of the quinone-form and the diradical-form. Further oxidation of them afforded another speaces having deep-red and deep-blue color respectively. Detailed study of these compouds are in progress.
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Research Products
(2 results)
