2007 Fiscal Year Final Research Report Summary
Development on the preparation of largely lc-conjugated compounds with high purity
| Project/Area Number |
17350022
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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 |
Organic chemistry
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| Research Institution | Ehime University |
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Principal Investigator |
UNO Hidemitsu Ehime University, Integrated Center for Sciences, Professor (20168735)
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| Project Period (FY) |
2005 – 2007
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| Keywords | Percivclic reaction / Retro-Diels-Alder reaction / p-Expanded porphvrinoids / Pentacenes / FET devices / Porphyrin oligomers / Molecular recognition / X-ray crystallographicanalyses |
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| Research Abstract |
Highly p-conjugated compounds have attracted great attention as highly functional organic materials such as field-effect transistors and sensors. However, there are many cases that fundamental properties of these compounds such as electronic and optical properties are unknown due to the difficulty of their preparation. I planned to solve this problem by developing highly pure synthesis of these largely π-conjugated compounds based on the pericyclic cycloreversion reactions in the final synthetic stages.
First, I planned to prepare the soluble pentacene precursors bearing removable bridging parts at the 6,13-positions in pericyclic cycloreversion reactions initiated by heat or light, because pentacene derivatives were reported to show high electron mobility in FET devices. By using these precursors, I succeeded in pentacene FET device preparation by Tin-coating the precursors on substrates followed by the cycloreversion to pentacene derivatives.
Second, I explore the synthon of very unsta
… More
ble isoindoles, namely bicyclo[2.2.2]octadiene-fused pyrroles, which quantitatively gave the isoindole derivatives via the cycloreversion by heat. This synthon opened the synthetic utility of isoindoles, which could have not been applicable for synthetic purpose. Starting from these synthons, I succeeded in preparation of porphyrinoids with novel is-systems and π-system-fused porphyrin oligomers. In these multi-step cycloreversion reactions of the precursors, the intermediary molecular structures were very important and the pericyclic cycloreversion reactions occurred sequentially. The precursors were proved to have a large cavity between the porphyrin rings and show a good molecular recognition with the fairly rigid cavities. For an example, they can distinguish the molecular sizes of fullerenes such as C60 and C70.
I explored a new synthesis of 4,5,6,7-tetrafluoroisoindole which was one of the stable isoindoles bearing no substituent on the five-membered ring. I succeeded to rationalize the remarkable stability of 4,5,6,7-tetrafluoroisoindole by its X-ray crystallographic analysis and employ the compound for the synthesis of a variety of highly π-conjugated compounds. Less
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Research Products
(104 results)
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[Journal Article] The Application of MCD Spectroscopy and TD-DFT to Non-Planar Core Modified. Tetrabenzoporphyrins. Effect of Reduced Symmetry on Non-Planar Porphyrinoids
Author(s)
J. Mack, M. Bunya, Y. Shimizu, H. Uoyama, N. Komobuchi, T. Okujima, H. Uno, S. Ito, M. I, Stillman, K, Ono, N. Kobayashi
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Journal Title
Chem. Eur. J 14(in press)
Description
「研究成果報告書概要(欧文)」より
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[Presentation] ベンゾサフィリンの合成2005
Author(s)
川上 沙織、清水 祐介、宇野 英満、小野 昇
Organizer
第35回複素環化学討論会
Place of Presentation
吹田
Year and Date
2005-10-26
Description
「研究成果報告書概要(和文)」より
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