2005 Fiscal Year Final Research Report Summary
Polynaphthylene : Development and Function of Precisely Nano-Structure Controlled Polymer
| Project/Area Number |
15350066
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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 |
Polymer chemistry
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| Research Institution | Yamagata University |
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Principal Investigator |
HABAUE Shigeki Yamagata University, Faculty of Engineering, Associate Professor, 工学部, 助教授 (30252266)
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| Project Period (FY) |
2003 – 2005
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| Keywords | binaphthol / polynaphthylene / polyaromatics / oxidative coupling / cross-coupling / optically active polymer / alternating coplymerization / asymmetric catalyat |
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| Research Abstract |
The asymmetric oxidative coupling polymerization (AOCP) leading to polybinaphthols in a highly cross-coupling selective or stereocontrolled manner was attained. The reaction of 2-naphthol and 3-hydroxy-2-naphthoate derivatives with the CuCl-(S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline) [(S)Phbox] catalyst proceeded in a highly cross-coupling selective manner with a moderate enantioselectivity. The AOCP of methyl 6,6'-dihydroxy-2,2'-binaphthalene-7-carboxylate with the CuCl-(S)Phbox catalyst gave a polymer with a high cross-coupling selectivity (head-to-tail regioselectivity). The copolymerization of 6,6'-dihydroxy-2,2'-binaphthalene and dihexyl 6,6'-dihydroxy-2,2'-binaphthalene-7,7'-dicarboxylate also afforded a polymer with the high cross-coupling selectivity, that is, a copolymer with a mainly alternating structure. Novel catalyst system, VOSO_4-(R)Phbox, for the AOCP of 2,3-dihydroxy-naphthalene (DHN) was developed. The enantioselectivity during the polymerization was evaluated to be 80% ee (S), a value much higher than that observed for the polymerizations with the copper(I)-based catalyst systems and the typical oxovanadium(IV) catalysts reported for the asymmetric oxidative homo-coupling producing the 1,1'-bi-2-naphthol derivatives. The OCP of DHN was also accomplished by the novel designed catalyst system, dinuclear copper(II) complexes. The polymerization proceeded under mild conditions to produce a polymer in a good yield.
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Research Products
(25 results)
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[Journal Article] Stereoselective Synthesis of (R,R)-, (S,S)-, and (R,S)-Poly(2,3-dihydroxy-1,4-naphthylene) Derivatives by Asymmetric Oxidative Coupling Polymerization2003
Author(s)
S.Habaue, T.Seko, M.Isonaga, H.Ajiro, Y.Okamoto
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Journal Title
Polym. J. 35(7)
Pages: 592-597
Description
「研究成果報告書概要(和文)」より
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[Journal Article] Stereoselective Synthesis of (R,R)-, (S,S)-, and (R,S)-Poly(2,3-dihydroxy-1,4-naphthylene) Derivatives by Asymmetric Oxidative Coupling Polymerization2003
Author(s)
S.Habaue, T.Seko, M.Isonaga, H.Ajiro, Y.Okamoto
-
Journal Title
Polym.J. 35(7)
Pages: 592-597
Description
「研究成果報告書概要(欧文)」より
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