Synthesis of novel substituted poly(arylene-vinylene)s by the palladium-catalyzed three-component coupling polymerization

Macromolecules

Volumn 30, Issue 15, 1997, Pages 4504-4506

  Miyaki, Nobuyuki ^a   Tomita, Ikuyoshi ^a   Kido, Junji ^a,b   Endo, Takeshi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b YAMAGATA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC POLYMERS; CHEMICAL ANALYSIS; ELECTRON TRANSPORT PROPERTIES; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PALLADIUM; POLYMERIZATION; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

HECK REACTION; POLYARYLENE VINYLENE; STILLE COUPLING; SUZUKI COUPLING; THREE COMPONENT COUPLING POLYMERIZATION;

VINYL RESINS;

EID: 0031186402     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma9702410     Document Type: Article

References (22)

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11. For instance, polymers containing internal double bonds can be obtained from appropriate nucleophiles. See: Miyaki, N.; Tomita, I.; Endo, T. J. Polym. Sci.: Part A: Polym. Chem. 1997, 35, 1211.
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13. The palladium-catalyzed three-component coupling reaction has been reported. See: (a) Shimizu, I.; Tsuji, J. Chem. Lett. 1984, 233. (b) Ahmar, M.; Cazes, B.; Gore, J. Tetrahedron Lett. 1984, 29, 4089. (c) Chaptal, N.; Colovray-Gotteland, V.; Grandjean, C.; Case, B.; Gore, J. Tetrahedron Lett. 1991, 32, 1795.
14. The palladium-catalyzed three-component coupling reaction has been reported. See: (a) Shimizu, I.; Tsuji, J. Chem. Lett. 1984, 233. (b) Ahmar, M.; Cazes, B.; Gore, J. Tetrahedron Lett. 1984, 29, 4089. (c) Chaptal, N.; Colovray-Gotteland, V.; Grandjean, C.; Case, B.; Gore, J. Tetrahedron Lett. 1991, 32, 1795.
15. 2 (0.0034 g, 0.015 mmol), 2a (0.203 g 0.5 mmol), 3 (0.392 g, 2.00 mmol), and 1,4-dioxane (1.1 mL), and the mixture was kept stirring at ambient temperature for 15 min under nitrogen. To the resulting solution, 1 (0.073 g, 0.50 mmol) in 1,4-dioxane (0.9 mL) was added and the tube was sealed under reduced pressure. After the reaction at 80 °C for 3 h, the reaction mixture was precipitated with methanol and then with n-hexane. The precipitate was freeze-dried from benzene. 4a: yield 92% (0.300 g, 0.460 mmol).
16. 8: C, 73.53; H, 6.74. Found: C, 73.26; H, 6.89. The obtained polymer (4a) contained three isomeric units (i.e., E-E, Z-Z, and E-Z) and the isomeric ratio of 4a was estimated as ca. 42:46:11.
17. max in shorter wavelength, probably due to the steric restriction caused by the side chain and the contamination of the Z-unit.
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21. -1.
22. -1.