Living polymerization of phenylacetylenes catalyzed by cationic rhodium complexes bearing tetrafluorobenzobarrelene

Polymer Journal

Volumn 43, Issue 1, 2011, Pages 51-57

  Shiotsuki, Masashi ^a   Onishi, Naoya ^a   Sanda, Fumio ^a   Masuda, Toshio ^b  

^a KYOTO UNIVERSITY   (Japan)

^b FUKUI UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

acidic diene ligand; living polymerization; substituted polyacetylene; transition metal catalyst

Indexed keywords

BINARY CATALYSTS; COUNTER ANIONS; DIENE LIGANDS; KINETIC PLOTS; NARROW MOLECULAR WEIGHT DISTRIBUTIONS; NUCLEAR MAGNETIC RESONANCE STUDIES; PHENYLACETYLENES; PHOSPHINE LIGANDS; POLY(PHENYLACETYLENE); RHODIUM COMPLEXES; SEQUENTIAL POLYMERIZATION; SUBSTITUTED POLYACETYLENES; TRANSITION METAL CATALYST;

ACETYLENE; AROMATIC HYDROCARBONS; BLOCK COPOLYMERS; CATALYSTS; CATIONIC POLYMERIZATION; LIGANDS; MAGNETIC RESONANCE; MOLECULAR WEIGHT DISTRIBUTION; OLEFINS; ORGANIC POLYMERS; PHOSPHORUS COMPOUNDS; POLYMERS; RHODIUM; RHODIUM COMPOUNDS; TRANSITION METALS;

LIVING POLYMERIZATION;

EID: 78651095281     PISSN: 00323896     EISSN: 13490540     Source Type: Journal    
DOI: 10.1038/pj.2010.98     Document Type: Article

References (24)

1. Liu, J., Lam, J. W. Y. & Tang, B. Z. Acetylenic polymers: syntheses, structures, and functions. Chem. Rev. 109, 5799-5867 (2009).
2. Masuda, T., Sanda, F. & Shiotsuki, M. Polymerization of acetylenes. in Comprehensive Organometallic Chemistry III (eds Michael, D., Mingos, P., & Crabtree, R. H.) 1st edn., Vol. 11, 557-593 (Elsevier, Oxford, 2007).
3. Tang, B. Z. & Lam, J. W. Y. Functional polyacetylenes. Acc. Chem. Res. 38, 745-754 (2005).
4. Masuda, T. & Sanda, F. in Handbook of Metathesis (ed. Grubbs, R. H.) Vol. 3, 375-406 (Wiley-VCH, Weinheim, 2003).
5. Sedlacek, J. & Vohlidal, J. Controlled and living polymerizations induced with rhodium catalysts. A review. Collect. Czech. Chem. Commun. 68, 1745-1790 (2003).
6. I complexes in reactions with phenylacetylene: synthesis of stereoregular poly(phenyl acetylene). J. Polym. Sci. Part A: Polym. Chem. 27, 75-86 (1989).
7. Furlani, A., Napoletano, C, Russo, M. V. & Feast, W. J. Stereoregular polyphenylace-tylene. Polym. Bull. 16, 311-317 (1986).
8. Tabata, M., Inaba, Y, Yokota, K. & Nozaki, Y Stereoregular polymerization of alkyl propiolate catalyzed by Rh complex. J. Macromol. Sci. PureAppl. Chem. 31, 465-475 (1994).
9. Nomura, R., Tabei, J. & Masuda, T. Biomimetic stabilization of helical structure in a synthetic polymer by means of intramolecular hydrogen bonds. J. Am. Chem. Soc. 123, 8430-8431 (2001).
10. Kishimoto, Y, Eckerle, P., Miyatake, T., Ikariya, T. & Noyori, R. Living polymerization of phenylacetylenes initiated by Rh(C=CC6H5)(2,5- norbornadiene)[P(C6H5)3]2. J. Am. Chem. Soc. 116, 12131-12132 (1994).
11. Kishimoto, Y, Eckerle, P., Miyatake, T., Kainosho, M., Ono, A., Ikariya, T. & Noyori, R. Well-controlled polymerization of phenylacetylenes with organorhodium(I) complexes: mechanism and structure of the polyenes. J. Am. Chem. Soc. 121, 12035-12044 (1999).
12. Kishimoto, Y, Itou, M., Miyatake, T., Ikariya, T. & Noyori, R. An efficient Rhodium(I) initiator for stereospecific living polymerization of phenylacetylenes. Macromolecules 29, 5054-5055 (1996).
13. Falcon, M., Farnetti, E. & Marsich, N. Stereoselective living polymerization of pheny-lacetylene promoted by rhodium catalysts with bidentate phosphines. J. Organomet. Chem. 629, 187-193 (2001).
14. Misumi, Y & Masuda, T. Living polymerization of phenylacetylene by novel rhodium catalysts. Quantitative initiation and introduction of functional groups at the initiating chain end. Macromolecules 31, 7572-7573 (1998).
15. Miyake, M., Misumi, Y & Masuda, T. Living polymerization of phenylacetylene by isolated rhodium complexes, Rh[C(C6H5)=C(C6H5)2](nbd)(4- XC6H4)3P (X=F, Cl). Macromolecules 33, 6636-6639 (2000).
16. Nakazato, A., Saeed, I., Shiotsuki, M., Sanda, F. & Masuda, T. Polymerization of N-propargylamides with a Rh-Vinyl complex: confirmation of the presence of long-lived active species. Macromolecules 37, 4044-4047 (2004).
17. Saeed, I., Shiotsuki, M. & Masuda, T. Effect of diene ligands in the rhodium-catalyzed polymerization of phenylacetylene. Macromolecules 39, 8977-8981 (2006).
18. Saeed, I., Shiotsuki, M. & Masuda, T. Living polymerization of phenylacetylene with tetrafluorobenzobarrelene ligand-containing rhodium catalyst systems featuring the synthesis of high molecular weight polymer. Macromolecules 39, 8567-8573 (2006).
19. Onishi, N., Shiotsuki, M., Sanda, F. & Masuda, T. Polymerization of phenylacetylenes with rhodium zwitterionic complexes: enhanced catalytic activity by p-acidic diene ligands. Macromolecules 42, 4071-4076 (2009).
20. 2-symmetric tetrafluorobenzobarrelene ligand. Organometallics 28, 4890-4893 (2009).
21. Shiotsuki, M., Onishi, N., Sanda, F & Masuda, T. Living polymerization of phenylacetylene catalyzed by a cationic Rh complex bearing tetrafluorobenzobarrelene. Chem. Lett. 39, 244-245 (2010).
22. Uson, R., Oro, L. A., Valderrama, M. & Rebullida, C. Preparation and catalytic activity of cationic rhodium tetrafluorobenzobarrelene complexes with nitrogen and phosphorus donor ligands. J. Organomet. Chem. 197, 87-93 (1980).
23. Schrock, R. R. & Osborn, J. A. Preparation and properties of some cationic complexes of Rhodium(I) and Rhodium(III). J. Am. Chem. Soc. 93, 2397-2407 (1971).
24. Jimenez, M. V, Perez-Torrente, J. J., Bartolome, M. I., Vispe, E., Laboz, F J. & Oro, L. A. Cationic rhodium complexes with hemilabile phosphine ligands as polymerization catalyst for high molecular weight stereoregular Poly(phenylacetylene). Macromolecules 42, 8146-8156 (2009).