Chain‐Growth Polymerization of Aryl Grignards Initiated by a Stabilized NHC‐Pd Precatalyst
dc.contributor.author | Bryan, Zachary J. | en_US |
dc.contributor.author | Smith, Mitchell L. | en_US |
dc.contributor.author | McNeil, Anne J. | en_US |
dc.date.accessioned | 2012-07-12T17:23:13Z | |
dc.date.available | 2013-07-01T14:33:05Z | en_US |
dc.date.issued | 2012-05-14 | en_US |
dc.identifier.citation | Bryan, Zachary J.; Smith, Mitchell L.; McNeil, Anne J. (2012). "Chain‐Growth Polymerization of Aryl Grignards Initiated by a Stabilized NHC‐Pd Precatalyst." Macromolecular Rapid Communications 33(9): 842-847. <http://hdl.handle.net/2027.42/92031> | en_US |
dc.identifier.issn | 1022-1336 | en_US |
dc.identifier.issn | 1521-3927 | en_US |
dc.identifier.uri | https://hdl.handle.net/2027.42/92031 | |
dc.description.abstract | An N‐heterocyclic carbene‐ligated palladium catalyst was discovered to mediate living, chain‐growth polymerizations of both phenylene‐ and thiophene‐based monomers. Polymerization of a fluorene‐based monomer, on the other hand, did not proceed through a living, chain‐growth pathway. Excitingly, block copolymerizations of phenylene and thiophene proceeded via a chain‐growth pathway, regardless of the order of monomer addition. Although some chain termination was observed during these copolymerizations, this pathway could be minimized when the second monomer was added shortly after consumption of the first monomer. These results suggest that the catalyst resting‐state at the end of polymerization is unstable. As a result, modifications to the NHC‐scaffold or the 3‐chloropyridine ligand will be necessary to generate an improved catalyst. A Pd catalyst that can mediate a living, chain‐growth polymerization of π‐conjugated monomers is reported. Using (IPr)Pd(3‐chloropyridine)Cl 2 as a precatalyst, both homopolymers and block copolymers of phenylene‐ and thiophene‐based monomers were prepared. Although a living, chain‐growth mechanism is observed during polymerization, the catalyst resting state is somewhat unstable after the monomer is consumed. | en_US |
dc.publisher | WILEY‐VCH Verlag | en_US |
dc.subject.other | Palladium Catalysts | en_US |
dc.subject.other | Conjugated Polymers | en_US |
dc.subject.other | Chain‐Growth Polymerization | en_US |
dc.subject.other | Block Copolymers | en_US |
dc.title | Chain‐Growth Polymerization of Aryl Grignards Initiated by a Stabilized NHC‐Pd Precatalyst | en_US |
dc.type | Article | en_US |
dc.rights.robots | IndexNoFollow | en_US |
dc.subject.hlbsecondlevel | Materials Science and Engineering | en_US |
dc.subject.hlbsecondlevel | Biological Chemistry | en_US |
dc.subject.hlbsecondlevel | Chemical Engineering | en_US |
dc.subject.hlbsecondlevel | Chemistry | en_US |
dc.subject.hlbtoplevel | Health Sciences | en_US |
dc.subject.hlbtoplevel | Science | en_US |
dc.subject.hlbtoplevel | Engineering | en_US |
dc.description.peerreviewed | Peer Reviewed | en_US |
dc.contributor.affiliationum | Department of Chemistry and Macromolecular Science and Engineering Program, University of Michigan, 930 North University Avenue, Ann Arbor, MI 48109‐1055, USA | en_US |
dc.contributor.affiliationum | Department of Chemistry and Macromolecular Science and Engineering Program, University of Michigan, 930 North University Avenue, Ann Arbor, MI 48109‐1055, USA. | en_US |
dc.identifier.pmid | 22488735 | en_US |
dc.description.bitstreamurl | http://deepblue.lib.umich.edu/bitstream/2027.42/92031/1/marc_201200096_sm_suppl.pdf | |
dc.description.bitstreamurl | http://deepblue.lib.umich.edu/bitstream/2027.42/92031/2/842_ftp.pdf | |
dc.identifier.doi | 10.1002/marc.201200096 | en_US |
dc.identifier.source | Macromolecular Rapid Communications | en_US |
dc.identifier.citedreference | For recent reviews, see:a) C. Valente, S. Çalimsiz, K. H. Hoi, D. Mallik, M. Sayah, M. G. Organ, Angew. Chem. Int. Ed. 2012, 51, 2; b) M. G. Organ, G. A. Chass, D.‐C. Fang, A. C. Hopkinson, C. Valente, Synthesis 2008, 17, 2776. | en_US |
dc.identifier.citedreference | M. Verswyvel, P. Verstappen, L. De Cremer, T. Verbiest, G. Koeckelberghs, J. Polym. Sci., Part A: Polym. Chem. 2011, 49, 5339. | en_US |
dc.identifier.citedreference | V. Senkovskyy, R. Tkachov, H. Komber, M. Sommer, M. Heuken, B. Voit, W. T. S. Huck, V. Kataev, A. Petr, A. Kiriy, J. Am. Chem. Soc. 2011, 133, 19966. | en_US |
dc.identifier.citedreference | a) C. J. O'Brien, E. A. B. Kantchev, C. Valente, N. Hadei, G. A. Chass, A. Lough, A. C. Hopkinson, M. G. Organ, Chem. Eur. J. 2006, 12, 4743; b) M. G. Organ, S. Avola, I. Dubovyk, N. Hadei, E. A. B. Kantchev, C. J. O'Brien, C. Valente, Chem. Eur. J. 2006, 12, 4749; c) M. G. Organ, M. Abdel‐Hadi, S. Avola, N. Hadei, J. Nasielski, C. J. O'Brien, C. Valente, Chem. Eur. J. 2007, 13, 150. | en_US |
dc.identifier.citedreference | I. Larrosa, C. Somoza, A. Banquy, S. M. Goldup, Org. Lett. 2011, 13, 146. | en_US |
dc.identifier.citedreference | a) M.‐T. Chen, D. A. Vicic, M. L. Turner, O. Navarro, Organometallics 2011, 30, 5052; b) See also, ref. 23. | en_US |
dc.identifier.citedreference | A. H. Roy, J. F. Hartwig, J. Am. Chem. Soc. 2003, 125, 13944; See also: A. H. Roy, J. F. Hartwig, Organometallics 2004, 23, 1533. | en_US |
dc.identifier.citedreference | a) S. Wu, L. Bu, L. Huang, X. Yu, Y. Han, Y. Geng, F. Wang, Polymer 2009, 50, 6245; b) R. Miyakoshi, A. Yokoyama, T. Yokozawa, Chem. Lett. 2008, 37, 1022; c) A. Yokoyama, A. Kato, R. Miyakoshi, T. Yokozawa, Macromolecules 2008, 41, 7271; e) See also, ref 3f. | en_US |
dc.identifier.citedreference | M. C. Stefan, A. E. Javier, I. Osaka, R. D. McCullough, Macromolecules 2009, 42, 30. | en_US |
dc.identifier.citedreference | Note that the radical‐based mechanisms have been proposed when iPrI is generated in situ. For reference, see:a) M. Kienle, P. Knochel, Org. Lett. 2010, 12, 2702; b) G. Manolikakes, P. Knochel, Angew. Chem. Int. Ed. 2009, 48, 205. | en_US |
dc.identifier.citedreference | For example, see ref. 1b. | en_US |
dc.identifier.citedreference | a) J.‐P. Lamps, J.‐M. Catala, Macromolecules. 2011, 44, 7962; b) See also, ref 21a. | en_US |
dc.identifier.citedreference | Excess iPrMgCl (or tBuMgCl) can be detrimental. For example, see: R. H. Lohwasser, M. Thelakkat, Macromolecules 2011, 44, 3388. | en_US |
dc.identifier.citedreference | a) L. Shi, Y. Chu, P. Knochel, H. Mayr, Org. Lett. 2009, 11, 3502; b) L. Shi, Y. Chu, P. Knochel, H. Mayr, J. Org. Chem. 2009, 74, 2760. | en_US |
dc.identifier.citedreference | J. Nasielski, N. Hadei, G. Achonduh, E. A. B. Kantchev, C. J. O'Brien, A. Lough, M. G. Organ, Chem. Eur. J. 2010, 16, 10844. | en_US |
dc.identifier.citedreference | a) E. L. Lanni, A. J. McNeil, Macromolecules. 2010, 43, 8039; b) E. L. Lanni, A. J. McNeil, J. Am. Chem. Soc. 2009, 131, 16573; c) See also, ref. 8. | en_US |
dc.identifier.citedreference | a) R. Tkachov, V. Senkovskyy, H. Komber, A. Kiriy, Macromolecules. 2011, 44, 2006; b) R. Tkachov, V. Senkovskyy, H. Komber, J.‐U. Sommer, A. Kiriy, J. Am. Chem. Soc. 2010, 132, 7803; c) T. Beryozkina, V. Senkovskyy, E. Kaul, A. Kiriy, Macromolecules 2008, 41, 7817; d) R. Miyakoshi, A. Yokoyama, T. Yokozawa, J. Am. Chem. Soc. 2005, 127, 17542; e) M. C. Iovu, E. E. Sheina, R. R. Gil, R. D. McCullough, Macromolecules 2005, 38, 8649. | en_US |
dc.identifier.citedreference | Unusually selective difunctionalizations have previously been observed with other Pd catalysts. Similar mechanisms have been proposed. For examples, see:a) S. K. Weber, F. Galbrecht, U. Scherf, Org. Lett.. 2006, 8, 4039; b) D. J. Sinclair, M. S. Sherburn, J. Org. Chem. 2005, 70, 3730; c) C.‐G. Dong, Q.‐S. Hu, J. Am. Chem. Soc. 2005, 127, 10006. | en_US |
dc.identifier.citedreference | a) E. E. Sheina, J. Liu, M. C. Iovu, D. W. Laird, R. D. McCullough, Macromolecules 2004, 37, 3526; b) A. Yokoyama, R. Miyakoshi, T. Yokozawa, Macromolecules 2004, 37, 1169; c) R. Miyakoshi, A. Yokoyama, T. Yokozawa, Macromol. Rapid Commun. 2004, 25, 1663. | en_US |
dc.identifier.citedreference | For recent reviews, see:a) A. Kiriy, V. Senkovskyy, M. Sommer, Macromol. Rapid Commun. 2011, 32, 1503; b) K. Okamoto, C. K. Luscombe, Polym. Chem. 2011, 2, 2424. | en_US |
dc.identifier.citedreference | For recent examples of block copolymers prepared via this method, see:a) M. Verswyvel, F. Monnaie, G. Koeckelberghs, Macromolecules 2011, 44, 9489; b) J. Kim, A. Siva, I. Y. Song, T. Park, Polymer. 2011, 52, 3704; c) T. Higashihara, K. Ohshimizu, Y. Ryo, T. Sakurai, A. Takahashi, S. Nojima, M. Ree, M. Ueda, Polymer 2011, 52, 3687; d) K. Ohshimizu, A. Takahashi, T. Higashihara, M. Ueda, J. Polym. Sci., Part A: Polym. Chem. 2011, 49, 2709; e) J. Hollinger, A. A. Jahnke, N. Coombs, D. S. Seferos, J. Am. Chem. Soc. 2010, 132, 8546; f) K. Van den Bergh, I. Cosemans, T. Verbiest, G. Koeckelberghs, Macromolecules 2010, 43, 3794; g) A. E. Javier, S. R. Varshney, R. D. McCullough, Macromolecules 2010, 43, 3233; h) S. Miyanishi, Y. Zhang, K. Tajima, K. Hashimoto, Chem. Commun. 2010, 46, 6723. | en_US |
dc.identifier.citedreference | J. R. Locke, A. J. McNeil, Macromolecules 2010, 43, 8709. | en_US |
dc.identifier.citedreference | For a recent review, see: N. Marshall, S. K. Sontag, J. Locklin, Chem. Commun. 2011, 47, 5681. | en_US |
dc.identifier.citedreference | For recent examples, see:a) N. Doubina, S. A. Paniagua, A. V. Soldatova, A. K. Y. Jen, S. R. Marder, C. K. Luscombe, Macromolecules 2011, 44, 512; b) A. Smeets, P. Willot, J. De Winter, P. Gerbaux, T. Verbiest, G. Koeckelberghs, Macromolecules 2011, 44, 6017. | en_US |
dc.identifier.citedreference | For a recent example of an non‐phosphine based Ni‐catalyst, see: H. D. Magurudeniya, P. Sista, J. K. Westbrook, T. E. Ourso, K. Nguyen, M. C. Maher, M. G. Alemseghed, M. C. Biewer, M. C. Stefan, Macromol. Rapid Commun. 2011, 32, 1748. | en_US |
dc.identifier.citedreference | E. L. Lanni, J. R. Locke, C. M. Gleave, A. J. McNeil, Macromolecules 2011, 44, 5136. | en_US |
dc.identifier.citedreference | S. R. Lee, Z. J. Bryan, A. M. Wagner, A. J. McNeil, Chem. Sci. 2012, DOI: 10.1039/C2SC00005A. | en_US |
dc.identifier.citedreference | a) A. R. Chianese, X. Li, M. C. Janzen, J. W. Faller, R. H. Crabtree, Organometallics 2003, 22, 1663; b) W. A. Herrmann, J. Schütz, G. D. Frey, E. Herdtweck, Organometallics 2006, 25, 2437. | en_US |
dc.identifier.citedreference | For recent reviews, see:a) G. C. Fortman, S. P. Nolan, Chem. Soc. Rev. 2011, 40, 5151; b) S. Díez‐González, N. Marion, S. P. Nolan, Chem. Rev. 2009, 109, 3612; c) E. A. B. Kantchev, C. J. O'Brien, M. G. Organ, Angew. Chem. Int. Ed. 2007, 46, 2768. | en_US |
dc.identifier.citedreference | S. Tamba, K. Shono, A. Sugie, A. Mori, J. Am. Chem. Soc. 2011, 133, 9700. | en_US |
dc.identifier.citedreference | a) T. Yokozawa, R. Suzuki, M. Nojima, Y. Ohta, A. Yokoyama, Macromol. Rapid Commun. 2011, 32, 801; b) E. Elmalem, A. Kiriy, W. T. S. Huck, Macromolecules 2011, 44, 9057; c) T. Yokozawa, H. Kohno, Y. Ohta, A. Yokoyama, Macromolecules 2010, 43, 7095; d) W. Huang, L. Su, Z. Bo, J. Am. Chem. Soc. 2009, 131, 10348; e) T. Beryozkina, K. Boyko, N. Khanduyeva, V. Senkovskyy, M. Horecha, U. Oertel, F. Simon, M. Stamm, A. Kiriy, Angew. Chem. Int. Ed. 2009, 48, 2695; f) A. Yokoyama, H. Suzuki, Y. Kubota, K. Ohuchi, H. Higashimura, T. Yokozawa, J. Am. Chem. Soc. 2007, 129, 7236. | en_US |
dc.identifier.citedreference | R. Grisorio, G. P. Suranna, P. Mastrorilli, Chem. Eur. J. 2010, 16, 8054. | en_US |
dc.owningcollname | Interdisciplinary and Peer-Reviewed |
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