A General Approach to Sequence-Controlled Polymers Using Macrocyclic Ring Opening Metathesis Polymerization

Journal of the American Chemical Society

Volumn 137, Issue 25, 2015, Pages 8038-8041

  Gutekunst, Will R ^a   Hawker, Craig J ^a,b  

^a University of California   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANIC POLYMERS; POLYMERS; SYNTHESIS (CHEMICAL);

DIVERSE RANGE; MACROCYCLIC RINGS; MACROCYCLIC STRUCTURE; SMALL MOLECULES;

RING OPENING POLYMERIZATION;

MACROCYCLIC COMPOUND; POLYMER; SACCHARIN; SWEETENING AGENT;

ARTICLE; CHEMICAL STRUCTURE; POLYMERIZATION; RING OPENING METATHESIS POLYMERIZATION; SEQUENCE ANALYSIS; SYNTHESIS; ALKYLATION; CATALYSIS; CHEMISTRY;

ALKYLATION; CATALYSIS; MACROCYCLIC COMPOUNDS; POLYMERIZATION; POLYMERS; SACCHARIN; SWEETENING AGENTS;

EID: 84934760274     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b04940     Document Type: Article

References (32)

1. Lutz, J.-F. Polym. Chem. 2010, 1, 55-62
2. Badi, N.; Lutz, J.-F. Chem. Soc. Rev. 2009, 38, 3383
3. Lutz, J.-F.; Ouchi, M.; Liu, D. R.; Sawamoto, M. Science 2013, 341, 1238149
4. Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149
5. Espeel, P.; Carrette, L. L. G.; Bury, K.; Capenberghs, S.; Martins, J. C.; Du Prez, F. E.; Madder, A. Angew. Chem., Int. Ed. 2013, 52, 13261
6. Pfeifer, S.; Zarafshani, Z.; Badi, N.; Lutz, J.-F. J. Am. Chem. Soc. 2009, 131, 9195
7. Rosales, A. M.; Segalman, R. A.; Zuckermann, R. N. Soft Matter 2013, 9, 8400
8. Chen, Y.; Guan, Z. J. Am. Chem. Soc. 2010, 132, 4577
9. Atallah, P.; Wagener, K. B.; Schulz, M. D. Macromolecules 2013, 46, 4735
10. Li, Z.-L.; Lv, A.; Du, F.-S.; Li, Z.-C. Macromolecules 2014, 47, 5942
11. Pfeifer, S.; Lutz, J.-F. J. Am. Chem. Soc. 2007, 129, 9542
12. Schmidt, B. V. K. J.; Fechler, N.; Falkenhagen, J.; Lutz, J.-F. Nat. Chem. 2011, 3, 234
13. Zamfir, M.; Lutz, J.-F. Nat. Commun. 2012, 3, 1138
14. Moatsou, D.; Hansell, C. F.; O'Reilly, R. K. Chem. Sci. 2014, 5, 2246
15. Hibi, Y.; Ouchi, M.; Sawamoto, M. Angew. Chem. 2011, 123, 7572
16. Niu, J.; Hili, R.; Liu, D. R. Nat. Chem. 2013, 5, 282
17. Zhang, J.; Matta, M. E.; Hillmyer, M. A. ACS Macro Lett. 2012, 1, 1383
18. Kobayashi, S.; Pitet, L. M.; Hillmyer, M. A. J. Am. Chem. Soc. 2011, 133, 5794
19. Gody, G.; Maschmeyer, T.; Zetterlund, P. B.; Perrier, S. Macromolecules 2014, 47, 3451
20. Anastasaki, A.; Nikolaou, V.; Pappas, G. S.; Zhang, Q.; Wan, C.; Wilson, P.; Davis, T. P.; Whittaker, M. R.; Haddleton, D. M. Chem. Sci. 2014, 5, 3536
21. Hoye, T. R.; Jeffrey, C. S.; Tennakoon, M. A.; Wang, J.; Zhao, H. J. Am. Chem. Soc. 2004, 126, 10210
22. Park, H.; Choi, T.-L. J. Am. Chem. Soc. 2012, 134, 7270
23. Park, H.; Lee, H.-K.; Choi, T.-L. J. Am. Chem. Soc. 2013, 135, 10769
24. Lee, O. S.; Kim, K. H.; Kim, J.; Kwon, K.; Ok, T.; Ihee, H.; Lee, H.-Y.; Sohn, J.-H. J. Org. Chem. 2013, 78, 8242
25. Kang, E.-H.; Yu, S. Y.; Lee, I. S.; Park, S. E.; Choi, T.-L. J. Am. Chem. Soc. 2014, 136, 10508
26. During polymerization a monomer isomerization process is observed (15-20%); see SI for discussion.
27. Li, J.; Rothstein, S. N.; Little, S. R.; Edenborn, H. M.; Meyer, T. Y. J. Am. Chem. Soc. 2012, 134, 16352
28. Li, J.; Stayshich, R. M.; Meyer, T. Y. J. Am. Chem. Soc. 2011, 133, 6910
29. Takizawa, K.; Nulwala, H.; Hu, J.; Yoshinaga, K.; Hawker, C. J. J. Poly. Sci., Part A: Polym. Chem. 2008, 46, 5977
30. Takizawa, K.; Tang, C.; Hawker, C. J. J. Am. Chem. Soc. 2008, 130, 1718
31. Fishman, J. M.; Kiessling, L. L. Angew. Chem., Int. Ed. 2013, 52, 5061
32. Leibfarth, F. A.; Moreno, N.; Hawker, A. P.; Shand, J. D. J. Poly. Sci., Part A: Polym. Chem. 2012, 50, 4814