Functional syndiotactic poly(ß-hydroxyalkanoate)s via stereoselective ring-opening copolymerization of rao-ß-butyrolactone and rac-allyl-ß-butyrolactone

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 47, Issue 12, 2009, Pages 3177-3189

  Ajellal, Noureddine ^a   Thomas, Christophe M ^a,b   Carpentier, Jean François ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

^b PSL RESEARCH UNIVERSITY   (France)

Author keywords

Catalysis; Copolymers; Functionalization; Functionalization of polymers; Metal organic catalysts organometallic catalysts; Poly(hydroxyalkanoate)s; Polyesters; Ring opening polymerization; Tacticity; Yttrium

Indexed keywords

FUNCTIONALIZATION; FUNCTIONALIZATION OF POLYMERS; METAL-ORGANIC CATALYSTS/ORGANOMETALLIC CATALYSTS; POLY(HYDROXYALKANOATE)S; TACTICITY;

CATALYSIS; CATALYSTS; COPOLYMERIZATION; COPOLYMERS; EPOXIDATION; ESTERS; MACROMOLECULES; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC POLYMERS; PHOTORESISTS; POLYDISPERSITY; POLYESTERS; POLYMERS; RING OPENING POLYMERIZATION; THERMODYNAMIC PROPERTIES; TOLUENE; YTTRIUM; YTTRIUM ALLOYS;

FUNCTIONAL POLYMERS;

EID: 67549124833     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.23418     Document Type: Article

References (41)

1. (a) Müller, H.-M.; Seebach, D. Angew Chem Int Ed Engl 1993, 32, 477-502;
2. (b) Lenz, R. W.; Marchessault, R. H. Biomacromolecules 2005, 6, 1-8.
3. Rieth, L. R.; Moore, D. R.; Lobkovsky, E. B.; Coates, G. W. J Am Chem Soc 2002, 124, 1523915248.
4. Highly isotactic PHB can be obtained when optically pure (R)- or (S)-BBL is involved; see:
5. (a) Yori, Y.; Suzuki, M.; Yamaguchi, A.; Nishishita, T. Macromolecules 1993, 26, 5533-5534.
6. For the synthesis of PHB enriched in isotactic diads from roc-BBL, see: (b) Zintl, M.; Moinar, F.; Urban, T.; Bernhart, V.; Preishuber-Pflügl, R; Rieger, B. Angew Chem Int Ed 2008, 47, 3458-3460;
7. (c) Le Borgne, A.; Spassky, N. Polymer 1989, 30, 2312-2319;
8. (d) Wu, B.; Lenz, R. W Macromolecules 1998, 31, 3473-3477;
9. (e) Bloembergen, S.; Holden, D. A.; Bluhm, T. L.; Hamer, G. K; Marchessault, R. H. Macromolecules 1989, 22, 1656-1663.
10. For the synthesis of PHB enriched in syndiotactic diads from roc-BBL, see: (f) Hori, Y.; Hagiwara, T Int J Biol Macromol 1999, 25, 237-245;
11. (g) Kricheldorf, H. R.; Eggerstedt, S. Macromolecules 1997, 30, 5693-5697;
12. (h) Arcana, M.; Giani Beaune, O.; Schue, F.; Amass, W.; Amass, A. Polymer Int 2000, 49, 1348-1355.
13. Kemnitzer, J. E.; McCarthy, S. R.; Gross, R. A. Macromolecules 1993, 26, 1221-1229.
14. (a) Cai, C-X.; Toupet, L.; Carpentier, J.-F. J Organomet Chem 2003, 683, 131-136;
15. (b) Cai, C.-X.; Amgoune, A.; Lehmann, C. W.; Carpentier, J.-F. Chem Commun 2004, 330-331;
16. (c) Amgoune, A.; Thomas, C. M.; Roisnel, T.; Carpentier, J.-F. Chem Eur J 2006, 12, 169-179;
17. (d) Amgoune, A.; Thomas, C. M.; Carpentier, J.-F. Pure Appl Chem 2007, 79, 2013-2030;
18. (e) Amgoune, A.; Thomas, C. M.; Carpentier, J.-F. Macromol Rap Commun 2007, 28, 693-697.
19. (a) Amgoune, A.; Thomas, C M.; Hinca, S.; Roisnel, T.; Carpentier, J.-F. Angew Chem Int Ed 2006, 45, 2782-2784;
20. (b) Ajellal, N.; Bouyahyi, M.; Amgoune, A.; Thomas, C. M.; Bondon, A.; Pillin, I.; Grohens, Y.; Carpentier, J.-F. Macromolecules 2009, 42, 987-993.
21. r up to 0.84) via a chain-end control mechanism, while they are surprisingly nonstereoselective for the ROP of roc-LA under strictly similar conditions; see: Ajellal, N.; Lyubov, D. M.; Sinenkov, M. A.; Fukin, G. K.; Cherkasov, A. V.; Thomas, C. M.; Carpentier, J.-F.; Trifonov, A. A. Chem Eur J 2008, 14, 5440-5448.
22. (a) Kim, O.; Gross, R. A.; Hammar, W. J.; Newmark, R. A. Macromolecules 1996, 29, 4572-4581;
23. (b) Mesiano, A. J.; Beckman, E. J.; Russell, A. J Biotechnol Prog 2000, 16, 64-68;
24. (c) Takagi, Y.; Yasuda, R.; Maehara, A.; Yamane, T. Eur Polym J 2004, 40, 1551-1557.
25. (a) Williams, S. F.; Martin, D. R In Biopolymers, Steinbuchel, A., Ed.; Wiley VCH, 2004; Vol. 4, pp 91-120;
26. (b) Kunioka, M.; Tamaki, A.; Doi, Y Macromolecules 1989, 22, 694-697;
27. (c) Noda, I.; Green, P. R.; Satkowski, M. M.; Schectman, L. A. Biomacromolecules 2005, 6, 580-586;
28. (d) Doi, Y.; Kanesawa, Y.; Kunioka, M.; Saito, T. Macromolecules 1990, 23, 26-31.
29. Kramer, J. W; Coates, G. W. Tetrahedron 2008, 64, 6973-6978.
30. Lee, J. T.; Thomas, P. J.; Alper, H. J Org Chem 2001, 66, 5424-5426.
31. 13C NMR spectroscopy from a random copolymer (see the Supporting Information).
32. allyl) copolymers were analyzed by GPC coupled with online two-angle laser light scattering (LS) and refractive index (RI) detectors, the light scattering at 45° (LS 45) and 90° (LS 90) traces revealed two additional signals corresponding to high molecular weight fragments (see the Supporting Information). Such high molecular weight fragments presumably arise from aggregation of macromolecules; see: Wang, X.; Xie, X.; Cai, C.; Rytting, E.; Steele, T.; Kissel T. Macromolecules 2008, 41, 2791-2799.
33. (a) Bloembergen, S.; Holden, D. A.; Bluhm, T. L.; Hamer, G. K.; Marchessault, R. H. Macromolecules 1987, 20, 3086-3089;
34. (b) lida, M.; Hayase, S.; Araki, T. Macromolecules 1978, 11, 490-493.
35. (a) Burgess, K.; Ohlmeyer, M. J. Chem Rev 1991, 91, 1179-1191;
36. (b) Westcott, S. A.; Blom, H. P.; Marder, T. B.; Baker, R. T. J Am Chem Soc 1992, 114, 8863-8869.
37. Bae, C.; Hartwig, J. F.; Harris, K. B. N.; Long, R. O.; Anderson, K. S.; Hillmyer, M. A. J Am Chem Soc 2005, 127, 767-776.
38. (a) Kolb, H. C.; Vannieuwenhuize, M. S.; Sharpless, K. B. Chem Rev 1994, 94, 2483-2547;
39. (b) Bolm, C.; Hildebrand, J. P.; Muniz, K. Recent Advances in Asymmetric Dihydroxylation and Aminohydroxylation in Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: Weinheim, 2000; pp 399-428;
40. (c) Sundermeier, U.; Döbler, C.; Beller, M. Modem Oxidation Methods; Bäckvall, J.-E., Ed.; Wiley-VCH: Weinheim, 2004; pp 1-20.
41. Haag, R.; Sunder, A.; Stumbe, J.-F. J Am Chem Soc 2000, 122, 2954-2955.