Boron-functionalized poly(3-hydroxybutyrate)s from hydroboration of poly(allyl-β-hydroxyalkanoate)s: Synthesis and insights into the microstructure

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 49, Issue 4, 2011, Pages 907-917

  Guillaume, Clémence ^a   Ajellal, Noureddine ^a   Carpentier, Jean François ^a   Guillaume, Sophie M ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

Author keywords

beta lactone; catalysis; functional polyesters; functionalization of polymers; hydroboration; poly(hydroxyalkanoate); ring opening polymerization; syndiotactic; tacticity

Indexed keywords

BETA-LACTONE; FUNCTIONAL POLYESTERS; FUNCTIONALIZATION OF POLYMERS; HYDROBORATION; POLYHYDROXYALKANOATES; SYNDIOTACTICS; TACTICITIES;

BORON; BORON COMPOUNDS; CATALYSIS; DIFFERENTIAL SCANNING CALORIMETRY; ESTERS; GLASS TRANSITION; ORGANIC POLYMERS; POLYESTERS; POLYMERS; RHODIUM; RING OPENING POLYMERIZATION; SIZE EXCLUSION CHROMATOGRAPHY; TOLUENE; YTTRIUM; ZINC;

FUNCTIONAL POLYMERS;

EID: 78751551793     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.24502     Document Type: Article

References (83)

1. (a), Lu, J.; Tappel, R. C.; Nomura, C. T. J., Polym Rev 2009, 49, 226-248
2. (b), Chen, G.-Q., Chem Soc Rev 2009, 38, 2434-2446
3. (c), Sudesh, K.; Abe, H.; Doi, Y., Prog Polym Sci 2000, 25, 1503-1555.
4. (a), Nair, L. S.; Laurencin, C. T., Prog Polym Sci 2007, 32, 762-798
5. (b), Albertsson, A.-C.; Varma, I. K., Biomacromolecules 2003, 4, 1466-1486
6. (c), Freier, T., Adv Polym Sci 2006, 203, 1-61
7. (d), Hakkarainen, M.; Albertsson A.-C., Adv Polym Sci 2008, 211, 85-116
8. (e), Zinn, M.; Witholt, B.; Egli, T., Adv Drug Deliv Rev 2001, 53, 5-21.
9. Carpentier, J.-F., Macromol Rapid Commun 2010, 31, 1696-1705 and references cited therein.
10. Thomas, C. M., Chem Soc Rev 2010, 39, 165-173.
11. (a), Le Borgne, A.; Spassky, N., Polymer 1989, 30, 2312-2319
12. (b), Zintl, M.; Molnar, F.; Urban, T.; Bernhart, V.; Preishuber- Pflügl, P.; Rieger, B., Angew Chem Int Ed 2008, 47, 3458-3460
13. (c), Wu, B.; Lenz, R. W., Macromolecules 1998, 31, 3473-3477
14. (d), Bloembergen, S.; Holden, D. A.; Bluhm, T. L.; Hamer, G. K.; Marchessault, R. H., Macromolecules 1989, 22, 1656-1663
15. (e), Yori, Y.; Suzuki, M.; Yamaguchi, A.; Nishishita, T., Macromolecules 1993, 26, 5533-5534
16. (f), Teranishi, K.; Iida, M.; Araki, T.; Yamashita, S.; Tani, H., Macromolecules 1974, 4, 421-427.
17. (a), Amgoune, A.; Thomas, C. M.; Ilinca, S.; Roisnel, T.; Carpentier, J.-F., Angew Chem Int Ed 2006, 45, 2782-2784
18. (b), 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
19. (c), Ajellal, N.; Bouyahyi, M.; Amgoune, A.; Thomas, C. M.; Bondon, A.; Pilin, I.; Grohens, Y.; Carpentier, J.-F., Macromolecules 2009, 42, 987-993
20. (d), Ajellal, N.; Thomas, C. M.; Carpentier, J.-F., J Polym Sci Part A: Polym Chem 2009, 47, 3177-3189
21. (e), Kramer, J. W.; Treiter, D. S.; Dunn, E. W.; Castro, P. M.; Roisnel, T.; Thomas, C. M.; Coates, G. W., J Am Chem Soc 2009, 131, 16042-16044
22. (f), Ajellal, N.; Durieux, G.; Delevoye, L.; Tricot, G.; Dujardin, C.; Thomas, C. M.; Gauvin, R. M., Chem Commun 2010, 46, 1032-1033
23. (g), Grunova, E.; Kirillov, E.; Roisnel, T.; Carpentier, J.-F., Dalton Trans 2010, 39, 6739-6752.
24. (a), Hori, Y.; Hagiwara, T., Int J Biol Macromol 1999, 25, 237-245
25. (b), Kricheldorf, H. R.; Eggerstedt, S., Macromolecules 1997, 30, 5693-5697
26. (c), Kemnitzer, J. E.; McCarthy, S. P.; Gross, R. A., Macromolecules 1993, 26, 1221-1229
27. (d), Kemnitzer, J. E.; McCarthy, S. P.; Gross, R. A., Macromolecules 1993, 26, 6143-6150
28. (e), Jedlinski, Z.; Kowalczuk, M.; Kurcok, P.; Adamus, G.; Matuszowicz, A.; Sikorska, W.; Gross, R. A.; Xu, J.; Lenz, R. W., Macromolecules 1996, 29, 3773-3777
29. (f), Kricheldorf, H. R.; Lee, S.-R.; Scharnagi, N., Macromolecules 1994, 27, 3139-3146
30. (g), Arcana, M.; Giani-Beaune, O.; Schue, F.; Amass, W.; Amass, A., Polym Int 2000, 49, 1348-1355.
31. (a), Guillaume, C.; Carpentier, J.-F.; Guillaume, S. M., Polymer 2009, 50, 5909-5917
32. (b), Rieth, L. R.; Moore, D. R.; Lobkovsky, E.; Coates, G. W., J Am Chem Soc 2002, 124, 15239-15248
33. (c), Grunova, E.; Roisnel, T.; Carpentier, J.-F., Dalton Trans 2009, 9010-9019
34. (d), Billingham, N. C.; Proctor, M. G.; Smith, J. D. J., Organomet Chem 1988 341, 83-93
35. (e), Moeller, M.; Kange, R.; Hedrick, J. L., J Polym Sci Part A: Polym Chem 2000, 38, 2067-2074
36. (f), Alaaedine, A.; Amgoune, A.; Thomas, C. M.; Dagorne, S.; Bellemin-Laponnaz, S.; Carpentier, J.-F., Eur J Inorg Chem 2006, 3652-3658
37. (g), Leborgne, A.; Pluta, C., Spassky, N,. Macromol Rapid Commun 1994, 15, 955-960
38. (h), Connor, E. F.; Nyce, G. W.; Myers, M.; Möck, A.; Hedrick, J. L., J Am Chem Soc 2002, 124, 914-915
39. (i), Kurock, P.; Smiga, M., Jedlinski, Z,. J Polym Sci Part A: Polym Chem 2002, 40, 2184-2189
40. (j), Gross, R. A.; Zhang, Y.; Konrad, G.; Lenz, R. W., Macromolecules 1988, 21, 2657-2668
41. (k), Kricheldorf, H. R.; Berl, M.; Scharnagl, N., Macromolecules 1988, 21, 286-293.
42. One must also keep in mind that β-butyrolactones are classified as carcinogens. This characteristic requires that special care must be paid for their handling and thorough removal from the final polymers. Such considerations are particularly appealing (but not necessarily disqualifying) should commercial/industrial production of PHB/PHAs via ROP of β-lactones be eventually considered.
43. For leading references on functionalized polyesters, see: (a), Coulembier, O.; Degee, P.; Hedrick, J. L.; Dubois, P., Prog Polym Sci 2006, 31, 723-747
44. (b), Williams, C. K., Chem Soc Rev 2007, 36, 1573-1580
45. (c), Pounder, R. J.; Dove, A. P., Polym Chem 2010, 1, 260-271.
46. Gauthier, M. A.; Gibson, M. I.; Klok, H.-A., Angew Chem Int Ed 2009, 48, 48-58.
47. (a), Sparks, J.; Scholz C,. Biomacromolecules 2008, 8, 2091-2096
48. (b), Stigers, D. J.; Tew, G. N., Biomacromolecules 2003, 2, 193-196
49. (c), Constantin, M.; Simionescu, C. I.; Carpov, A.; Samain, E.; Driguez, H., Macromol Rapid Commun 1999, 20, 91-94
50. (d), Timbart, L.; Renard, E.; Tessier, M.; Langlois, V., Biomacromolecules 2007, 8, 1255-1265
51. (e), Babinot, J.; Renard, E.,; Langlois, Macromol Rapid Commun 2010, 31, 619-624
52. (f), Arkin, A. H.; Hazer, B.; Borcakli, M., Macromolecules 2000, 33, 3219-3223
53. (g), Erduranhi, H.; Hazer, B.; Borcakli, M., Macromol Symp 2008, 269, 161-169.
54. (a), Soloway, A. H.; Tjarks, W.; Barnum, B. A.; Rong, F.-G.; Barth, R. F.; Codogni, I. M.; Wilson, J. G., Chem Rev 1998, 98, 1515-1562
55. (b), Hawthorne, M. F., Mol Med Today 1998, 174-181
56. (c), Barth, R. F.; Coderre, J. A.; Vicente, M. G. H.; Blue, T. E., Clin Cancer Res 2005, 11, 3987-4002
57. (d), Hawthorne, M. F., Angew Chem Int Ed 1993, 32, 950-984.
58. (a), Sezgin, A.; Akbey, U.; Hansen, M. R.; Graf, R.; Bozkurt, A.; Baykal, A., Polymer 2008, 49, 3859-3864
59. (b) Smart Polymers: Applications in Biotechnology and Biomedicine, 2nd ed.;, Ivanov, A. E.; Galaev, I. Y.; Mattiasson, B., Eds.; CRC Press: Boca Raton, FL, USA, 2008; Chapter 10, pp 299-329.
60. (a), Deore, B. A.; Yu, I.; Woodmass, J.; Freund, M. S., Macromol Chem Phys 2008, 209, 1094-1105
61. (b), Akram, D.; Sharmin, E.; Ahmad, S., Macromol Chem Phys 2009, 277, 130-137
62. (c), Budhathoki, J.; Novak, B. M., Polymer 2010, 51, 2140-2146.
63. 3,6(a,c)
64. Burgess, K.; van der Donk, W. A.; Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C., J Am Chem Soc 1992, 114, 9350-9359.
65. Kramer, J. W.; Coates, G. W., Tetrahedron 2008, 64, 6973-6978.
66. (a), Helou, M.; Miserque, O.; Brusson, J.-M.; Carpentier, J.-F.; Guillaume, S. M., Chem Eur J 2008, 14, 8772-8775
67. (b), Helou, M.; Miserque, O.; Brusson, J.-M.; Carpentier, J.-F.; Guillaume, S. M., Adv Synth Catal 2009, 351, 1312-1324
68. (c), Helou, M.; Miserque, O.; Brusson, J.-M.; Carpentier, J.-F.; Guillaume, S. M., Macromol Rapid Commun 2009, 30, 2128-2135
69. (d), Carpentier, J.-F.; Guillaume, S.; Helou, M.; Miserque, O.; Sarazin, Y., Eur Pat Appl 082,901,877 (2008)
70. (e), Carpentier, J.-F.; Guillaume, C.; Guillaume, S. M.; Helou, M.; Poirier, V.; Sarazin, Y., J Chem Soc Dalton Trans 2010, 39, 8363-8376
71. (f), Helou, M.; Miserque, O.; Brusson, J.-M.; Carpentier, J.-F.; Guillaume, S. M., Chem Cat Chem 2010, 2, 306-313
72. (g), Carpentier, J.-F.; Guillaume, S. M.; Helou, M.; Miserque, O., Eur Pat Appl 082,907,494 (2008)
73. (h), Helou, M.; Miserque, O.; Brusson, J.-M.; Carpentier, J.-F.; Guillaume, S. M., Chem Eur J 2010, DOI: 10.1002/chem.201001111
74. (i), Poirier, V.; Roisnel, T.; Carpentier, J.-F.; Sarazin, Y., Dalton Trans 2009, 9820-9827
75. (j), Poirier, V.; Roisnel, T.; Carpentier, J.-F.; Sarazin, Y., Dalton Trans 2011, DOI: 10.1039/c0dt01219j.
76. allyl. This loss of allyl moiety, therefore, most likely occurs during the ionization process of the MS analysis.
77. allyl. On the other hand, it can not be excluded that the slight broadening of the molecular mass distributions reflects minor detrimental side reactions.
78. (a), Bloembergen, S.; Holde, D. A.; Bluhm, T. L.; Hamer, G. K.; Merchessault, R. H., Macromolecules 1987, 20, 3086-3089
79. (b), Iida, M.; Hayasse, S.; Araki, T., Macromolecules 1978, 11, 490-493
80. (c), Hocking, P. J.; Marchessault, R. H., Macromolecules 1995, 28, 6401-6409.
81. Lee, J. T.; Thomas, P. J.; Alper, H., J Org Chem 2001, 66, 5424-5426.
82. (a), Cai, C.-X.; Toupet, L.; Carpentier, J.-F., J Organomet Chem 2003, 683, 131-136
83. (b), Amgoune, A.; Thomas, C. M.; Roisnel, T.; Carpentier, J.-F., Chem Eur J 2006, 12, 169-179.