Unequal siblings: Adverse characteristics of naphtalene-based hoveyda-type second generation initiators in ring opening metathesis polymerization

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 49, Issue 15, 2011, Pages 3448-3454

  Leitgeb, Anita ^a   Szadkowska, Anna ^b   Michalak, Michal ^c   Barbasiewicz, Michaå ^c   Grela, Karol ^b,c   Slugovc, Christian ^a  

^a GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

^b INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^c UNIVERSITY OF WARSAW   (Poland)

Author keywords

DCPD; differential scanning calorimetry (DSC) gel permeation chromatography (GPC); latent initiators; ring opening metathesis polymerization (ROMP)

Indexed keywords

CARBENE LIGANDS; CONTROLLED POLYMERIZATION; DCPD; DICYCLOPENTADIENE; HIGH ACTIVITY; HOVEYDA-GRUBBS CATALYST; LATENT INITIATORS; NORBORNENE DERIVATIVES; RING OPENING METATHESIS POLYMERIZATION; ROOM TEMPERATURE; SECOND GENERATION;

DIFFERENTIAL SCANNING CALORIMETRY; GEL PERMEATION CHROMATOGRAPHY; LIGANDS; ORGANIC POLYMERS; SIZE EXCLUSION CHROMATOGRAPHY;

RING OPENING POLYMERIZATION;

EID: 79959687202     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.24776     Document Type: Article

References (44)

1. (a) Handbook of Metathesis;, Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003
2. Bielawski, C. W.,;, Grubbs, R. H., Prog Polym Sci 2007, 32, 1-29
3. Slugovc, C., Macromol Rapid Commun 2004, 25, 1283-1297
4. Leitgeb, A.,;, Wappel, J.,;, Slugovc, C., Polymer 2010, 51, 2927-2946.
5. Choi, T.-L.,;, Grubbs, R. H., Angew Chem Int Ed Engl 2003, 42, 1743-1746
6. Slugovc, C.,;, Riegler, S.,;, Hayn, G.,;, Saf, R.,;, Stelzer, F., Macromol Rapid Commun 2003, 24, 435-439
7. Riegler, S.,;, Demel, S.,;, Trimmel, G.,;, Slugovc, C.,;, Stelzer, F., J Mol Catal A 2006, 257, 53-58
8. Burtscher, D.,;, Saf, R.,;, Slugovc, C., J Polym Sci Part A: Polym Chem 2006, 44, 6136-6145
9. Burtscher, D.,;, Lexer, C.,;, Mereiter, K.,;, Winde, R.,;, Karch, R.,;, Slugovc C., J Polym Sci Part A: Polym Chem 2008, 46, 4630-4635.
10. Mol, J. C., J Mol Catal A: Chem 2004, 213, 39-45
11. Khosravi, E., In Ring Opening Metathesis Polymerisation and Related Chemistry;, Khsravi, E.,;, Szymanska-Buzar, T., Eds.; Kluver Academic Publishers: Dortrecht, Boston, London, 2002; pp 105-115.
12. Wang, D.,;, Wurst, K.,;, Knolle, W.,;, Decker, U.,;, Prager, L.,;, Naumov, S.,;, Buchmeiser, M. R., Angew Chem Int Ed Engl 2008, 47, 3267-3270
13. Wang, D. R.,;, Wurst, K.,;, Buchmeiser, M. R., Chem-Eur J 2010, 16, 12928-12934
14. Vidavsky, Y.,;, Lemcoff, N. G., Beilstein J Org Chem 2010, 6, 1106-1109.
15. Monsaert, S.,;, Lozano Vila, A.,;, Drozdzak, R.,;, Van Der Voort, P.,;, Verpoort, F., Chem Soc Rev 2009, 38, 3360-3372
16. Diesendruck, C. E.,;, Iliashevsky, O.,;, Ben-Asuly, A.,;, Goldberg, I.,;, Lemcoff, N. G., Macromol Symp 2010, 293, 33-38.
17. Gstrein, X.,;, Burtscher, D.,;, Szadkowska, A.,;, Barbasiewicz, M.,;, Stelzer, F.,;, Grela, K.,;, Slugovc, C.,; J Polym Sci Part A: Polym Chem 2007, 45, 3494-3500
18. Hejl, A.,;, Day, M. W.,;, Grubbs, R. H., Organometallics 2006, 25, 6149-6154.
19. Garber, S. B.,;, Kingsbury, J. S.,;, Gray, B. L.,;, Hoveyda, A. H.,; J Am Chem Soc 2000, 122, 8168-8179.
20. Michrowska, A.,;, Bujok, R.,;, Harutyunyan, S.,;, Sashuk, V.,;, Dolgonos, G.,;, Grela, K., J Am Chem Soc 2004, 126, 9318-9325
21. Wappel, J.,;, Urbina-Blanco, C. A.,;, Abbas, M.,;, Albering, J. H.,;, Saf, R.,;, Nolan, S. P.,;, Slugovc, C., Beilstein J Org Chem 2010, 6, 1091-1098.
22. Slugovc, C.,;, Perner, B.,;, Mereiter, K.,;, Stelzer, F., Organometallics 2004, 23, 3622-3626
23. Zirngast, M.,;, Pump, E.,;, Leitgeb, A.,;, Albering, J. H.,;, Slugovc, C., Chem Commun 2011, 47, 2261-2263.
24. Slugovc, C.,;, Burtscher, D.,;, Mereiter, K.,;, Stelzer, F.,; Organometallics 2005, 24, 2255-2258.
25. Gstrein, X.,;, Burtscher, D.,;, Szadkowska, A.,;, Barbasiewicz, M.,;, Stelzer, F.,;, Grela, K.,;, Slugovc, C.,; J Polym Sci Part A: Polym Chem 2007, 45, 3494-3500
26. Burtscher, D.,;, Perner, B.,;, Mereiter, K.,;, Slugovc, C., J Organomet Chem 2006, 691, 5423-5430
27. Ung, T.,;, Hejl, A.,;, Grubbs, R. H.,;, Schrodi, Y., Organometallics 2004, 23, 5399-5401
28. Diesendruck, C. E.,;, Vidavsky, Y.,;, Ben-Asuly, A.,;, Lemcoff, N. G., J Polym Sci Part A: Polym Chem 2009, 47, 4209-4213
29. Szadkowska, A.,;, Makal, A.,;, Wozniak, K.,;, Kadyrov, R.,;, Grela, K., Organometallics 2009, 28, 2693-2700
30. Kost, T.,;, Sigalov, M.,;, Goldberg, I.,;, Ben-Asuly, A.,;, Lemcoff, N. G., J Organomet Chem 2008, 693, 2200-2203
31. Ben-Asuly, A.,;, Tzur, E.,;, Diesendruck, C. E.,;, Sigalov, M.,;, Goldberg, I.,;, Lemcoff, N. G., Organometallics 2008, 27, 811-813
32. Ben-Asuly, A.,;, Aharoni, A.,;, Diesendruck, C. E.,;, Vidavsky, Y.,;, Goldberg, I.,;, Straub, B. F.,;, Lemcoff, N. G., Organometallics 2009, 28, 4652-4655
33. Diesendruck, C. E.,;, Tzur, E.,;, Ben-Asuly, A.,;, Goldberg, I.,;, Straub, B. F.,;, Lemcoff, N. G., Inorg Chem 2009, 48, 10819-10825
34. Tzur, E.,;, Szadkowska, A.,;, Ben-Asuly, A.,;, Makal, A.,;, Goldberg, I.,;, Wozniak, K.,;, Grela, K.,;, Lemcoff, N. G., Chem-Eur J 2010, 16, 8726-8737
35. Aharoni, A.,;, Vidavsky, Y.,;, Diesendruck, C. E.,;, Ben-Asuly, A.,;, Goldberg, I.,;, Lemcoff, N. G., Organometallics 2011, 30, 1607-1615.
36. Szadkowska, A.,;, Gstrein, X.,;, Burtscher, D.,;, Jarzembska, K.,;, Wozniak, K.,;, Slugovc, C.,;, Grela, K., Organometallics 2010, 29, 117-124.
37. Barbasiewicz, M.,;, Szadkowska, A.,;, Makal, A.,;, Jarzembska, K.,;, Woźniak, K.,;, Grela, K., Chem Eur J 2008, 14, 9330-9337
38. (b) see also:, Solans-Monfort, X.,;, Pleixats, R.,;, Sodupe, M., Chem Eur J 2010, 16, 7331-7343.
39. Molecular weight and molecular weight distribution might be changed by secondary metathesis reactions such as back-biting.
40. Slugovc, C.,;, Demel, S.,;, Riegler, S.,;, Hobisch. J.,;, Stelzer, F., Macromol Rapid Commun 2004, 25, 475-480.
41. Demel, S.,;, Schoefberger, W.,;, Slugovc, C.,;, Stelzer, F., J Mol Catal A 2003, 200, 11-19
42. Broggi, J.,;, Urbina-Blanco, C. A.,;, Clavier, H.,;, Leitgeb, A.,;, Slugovc, C.,;, Slawin, A. M. Z.,;, Nolan, S. P., Chem Eur J 2010, 16, 9215-9225.
43. A loading of 20 ppm of M2 was found appropriate for the polymerization of Mon4 under said conditions (cf. Supporting Information). The higher loading of 40 ppm of 2, 3, and 4 was selected as it is a compromise of two reasons: (a) as high as possible loadings were intended to be applied because of the pronounced latency of the initiators and (b) the solubility of the initiators in Mon4 should be assured, cf., Jeong, W.,;, Kessler, M. R., Chem Mater 2008, 20, 7060-7068.
44. Rickborn B,. The retro-Diels-Alder Reaction. Part I. C-C Dienophiles in: Organic Reactions, Hoboken, NJ, United States, 1998; 52.