Homo- and copolymerization of aromatic diynes by ruthenium/acid-promoted (rap) catalysis

European Journal of Organic Chemistry

Volumn , Issue 30, 2009, Pages 5224-5231

  Pasquini, Chiara ^a,b   Fratoddi, Ilaria ^a,b   Bassetti, Mauro ^a,b  

^a CNR Consiglio Nazionale delle Ricerche   (Italy)

^b SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

C c coupling; Enynes; Homogeneous catalysis; Polymerization; Ruthenium

Indexed keywords

EID: 70350180835     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200900748     Document Type: Article

References (40)

1. A. C. Grimsdale, K. L. Chan, R. E. Martin, P. G. Jokisz, A. B. Holmes, Chem. Rev. 2009, 109, 897-1091.
2. a) A. Mori, M. S. M. Ahmed in Comprehensive Organometallic Chemistry III (Eds.: D. M. P. Mingos, R. H. Crabtree, T. Hiyama), Elsevier, Oxford, 2007, vol.11, chapter 19;
3. b) F. Babudri, G. M. Farinola, F. Naso, J. Mater. Chem. 2004, 14, 11-34.
4. M. S. Taylor, T. M. Swager, Angew. Chem. Int. Ed. 2007, 46, 8480-8483.
5. D. Venkatesan, M. Yoneda, M. Ueda, React. Funct. Polym. 1996, 30, 341-352.
6. a) H. Katayama, M. Nakayama, T. Nakano, C. Wada, K. Akamatsu, F. Ozawa, Macromolecules 2004, 37, 13-17;
7. b) M. Nishiura, Z. Hou, J. Mol. Catal. A 2004, 213. 101-106;
8. (c) M. Ueda, I. Tomita, Polym. Bull. 2004, 51, 359-364;
9. (d) V. F. Quiroga Norambuena, University of Groningen, The Nederlands, Ph. D. Dissertation, 2006, chapter 6.
10. E. Bustelo, P. H. Dixneuf, in Handbook of C-H Transformations (Ed.: G. Dyker), Wiley-VCH, Weinheim, 2005, vol.1, chapter II, p. 62.
11. M. Bassetti, C. Pasquini, A. Raneri, D. Rosato, J. Org. Chem. 2007, 72, 4558-4561.
12. C. Pasquini, I. Fratoddi, D. Capitani, L. Mannina, M. Bassetti, J. Org. Chem. 2008, 73, 3892-3899.
13. Selected references of fluorene-based polymers: a) M. Fukuda, K. Sawada, K. Yoshino, J. Polym. Sci., Part A: Polym. Chem. 1993, 31, 2465-2471;
14. b) M. Grell, D. D. C. Bradley, G. Ungar, J. Hill, K. S. Whitehead, Macromolecules 1999, 32, 5810-5817;
15. (c) M. Leclerc, J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 2867-2873;
16. (d) K. Zhan, Y. Liu, D. Zhu, W. Huang, Q. Gong, Chem. Mater. 2001, 13, 1540-1544;
17. e) S.-H. Jin, S.-Y Kang, M. Y. Kim, Y. U. Chan, J. Y Kim, K. Lee, Y-S. Gal, Macromolecules 2003, 36, 3841-3847;
18. f) T. Okamoto, Y. Jiang, F. Qu, A. C. Mayer, J. E. Parmer, M. D. McGehee, Z. Bao, Macromolecules 2008, 41, 6977-6980.
19. Selected references of MEH-PPV polymers: a) P. L. Burn, A. Kraft, D. R. Baigent, D. D. C Bradley, A. R. Brown, R. H. Friend, R. W Gymer, A. B. Holmes, R. W. Jackson, J. Am. Chem. Soc. 1993, 115, 10117-10124;
20. b) B. R. Hsieh, Y. Yu, A. C. VanLaeken, H. Lee, Macromolecules 1997, 30, 8094-8095;
21. (c) C. J. Neef, J. P. Ferraris, Macromolecules 2000, 33, 2311-2314;
22. (d) Y.-Z. Lee, X. Chen, S.-A. Chen, P-K. Wei, W.S. Fann, J. Am. Chem. Soc. 2001, 123, 2296-2307.
23. Fluorene-PPE polymers: N. G. Pschirer, U. H. F. Bunz, Macromolecules 2000, 33, 3961-3963.
24. MEH-PPE polymers: a) S. Dellsperger, F. Dötz, P. Smith, C. Weder, Macromol. Chem. Phys. 2000, 201, 192-198;
25. b) D. A. M. Egbe, A. Wild, E. Birckner, U.-W. Grummt, U. S. Schubert, Macromol. Symp. 2008, 268, 25-27.
26. 3 (4 equiv.) (SIMes·HCl = 1,3-dimesitylimidazolium chloride).[5a]
27. a) C. Weder, M. S. Wrighton, Macromolecules 1996, 29, 5157-5165;
28. b) S. Setayesh, A. C. Grimsdale, T Weil, V. Enkelniann, Müllen, F. Meghdadi, E. J. W. List, G. Leising, J. Am. Chem. Soc. 2001, 123, 946-953.
29. G. Hughes, M. R. Bryce, J. Mater. Chem. 2005, 15, 94-107.
30. Soxhlet extraction from the bulk did not improve the yield of the soluble components with respect to filtration through silica. [17] P.-S. Wang, H.-H. Lu, C.-Y. Liu, S.-A. Chen, Macromolecules 2008, 41, 6500-6504.
31. The ethynyl groups of the diyne 2 appear as two singlets at S = 3.39, 3.33 ppm. The PPEVs. obtained from symmetric 1,4-dialkoxy-2,5-diethynylbenzene derivatives afforded, two distinct signals due to the different C=CH protons.[8]
32. R. Traiphol, P. Sanguansat, T Srikhirin, T. Kerdcharoen, T. Osotchan, Macromolecules 2006, 39, 1165-1172.
33. P. F. Barbara, A. J. Gesquiere, S.-J. Park, Y. J. Lee, Acc. Chem. Res. 2005, 38, 602-610.
34. The similar reactivity of the monomers 1 and 2, as judged by the comparable reaction times observed, in the homopolymerization, suggests that P3 is a random copolymer, rather than a block polymer formed by coupling of Pl and P2 oligomers.
35. In order to exclude that the photoluminescent spectrum of P3 is merely due to the linear combination of the emission spectra of the homopolymers, a chloroform, solution of Pl and P2 in a 7:3 molar ratio was studied as a control, experiment. The resulting sample exhibited an emission spectrum markedly dependent on the chosen excitation wavelength, as expected for a solution containing two independent chromophores (see Figures in the Supporting Information), in contrast with the behaviour of P3. This confirms that the P3 sample is formed by molecular species including the fluorene and the MEH subunits in the same chain. The absence of intramolecular and intermolecular energy transfer between the two chromophores in the control sample further confirms that intramolecular resonance energy transfer processes are involved in the photoluminescence of P3.
36. The polymerizations of the l,4-dialkoxy-2,5-diethynylbenzene derivatives were characterized by extensive precipitation of material during the course of the reaction, as the result of limited solubility at increasing chain length.
37. P. C Hiemenz in Polymer Chemistry The Basic Concepts, Marcel Dekker, Inc., New York, 1984.
38. Y Guillaneuf, P. Castignolles, J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 897-911.
39. M. S. Khan, M. R. A. Al-Mandhary, M. K. Al-Suti, P. Raithby, B. Ahrens, L. Male, R. H. Friend, A. Köhler, J. Wilson, Dalton Trans. 2003, 65-73.
40. H. Meier, D. Ickenroth, U. Stalmach, K. Koynov, A. Bahtiar, C. Bubeck, Eur. J. Org. Chem. 2001, 4431-4443.