Benzyl bromide functionalized poly(phenyleneethynylene)s as macroinitiators in the atom transfer radical polymerization of methyl methacrylate

Journal of Macromolecular Science - Pure and Applied Chemistry

Volumn 41 A, Issue 6, 2004, Pages 637-647

  Wagner, Martin ^a   Nuyken, Oskar ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

ATRP; Conjugated polymer; Graft copolymer; Macroinitiator; Methyl methacrylate; Poly(phenyleneethynylene)

Indexed keywords

ATOMS; GEL PERMEATION CHROMATOGRAPHY; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC POLYMERS; POLYMERIZATION; ULTRAVIOLET SPECTROSCOPY;

ATOM TRANSFER RADICAL POLYMERIZATION (ATRP); MACROINITIATOR; METHYL METHACRYLATE; POLY(PHENYLENEETHYNYLENE);

GRAFT COPOLYMERS;

EID: 3042690574     PISSN: 10601325     EISSN: None     Source Type: Journal    
DOI: 10.1081/MA-120034196     Document Type: Article

References (23)

1. Wang, J.-S.; Matyjaszewski, K. Controlled/"living" radical polymerization: atom transfer radical polymerization in the presence of transition-metal complexes. J. Am. Chem. Soc. 1995, 117, 5614-5615.
2. Kato, M.; Kamigaito, M.; Sawamoto, M.; Higashirnura, T. Polymerization of methyl methacrylate with the carbon tetrachloride/ dichlorotris(triphenylphosphine)ruthenium(II)/methylaluminium bis(2,6-di-tert-butylphenoxide) initiating system: possibility of living radical polymerization. Macromolecules 1995, 28, 1721-1723.
3. Matyjaszewski, K.; Xia, J. Atom transfer radical polymerization. Chem. Rev. 2001, 101, 2921-2990.
4. Kamigaito, M.; Ando, T.; Sawamoto, M. Metal-catalyzed living radical polymerization. Chem. Rev. 2001, 101, 3689-3745.
5. Wagner, M.; Nuyken, O. Benzyl bromide functionalized poly(phenyleneethynylene)s: a novel approach toward conjugated polymers with a well-defined chemical reactivity. Macromolecules 2003, 36, 6716-6721.
6. Skotheim, T.A.; Elsenbaumer, R.L.; Reynolds, J., Eds.; Handbook of Conducting Polymers, 2nd Ed.; Marcel Dekker: New York, 1997.
7. Hadziioannou, G.; van Hutten, P.F., Eds.; Semiconducting Polymers; Viley-VCH: Weinheim, 2000.
8. Horowitz, G. Organic field-effect transistors. Adv. Mater. 1998, 10, 365-377.
9. Hide, F.; Díaz-García, M.A.; Schwartz, B.J.; Heeger, A.J. New developments in the photonic applications of conjugated polymers. Ace. Chem. Res. 1997, 30, 430-436.
10. McGehee, M.D.; Heeger, A.J. Semiconducting (conjugated) polymers as materials for solid-state lasers. Adv. Mater. 2000, 12, 1655-1668.
11. Yu, G.; Gao, J.; Hummelen, J.C.; Wudl, F.; Heeger, A.J. Polymer photovoltaic cells: enhanced efficiencies via a network of internal donor-acceptor heterojunctions. Science 1995, 270, 1789-1791.
12. Brabec, C.J.; Sariciftci, N.S.; Hummelen, J.C. Plastic solar cells. Adv. Func. Mater. 2001, 11, 15-26.
13. Kraft, A.; Grimsdale, A.C.; Holmes, A.B. Electroluminescent conjugated polymers-seeing polymers in a new light. Angew. Chem. Int. Ed. 1998, 37, 402-428.
14. Dai, L.; Winkler, B.; Dong, L.; Tong, L.; Mau, A.W.H. Conjugated polymers for light emitting applications. Adv. Mater. 2001, 13, 915-925.
15. Becker, H.; Spreizer, H.; Kreuder, W.; Kluge, E.; Vestweber, H.; Schenk, H.; Treacher, K. Advances in polymers for PLEDs: from a polymerization mechanism to industrial manufacturing. Syn. Met. 2001, 122, 105-110.
16. Matyjaszewski, K.; Patten, T.E.; Xia, J. Controlled/"living" radical polymerization: kinetics of the homogeneous atom transfer radical polymerization of styrene. J. Am. Chem. Soc. 1997, 119, 674-680.
17. Patten, T.E.; Xia, J.; Abernathy, T.; Matyjaszewski, K. Polymers with very low poly-dispersities from atom transfer radical polymerization. Science 1996, 272, 866-868.
18. Matyjaszewski, K.; Wang, J.-L.; Grimaud, T.; Shipp, D.A. Controlled/"living" atom transfer radical polymerization of methyl methacrylate using various initiation systems. Macromolecules 1998, 31, 1527-1534.
19. Matyjaszewski, K.; Shipp, D.A.; Wang, J.-L.; Grimaud, T.; Patten, T.E. Utilizing halide exchange to improve control of atom transfer radical polymerization. Macromolecules 1998, 31, 6836-6840.
20. Trumbo, D.L.; Marvel, C.S. Polymerization using palladium(II) salts: homopolymers and copolymers from phenylethynyl compounds and aromatic bromides. J. Polym. Sci., Part A: Polym. Chem. 1986, 24, 2311-2326.
21. Schumm, J.S.; Pearson, D.L.; Tour, J.M. Iterative divergent/convergent approach to linear conjugated oligomers by successive doubling of the molecular length: a rapid route to a 128 A-long potential molecular wire. Angew. Chem. Int. Ed. Engl. 1994, 33, 1360-1363.
22. Francke, V.; Mangel, T.; Müllen, K. Synthesis of α,ω-difunctionalized oligo- and poly(p-phenlyenethynylene)s. Macromolecules 1998, 31, 2447-2453.
23. Huang, S.; Tour, J.M. Rapid solid-phase synthesis of oligo(1,4- phenyleneethynylene)s by a divergent/convergent tripling strategy. J. Am. Chem. Soc. 1999, 121, 4908-4909.