New insights into the microstructure of GILCH-polymerized PPVs

Macromolecules

Volumn 32, Issue 15, 1999, Pages 4925-4932

  Becker, Heinrich ^a   Spreitzer, Hubert ^a   Ibrom, Kerstin ^b   Kreuder, Willi ^a  

^a G865 ^*  (Germany)

^b OTTO VON GUERICKE UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTAL DEFECTS; MICROSTRUCTURE; MONOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; SOLUTIONS; SYNTHESIS (CHEMICAL);

POLYPHENYLENEVINYLENE; TOLANE BISBENZYL MOIETIES;

ORGANIC POLYMERS;

EID: 0033154103     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma990347q     Document Type: Article

References (23)

1. Burroughes, J. H.; Bradley, D. D. C.; Brown, A. R.; Marks, R. N.; Mackay, K.; Friend, R. H.; Burn, P. L.; Holmes, A. B. Nature 1990, 347, 539.
2. Granstrom, M.; Petritsch, K.; Arias, A. C.; Lux, A.; Andersson, M. R.; Friend, R. H. Nature 1998, 395, 257.
3. Kraft, A.; Grimsdale, A. C.; Holmes, A. B. Angew. Chem., Int. Ed. Engl. 1998, 37, 402.
4. (a) Spreitzer, H.; Becker, H.; Kluge, E.; Kreuder, W.; Schenk, H.; Demandt, R.; Schoo, H. Adv. Mater. 1998, 10, 1340.
5. (b) Spreitzer, H.; Kreuder, W.; Becker, H.; Schoo, H.; Demandt, R. PCT Patent Application WO 98/27136, 1996.
6. In the GILCH procedure, 1,4-bis(halomethyl)benzenes are polymerized by the addition of a base: Gilch, H. G.; Wheelwright, W. L. J. Polym. Sci., Part A: Polym. Chem. 1966, 4, 1337.
7. Wessling, R. A. J. Polym. Sci., Polym. Symp. 1985, 72, 55.
8. (a) Hsieh, B. R.; Yu, Y.; Forsythe, E. W.; Schaaf, G. M.; Field, W. A. J. Am. Chem. Soc. 1998, 120, 231.
9. (b) Wan, W. C.; Antoniadis, H.; Choong, V. E.; Razafitrimo, H.; Gao, Y.; Field, W. A.; Hsieh, B. R. Macromolecules 1997, 30, 6567.
10. Son, S.; Dodabalapur, A.; Lovinger, A. J.; Galvin, M. E. Science 1995, 269, 376.
11. Issaris, A.; Vanderzande, D.; Gelan, J. Polymer 1997, 38, 2571.
12. 5 Also, our own measurements-which demonstrate very high molecular weight already well below 100% conversion-contradict such a speculation (see Supporting Information).
13. (a) Schoo, H.; Demandt, R. Philips J. Res. 1998, 57, 527.
14. (b) Vaeth, K. M.; Jensen, K. F. Macromolecuks 1998, 31, 6789.
15. Gelinck, G. H.; Warman, J. M.; Staring, E. G. J. J. Phys. Chem. 1996, 100, 5485.
16. Braun, S.; Kalinowski, H.-O.; Berger, S. 150 and More Basic NMR Experiments, 2nd ed.; Wiley-VCH: Weinheim, 1998; (a) p 180, (b) p 485, (c) p 489.
17. Davis, A. L.; Keeler, J.; Laue, E. D.; Moskau, D. J. Magn. Reson. 1992, 98, 207.
18. 1H NMRs of soluble PPVs in the literature are rare. One example (also exhibiting the 2.9 ppm peak) is: Holmes, A.; Bradley, D. D.; Friend, R. H.; Kraft, A.; Burn, P.; Brown, A. (all of CDT, Cambridge, UK), US patent US 5,328,809, granted 12.6.94; priority 22.8.91, Figure 24.
19. The intensity of the signal around 2.9 ppm is not influenced by the degree of purification, and therefore the corresponding structure must be an integral part of the polymer. The amount of this defect is dependent on the type of polymer and the polymerization conditions.
20. The residual chlorine content of the polymers was determined by incineration and subsequent argentometric titration.
21. 2OR: 75.8 ppm; cf. p 165.
22. Berntsen, A.; Croonen, Y.; Liedenbaum, C.; Schoo, H.; Visser, R.-J.; Vleggaar, J.; van de Weijer, P. Opt. Mater. 1998, 9, 125.
23. The estimated amount of these groups corresponds to the degree of polymerization (∼1000). Assuming that further end groups are negligible, the number of branches present is likely to be low.