Preparation and characterization of conjugated polymers made by postpolymerization reactions of alternating polyketones

Journal of the American Chemical Society

Volumn 133, Issue 25, 2011, Pages 9658-9661

  Cheng, Chen ^a   Guironnet, Damien ^a   Barborak, James ^b   Brookhart, Maurice ^a  

^a University of North Carolina at Chapel Hill   (United States)

^b UNIVERSITY OF NORTH CAROLINA AT GREENSBORO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION PEAKS; CARBON BACKBONE; LARGE SCALE PREPARATION; NIR REGIONS; ONE-POT REACTION; POLYKETONES; POST-POLYMERIZATION; REPEATING UNIT; UV-VIS SPECTROSCOPY; VISIBLE REGION;

ABSORPTION; BROMINE; KETONES; SYNTHESIS (CHEMICAL);

CONJUGATED POLYMERS;

KETONE DERIVATIVE; POLY(2,5 DIMETHYLENE 2,5 DIHYDROFURAN); POLY(2,5 DIMETHYLENETETRAHYDROFURAN); POLY(PHENYLENEVINYLENE); POLYACETYLENE; POLYKETONE; POLYMER; POLYTHIOPHENE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; BROMINATION; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CONJUGATION; CYCLIC POTENTIOMETRY; DIASTEREOISOMER; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; POSTPOLYMERIZATION; PROTON TRANSPORT; ULTRAVIOLET SPECTROSCOPY;

EID: 79959531785     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja202361k     Document Type: Article

References (49)

1. Coakley, K. M.; McGehee, M. D. Chem. Mater. 2004, 16, 4533-4542
2. Cheng, Y.; Yang, S.; Hsu, C. Chem. Rev. 2009, 109, 5868-5923
3. Po, R; Maggini, M.; Camaioni, N. J. Phys. Chem. C 2010, 114, 695-706
4. Yang, X; Loos, J. Macromolecules 2007, 40, 1353-1362
5. Li, C.; Liu, M.; Pschirer, N. G.; Baumgarten, M.; Müllen, K. Chem. Rev. 2010, 110, 6817-6855
6. Clem, T. A.; Kavulak, D. F. J.; Westling, E. J.; Fréchet, J. M. J. Chem. Mater. 2010, 22, 1977-1987
7. Günes, S.; Neugebauer, H.; Sariciftci, N. S. Chem. Rev. 2007, 107, 1324-1338
8. Baek, N. S.; Hau, S. K.; Yip, H.; Acton, O.; Chen, K.; Jen, A. K.-Y. Chem. Mater. 2008, 20, 5734-5736
9. Beaujuge, P. M.; Reynolds, J. R. Chem. Rev. 2010, 110, 268-320
10. Argun, A. A.; Aubert, P.; Thompson, B. C.; Schwendeman, I.; Gaupp, C. L.; Hwang, J.; Pinto, N. J.; Tanner, D. B.; MacDiarmid, A. G.; Reynolds, J. R. Chem. Mater. 2004, 16, 4401-4412
11. Kummar, A.; Welsh, D. M.; Morvant, M. C.; Piroux, F.; Abboud, K. A.; Reynolds, J. R. Chem. Mater. 1998, 10, 896-902
12. Dyer, A. L.; Craig, M. R.; Babiarz, J. E.; Kiyak, K.; Reynolds, J. R. Macromolecules 2010, 43, 4460-4467
13. Nielsen, C. B.; Angerhofer, A.; Abboud, K. A.; Reynolds, J. R. J. Am. Chem. Soc. 2008, 130, 9734-9746
14. Dyer, A. L.; Reynolds, J. R. Handbook of Conducting Polymers 3 rd ed.; CRC Press: Boca Raton, FL, 2007; Chapter 20, pp 1-63.
15. Grimsdale, A. C.; Chan, K. L.; Martin, R. E.; Jokisz, P. G.; Holmes, A. B. Chem. Rev. 2009, 109, 897-1091
16. Kulkarni, A. P.; Tonzola, C. J.; Babel, A.; Jenekhe, S. A. Chem. Mater. 2004, 16, 4556-4573
17. Chen, C. Chem. Mater. 2004, 16, 4389-4400
18. Veinot, J. G. C.; Marks, T. J. Acc. Chem. Res. 2005, 38, 632-643
19. Huebner, C. F.; Foulger, S. H. Langmuir 2010, 26, 2945-2950
20. Pei, J.; Yu, W.; Huang, W.; Heeger, A. J. Macromolecules 2000, 33, 2462-2471
21. Heinze, J.; Frontana-Uribe, B. A.; Ludwigs, S. Chem. Rev. 2010, 110, 4724-4771
22. Gangopadhyay, R.; De, A. Chem. Mater. 2000, 12, 608-622
23. Hopkins, A. R.; Reynolds, J. R. Macromolecules 2000, 33, 5221-5226
24. Naebe, M.; Lin, T.; Feng, L.; Dai, L.; Abramson, A.; Prakash, V.; Wang, X. Nanoscience and Nanotechnology for Chemical and Biological Defense; American Chemical Society: Washington, DC, 2009; Chapter 4, pp 39-58.
25. Rasmussen, S. C.; Martin, P. Handbook of Conducting Polymers 3 rd ed.; CRC Press: Boca Raton, FL, 2007; Chapter 12, pp 421-462.
26. Groenendaal, L. B.; Jonas, F.; Freitag, D.; Pielartzik, H.; Reynolds, J. R. Adv. Mater. 2000, 12, 481-494
27. Jiang, H.; Taranekar, P.; Reynolds, J. R.; Schanze, K. S. Angew. Chem., Int. Ed. 2009, 48, 4300-4316
28. Babudri, F.; Farinola, G. M.; Naso, F. J. Mater. Chem. 2004, 14, 11-34
29. Yokoyama, A; Yokozawa, T. Macromolecules 2007, 40, 4093-4101
30. Drent, E.; Budzelaar, P. H. M. Chem. Rev. 1996, 96, 663-682
31. Anselment, T. M. J.; Vagin, S. I.; Rieger, B. Dalton Trans. 2008, 4537-4548
32. Brookhart, M.; F. C. Rix, F. C.; DeSimone, J. M.; Barborak, J. C. J. Am. Chem. Soc. 1992, 114, 5894-5895
33. Rix, F. C.; Rachita, M. J.; Wagner, M. I.; Brookhart, M.; Milani, B.; Barborak, J. C. Dalton Trans. 2009, 41, 8977-8992
34. Durand, J.; Milani, B. Coord. Chem. Rev. 2006, 250, 542-560
35. Milani, B.; Mestroni, G. Comments Inorg. Chem. 1999, 20, 301-326
36. Flory, P. J. J. Am. Chem. Soc. 1939, 61, 1518-1521
37. 13C signal at 109 ppm assigned to C1, there is a minor resonance at 108 ppm which may correspond to a minor diastereomer.
38. Paal, C. Ber. Dtsch. Chem. Ges. 1884, 17, 2756-2767
39. King, S. M.; Bauer, C. R.; Lutz, R. E. J. Am. Chem. Soc. 1951, 73, 2253-2256
40. Derenberg, M.; Hodge, P. J. Chem. Soc. D 1971, 233-234
41. Gubina, T. I.; Pankratov, A. N.; Labunskaya, V. I.; Rogacheva, S. M. Chem. Heterocycl. Compd. 2004, 40, 1396-1401
42. Scheme 2 is one of several possible pathways leading to 2. Furan units and/or endocyclic double bonds could be formed, but under acid conditions rearrangement to more stable exocyclic, conjugated structures could occur.
43. Han, C. C.; Elsenbaumer, R. L. Synth. Met. 1989, 30, 123-139
44. Clarke, T. C.; McQuillan, B. W.; Rabolt, J. F.; Scott, J. C.; Street, G. B. Mol. Cryst. Liq. Cryst. 1982, 83, 1-16
45. Chen, S.; Hua, M. Macromolecules 1993, 26, 7108-7110
46. Wang, F.; Lai, Y. Macromolecules 2003, 36, 536-538
47. Wang, F.; Lai, Y.; Han, M. Macromolecules 2004, 37, 3222-3230
48. Ohlan, A.; Singh, K.; Dhawan, S. K. J. Appl. Polym. Chem. 2010, 115, 498-503
49. Brédas, J. L.; Heeger, A. J. Chem. Phys. Lett. 1994, 217, 507-512