A new family of color-tunable light-emitting polymers with high quantum yields via the controlled oxidation of MEH-PPV

Journal of Physical Chemistry B

Volumn 113, Issue 40, 2009, Pages 13216-13221

  Duncan, Timothy V ^a   Park, So Jung ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CONJUGATED POLYMERS; ETHYLENE; FLUOROPHORES; LIGHT EMISSION; OXIDATION;

DIOXYGENS; EMISSION WAVELENGTH; FLUORESCENCE QUANTUM YIELD; LIGHT EMITTING POLYMER; MEH-PPV; METHOXY; ORGANIC FLUOROPHORES; PHENYLENEVINYLENE; PRISTINE POLYMERS; REACTION TIME; WAVELENGTH RANGES;

POLYMERS;

3 CHLOROPERBENZOIC ACID; 3-CHLOROPERBENZOIC ACID; CHLOROBENZOIC ACID DERIVATIVE; FLUORESCENT DYE; OXIDIZING AGENT; POLY(2 METHOXY 5 (2' ETHYLHEXYLOXY) P PHENYLENEVINYLENE); POLY(2-METHOXY-5-(2'-ETHYLHEXYLOXY)-P-PHENYLENEVINYLENE); POLYMER; VINYL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COLOR; LIGHT; METHODOLOGY; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY;

CHLOROBENZOATES; COLOR; FLUORESCENT DYES; LIGHT; MOLECULAR STRUCTURE; OXIDANTS; OXIDATION-REDUCTION; PHOTOCHEMISTRY; POLYMERS; VINYL COMPOUNDS;

EID: 70349967671     PISSN: 15206106     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp907720a     Document Type: Article

References (52)

1. Lavigne, J. J.; Anslyn, E. V. Angew. Chem., Int. Ed. 2001, 40, 3118.
2. Zhang, J.; Campbell, R. E.; Ting, A. Y.; Tsien, R. Y. Nat. Rev. Mol. Cell. Biol. 2002, 3, 906.
3. Frangioni, J. V. Curr. Opin. Chem. Biol. 2003, 7, 626.
4. Giepmans, B. N. G.; Adams, S. R.; Ellisman, M. H.; Tsien, R. Y. Science 2006, 312, 217.
5. Lakowicz, J. R. Principles of Fluorescence Spectroscopy, 3rd ed.; Springer: New York, 2006.
6. Rao, J.; Dragulescu-Andrasi, A.; Yao, H. Curr. Opin. Biotechnol. 2007, 18, 17.
7. Johnsson, N.; Johnsson, K. ACS Chem. Biol. 2007, 2, 31.
8. Lavis, L. D.; Raines, R. T. ACS Chem. Biol. 2008, 3, 142.
9. Tang, C. W.; Van Slyke, S. A. Appl. Phys. Lett. 1987, 51, 913.
10. Burroughes, J. H.; Bradley, D. D. C; Brown, A. R.; Marks, R. N.; Mackay, K.; Friend, R. H.; Burns, P. L.; Holmes, A. B. Nature 1990, 347, 539.
11. Friend, R. H.; Gymer, R. W.; Holmes, A. B.; Burroughes, J. H.; Marks, R. N.; Taliani, C; Bradley, D. D. C; Dos Santos, D. A.; Brédas, J. L.; Lögdlund, M.; Salaneck, W. R. Nature 1999, 397, 121.
12. Nalwa, H. S., Ed. Handbook of Luminescence, Display Materials and Devices; American Scientific Publishers: Los Angeles, CA, 2003; Vol.1-3.
13. Jaska, C. A.; Piers, W. E.; McDonald, R.; Parvez, M. J. Org. Chem. 2007, 72, 5234.
14. Murray, C. B.; Kagan, C. R.; Bawendi, M. G. Annu. Rev. Mater. Sci. 2000, 30, 545.
15. Hoshino, A.; Fujioka, K.; Oku, T.; Suga, M.; Sasaki, Y. F.; Ohta, T.; Yasuhara, M.; Suzuki, K.; Yamamoto, K. Nano Lett. 2004, 4, 2163.
16. Shiohara, A.; Hoshino, A.; Hanaki, K.; Suzuki, K.; Yamamoto, K. Microbiol. Immunol. 2004, 48, 669.
17. Derfus, A. M.; Chan, W. C. W.; Bhatia, S. N. Nano Lett. 2004, 4, 11.
18. Oberdörster, G.; Oberdörster, E.; Oberdörster, J. Environ. Health Perspect. 2005, 113, 823.
19. Hardman, R. Environ. Health Perspect. 2006, 114, 165.
20. Briehn, C. A.; Schiedel, M.-S.; Bonsen, E. M.; Schuhmann, W.; Bauerle, P. Angew. Chem., Int. Ed. 2001, 40, 4680.
21. Schiedel, M.-S.; Briehn, C. A.; Bauerle, P. Angew. Chem., Int. Ed. 2001, 40, 4677.
22. Lavastre, O.; Illitchev, I.; Jegou, G.; Dixneuf, P. H. J. Am. Chem. Soc. 2002, 124, 5278.
23. Zhu, Q.; Yoon, H.-S.; Parikh, P. B.; Chang, Y.-T.; Yao, S. Q. Tetrahedron Lett. 2002, 43, 5083.
24. Li, Q.; Lee, J.-S.; Ha, C; Park, C. B.; Yang, G.; Gan, W. B.; Chang, Y.-T. Angew. Chem., Int. Ed. 2004, 43, 6331.
25. Mello, J.; Finney, N. S. J. Am. Chem. Soc. 2005, 127, 10124.
26. Wang, S.; Chang, Y.-T. J. Am. Chem. Soc. 2006, 128, 10380.
27. An, Y.-H.; Lee, J.-S.; Chang, Y.-T. J. Am. Chem. Soc. 2007, 129, 4510.
28. Finney, N. S. Curr. Opin. Chem. Biol. 2008, 10, 238.
29. Kim, E.; Koh, M.; Ryu, J.; Park, S. B. J. Am. Chem. Soc. 2008, 130, 12206.
30. Andersson, M. R.; Berggren, M.; Inganäs, O.; Gustafsson, G.; Gustaffson-Carlberg, J. C; Seise, D.; Hjertberg, T.; Wennerström, O. Macromolecules 1995, 28, 7525.
31. Andersson, M. R.; Thomas, O.; Mammo, W.; Svensson, M.; Theander, M.; Inganäs, O. J. Mater. Chem. 1999, 9, 1933.
32. Perepichka, I. F.; Perepichka, D. F.; Meng, H.; Wudl, F. Adv. Mater. 2005, 17, 2281.
33. Turro, N. J. Modern Molecular Photochemistry; University Science Books: Sausolito, CA, 1991.
34. Kubin, R. F.; Fletcher, A. N. J. Lumin. 1982, 27, 455.
35. Jones, G.; Rahman, M. A. J. Phys. Chem. 1994, 98, 13028.
36. Reynolds, G. A.; Drexhage, K. H. Opt. Commun. 1975, 13, 222.
37. The additional samples were the aliquots removed from the 0.7 mM m-CPBA experiment shown in Figure 3A (blue triangles), which is discussed in section IIIC of this paper.
38. Kim, C; Traylor, T. G.; Perrin, C. L. J. Am. Chem. Soc. 1998, 120, 9513.
39. Solomons, T. W. G. Organic Chemistry, 6th ed.; John Wiley and Sons: New York, NY, 1996.
40. Lynch, B. M.; Pausacker, K. H. J. Chem. Soc. 1955, 1525.
41. Voss, K. F.; Foster, C. M.; Smilowitz, L.; Mihailović, D.; Askari, S.; Srdanov, G.; Ni, Z.; Shi, S.; Heeger, A. J.; Wudl, F. Phys. Rev. B 1991, 43, 5109.
42. Silvertein, R. M.; Webster, F. X. Spectroscopic Identification of Organic Compounds, 6th ed.; John Wiley and Sons, Inc.: New York, 1998.
43. The epoxide groups in these oxidized polymers are fairly stable, as the epoxide-derived peak is observed in the IR spectra several days after quenching the m-CPBA. In principle, exposure of the epoxide-elaborated polymers to acidic solutions or other nucleophiles could result in ring- opening reactions. However, we have observed no evidence of such reactions at ambient condition, and in any case, it is not anticipated that such reactions would significantly affect the optical properties of these polymers.
44. Papadimitrakopoulos, F.; Konstadinidis, K.; Miller, T. M.; Opila, R.; Chandross, E. A.; Galvin, M. E. Chem. Mater. 1994, 6, 1563.
45. Sarkas, H. W.; Kwan, W.; Flom, S. R.; Merritt, C. D.; Kafafi, Z. H. J. Phys. Chem. 1996, 100, 5169.
46. Meier, H.; Stalmach, U.; Kolshorn, H. Acta Polym. 1997, 48, 379.
47. Note that oligomeric model compounds can also be used to rationalize the QY trends observed in Figure ID. A brief explanation of this is provided in the Supporting Information.
48. Barbara, P. F.; Gesquire, A. J.; Park, S.-J.; Lee, Y. J. Acc. Chem. Res. 2005, 38, 602.
49. Berlman, I. B. Handbook of Fluorescence Spectra of Aromatic Molecules; Academic Press: New York, NY, 1965.
50. Nguyen, T.-Q.; Doan, V.; Schwartz, B. J. J. Chem. Phys. 1999, 110, 4068.
51. Traiphol, R.; Sanguansat, P.; Srikhirin, T.; Kerdcharoen, T.; Osotchan, T. Macromolecules 2006, 39, 1165.
52. Schwartz, B. J. Annu. Rev. Phys. Chem. 2003, 54, 141.