Pyrene as chromophore and electrophore: Encapsulation in a rigid polyphenylene shell

Chemistry - A European Journal

Volumn 12, Issue 23, 2006, Pages 6117-6128

  Bernhardt, Stefan ^a   Kastler, Marcel ^a   Enkelmann, Volker ^a   Baumgarten, Martin ^a   Müllen, Klaus ^a  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

Author keywords

Dendrimers; EPR spectroscopy; Fluorescence; Pyrenes; Substituent effects

Indexed keywords

CHROMOPHORES; ENCAPSULATION; FLUORESCENCE; GROWTH KINETICS; PARAMAGNETIC RESONANCE; QUANTUM EFFICIENCY;

ALKYL CHAINS; EPR SPECTROSCOPY; PYRENES; SUBSTITUENT EFFECTS;

DENDRIMERS;

EID: 33747183916     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200500999     Document Type: Article

References (69)

1. a) I. Carmichael, G. L. Hug, Handbook of Photochemistry, 2nd ed., Marcel Dekker, New York, 1993;
2. b) J. B. Birks, Photophysics of Aromatic Molecules, Wiley Interscience, London, 1970.
3. a) E. M. S. Castanheira, J. M. G. Martinho, Chem. Phys. Lett. 1991, 185, 319-323;
4. b) D. C. Dong, M. A. Winnik, Can. J. Chem. 1984, 62, 2560-2565.
5. A. Thomas, S. Polarz, M. Antonietti, J. Phys. Chem. B 2003, 107, 5081-5087.
6. a) C. M. Cardona, T. Wilkes, W. Ong, A. E. Kaifer, T. D. McCarley, S. Pandey, G. A. Baker, M. N. Kane, S. N. Baker, F. V. Bright, J. Phys. Chem. B 2002, 106, 8649-8656;
7. b) S. Hecht, N. Vladimirov, J. M. J. Fréchet, J. Am. Chem. Soc. 2001, 123, 18-25;
8. c) L. A. Baker, R. M. Crooks, Macromolecules 2000, 33, 9034-9039;
9. d) R. Wilken, J. Adams, Macromol. Rapid Commun. 1997, 18, 659-665.
10. For OLEDs in general see, for example: a) A. P. Kulkarni, C. J. Tonzola, A. Babel, S.A. Jenekhe, Chem. Mater. 2004, 16, 4556-4573;
11. b) L. S. Hung, C.H. Chen, Mater. Sci. Eng. R 2002, 39, 143-222;
12. c) M. T. Bernius, M. Inbasekaran, J. O'Brien, W. S. Wu, Adv. Mater. 2000, 12, 1737-1750;
13. d) Y. Cao, I. D. Parker, G. Yu, C. Zhang, A. J. Heeger, Nature 1999, 397, 414-417. For pyrene containing devices, see:
14. e) W. L. Jia, T. McCormick, Q. D. Liu, H. Fukutani, M. Motala, R. Y. Wang, Y. Tao, S. N. Wang, J. Mater. Chem. 2004, 14, 3344-3350;
15. f) V. Cimrová, D. Výprachtický, Appl. Phys. Lett. 2003, 82, 642-644;
16. g) Y. Aso, T. Okai, Y. Kawaguchi, T. Otsubo, Chem. Lett. 2001, 420-421.
17. a) M. Wind, U. M. Wiesler, K. Saalwächter, K. Müllen, H. W. Spiess, Adv. Mater. 2001, 13, 752-756;
18. b) H. Zhang, P. C. M. Grim, P. Foubert, T. Vosch, P. Vanoppen, U.M. Wiesler, A.J. Berresheim, K. Müllen, F. C. De Schryver, Langmuir 2000, 16, 9009-9014;
19. c) S. Rosenfeldt, N. Dingenouts, D. Potschke, M. Ballauff, A. J. Berre sheim, K. Müllen, P. Lindner, Angew. Chem. 2003, 115, 111-114;
20. Angew. Chem. Int. Ed. 2004, 43, 109-112;
21. d) M. Wind, K. Saalwächter, U.M. Wiesler, K. Müllen, H.W. Spiess, Macromolecules 2002, 35, 10071-10086.
22. a) D. J. Liu, S. De Feyter, M. Cotlet, A. Stefan, U. M. Wiesler, A. Herrmann, D. Grebel-Koehler, J. Q. Qu, K. Müllen, F. C. De Schryver, Macromolecules 2003, 36, 5918-5925;
23. b) A. Herrmann, T. Weil, V. Sinigersky, U. M. Wiesler, T. Vosch, J. Hofkens, F. C. De Schryver, K. Müllen, Chem. Eur. J. 2001, 7, 4844-4853.
24. a) J. N. G. Pillow, M. Halim, J. M. Lupton, P. L. Burn, I. D. W. Samuel, Macromolecules 1999, 32, 5985-5993;
25. b) P.W. Wang, Y. J. Liu, C. Devadoss, P. Bharathi, J. S. Moore, Adv. Mater. 1996, 8, 237.
26. J. Q. Qu, D. J. Liu, S. De Feyter, J. Y. Zhang, F. C. De Schryver, K. Müllen, J. Org. Chem. 2003, 68, 9802-9808.
27. a) E. M. Harth, S. Hecht, B. Helms, E. E. Malmström, J. M. J. Frechet, C. J. Hawker, J. Am. Chem. Soc. 2002, 124, 3926-3938;
28. b) V. Rozhkov, D. Wilson, S. Vinogradov, Macromolecules 2002, 35, 1991-1993.
29. C. B. Gorman, J. C. Smith, M. W. Hager, B. L. Parkhurst, H. Sierzputowska-Gracz, C. A. Haney, J. Am. Chem. Soc. 1999, 121, 9958-9966.
30. a) K. Ogino, S. Iwashima, H. Inokuchi, Y. Harada, Bull. Chem. Soc. Jpn. 1965, 38, 473-477;
31. b) Vollmann, Liebigs Ann. Chem. 1937, 531, 1.
32. a) Y. F. Wang, W. Deng, L. Liu, Q. X. Quo, Chin. J. Org. Chem. 2005, 25, 8-24;
33. b) K. Sonogashira, S. Takahashi, J. Synth. Org. Chem. Jpn. 1993, 51, 1053-1063;
34. c) H. A. Dieck, F. R. Heck, J. Organomet. Chem. 1975, 93, 259-263.
35. a) U. M. Wiesler, T. Weil, K. Müllen, Top. Curr. Chem. 2001, 272, 1-40;
36. b) F. Morgenroth, E. Reuther, K. Müllen, Angew. Chem. 1997, 109, 647-649;
37. Angew. Chem. Int. Ed. Engl. 1997, 36, 631-634.
38. F. Morgenroth, K. Müllen, Tetrahedron 1997, 55, 15349-15366.
39. U. M. Wiesler, K. Müllen, Chem. Commun. 1999, 2293-2294.
40. W. Pisula, M. Kastler, D. Wasserfallen, T. Pakula, K. Müllen, J. Am. Chem. Soc. 2004, 126, 8074-8075.
41. R.E. Bauer, V. Enkelmann, U.M. Wiesler, A.J. Berresheim, K. Müllen, Chem. Eur. J. 2002, 8, 3858-3864.
42. CCDC-285925 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_ request/cif.
43. max em and corresponding molar extinction coefficients e for unsubstituted pyrene and the dendronized pyrenes are given in the Supporting Information.
44. I. B. Berlman, J. Phys. Chem. 1970, 74, 3085-3093.
45. Extinction coefficients are in line with values reported by others: a) F. M. Winnik, M. A. Winnik, S. Tazuke, C. K. Ober, Macromolecules 1987, 20, 38-44;
46. b) K. Kara, W. R. Ware, Chem. Phys. 1980, 57, 61-68.
47. f: 0.90, solvent: cyclohexane, excitation wavelength: 350 nm.
48. D. C. Dong, M. A. Winnik, Can. J. Chem. 1984, 62, 2560-2565.
49. a) M. Stepanek, K. Krijtova, K. Prochazka, Y. Teng, S. E. Webber, P. Munk, Acta Polym. 1998, 49, 96-102;
50. b) M. Stepanek, K. Krijtova, Z. Limpouchova, K. Prochazka, Y. Teng, P. Munk, S. E. Webber, Acta Polym. 1998, 49, 103-107.
51. T. Förster, Angew. Chem. 1969, 81, 364-374;
52. Angew. Chem. Int. Ed. Engl. 1969, 8, 333-343.
53. T. Keeling-Tucker, J. D. Brennan, Chem. Mater. 2001, 13, 3331-3350.
54. Compound 10 was chosen instead of 6 due to its better solubility. The peripheral ethynyl groups were not expected to significantly enlarge the dendrimer dimensions. The absorption maxima of 10 and lia did not shift with increasing temperature.
55. a) J. Zhang, R. E. Campbell, A. Y. Ting, R. Y. Tsien, Nat. Rev. Mol. Cell Biol. 2002, 3, 906-918;
56. b) D. L. Taylor, Y. L. Wang, Nature 1980, 284, 405-410.
57. M. Baumgarten, K. Müllen, Top. Curr. Chem. 1994, 169, 1-103.
58. K. H. J. Buschow, J. Dieleman, G. J. Hoijtink, J. Chem. Phys. 1965, 42, 1993-1998.
59. I. C. Lewis, L. S. Singer, J. Chem. Phys. 1965, 43, 2712-2727.
60. For ease of comparison the EPR spectra of 7, lia, and 21 are collected in the Supporting Information.
61. R. Pilot, E. Fron, F. C. De Schryver, Katholieke Universiteit Leuven (Belgium), personal communication.
62. -1.
63. U. M. Wiesler, Dissertation, Johannes Gutenberg Universität Mainz (Germany), 2001.
64. Distances were derived from three-dimensional structures calculated by the MMFF method. T. A. Halgren, J. Comput. Chem. 1996, 17, 490-519.
65. a)T. Shida, S. Iwata, J. Am. Chem. Soc. 1973, 95, 3473-3483;
66. b) D. F. Lindow, C. N. Cortez, R. G. Harvey, J. Am. Chem. Soc. 1972, 94, 5406;
67. c) T. Shida, S. Iwata, J. Chem. Phys. 1972, 56, 2858;
68. T. Shida, S. Iwata, J. Phys. Chem. 1971, 75, 2591;
69. e) P. Balk, S. Debruijn, G. J. Hoijtink, Reel. Trav. Chim. Pays-Bas 1957, 76, 907-918.