Supramolecular p-n-heterojunctions by co-self-organization of oligo(p-phenylene vinylene) and perylene bisimide dyes

Journal of the American Chemical Society

Volumn 126, Issue 34, 2004, Pages 10611-10618

  Würthner, Frank ^a   Chen, Zhijian ^a   Hoeben, Freek J M ^b   Osswald, Peter ^a   You, Chang Cheng ^a   Jonkheijm, Pascal ^b   Herrikhuyzen, Jeroen V ^b   Schenning, Albertus P H J ^b   Van Der Schoot, Paul P A M ^b   Meijer, E W ^b   Beckers, Edwin H A ^b   Meskers, Stefan C J ^b   Janssen, René A J ^b  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ARRAYS; DYES; ELECTRONS; HETEROJUNCTIONS; HYDROGEN BONDS; SPECTROSCOPIC ANALYSIS;

HYDROGEN-BONDED ARRAYS; METHYLCYCLOHEXANE; PHOTOINDUCED ELECTRON TRANSFER; SUBPICOSECOND TIME SCALE;

SUPRAMOLECULAR CHEMISTRY;

DYE; HEXANE; METHYLCYCLOHEXANE; OLIGO(4 PHENYLENE VINYLENE); PERYLENE; PERYLENE BISIMIDE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; ATOMIC FORCE MICROSCOPY; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; COVALENT BOND; ELECTRON TRANSPORT; HYDROGEN BOND; MOLECULAR STABILITY; SOLID STATE; STRUCTURE ANALYSIS; SUPRAMOLECULAR CHEMISTRY;

EID: 4344627317     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0475353     Document Type: Article

References (58)

1. (a) Scheibe, G. Angew. Chem. 1936, 49, 563.
2. (b) Scheibe, G. Angew. Chem. 1937, 50, 212-219.
3. (c) Jelley, E. Nature 1936, 138, 1009-1010.
4. (a) Wolthaus, L.; Schaper, A.; Möbius, D. Chem. Phys. Lett. 1994, 225, 322-326.
5. (b) Koti, A. S. R.; Periasamy, N. J. Mater. Chem. 2002, 12, 2313-2317 and references therein.
6. Adam, D.; Schuhmacher, P.; Simmerer, J.; Häussling, L.; Siemensmeyer, K.; Etzbach, K.-H.; Ringsdorf, H.; Haarer, D. Nature 1994, 371, 141-143.
7. Schenning, A. P. H. J.; Benneker, F. B. G.; Geurts, H. P. M.; Liu, X. Y.; Nolte, R. J. M. J. Am. Chem. Soc. 1996, 118, 8549-8552.
8. (a) van Nostrum, C. F.; Picken, S. J.; Schouten, A.-J.; Nolte, R. J. M. J. Am. Chem. Soc. 1995, 117, 9957-9965.
9. (b) Engelkamp, H.; Middelbeek, S.; Nolte, R. J. M. Science 1999, 284, 785-788.
10. Law, K.-Y. Chem. Rev. 1993, 93, 449-486.
11. (a) Chen, L.; McBranch, D. W.; Wang, H.-L.; Helgeson, R.; Wudl, F.; Whitten, D. G. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 12287-12292.
12. (b) Jones, R. M.; Lu, L.; Helgeson, R.; Bergstedt, T. S.; McBranch, D. W.; Whitten, D. G. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 14769-14772.
13. (a) Würthner, F. Angew. Chem., Int. Ed. 2001, 40, 1037-1039.
14. (b) Kraft, A. ChemPhysChem 2001, 2, 163-165.
15. Wöhrle, D.; Meissner, D. Adv. Mater. 1991, 3, 129-138.
16. Hagfeld, A.; Grätzel, M. Acc. Chem. Res. 2000, 33, 269-277.
17. (a) Nelson, J. Curr. Opin. Solid State Mater. Sci. 2002, 6, 87-95.
18. (b) Brabec, C. J.; Winder, C.; Sariciftci, N. S.; Hummelen, J. C.; Dhanabalan, A.; van Hal, P. A.; Janssen, R. A. J. Adv. Funct. Mater. 2002, 12, 709-712.
19. (a) Schmidt-Mende, L.; Fechtenkötter, A.; Müllen, K.; Moons, E.; Friend, R. H.; MacKenzie, J. D. Science 2001, 293, 1119-1122.
20. For other works on organic solar cell that apply perylene bisimide dyes, see: (b) Tang, C. W. Appl. Phys. Lett. 1986, 48, 183-185.
21. (c) Breeze, A. J.; Salomon, A.; Ginley, D. S.; Gregg, B. A.; Tillmann, H.; Hörhold, H.-H. Appl. Phys. Lett. 2002, 81, 3085-3087.
22. (d) Park, L. Y.; Hamilton, D. G.; McGehee, E. A.; McMenimen, K. A. J. Am. Chem. Soc. 2003, 125, 10586-10590.
23. A short communication of this work has been published: Schenning, A. P. H. J.; van Herrikhuyzen, J.; Jonkbeijm, P.; Chen, Z.; Würthner, F.; Meijer, E. W. J. Am. Chem. Soc. 2002, 124, 10252-10253.
24. (a) Schenning, A. P. H. J.; Jonkheijm, P.; Peeters, E.; Meijer, E. W. J. Am. Chem. Soc. 2001, 123, 409-416.
25. (b) El-ghayoury, A.; Schenning, A. P. H. J.; van Hal, P. A.; van Duren, J. K. J.; Janssen, R. A. J.; Meijer, E. W. Angew. Chem., Int. Ed. 2001, 40, 3660-3663.
26. (c) Jonkheijm, P.; Hoeben, F. J. M.; Kleppinger, R.; van Herrikhuyzen, J.; Schenning, A. P. H. J.; Meijer, E. W. J. Am. Chem. Soc. 2003, 125, 15941-15949.
27. (d) Jonkheijm, P.; Miura, A.; Zdanowska, M.; Hoeben, F. J. M.; de Feyter, S.; Schenning, A. P. H. J.; de Schryver, F.; Meijer, E. W. Angew. Chem., Int. Ed. 2004, 43, 74-78.
28. (a) Würthner, F.; Thalacker, C.; Sautter, A. Adv. Mater. 1999, 11, 754-758.
29. (b) Würthner, F.; Thalacker, C.; Sautter, A.; Schärtl, W.; Ibach, W.; Hollricher, O. Chem.-Eur. J. 2000, 6, 3871-3885.
30. (c) Würthner, F.; Thalacker, C.; Diele, S.; Tschierske, C. Chem.-Eur. J. 2001, 7, 2245-2253.
31. (d) Thalacker, C.; Würthner, F. Adv. Funct. Mater. 2002, 12, 209-218.
32. (e) Sautter, A.; Thalacker, C.; Heise, B.; Würthner, F. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4993-4996.
33. (f) Würthner, F. Chem. Commun. 2004, 1564-1579.
34. Piotrowiak, P. Chem. Soc. Rev. 1999, 28, 143-150.
35. (a) Miura, A.; Chen, Z.; Uji-i, H.; De Feyter, S.; Zdanowska, M.; Jonkheijm, P.; Schenning, A. P. H. J.; Meijer, E. W.; Würthner, F.; de Schryver, F. J. Am. Chem. Soc. 2003, 125, 14968-14969.
36. (b) Beckers, E. H. A.; Meskers, S. C. J.; Schenning, A. P. H. J.; Chen, Z.; Würthner, F.; Janssen, R. A. J. J. Phys. Chem. A, published online Aug 3, 2004. http://dx.doi.org/10.1021/ jp048980n.
37. Hirschberg, J. H. K. K.; Ramzi, A.; Sijbesma, R. P.; Meijer, E. W. Macromolecules 2003, 36, 1429-1432.
38. Gvishi, R.; Reisfeld, R.; Burshtein, Z. Chem. Phys. Lett. 1993, 213, 338-344.
39. (a) Martin, R. B. Chem. Rev. 1996, 96, 3043-3064.
40. (b) Baxter, N. J.; Williamson, M. P.; Lilley, T. H.; Haslan, E. J. Chem. Soc., Faraday Trans. 2 1996, 92, 231-234.
41. Peeters, E.; van Hal, P. A.; Meskers, S. C. J.; Janssen, R. A. J.; Meijer, E. W. Chem.-Eur. J. 2002, 8, 4470-4474.
42. Reichardt, C. Chem. Rev. 1994, 94, 2319-2358.
43. 3 was determined for 1b and a related diimide acceptor, e.g., N-(2,5-di-tert-butylphenyl)-1,8-dicarboxy-N′-hydrogen-4,5- dicarboxy-naphthalenediimide.
44. (a) Czikkely, V.; Försterling, H. D.; Kuhn, H. Chem. Phys. Lett. 1970, 6, 11-14; 207-210.
45. (b) Bohn, P. W. Annu. Rev. Phys. Chem. 1993, 44, 37-60.
46. (c) J-Aggregates; Kobayashi, T., Ed.; World Scientific: Singapore, 1996.
47. Kasha, M.; Rawls, H. R.; El-Bayoumi, M. A. Pure. Appl. Chem. 1965, 11, 371-392.
48. West, W.; Pearce, S. J. Phys. Chem. 1965, 69, 1894-1903.
49. However, the aggregation strength of 4 is higher than that of 5-2-5, which might be explained in terms of the different aliphatic chains of the trialkoxybenzene wedges used. For π-π interactions of water soluble derivatives of parent perylene bisimide, see: (a) Wang, W.; Han, J. J.; Wang, L.-Q.; Li, L.-S.; Shaw, W. J.; Li, A. D. Q. Nano Lett. 2003, 3, 455-458.
50. (b) Wang, W.; Li, L.-S.; Helms, G.; Zhou, H.-H.; Li, A. D. Q. J. Am. Chem. Soc. 2003, 125, 1120-1121.
51. (c) Wang, W.; Wan, W.; Zhou, H.-H.; Niu, S.; Li, A. D. Q. J. Am. Chem. Soc. 2003, 125, 5248-5249.
52. van der Schoot, P.; Michels, M. A J.; Brunsveld, L.; Sijbesma, R. P.; Ramzi, A. Langmuir 2000, 16, 10076-10083.
53. The crystal structure of a tetrachloro-substituted perylene bisimide with 4-dodecylphenyl substituents at imide N atoms shows an average torsion angle of 79° between the plane of the phenyl groups and the imide units: Chen, Z.; Debije, M. G.; Debaerdemaeker, T.; Osswald, P.; Würthner, F. ChemPhysChem 2004, 5, 137-140.
54. Würthner, F.; Sautter, A.; Schilling, J. J. Org. Chem. 2002, 67, 3037-3044.
55. Langeveld-Voss, B. M. W.; Beljonne, D.;: Shuai, Z.; Janssen, R. A. J.; Meskers, S. C. J.; Meijer, E. W.; Brédas, J.-L. Adv. Mater. 1998, 10, 1343-1348.
56. Harada, N.; Nakanishi, K. Circular Dichroism Spectroscopy; Oxford University Press: Oxford, 1983.
57. Stacking model studies show that owing to the steric effect of the bay-substituents, for M enantiomers a left-handed and for P enantiomers a right-handed helical stacking is preferred.
58. Samori, P.; Franke, V.; Mangel, T.; Müllen, K.; Rabe, J. Opt. Mater. 1998, 9, 390-394.