Highly ordered merocyanine dye assemblies by supramolecular polymerization and hierarchical self-organization

Angewandte Chemie - International Edition

Volumn 42, Issue 28, 2003, Pages 3247-3250

  Würthner, Frank ^a   Yao, Sheng ^a,c   Beginn, Uwe ^b  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b RWTH AACHEN UNIVERSITY   (Germany)

^c UNIVERSITY OF CENTRAL FLORIDA   (United States)

Author keywords

Aggregation; Dyes pigments; Polymethines; Self assembly; Supramolecular polymers

Indexed keywords

CHROMOPHORES; GELS; LIQUID CRYSTALS; POLYMERIZATION; SUPRAMOLECULAR CHEMISTRY;

SUPERSTRUCTURES;

DYES;

BIS(MEROCYANINE); CARBON TETRACHLORIDE; CHLOROPHYLL; DIOXANE; DYE; MEROCYANINE; POLYMER; SOLVENT; TRICHLOROETHYLENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL INTERACTION; CHROMATOPHORE; CONFORMATION; DIMERIZATION; DIPOLE; ELECTRON TRANSPORT; GEL; LIQUID CRYSTAL; MACROMOLECULE; PHOTOSYNTHESIS; POLARIZATION; POLYMERIZATION; SCHEIE SYNDROME; SUPRAMOLECULAR CHEMISTRY; VISCOSITY; X RAY DIFFRACTION;

EID: 0042768525     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200351414     Document Type: Article

References (32)

1. R. Huber, Angew. Chem. 1989, 101, 849-871; Angew. Chem. Int. Ed. Engl. 1989, 28, 848-869.
2. R. Huber, Angew. Chem. 1989, 101, 849-871; Angew. Chem. Int. Ed. Engl. 1989, 28, 848-869.
3. T. Pullerits, V. Sundstöm, Acc. Chem. Res. 1999, 29, 381-389.
4. A. R. Holzwarth, M. Katterle, M. G. Müller, Y.-Z. Ma, V. I. Prokhorenko, Pure Appl. Chem. 2001, 73, 469-474.
5. a) G. M. Whitesides, J. P. Matthias, C. T. Seto, Science 1991, 254, 1312-1319;
6. b) J.-M. Lehn, Science 2002, 295, 2400-2403;
7. c) O. Ikkala, G. ten Brinke, Science 2002, 295, 2407-2409.
8. a) H. Engelkamp, S. Middelbeck, R. J. M. Nolte, Science 1999, 284, 785-788;
9. b) E S. Schoonbeek, J. H. van Esch, B. Wegewijs, D. B. A. Rep, M. P. de Haas, T. M. Klapwijk, R. M. Kellogg, B. L. Feringa, Angew. Chem. 1999, 111, 1486-1490; Angew. Chem. Int. Ed. 1999, 38, 1393-1397;
10. b) E S. Schoonbeek, J. H. van Esch, B. Wegewijs, D. B. A. Rep, M. P. de Haas, T. M. Klapwijk, R. M. Kellogg, B. L. Feringa, Angew. Chem. 1999, 111, 1486-1490; Angew. Chem. Int. Ed. 1999, 38, 1393-1397;
11. c) F. Würthner, C. Thalacker, A. Sautter, Adv. Mater. 1999, 11, 754-758;
12. d) A. P, H. J. Schenning, P. Jonkheijm, E. Peeters, E. W. Meijer, J. Am. Chem. Soc, 2001, 123, 409-416;
13. e) A. Ajayaghosh, S. J. George, J. Am. Chem. Soc. 2001, 123, 5148-5149.
14. a) C. F. van Nostrum, Adv. Mater. 1996, 8, 1027-1030;
15. b) J. Vacus, J. Simon, Adv, Mater. 1995, 7, 797-800;
16. c) F. Würthner, C. Thalacker, S. Diele, C. Tschierske, Chem. Eur. J. 2001, 7, 2245-2253.
17. a) E. Jelley, Nature 1936, 138, 1009;
18. b) G. Scheibe Angew. Chem. 1936, 49, 563-563;
19. c) D. Möbius, Adv. Mater. 1995, 7, 437-444;
20. d) A. Mishra, R, K. Behera, P. K. Behera, B. K. Mishra, G. B. Behera, Chem. Rev. 2000, 100, 1973-2011;
21. e) A. Pawlik, S. Kirstein, U. De Rossi, S. Dähne, J. Phys. Chem. B 1997, 101, 5646-5651;
22. f) H. von Berlepsch, C. Böttcher, L. Dähne, J. Phys. Chem. B 2000, 104, 8792-8799.
23. Merocyanine dye aggregates have been observed before in water and on surfaces. However, the structural properties of these aggregates remained unclear and their formation was attributed to a different kind of intermolecular interaction, that is, dispersion forces as for cationic cyanine dye aggregates: M. Kussler, H. Balli, Helv. Chim. Acta 1989, 72, 17-28.
24. a) F. Dietz, J. Signalaufzeichnungsmater. 1973, 3, 157-180;
25. b) A. H. Herz, Adv. Colloid and Interface Science 1977, 8, 237-298.
26. L. Brunsveld, B. J. B. Folmer, E. W. Meijer, R. P. Sijbesma, Chem. Rev. 2001, 101, 4071-4097.
27. F. Würthner, S. Yao, T. Debaerdemaeker, R. Wortmann, J. Am. Chem. Soc, 2002, 124, 9431-9447.
28. 1H NMR spectroscopy, mass spectrometry, and elemental analysis.
29. The formation of the D band could be also related to the formation of a cyclic oligomeric aggregate that opens to the extended polymeric form upon further self-assembly to the H-aggregated state. For concentration-dependent equilibria between supramolecular polymers and cycles, see a) X. Chi, A. J. Guerin, R. A. Haycock, C. A. Hunter, L. D. Sarson, J. Chem. Soc. Chem. Commun. 1995, 2563-2565;
30. b) G. Ercolani, J. Phys. Chem. B 1998, 102, 5699-5703;
31. c) G. Ercolani, M. Ioele, D. Monti, New. J. Chem. 2001, 25, 783-789.
32. Ka radiation) at 2Θ = 2.35° (100), 4.06° (110), 4.67° (200), 8.04° (220), 7.01° (300), 8.36° (310), and 12.23° (330) provide evidence for an ordered hexagonal lattice composed of rods of 4.34 nm diameter. We note that the resolution of the TEM micrograph provides only an upper limit of 15 nm for these rods.