Dipolar dye aggregates: A problem for nonlinear optics, but a chance for supramolecular chemistry

Angewandte Chemie - International Edition

Volumn 39, Issue 11, 2000, Pages 1978-1981

  Würthner, Frank ^a   Yao, Sheng ^a  

^a UNIVERSITY OF ULM   (Germany)

Author keywords

Aggregations; Dyes; Noncovalent interactions; Nonlinear optics; Supramolecular chemistry

Indexed keywords

DYE;

ARTICLE; CHEMICAL STRUCTURE; ELECTRON DIFFRACTION; ORGANIC CHEMISTRY; PHOTODYNAMICS; POLARIMETRY; REACTION ANALYSIS; SYNTHESIS;

EID: 0039001658     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000602)39:11<1978::AID-ANIE1978>3.0.CO;2-0     Document Type: Article

References (37)

1. a) J. J. Wolff, R. Wortmann, Adv. Phys. Org. Chem. 1999, 32, 121-217;
2. b) T. Verbiest, S. Houbrechts, M. Kauranen, K. Clays, A. Persoons, J. Mater. Chem. 1997, 7, 2175-2189;
3. c) D. R. Kanis, M. A. Ratner, T. J. Marks, Chem. Rev. 1994, 94, 191-242.
4. a) C. Bosshard, F. Pan, M. S. Wong, S. Manetta, R. Spreiter, C. Cai, P. Günter, V. Gramlich, Chem. Phys. 1999, 245, 377-394;
5. b) S. Yitzchaik, S. Di Bella, P. M. Lundquist, G. K. Wong, T. J. Marks, J. Am. Chem. Soc. 1997, 119, 2995-3002;
6. c) P. J. A. Kenis, O. F. J. Noordman, H. Schönherr, E. G. Kerver, B. H. M. Snellink-Ruel, G. J. van Hummel, S. Harkema, C. P. J. M. van der Vorst, J. Hare, S. J. Picken, J. F. J. Engbersen, N. F. van Hulst, G. J. Vansco, D. N. Reinhoudt, Chem. Eur. J. 1998, 4, 1225-1234.
7. a) D. M. Burland, R. D. Miller, C. A. Walsh, Chem. Rev. 1994, 94, 31-75;
8. b) H.-T. Man, H. N. Yoon, Adv. Mater. 1992, 4, 159-168.
9. a) W. E. Moerner, S. M. Silence, Chem. Rev. 1994, 94, 127-155;
10. b) K. Meerholz, Angew. Chem. 1997, 109, 981-985; Angew. Chem. Int. Ed. Engl. 1997, 36, 945-948.
11. b) K. Meerholz, Angew. Chem. 1997, 109, 981-985; Angew. Chem. Int. Ed. Engl. 1997, 36, 945-948.
12. a) M. Dörr, R. Zentel, R. Dietrich, K. Meerholz, C. Bräuchle, J. Wichern, S. Zippel, P. Boldt, Macromolecules 1998, 31, 1454-1465;
13. b) R. Hagen, O. Zobel, O. Sahr, M. Biber, M. Eckl, P. Strohriegl, C.-D. Eisenbach, D. Haarer, J. Appl. Phys. 1996, 80, 3162-3166;
14. c) It may be assumed that many studies have not been published if aggregation led to completely inactive materials. This was also the case for a number of polymers based on azo and methine dyes in our own earlier work.
15. a) L. R. Dalton, A. W. Harper, B. H. Robinson, Proc. Natl. Acad. Sci. USA 1997, 94, 4842-4847;
16. b) T. Katoh, Y. Inagaki, R. Okazaki, J. Am. Chem. Soc. 1998, 120, 3623-3628.
17. a) C. P. J. M. van der Vorst, S. J. Picken in Polymers as electrooptical and photooptical active media (Ed.: V. P. Shibaev), Springer, Berlin, 1996, pp. 173-211;
18. b) C. F. J. Böttcher, Theory of electric polarization, Elsevier, New York, 1973.
19. a) S. Beckmann, K.-H. Etzbach, P. Krämer, K. Lukaszuk, R. Matschiner, A. J. Schmidt, P. Schuhmacher, R. Sens, G. Seybold, R. Wortmann, F. Würthner, Adv. Mater. 1999, 11, 536-541;
20. b) R. Wortmann, F. Würthner, A. Sautter, K. Lukaszuk, R. Matschiner, K. Meerholz, Proc. SPIE 1998, 3471, 41-49.
21. a) F. Würthner, R. Wortmann, R. Matschiner, K. Lukaszuk, K. Meerholz, Y. De Nardin, R. Bittner, C. Bräuchle, R. Sens, Angen. Chem. 1997, 109, 2933-2936; Angew. Chem. Int. Ed. Engl. 1997, 36, 2765-2768;
22. a) F. Würthner, R. Wortmann, R. Matschiner, K. Lukaszuk, K. Meerholz, Y. De Nardin, R. Bittner, C. Bräuchle, R. Sens, Angen. Chem. 1997, 109, 2933-2936; Angew. Chem. Int. Ed. Engl. 1997, 36, 2765-2768;
23. b) K. Meerholz, Y. De Nardin, R. Bittner, R. Wortmann, F. Würthner, Appl. Phys. Lett. 1998, 73, 4-6.
24. 1 in dioxane at 60 C using benzil for calibration) afforded a molecular weight of 950 for compound 1h (calculated for dimer: 955.4).
25. The small absorption hand which is revealed in the calculated spectrum of the dimer at longer wavelengths indicates a small deviation from parallelism, see M. Kasha, H. R. Rawls, M. Ashraf El-Bayoumi, Pure Appl. Chem. 1965, 11, 371-392.
26. F. Würthner, C. Thalacker, A. Sautter, Adv. Mater. 1999, 11, 754-758, and references therein.
27. 2 (477.7): C 75.43, H 9.07, N 8.80; found: C 75.13, H 8.80, N 8.84.
28. a) E. A. Guggenheim, Trans. Faraday Soc. 1949, 45, 714-720;
29. b) G. M. Janini, A. H. Katrib, J. Chem. Educ. 1983, 60, 1087-1088.
30. CAChe for Windows, Version 3.2, Oxford Molecular Group, Inc., USA, 1999.
31. C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, 2nd ed., VCH, Weinheim, 1990.
32. r because of a substantial quadrupole moment, see W. Baumann in Physical Methods of Chemistry, Vol. 3B (Eds.: B.W. Rossiter, J. F. Hamilton), Wiley, New York, 1989, p. 45.
33. a) A. H. Herz, Adv. Colloid Interface Sci. 1977, 8, 237-298;
34. b) D. Möbius, Adv. Mater. 1995, 7, 437-444;
35. c) H. Nakahara, K. Fukuda, D. Möbius, H. Kuhn, J. Phys. Chem. 1986, 90, 6144-6148;
36. d) F. Mizutani, S. Iijima, K. Tsuda, Bull. Chem. Soc. Jpn. 1982, 55, 1295-1299;
37. e) M. Kussler. H. Balli, Helv. Chim. Acta 1989, 72, 17-28.