Synthesis, (non)linear optical and redox properties of a donor- substituted truxenone derivative

Chemistry - A European Journal

Volumn 4, Issue 11, 1998, Pages 2129-2135

  Lambert, Christoph ^a   Nöll, Gilbert ^a   Schmälzlin, Elmar ^b   Meerholz, Klaus ^b   Bräuchle, Christoph ^b  

^a UNIVERSITY OF REGENSBURG   (Germany)

^b UNIVERSITY OF MUNICH   (Germany)

Author keywords

Cross coupling; Cyclic voltammetry; Cyclotrimerisation; Nonlinear optics; Semiempirical calculations

Indexed keywords

ARTICLE; ELECTROCHEMICAL ANALYSIS; OPTICS; OXIDATION REDUCTION POTENTIAL; OXIDATION REDUCTION REACTION; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 0031796720     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19981102)4:11<2129::AID-CHEM2129>3.0.CO;2-0     Document Type: Article

References (78)

1. For general introduction to nonlinear optics in organic materials, see: a) P. N. Prasad, D. J. Williams, Nonlinear Optical Effects in Molecules and Polymers, Wiley, New York, 1991; b) Principles and Applications of Nonlinear Optical Materials (Eds.: R. W. Munn, C. N. Ironside) Blackie Academic and Professional, Glasgow, 1993; c) Nonlinear Optics of Organic Molecules and Polymers (Eds.: H. S. Nalwa, S. Miyata) CRC, Boca Raton. 1997; d) T. J. Marks, M. A. Ratner, Angew. Chem. 1995, 107, 167; Angew. Chem. Int. Ed. Engl 1995, 34, 155; e) N. J. Long, Angew. Chem. 1995, 107, 37; Angew. Chem. Int. Ed. Engl. 1995, 34.905; f) C. Bosshard, K. Sutler. P. Prêtre, J. Hulliger, M. Flörsheimer, P. Kaatz, P. Günther, Organic Nonlinear Optical Materials, Gordon and Breach, Basel, 1995; g) S. R. Marder, J. W. Perry, Adv. Mater. 1993, 5, 804.
2. For general introduction to nonlinear optics in organic materials, see: a) P. N. Prasad, D. J. Williams, Nonlinear Optical Effects in Molecules and Polymers, Wiley, New York, 1991; b) Principles and Applications of Nonlinear Optical Materials (Eds.: R. W. Munn, C. N. Ironside) Blackie Academic and Professional, Glasgow, 1993; c) Nonlinear Optics of Organic Molecules and Polymers (Eds.: H. S. Nalwa, S. Miyata) CRC, Boca Raton. 1997; d) T. J. Marks, M. A. Ratner, Angew. Chem. 1995, 107, 167; Angew. Chem. Int. Ed. Engl 1995, 34, 155; e) N. J. Long, Angew. Chem. 1995, 107, 37; Angew. Chem. Int. Ed. Engl. 1995, 34.905; f) C. Bosshard, K. Sutler. P. Prêtre, J. Hulliger, M. Flörsheimer, P. Kaatz, P. Günther, Organic Nonlinear Optical Materials, Gordon and Breach, Basel, 1995; g) S. R. Marder, J. W. Perry, Adv. Mater. 1993, 5, 804.
3. For general introduction to nonlinear optics in organic materials, see: a) P. N. Prasad, D. J. Williams, Nonlinear Optical Effects in Molecules and Polymers, Wiley, New York, 1991; b) Principles and Applications of Nonlinear Optical Materials (Eds.: R. W. Munn, C. N. Ironside) Blackie Academic and Professional, Glasgow, 1993; c) Nonlinear Optics of Organic Molecules and Polymers (Eds.: H. S. Nalwa, S. Miyata) CRC, Boca Raton. 1997; d) T. J. Marks, M. A. Ratner, Angew. Chem. 1995, 107, 167; Angew. Chem. Int. Ed. Engl 1995, 34, 155; e) N. J. Long, Angew. Chem. 1995, 107, 37; Angew. Chem. Int. Ed. Engl. 1995, 34.905; f) C. Bosshard, K. Sutler. P. Prêtre, J. Hulliger, M. Flörsheimer, P. Kaatz, P. Günther, Organic Nonlinear Optical Materials, Gordon and Breach, Basel, 1995; g) S. R. Marder, J. W. Perry, Adv. Mater. 1993, 5, 804.
4. For general introduction to nonlinear optics in organic materials, see: a) P. N. Prasad, D. J. Williams, Nonlinear Optical Effects in Molecules and Polymers, Wiley, New York, 1991; b) Principles and Applications of Nonlinear Optical Materials (Eds.: R. W. Munn, C. N. Ironside) Blackie Academic and Professional, Glasgow, 1993; c) Nonlinear Optics of Organic Molecules and Polymers (Eds.: H. S. Nalwa, S. Miyata) CRC, Boca Raton. 1997; d) T. J. Marks, M. A. Ratner, Angew. Chem. 1995, 107, 167; Angew. Chem. Int. Ed. Engl 1995, 34, 155; e) N. J. Long, Angew. Chem. 1995, 107, 37; Angew. Chem. Int. Ed. Engl. 1995, 34.905; f) C. Bosshard, K. Sutler. P. Prêtre, J. Hulliger, M. Flörsheimer, P. Kaatz, P. Günther, Organic Nonlinear Optical Materials, Gordon and Breach, Basel, 1995; g) S. R. Marder, J. W. Perry, Adv. Mater. 1993, 5, 804.
5. For general introduction to nonlinear optics in organic materials, see: a) P. N. Prasad, D. J. Williams, Nonlinear Optical Effects in Molecules and Polymers, Wiley, New York, 1991; b) Principles and Applications of Nonlinear Optical Materials (Eds.: R. W. Munn, C. N. Ironside) Blackie Academic and Professional, Glasgow, 1993; c) Nonlinear Optics of Organic Molecules and Polymers (Eds.: H. S. Nalwa, S. Miyata) CRC, Boca Raton. 1997; d) T. J. Marks, M. A. Ratner, Angew. Chem. 1995, 107, 167; Angew. Chem. Int. Ed. Engl 1995, 34, 155; e) N. J. Long, Angew. Chem. 1995, 107, 37; Angew. Chem. Int. Ed. Engl. 1995, 34.905; f) C. Bosshard, K. Sutler. P. Prêtre, J. Hulliger, M. Flörsheimer, P. Kaatz, P. Günther, Organic Nonlinear Optical Materials, Gordon and Breach, Basel, 1995; g) S. R. Marder, J. W. Perry, Adv. Mater. 1993, 5, 804.
6. For general introduction to nonlinear optics in organic materials, see: a) P. N. Prasad, D. J. Williams, Nonlinear Optical Effects in Molecules and Polymers, Wiley, New York, 1991; b) Principles and Applications of Nonlinear Optical Materials (Eds.: R. W. Munn, C. N. Ironside) Blackie Academic and Professional, Glasgow, 1993; c) Nonlinear Optics of Organic Molecules and Polymers (Eds.: H. S. Nalwa, S. Miyata) CRC, Boca Raton. 1997; d) T. J. Marks, M. A. Ratner, Angew. Chem. 1995, 107, 167; Angew. Chem. Int. Ed. Engl 1995, 34, 155; e) N. J. Long, Angew. Chem. 1995, 107, 37; Angew. Chem. Int. Ed. Engl. 1995, 34.905; f) C. Bosshard, K. Sutler. P. Prêtre, J. Hulliger, M. Flörsheimer, P. Kaatz, P. Günther, Organic Nonlinear Optical Materials, Gordon and Breach, Basel, 1995; g) S. R. Marder, J. W. Perry, Adv. Mater. 1993, 5, 804.
7. For general introduction to nonlinear optics in organic materials, see: a) P. N. Prasad, D. J. Williams, Nonlinear Optical Effects in Molecules and Polymers, Wiley, New York, 1991; b) Principles and Applications of Nonlinear Optical Materials (Eds.: R. W. Munn, C. N. Ironside) Blackie Academic and Professional, Glasgow, 1993; c) Nonlinear Optics of Organic Molecules and Polymers (Eds.: H. S. Nalwa, S. Miyata) CRC, Boca Raton. 1997; d) T. J. Marks, M. A. Ratner, Angew. Chem. 1995, 107, 167; Angew. Chem. Int. Ed. Engl 1995, 34, 155; e) N. J. Long, Angew. Chem. 1995, 107, 37; Angew. Chem. Int. Ed. Engl. 1995, 34.905; f) C. Bosshard, K. Sutler. P. Prêtre, J. Hulliger, M. Flörsheimer, P. Kaatz, P. Günther, Organic Nonlinear Optical Materials, Gordon and Breach, Basel, 1995; g) S. R. Marder, J. W. Perry, Adv. Mater. 1993, 5, 804.
8. For general introduction to nonlinear optics in organic materials, see: a) P. N. Prasad, D. J. Williams, Nonlinear Optical Effects in Molecules and Polymers, Wiley, New York, 1991; b) Principles and Applications of Nonlinear Optical Materials (Eds.: R. W. Munn, C. N. Ironside) Blackie Academic and Professional, Glasgow, 1993; c) Nonlinear Optics of Organic Molecules and Polymers (Eds.: H. S. Nalwa, S. Miyata) CRC, Boca Raton. 1997; d) T. J. Marks, M. A. Ratner, Angew. Chem. 1995, 107, 167; Angew. Chem. Int. Ed. Engl 1995, 34, 155; e) N. J. Long, Angew. Chem. 1995, 107, 37; Angew. Chem. Int. Ed. Engl. 1995, 34.905; f) C. Bosshard, K. Sutler. P. Prêtre, J. Hulliger, M. Flörsheimer, P. Kaatz, P. Günther, Organic Nonlinear Optical Materials, Gordon and Breach, Basel, 1995; g) S. R. Marder, J. W. Perry, Adv. Mater. 1993, 5, 804.
9. For general introduction to nonlinear optics in organic materials, see: a) P. N. Prasad, D. J. Williams, Nonlinear Optical Effects in Molecules and Polymers, Wiley, New York, 1991; b) Principles and Applications of Nonlinear Optical Materials (Eds.: R. W. Munn, C. N. Ironside) Blackie Academic and Professional, Glasgow, 1993; c) Nonlinear Optics of Organic Molecules and Polymers (Eds.: H. S. Nalwa, S. Miyata) CRC, Boca Raton. 1997; d) T. J. Marks, M. A. Ratner, Angew. Chem. 1995, 107, 167; Angew. Chem. Int. Ed. Engl 1995, 34, 155; e) N. J. Long, Angew. Chem. 1995, 107, 37; Angew. Chem. Int. Ed. Engl. 1995, 34.905; f) C. Bosshard, K. Sutler. P. Prêtre, J. Hulliger, M. Flörsheimer, P. Kaatz, P. Günther, Organic Nonlinear Optical Materials, Gordon and Breach, Basel, 1995; g) S. R. Marder, J. W. Perry, Adv. Mater. 1993, 5, 804.
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11. a) M. S. Wong, C. Bosshard, F. Pan, P. Günther, Adv. Mater. 1996, 8, 677;
12. b) T. Verbiest, S. Houbrechts, M. Kauranen, K. Clays, A. Persoons, J. Mater. Chem. 1997, 7, 2157.
13. For reviews on nonlinear optics in multipolar media, see a) J. Zyss, I. Ledoux, Chem. Rev. 1994, 94, 77; b) J. J. Wolff, R. Wortmann, J. Prakt. Chem. 1998, 340, 99.
14. For reviews on nonlinear optics in multipolar media, see a) J. Zyss, I. Ledoux, Chem. Rev. 1994, 94, 77; b) J. J. Wolff, R. Wortmann, J. Prakt. Chem. 1998, 340, 99.
15. 2v symmetry: a) R. Wortmann, P. Krämer, C. Glania, S. Lebus, N. Detzer, Chem. Phys. 1993, 173, 99; b) H. S. Nalwa, T. Watanabe, S. Miyata, Adv. Mater. 1995, 7, 754; c) C. R. Moylan, S. Ermer, S. M. Lovejoy, I.-H. McComb, D. S. Leung, R. Wortmann, P. Krämer, R. J. Twieg, J. Am. Chem. Soc. 1996, 118, 12950; d) J. J. Wolff, D. Längle, D. Hillenbrand, R. Wortmann, R. Matschiner, C Glania, P. Krämer, Adv. Mater. 1997, 9, 138.
16. 2v symmetry: a) R. Wortmann, P. Krämer, C. Glania, S. Lebus, N. Detzer, Chem. Phys. 1993, 173, 99; b) H. S. Nalwa, T. Watanabe, S. Miyata, Adv. Mater. 1995, 7, 754; c) C. R. Moylan, S. Ermer, S. M. Lovejoy, I.-H. McComb, D. S. Leung, R. Wortmann, P. Krämer, R. J. Twieg, J. Am. Chem. Soc. 1996, 118, 12950; d) J. J. Wolff, D. Längle, D. Hillenbrand, R. Wortmann, R. Matschiner, C Glania, P. Krämer, Adv. Mater. 1997, 9, 138.
17. 2v symmetry: a) R. Wortmann, P. Krämer, C. Glania, S. Lebus, N. Detzer, Chem. Phys. 1993, 173, 99; b) H. S. Nalwa, T. Watanabe, S. Miyata, Adv. Mater. 1995, 7, 754; c) C. R. Moylan, S. Ermer, S. M. Lovejoy, I.-H. McComb, D. S. Leung, R. Wortmann, P. Krämer, R. J. Twieg, J. Am. Chem. Soc. 1996, 118, 12950; d) J. J. Wolff, D. Längle, D. Hillenbrand, R. Wortmann, R. Matschiner, C Glania, P. Krämer, Adv. Mater. 1997, 9, 138.
18. 2v symmetry: a) R. Wortmann, P. Krämer, C. Glania, S. Lebus, N. Detzer, Chem. Phys. 1993, 173, 99; b) H. S. Nalwa, T. Watanabe, S. Miyata, Adv. Mater. 1995, 7, 754; c) C. R. Moylan, S. Ermer, S. M. Lovejoy, I.-H. McComb, D. S. Leung, R. Wortmann, P. Krämer, R. J. Twieg, J. Am. Chem. Soc. 1996, 118, 12950; d) J. J. Wolff, D. Längle, D. Hillenbrand, R. Wortmann, R. Matschiner, C Glania, P. Krämer, Adv. Mater. 1997, 9, 138.
19. 3 symmetry: a) I. Ledoux, J. Zyss, J. S. Siegel, J. Bienne, J.-M. Lehn, Chem. Phys. Lett. 1990, 172, 440; b) M. Joffre, D. Yaron, R. J. Silbey, J. Zyss, J. Chem. Phys. 1992, 97, 5607; c) J. L. Bredas, F. Meyers, B. M. Pierce, J. Zyss, J. Am. Chem. Soc. 1992, 114, 4928; d) J. Zyss, T. C. Van, C. Dhenaut, I. Ledoux, Chem. Phys. 1993, 177, 281; e) T. Verbiest, K. Clays, C. Samyn, J. Wolff, D. Reinhoudt, A. Persoons, J. Am. Chem. Soc. 1994, 116, 9320; f) S. Stadler, F. Feiner, C. Bräuchle, S. Brandl, R. Gompper, Chem. Phys. Lett. 1995, 245, 292; g) Y. Luo, A. Cesar, H. Agren, Chem. Phys. Lett. 1996, 252, 389; h) S. Stadler, R. Dietrich, G. Bourhill, C. Bräuchle, Opt. Lett. 1996, 21, 251; i) A. Sastre, T. Torres, M. A. Diaz-Garcia, F. Agullo-Lopez, C. Denhaut, S. Brasselet, I. Ledoux, J. Zyss, J. Am. Chem. Soc. 1996, 118, 2746; j) G. de al Torre, T. Torres, F. Agullo-Lopez, Adv. Mater. 1997, 9, 265; k) P. Kaatz, D. P. Shelton, J. Chem. Phys. 1996, 105, 3918; 1) R. Wortmann, C. Glania, P. Krämer, R. tschiner, J. J. Wolff, S. Kraft, B. Treptow, E. Barbu, D. Längle, G. Görlitz, Chew. Eur. J. 1997, 3, 1765.
20. 3 symmetry: a) I. Ledoux, J. Zyss, J. S. Siegel, J. Bienne, J.-M. Lehn, Chem. Phys. Lett. 1990, 172, 440; b) M. Joffre, D. Yaron, R. J. Silbey, J. Zyss, J. Chem. Phys. 1992, 97, 5607; c) J. L. Bredas, F. Meyers, B. M. Pierce, J. Zyss, J. Am. Chem. Soc. 1992, 114, 4928; d) J. Zyss, T. C. Van, C. Dhenaut, I. Ledoux, Chem. Phys. 1993, 177, 281; e) T. Verbiest, K. Clays, C. Samyn, J. Wolff, D. Reinhoudt, A. Persoons, J. Am. Chem. Soc. 1994, 116, 9320; f) S. Stadler, F. Feiner, C. Bräuchle, S. Brandl, R. Gompper, Chem. Phys. Lett. 1995, 245, 292; g) Y. Luo, A. Cesar, H. Agren, Chem. Phys. Lett. 1996, 252, 389; h) S. Stadler, R. Dietrich, G. Bourhill, C. Bräuchle, Opt. Lett. 1996, 21, 251; i) A. Sastre, T. Torres, M. A. Diaz-Garcia, F. Agullo-Lopez, C. Denhaut, S. Brasselet, I. Ledoux, J. Zyss, J. Am. Chem. Soc. 1996, 118, 2746; j) G. de al Torre, T. Torres, F. Agullo-Lopez, Adv. Mater. 1997, 9, 265; k) P. Kaatz, D. P. Shelton, J. Chem. Phys. 1996, 105, 3918; 1) R. Wortmann, C. Glania, P. Krämer, R. tschiner, J. J. Wolff, S. Kraft, B. Treptow, E. Barbu, D. Längle, G. Görlitz, Chew. Eur. J. 1997, 3, 1765.
21. 3 symmetry: a) I. Ledoux, J. Zyss, J. S. Siegel, J. Bienne, J.-M. Lehn, Chem. Phys. Lett. 1990, 172, 440; b) M. Joffre, D. Yaron, R. J. Silbey, J. Zyss, J. Chem. Phys. 1992, 97, 5607; c) J. L. Bredas, F. Meyers, B. M. Pierce, J. Zyss, J. Am. Chem. Soc. 1992, 114, 4928; d) J. Zyss, T. C. Van, C. Dhenaut, I. Ledoux, Chem. Phys. 1993, 177, 281; e) T. Verbiest, K. Clays, C. Samyn, J. Wolff, D. Reinhoudt, A. Persoons, J. Am. Chem. Soc. 1994, 116, 9320; f) S. Stadler, F. Feiner, C. Bräuchle, S. Brandl, R. Gompper, Chem. Phys. Lett. 1995, 245, 292; g) Y. Luo, A. Cesar, H. Agren, Chem. Phys. Lett. 1996, 252, 389; h) S. Stadler, R. Dietrich, G. Bourhill, C. Bräuchle, Opt. Lett. 1996, 21, 251; i) A. Sastre, T. Torres, M. A. Diaz-Garcia, F. Agullo-Lopez, C. Denhaut, S. Brasselet, I. Ledoux, J. Zyss, J. Am. Chem. Soc. 1996, 118, 2746; j) G. de al Torre, T. Torres, F. Agullo-Lopez, Adv. Mater. 1997, 9, 265; k) P. Kaatz, D. P. Shelton, J. Chem. Phys. 1996, 105, 3918; 1) R. Wortmann, C. Glania, P. Krämer, R. tschiner, J. J. Wolff, S. Kraft, B. Treptow, E. Barbu, D. Längle, G. Görlitz, Chew. Eur. J. 1997, 3, 1765.
22. 3 symmetry: a) I. Ledoux, J. Zyss, J. S. Siegel, J. Bienne, J.-M. Lehn, Chem. Phys. Lett. 1990, 172, 440; b) M. Joffre, D. Yaron, R. J. Silbey, J. Zyss, J. Chem. Phys. 1992, 97, 5607; c) J. L. Bredas, F. Meyers, B. M. Pierce, J. Zyss, J. Am. Chem. Soc. 1992, 114, 4928; d) J. Zyss, T. C. Van, C. Dhenaut, I. Ledoux, Chem. Phys. 1993, 177, 281; e) T. Verbiest, K. Clays, C. Samyn, J. Wolff, D. Reinhoudt, A. Persoons, J. Am. Chem. Soc. 1994, 116, 9320; f) S. Stadler, F. Feiner, C. Bräuchle, S. Brandl, R. Gompper, Chem. Phys. Lett. 1995, 245, 292; g) Y. Luo, A. Cesar, H. Agren, Chem. Phys. Lett. 1996, 252, 389; h) S. Stadler, R. Dietrich, G. Bourhill, C. Bräuchle, Opt. Lett. 1996, 21, 251; i) A. Sastre, T. Torres, M. A. Diaz-Garcia, F. Agullo-Lopez, C. Denhaut, S. Brasselet, I. Ledoux, J. Zyss, J. Am. Chem. Soc. 1996, 118, 2746; j) G. de al Torre, T. Torres, F. Agullo-Lopez, Adv. Mater. 1997, 9, 265; k) P. Kaatz, D. P. Shelton, J. Chem. Phys. 1996, 105, 3918; 1) R. Wortmann, C. Glania, P. Krämer, R. tschiner, J. J. Wolff, S. Kraft, B. Treptow, E. Barbu, D. Längle, G. Görlitz, Chew. Eur. J. 1997, 3, 1765.
23. 3 symmetry: a) I. Ledoux, J. Zyss, J. S. Siegel, J. Bienne, J.-M. Lehn, Chem. Phys. Lett. 1990, 172, 440; b) M. Joffre, D. Yaron, R. J. Silbey, J. Zyss, J. Chem. Phys. 1992, 97, 5607; c) J. L. Bredas, F. Meyers, B. M. Pierce, J. Zyss, J. Am. Chem. Soc. 1992, 114, 4928; d) J. Zyss, T. C. Van, C. Dhenaut, I. Ledoux, Chem. Phys. 1993, 177, 281; e) T. Verbiest, K. Clays, C. Samyn, J. Wolff, D. Reinhoudt, A. Persoons, J. Am. Chem. Soc. 1994, 116, 9320; f) S. Stadler, F. Feiner, C. Bräuchle, S. Brandl, R. Gompper, Chem. Phys. Lett. 1995, 245, 292; g) Y. Luo, A. Cesar, H. Agren, Chem. Phys. Lett. 1996, 252, 389; h) S. Stadler, R. Dietrich, G. Bourhill, C. Bräuchle, Opt. Lett. 1996, 21, 251; i) A. Sastre, T. Torres, M. A. Diaz-Garcia, F. Agullo-Lopez, C. Denhaut, S. Brasselet, I. Ledoux, J. Zyss, J. Am. Chem. Soc. 1996, 118, 2746; j) G. de al Torre, T. Torres, F. Agullo-Lopez, Adv. Mater. 1997, 9, 265; k) P. Kaatz, D. P. Shelton, J. Chem. Phys. 1996, 105, 3918; 1) R. Wortmann, C. Glania, P. Krämer, R. tschiner, J. J. Wolff, S. Kraft, B. Treptow, E. Barbu, D. Längle, G. Görlitz, Chew. Eur. J. 1997, 3, 1765.
24. 3 symmetry: a) I. Ledoux, J. Zyss, J. S. Siegel, J. Bienne, J.-M. Lehn, Chem. Phys. Lett. 1990, 172, 440; b) M. Joffre, D. Yaron, R. J. Silbey, J. Zyss, J. Chem. Phys. 1992, 97, 5607; c) J. L. Bredas, F. Meyers, B. M. Pierce, J. Zyss, J. Am. Chem. Soc. 1992, 114, 4928; d) J. Zyss, T. C. Van, C. Dhenaut, I. Ledoux, Chem. Phys. 1993, 177, 281; e) T. Verbiest, K. Clays, C. Samyn, J. Wolff, D. Reinhoudt, A. Persoons, J. Am. Chem. Soc. 1994, 116, 9320; f) S. Stadler, F. Feiner, C. Bräuchle, S. Brandl, R. Gompper, Chem. Phys. Lett. 1995, 245, 292; g) Y. Luo, A. Cesar, H. Agren, Chem. Phys. Lett. 1996, 252, 389; h) S. Stadler, R. Dietrich, G. Bourhill, C. Bräuchle, Opt. Lett. 1996, 21, 251; i) A. Sastre, T. Torres, M. A. Diaz-Garcia, F. Agullo-Lopez, C. Denhaut, S. Brasselet, I. Ledoux, J. Zyss, J. Am. Chem. Soc. 1996, 118, 2746; j) G. de al Torre, T. Torres, F. Agullo-Lopez, Adv. Mater. 1997, 9, 265; k) P. Kaatz, D. P. Shelton, J. Chem. Phys. 1996, 105, 3918; 1) R. Wortmann, C. Glania, P. Krämer, R. tschiner, J. J. Wolff, S. Kraft, B. Treptow, E. Barbu, D. Längle, G. Görlitz, Chew. Eur. J. 1997, 3, 1765.
25. 3 symmetry: a) I. Ledoux, J. Zyss, J. S. Siegel, J. Bienne, J.-M. Lehn, Chem. Phys. Lett. 1990, 172, 440; b) M. Joffre, D. Yaron, R. J. Silbey, J. Zyss, J. Chem. Phys. 1992, 97, 5607; c) J. L. Bredas, F. Meyers, B. M. Pierce, J. Zyss, J. Am. Chem. Soc. 1992, 114, 4928; d) J. Zyss, T. C. Van, C. Dhenaut, I. Ledoux, Chem. Phys. 1993, 177, 281; e) T. Verbiest, K. Clays, C. Samyn, J. Wolff, D. Reinhoudt, A. Persoons, J. Am. Chem. Soc. 1994, 116, 9320; f) S. Stadler, F. Feiner, C. Bräuchle, S. Brandl, R. Gompper, Chem. Phys. Lett. 1995, 245, 292; g) Y. Luo, A. Cesar, H. Agren, Chem. Phys. Lett. 1996, 252, 389; h) S. Stadler, R. Dietrich, G. Bourhill, C. Bräuchle, Opt. Lett. 1996, 21, 251; i) A. Sastre, T. Torres, M. A. Diaz-Garcia, F. Agullo-Lopez, C. Denhaut, S. Brasselet, I. Ledoux, J. Zyss, J. Am. Chem. Soc. 1996, 118, 2746; j) G. de al Torre, T. Torres, F. Agullo-Lopez, Adv. Mater. 1997, 9, 265; k) P. Kaatz, D. P. Shelton, J. Chem. Phys. 1996, 105, 3918; 1) R. Wortmann, C. Glania, P. Krämer, R. tschiner, J. J. Wolff, S. Kraft, B. Treptow, E. Barbu, D. Längle, G. Görlitz, Chew. Eur. J. 1997, 3, 1765.
26. 3 symmetry: a) I. Ledoux, J. Zyss, J. S. Siegel, J. Bienne, J.-M. Lehn, Chem. Phys. Lett. 1990, 172, 440; b) M. Joffre, D. Yaron, R. J. Silbey, J. Zyss, J. Chem. Phys. 1992, 97, 5607; c) J. L. Bredas, F. Meyers, B. M. Pierce, J. Zyss, J. Am. Chem. Soc. 1992, 114, 4928; d) J. Zyss, T. C. Van, C. Dhenaut, I. Ledoux, Chem. Phys. 1993, 177, 281; e) T. Verbiest, K. Clays, C. Samyn, J. Wolff, D. Reinhoudt, A. Persoons, J. Am. Chem. Soc. 1994, 116, 9320; f) S. Stadler, F. Feiner, C. Bräuchle, S. Brandl, R. Gompper, Chem. Phys. Lett. 1995, 245, 292; g) Y. Luo, A. Cesar, H. Agren, Chem. Phys. Lett. 1996, 252, 389; h) S. Stadler, R. Dietrich, G. Bourhill, C. Bräuchle, Opt. Lett. 1996, 21, 251; i) A. Sastre, T. Torres, M. A. Diaz-Garcia, F. Agullo-Lopez, C. Denhaut, S. Brasselet, I. Ledoux, J. Zyss, J. Am. Chem. Soc. 1996, 118, 2746; j) G. de al Torre, T. Torres, F. Agullo-Lopez, Adv. Mater. 1997, 9, 265; k) P. Kaatz, D. P. Shelton, J. Chem. Phys. 1996, 105, 3918; 1) R. Wortmann, C. Glania, P. Krämer, R. tschiner, J. J. Wolff, S. Kraft, B. Treptow, E. Barbu, D. Längle, G. Görlitz, Chew. Eur. J. 1997, 3, 1765.
27. 3 symmetry: a) I. Ledoux, J. Zyss, J. S. Siegel, J. Bienne, J.-M. Lehn, Chem. Phys. Lett. 1990, 172, 440; b) M. Joffre, D. Yaron, R. J. Silbey, J. Zyss, J. Chem. Phys. 1992, 97, 5607; c) J. L. Bredas, F. Meyers, B. M. Pierce, J. Zyss, J. Am. Chem. Soc. 1992, 114, 4928; d) J. Zyss, T. C. Van, C. Dhenaut, I. Ledoux, Chem. Phys. 1993, 177, 281; e) T. Verbiest, K. Clays, C. Samyn, J. Wolff, D. Reinhoudt, A. Persoons, J. Am. Chem. Soc. 1994, 116, 9320; f) S. Stadler, F. Feiner, C. Bräuchle, S. Brandl, R. Gompper, Chem. Phys. Lett. 1995, 245, 292; g) Y. Luo, A. Cesar, H. Agren, Chem. Phys. Lett. 1996, 252, 389; h) S. Stadler, R. Dietrich, G. Bourhill, C. Bräuchle, Opt. Lett. 1996, 21, 251; i) A. Sastre, T. Torres, M. A. Diaz-Garcia, F. Agullo-Lopez, C. Denhaut, S. Brasselet, I. Ledoux, J. Zyss, J. Am. Chem. Soc. 1996, 118, 2746; j) G. de al Torre, T. Torres, F. Agullo-Lopez, Adv. Mater. 1997, 9, 265; k) P. Kaatz, D. P. Shelton, J. Chem. Phys. 1996, 105, 3918; 1) R. Wortmann, C. Glania, P. Krämer, R. tschiner, J. J. Wolff, S. Kraft, B. Treptow, E. Barbu, D. Längle, G. Görlitz, Chew. Eur. J. 1997, 3, 1765.
28. 3 symmetry: a) I. Ledoux, J. Zyss, J. S. Siegel, J. Bienne, J.-M. Lehn, Chem. Phys. Lett. 1990, 172, 440; b) M. Joffre, D. Yaron, R. J. Silbey, J. Zyss, J. Chem. Phys. 1992, 97, 5607; c) J. L. Bredas, F. Meyers, B. M. Pierce, J. Zyss, J. Am. Chem. Soc. 1992, 114, 4928; d) J. Zyss, T. C. Van, C. Dhenaut, I. Ledoux, Chem. Phys. 1993, 177, 281; e) T. Verbiest, K. Clays, C. Samyn, J. Wolff, D. Reinhoudt, A. Persoons, J. Am. Chem. Soc. 1994, 116, 9320; f) S. Stadler, F. Feiner, C. Bräuchle, S. Brandl, R. Gompper, Chem. Phys. Lett. 1995, 245, 292; g) Y. Luo, A. Cesar, H. Agren, Chem. Phys. Lett. 1996, 252, 389; h) S. Stadler, R. Dietrich, G. Bourhill, C. Bräuchle, Opt. Lett. 1996, 21, 251; i) A. Sastre, T. Torres, M. A. Diaz-Garcia, F. Agullo-Lopez, C. Denhaut, S. Brasselet, I. Ledoux, J. Zyss, J. Am. Chem. Soc. 1996, 118, 2746; j) G. de al Torre, T. Torres, F. Agullo-Lopez, Adv. Mater. 1997, 9, 265; k) P. Kaatz, D. P. Shelton, J. Chem. Phys. 1996, 105, 3918; 1) R. Wortmann, C. Glania, P. Krämer, R. tschiner, J. J. Wolff, S. Kraft, B. Treptow, E. Barbu, D. Längle, G. Görlitz, Chew. Eur. J. 1997, 3, 1765.
29. 3 symmetry: a) I. Ledoux, J. Zyss, J. S. Siegel, J. Bienne, J.-M. Lehn, Chem. Phys. Lett. 1990, 172, 440; b) M. Joffre, D. Yaron, R. J. Silbey, J. Zyss, J. Chem. Phys. 1992, 97, 5607; c) J. L. Bredas, F. Meyers, B. M. Pierce, J. Zyss, J. Am. Chem. Soc. 1992, 114, 4928; d) J. Zyss, T. C. Van, C. Dhenaut, I. Ledoux, Chem. Phys. 1993, 177, 281; e) T. Verbiest, K. Clays, C. Samyn, J. Wolff, D. Reinhoudt, A. Persoons, J. Am. Chem. Soc. 1994, 116, 9320; f) S. Stadler, F. Feiner, C. Bräuchle, S. Brandl, R. Gompper, Chem. Phys. Lett. 1995, 245, 292; g) Y. Luo, A. Cesar, H. Agren, Chem. Phys. Lett. 1996, 252, 389; h) S. Stadler, R. Dietrich, G. Bourhill, C. Bräuchle, Opt. Lett. 1996, 21, 251; i) A. Sastre, T. Torres, M. A. Diaz-Garcia, F. Agullo-Lopez, C. Denhaut, S. Brasselet, I. Ledoux, J. Zyss, J. Am. Chem. Soc. 1996, 118, 2746; j) G. de al Torre, T. Torres, F. Agullo-Lopez, Adv. Mater. 1997, 9, 265; k) P. Kaatz, D. P. Shelton, J. Chem. Phys. 1996, 105, 3918; 1) R. Wortmann, C. Glania, P. Krämer, R. tschiner, J. J. Wolff, S. Kraft, B. Treptow, E. Barbu, D. Längle, G. Görlitz, Chew. Eur. J. 1997, 3, 1765.
30. 3 symmetry: a) I. Ledoux, J. Zyss, J. S. Siegel, J. Bienne, J.-M. Lehn, Chem. Phys. Lett. 1990, 172, 440; b) M. Joffre, D. Yaron, R. J. Silbey, J. Zyss, J. Chem. Phys. 1992, 97, 5607; c) J. L. Bredas, F. Meyers, B. M. Pierce, J. Zyss, J. Am. Chem. Soc. 1992, 114, 4928; d) J. Zyss, T. C. Van, C. Dhenaut, I. Ledoux, Chem. Phys. 1993, 177, 281; e) T. Verbiest, K. Clays, C. Samyn, J. Wolff, D. Reinhoudt, A. Persoons, J. Am. Chem. Soc. 1994, 116, 9320; f) S. Stadler, F. Feiner, C. Bräuchle, S. Brandl, R. Gompper, Chem. Phys. Lett. 1995, 245, 292; g) Y. Luo, A. Cesar, H. Agren, Chem. Phys. Lett. 1996, 252, 389; h) S. Stadler, R. Dietrich, G. Bourhill, C. Bräuchle, Opt. Lett. 1996, 21, 251; i) A. Sastre, T. Torres, M. A. Diaz-Garcia, F. Agullo-Lopez, C. Denhaut, S. Brasselet, I. Ledoux, J. Zyss, J. Am. Chem. Soc. 1996, 118, 2746; j) G. de al Torre, T. Torres, F. Agullo-Lopez, Adv. Mater. 1997, 9, 265; k) P. Kaatz, D. P. Shelton, J. Chem. Phys. 1996, 105, 3918; 1) R. Wortmann, C. Glania, P. Krämer, R. tschiner, J. J. Wolff, S. Kraft, B. Treptow, E. Barbu, D. Längle, G. Görlitz, Chew. Eur. J. 1997, 3, 1765.
31. 2 or T symmetry: a) T. Thami, P. Bassoul, M. A. Petit, J. Simon, A. Fort, M. Barzoukas, A. Villaeys, J. Am. Chem. Soc. 1992, 114, 915; b) M. Lequan, C. Branger, J. Simon, T. Thami, E. Chauchard, A. Persoons, Chem. Phys. Lett. 1994, 229, 101; c) M. Lequan, C. Branger, J. Simon, T. Thami, E. Chauchard, A. Persoons, Adv. Mater. 1994, 6, 851; d) C. Lambert, E. Schmälzlin, K. Meerholz, C. Bräuchle, Chem. Eur. J. 1998, 4, 512.
32. 2 or T symmetry: a) T. Thami, P. Bassoul, M. A. Petit, J. Simon, A. Fort, M. Barzoukas, A. Villaeys, J. Am. Chem. Soc. 1992, 114, 915; b) M. Lequan, C. Branger, J. Simon, T. Thami, E. Chauchard, A. Persoons, Chem. Phys. Lett. 1994, 229, 101; c) M. Lequan, C. Branger, J. Simon, T. Thami, E. Chauchard, A. Persoons, Adv. Mater. 1994, 6, 851; d) C. Lambert, E. Schmälzlin, K. Meerholz, C. Bräuchle, Chem. Eur. J. 1998, 4, 512.
33. 2 or T symmetry: a) T. Thami, P. Bassoul, M. A. Petit, J. Simon, A. Fort, M. Barzoukas, A. Villaeys, J. Am. Chem. Soc. 1992, 114, 915; b) M. Lequan, C. Branger, J. Simon, T. Thami, E. Chauchard, A. Persoons, Chem. Phys. Lett. 1994, 229, 101; c) M. Lequan, C. Branger, J. Simon, T. Thami, E. Chauchard, A. Persoons, Adv. Mater. 1994, 6, 851; d) C. Lambert, E. Schmälzlin, K. Meerholz, C. Bräuchle, Chem. Eur. J. 1998, 4, 512.
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