Syntheses and NLO Properties of Chromium Carbonyl Arene Complexes with Conjugated Side Chains: The Amphoteric Nature of Chromium Carbonyl Complexation in Push-Pull Chromophores

Organometallics

Volumn 18, Issue 24, 1999, Pages 5066-5074

  Müller, Thomas J J ^a   Netz, Astrid ^a   Ansorge, Markus ^a   Schmälzlin, Elmar ^a   Bräuchle, Christoph ^a   Meerholz, Klaus ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0037571087     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9904551     Document Type: Article

References (72)

1. For recent reviews on NLO materials see, e.g.: (a) Long, N. J. Angew. Chem. 1995, 107, 37; Angew. Chem., Int. Ed. Engl. 1995, 34, 6. (b) Marder, S. R.; Perry, J. W. Adv. Mater. 1993, 5, 804. (c) Nie, W. Adv. Mater. 1993, 5, 520. (d) Kanis, D. R.; Ratner, M. A.; Marks, T. J. Chem. Rev. 1994, 94, 195. (e) Marks, T. J.; Ratner, M. A. Angew. Chem. 1995, 107, 167; Angew. Chem., Int. Ed. Engl. 1995, 34, 155.
2. For recent reviews on NLO materials see, e.g.: (a) Long, N. J. Angew. Chem. 1995, 107, 37; Angew. Chem., Int. Ed. Engl. 1995, 34, 6. (b) Marder, S. R.; Perry, J. W. Adv. Mater. 1993, 5, 804. (c) Nie, W. Adv. Mater. 1993, 5, 520. (d) Kanis, D. R.; Ratner, M. A.; Marks, T. J. Chem. Rev. 1994, 94, 195. (e) Marks, T. J.; Ratner, M. A. Angew. Chem. 1995, 107, 167; Angew. Chem., Int. Ed. Engl. 1995, 34, 155.
3. For recent reviews on NLO materials see, e.g.: (a) Long, N. J. Angew. Chem. 1995, 107, 37; Angew. Chem., Int. Ed. Engl. 1995, 34, 6. (b) Marder, S. R.; Perry, J. W. Adv. Mater. 1993, 5, 804. (c) Nie, W. Adv. Mater. 1993, 5, 520. (d) Kanis, D. R.; Ratner, M. A.; Marks, T. J. Chem. Rev. 1994, 94, 195. (e) Marks, T. J.; Ratner, M. A. Angew. Chem. 1995, 107, 167; Angew. Chem., Int. Ed. Engl. 1995, 34, 155.
4. For recent reviews on NLO materials see, e.g.: (a) Long, N. J. Angew. Chem. 1995, 107, 37; Angew. Chem., Int. Ed. Engl. 1995, 34, 6. (b) Marder, S. R.; Perry, J. W. Adv. Mater. 1993, 5, 804. (c) Nie, W. Adv. Mater. 1993, 5, 520. (d) Kanis, D. R.; Ratner, M. A.; Marks, T. J. Chem. Rev. 1994, 94, 195. (e) Marks, T. J.; Ratner, M. A. Angew. Chem. 1995, 107, 167; Angew. Chem., Int. Ed. Engl. 1995, 34, 155.
5. For recent reviews on NLO materials see, e.g.: (a) Long, N. J. Angew. Chem. 1995, 107, 37; Angew. Chem., Int. Ed. Engl. 1995, 34, 6. (b) Marder, S. R.; Perry, J. W. Adv. Mater. 1993, 5, 804. (c) Nie, W. Adv. Mater. 1993, 5, 520. (d) Kanis, D. R.; Ratner, M. A.; Marks, T. J. Chem. Rev. 1994, 94, 195. (e) Marks, T. J.; Ratner, M. A. Angew. Chem. 1995, 107, 167; Angew. Chem., Int. Ed. Engl. 1995, 34, 155.
6. For recent reviews on NLO materials see, e.g.: (a) Long, N. J. Angew. Chem. 1995, 107, 37; Angew. Chem., Int. Ed. Engl. 1995, 34, 6. (b) Marder, S. R.; Perry, J. W. Adv. Mater. 1993, 5, 804. (c) Nie, W. Adv. Mater. 1993, 5, 520. (d) Kanis, D. R.; Ratner, M. A.; Marks, T. J. Chem. Rev. 1994, 94, 195. (e) Marks, T. J.; Ratner, M. A. Angew. Chem. 1995, 107, 167; Angew. Chem., Int. Ed. Engl. 1995, 34, 155.
7. For recent reviews on NLO materials see, e.g.: (a) Long, N. J. Angew. Chem. 1995, 107, 37; Angew. Chem., Int. Ed. Engl. 1995, 34, 6. (b) Marder, S. R.; Perry, J. W. Adv. Mater. 1993, 5, 804. (c) Nie, W. Adv. Mater. 1993, 5, 520. (d) Kanis, D. R.; Ratner, M. A.; Marks, T. J. Chem. Rev. 1994, 94, 195. (e) Marks, T. J.; Ratner, M. A. Angew. Chem. 1995, 107, 167; Angew. Chem., Int. Ed. Engl. 1995, 34, 155.
8. For excellent reviews on organometallic NLO chromophores see, e.g. (a) Whittall, I. R.; McDonagh, A. M.; Humphrey, M. G.; Samoc, M. Adv. Organomet. Chem. 1998, 42, 291. (b) Whittall, I. R.; McDonagh, A. M.; Humphrey, M. G.; Samoc, M. Adv. Organomet. Chem. 1998, 43, 349. For representative novel organometallic NLO chromophores see, e.g.: (c) Behrens, U.; Bruesaard, H.; Hagenau, U.; Heck, J.; Hendrickx, E.; Körnich, J.; van der Linden, J. G. M.; Persoons, A.; Spek, A. L.; Veldman, N.; Voss, B.; Wong, H. Chem. Eur. J. 1996, 2, 98. (d) Dhenaut, C.; Ledoux, I.; Samuel, I. D. W.; Zyss, J.; Bourgault, M.; Le Bozec, H. Nature 1995, 374, 339. (e) Tamm, M.; Grzegorzeweski, A.; Steiner, T.; Jentzsch, T.; Werncke, W. Organometallics 1996, 15, 4984. (f) Whittall, I. R.; Humphrey, M. G.; Houbrechts, S.; Persoons, A.; Hockless, D. C. R. Organometallics 1996, 15, 5738. (g) Whittall, I. R.; Cifuentes, M. P.; Humphrey, M. G.; Luther-Davies, B.; Samoc, M.; Houbrechts, S.; Persoons, A.; Heath, G. A.; Hockless, D. C. R. J. Organomet. Chem. 1997, 549, 127.
9. For excellent reviews on organometallic NLO chromophores see, e.g. (a) Whittall, I. R.; McDonagh, A. M.; Humphrey, M. G.; Samoc, M. Adv. Organomet. Chem. 1998, 42, 291. (b) Whittall, I. R.; McDonagh, A. M.; Humphrey, M. G.; Samoc, M. Adv. Organomet. Chem. 1998, 43, 349. For representative novel organometallic NLO chromophores see, e.g.: (c) Behrens, U.; Bruesaard, H.; Hagenau, U.; Heck, J.; Hendrickx, E.; Körnich, J.; van der Linden, J. G. M.; Persoons, A.; Spek, A. L.; Veldman, N.; Voss, B.; Wong, H. Chem. Eur. J. 1996, 2, 98. (d) Dhenaut, C.; Ledoux, I.; Samuel, I. D. W.; Zyss, J.; Bourgault, M.; Le Bozec, H. Nature 1995, 374, 339. (e) Tamm, M.; Grzegorzeweski, A.; Steiner, T.; Jentzsch, T.; Werncke, W. Organometallics 1996, 15, 4984. (f) Whittall, I. R.; Humphrey, M. G.; Houbrechts, S.; Persoons, A.; Hockless, D. C. R. Organometallics 1996, 15, 5738. (g) Whittall, I. R.; Cifuentes, M. P.; Humphrey, M. G.; Luther-Davies, B.; Samoc, M.; Houbrechts, S.; Persoons, A.; Heath, G. A.; Hockless, D. C. R. J. Organomet. Chem. 1997, 549, 127.
10. For excellent reviews on organometallic NLO chromophores see, e.g. (a) Whittall, I. R.; McDonagh, A. M.; Humphrey, M. G.; Samoc, M. Adv. Organomet. Chem. 1998, 42, 291. (b) Whittall, I. R.; McDonagh, A. M.; Humphrey, M. G.; Samoc, M. Adv. Organomet. Chem. 1998, 43, 349. For representative novel organometallic NLO chromophores see, e.g.: (c) Behrens, U.; Bruesaard, H.; Hagenau, U.; Heck, J.; Hendrickx, E.; Körnich, J.; van der Linden, J. G. M.; Persoons, A.; Spek, A. L.; Veldman, N.; Voss, B.; Wong, H. Chem. Eur. J. 1996, 2, 98. (d) Dhenaut, C.; Ledoux, I.; Samuel, I. D. W.; Zyss, J.; Bourgault, M.; Le Bozec, H. Nature 1995, 374, 339. (e) Tamm, M.; Grzegorzeweski, A.; Steiner, T.; Jentzsch, T.; Werncke, W. Organometallics 1996, 15, 4984. (f) Whittall, I. R.; Humphrey, M. G.; Houbrechts, S.; Persoons, A.; Hockless, D. C. R. Organometallics 1996, 15, 5738. (g) Whittall, I. R.; Cifuentes, M. P.; Humphrey, M. G.; Luther-Davies, B.; Samoc, M.; Houbrechts, S.; Persoons, A.; Heath, G. A.; Hockless, D. C. R. J. Organomet. Chem. 1997, 549, 127.
11. For excellent reviews on organometallic NLO chromophores see, e.g. (a) Whittall, I. R.; McDonagh, A. M.; Humphrey, M. G.; Samoc, M. Adv. Organomet. Chem. 1998, 42, 291. (b) Whittall, I. R.; McDonagh, A. M.; Humphrey, M. G.; Samoc, M. Adv. Organomet. Chem. 1998, 43, 349. For representative novel organometallic NLO chromophores see, e.g.: (c) Behrens, U.; Bruesaard, H.; Hagenau, U.; Heck, J.; Hendrickx, E.; Körnich, J.; van der Linden, J. G. M.; Persoons, A.; Spek, A. L.; Veldman, N.; Voss, B.; Wong, H. Chem. Eur. J. 1996, 2, 98. (d) Dhenaut, C.; Ledoux, I.; Samuel, I. D. W.; Zyss, J.; Bourgault, M.; Le Bozec, H. Nature 1995, 374, 339. (e) Tamm, M.; Grzegorzeweski, A.; Steiner, T.; Jentzsch, T.; Werncke, W. Organometallics 1996, 15, 4984. (f) Whittall, I. R.; Humphrey, M. G.; Houbrechts, S.; Persoons, A.; Hockless, D. C. R. Organometallics 1996, 15, 5738. (g) Whittall, I. R.; Cifuentes, M. P.; Humphrey, M. G.; Luther-Davies, B.; Samoc, M.; Houbrechts, S.; Persoons, A.; Heath, G. A.; Hockless, D. C. R. J. Organomet. Chem. 1997, 549, 127.
12. For excellent reviews on organometallic NLO chromophores see, e.g. (a) Whittall, I. R.; McDonagh, A. M.; Humphrey, M. G.; Samoc, M. Adv. Organomet. Chem. 1998, 42, 291. (b) Whittall, I. R.; McDonagh, A. M.; Humphrey, M. G.; Samoc, M. Adv. Organomet. Chem. 1998, 43, 349. For representative novel organometallic NLO chromophores see, e.g.: (c) Behrens, U.; Bruesaard, H.; Hagenau, U.; Heck, J.; Hendrickx, E.; Körnich, J.; van der Linden, J. G. M.; Persoons, A.; Spek, A. L.; Veldman, N.; Voss, B.; Wong, H. Chem. Eur. J. 1996, 2, 98. (d) Dhenaut, C.; Ledoux, I.; Samuel, I. D. W.; Zyss, J.; Bourgault, M.; Le Bozec, H. Nature 1995, 374, 339. (e) Tamm, M.; Grzegorzeweski, A.; Steiner, T.; Jentzsch, T.; Werncke, W. Organometallics 1996, 15, 4984. (f) Whittall, I. R.; Humphrey, M. G.; Houbrechts, S.; Persoons, A.; Hockless, D. C. R. Organometallics 1996, 15, 5738. (g) Whittall, I. R.; Cifuentes, M. P.; Humphrey, M. G.; Luther-Davies, B.; Samoc, M.; Houbrechts, S.; Persoons, A.; Heath, G. A.; Hockless, D. C. R. J. Organomet. Chem. 1997, 549, 127.
13. For excellent reviews on organometallic NLO chromophores see, e.g. (a) Whittall, I. R.; McDonagh, A. M.; Humphrey, M. G.; Samoc, M. Adv. Organomet. Chem. 1998, 42, 291. (b) Whittall, I. R.; McDonagh, A. M.; Humphrey, M. G.; Samoc, M. Adv. Organomet. Chem. 1998, 43, 349. For representative novel organometallic NLO chromophores see, e.g.: (c) Behrens, U.; Bruesaard, H.; Hagenau, U.; Heck, J.; Hendrickx, E.; Körnich, J.; van der Linden, J. G. M.; Persoons, A.; Spek, A. L.; Veldman, N.; Voss, B.; Wong, H. Chem. Eur. J. 1996, 2, 98. (d) Dhenaut, C.; Ledoux, I.; Samuel, I. D. W.; Zyss, J.; Bourgault, M.; Le Bozec, H. Nature 1995, 374, 339. (e) Tamm, M.; Grzegorzeweski, A.; Steiner, T.; Jentzsch, T.; Werncke, W. Organometallics 1996, 15, 4984. (f) Whittall, I. R.; Humphrey, M. G.; Houbrechts, S.; Persoons, A.; Hockless, D. C. R. Organometallics 1996, 15, 5738. (g) Whittall, I. R.; Cifuentes, M. P.; Humphrey, M. G.; Luther-Davies, B.; Samoc, M.; Houbrechts, S.; Persoons, A.; Heath, G. A.; Hockless, D. C. R. J. Organomet. Chem. 1997, 549, 127.
14. For excellent reviews on organometallic NLO chromophores see, e.g. (a) Whittall, I. R.; McDonagh, A. M.; Humphrey, M. G.; Samoc, M. Adv. Organomet. Chem. 1998, 42, 291. (b) Whittall, I. R.; McDonagh, A. M.; Humphrey, M. G.; Samoc, M. Adv. Organomet. Chem. 1998, 43, 349. For representative novel organometallic NLO chromophores see, e.g.: (c) Behrens, U.; Bruesaard, H.; Hagenau, U.; Heck, J.; Hendrickx, E.; Körnich, J.; van der Linden, J. G. M.; Persoons, A.; Spek, A. L.; Veldman, N.; Voss, B.; Wong, H. Chem. Eur. J. 1996, 2, 98. (d) Dhenaut, C.; Ledoux, I.; Samuel, I. D. W.; Zyss, J.; Bourgault, M.; Le Bozec, H. Nature 1995, 374, 339. (e) Tamm, M.; Grzegorzeweski, A.; Steiner, T.; Jentzsch, T.; Werncke, W. Organometallics 1996, 15, 4984. (f) Whittall, I. R.; Humphrey, M. G.; Houbrechts, S.; Persoons, A.; Hockless, D. C. R. Organometallics 1996, 15, 5738. (g) Whittall, I. R.; Cifuentes, M. P.; Humphrey, M. G.; Luther-Davies, B.; Samoc, M.; Houbrechts, S.; Persoons, A.; Heath, G. A.; Hockless, D. C. R. J. Organomet. Chem. 1997, 549, 127.
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22. (a) For side chain activation see, e.g.: Davies, S. G.; McCarthy, T. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 12, p 1039. (b) For application in asymmetric syntheses see, e.g.: Uemura, M. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: London, 1991; Vol. 2, p 195. (c) For nucleophilic additions see, e.g.: Semmelhack, M. F. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 12, p 979. (d) For ring lithiations see, e.g.: Semmelhack, M. F. In Comprehensive Organometallic Chemistry II, Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K. 1995; Vol. 12, p 1017. (e) For stabilization of benzylic carbanions see, e.g.: Davies, S. G.; Coote, S. J.; Goodfellow, C. L. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: London, 1991; Vol. 2, p 1. (f) For stabilization of benzylic carbocations see, e.g.: Davies, S. G.; Donohoe, T. J. Synlett 1993, 323.
23. (a) For side chain activation see, e.g.: Davies, S. G.; McCarthy, T. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 12, p 1039. (b) For application in asymmetric syntheses see, e.g.: Uemura, M. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: London, 1991; Vol. 2, p 195. (c) For nucleophilic additions see, e.g.: Semmelhack, M. F. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 12, p 979. (d) For ring lithiations see, e.g.: Semmelhack, M. F. In Comprehensive Organometallic Chemistry II, Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K. 1995; Vol. 12, p 1017. (e) For stabilization of benzylic carbanions see, e.g.: Davies, S. G.; Coote, S. J.; Goodfellow, C. L. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: London, 1991; Vol. 2, p 1. (f) For stabilization of benzylic carbocations see, e.g.: Davies, S. G.; Donohoe, T. J. Synlett 1993, 323.
24. (a) For side chain activation see, e.g.: Davies, S. G.; McCarthy, T. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 12, p 1039. (b) For application in asymmetric syntheses see, e.g.: Uemura, M. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: London, 1991; Vol. 2, p 195. (c) For nucleophilic additions see, e.g.: Semmelhack, M. F. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 12, p 979. (d) For ring lithiations see, e.g.: Semmelhack, M. F. In Comprehensive Organometallic Chemistry II, Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K. 1995; Vol. 12, p 1017. (e) For stabilization of benzylic carbanions see, e.g.: Davies, S. G.; Coote, S. J.; Goodfellow, C. L. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: London, 1991; Vol. 2, p 1. (f) For stabilization of benzylic carbocations see, e.g.: Davies, S. G.; Donohoe, T. J. Synlett 1993, 323.
25. (a) For side chain activation see, e.g.: Davies, S. G.; McCarthy, T. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 12, p 1039. (b) For application in asymmetric syntheses see, e.g.: Uemura, M. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: London, 1991; Vol. 2, p 195. (c) For nucleophilic additions see, e.g.: Semmelhack, M. F. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K., 1995; Vol. 12, p 979. (d) For ring lithiations see, e.g.: Semmelhack, M. F. In Comprehensive Organometallic Chemistry II, Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K. 1995; Vol. 12, p 1017. (e) For stabilization of benzylic carbanions see, e.g.: Davies, S. G.; Coote, S. J.; Goodfellow, C. L. In Advances in Metal-Organic Chemistry; Liebeskind, L. S., Ed.; JAI Press: London, 1991; Vol. 2, p 1. (f) For stabilization of benzylic carbocations see, e.g.: Davies, S. G.; Donohoe, T. J. Synlett 1993, 323.
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