Synthesis and photophysical studies of bis-enediynes as tunable fluorophores

Journal of the American Chemical Society

Volumn 125, Issue 37, 2003, Pages 11241-11248

  Hwang, Gil Tae ^a   Son, Hyung Su ^a   Ku, Ja Kang ^a   Kim, Byeang Hyean ^a  

^a Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

PHOTOPHYSICAL STUDIES;

ABSORPTION; FLUORESCENCE; QUANTUM THEORY; SYNTHESIS (CHEMICAL);

AROMATIC HYDROCARBONS;

ALKYNE; BROMIDE; PALLADIUM;

ANALYTIC METHOD; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; COUPLING FACTOR; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM CHEMISTRY; REACTION ANALYSIS; SYNTHESIS;

EID: 0042192050     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0349148     Document Type: Article

References (32)

1. (a) Joshi, H. S.; Jamshidi, R.; Tor, Y. Angew. Chem., Int. Ed. Engl. 1999, 38, 2722.
2. (b) Meng, H.; Huang, W. J. Org. Chem. 2000, 65, 3894.
3. (c) Mori, A.; Sekiguchi, A.; Masui, K.; Shimada, T.; Horie, M.; Osakada, K.; Kawamoto, M.; Ikeda, T. J. Am. Chem. Soc. 2003, 125, 1700.
4. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769.
5. Uenishi, J.; Kawahama, R.; Yonemitsu, O.; Tsuji, J. J. Org. Chem. 1998, 63, 8965.
6. (a) Roush, W. R.; Moriarty, K. J.; Brown, B. B. Tetrahedron Lett. 1990, 31, 6509.
7. (b) Zapata, A. J.; Ruíz, J. J. Organomet. Chem. 1994, 479, C6.
8. (c) Shen, W.; Wang, L. J. Org. Chem. 1999, 64, 8873.
9. Shen, W.; Thomas, S. A. Org. Lett. 2000, 2, 2857, and references therein.
10. (a) Sonogashira. K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998.
11. (b) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467.
12. (a) Anthony, J.; Boldi, A. M.; Rubin, Y.; Hobi, M.; Gramlich, V.; Knobler, C. B.; Sciler, P.; Diederich, F. Helv. Chim. Acta 1995, 78, 13.
13. (b) Faust, R.; Diederich, F.; Gramlich, V.; Seiler, P. Chem. Eur. J. 1995, 1, 111.
14. (c) Zhao, Y.; Campbell, K.; Tykwinski, R. R. J. Org. Chem. 2002, 67, 336.
15. (a) Kaafarani, B. R.; Neckers, D. C. Tetrahedron Lett. 2001, 42, 4099.
16. (b) Kaafarani, B. R.; Pinkerton, A. A.; Neckers, D. C. Tetrahedron Lett. 2001, 42, 8137.
17. (c) Kaafarani, B. R.; Wex, B.; Strehmel, B.; Neckers, D. C. Photochem. Photobiol. Sci. 2002, 1, 942.
18. Hwang, G. T.; Son, H. S.; Ku, J. K.; Kim, B. H. Org. Lett. 2001, 3, 2469.
19. (a) Blanchette, H. S.; Brand, S. C.; Naruse, H.; Weakley, T. J. R.; Haley, M. M. Tetrahedron 2000, 56, 9581.
20. (b) Benites, P. J.; Rawat, D. S.; Zaleski, J. M. J. Am. Chem. Soc. 2000, 122, 7208.
21. See Supporting Information.
22. Parker, C. A. In Photoluminescence of Solutions; Elsevier: Amsterdam, 1968.
23. Shetty, A. S.; Zhang, J.; Moore. J. S. J. Am. Chem. Soc. 1996, 118, 1019.
24. The following dialdehydes and 1,1-dibromo-1-alkenes have been reported previously. 4, 4′-diformylbiphenyl: Parrish, J. P.; Flanders, V. L.; Floyd, R. J.; Jung, K. W. Tetrahedron Lett. 2001, 42, 7729; 2-nitroterephthaldicarboxaldehyde: Saikachi, H.; Muto, H. Chem. Pharm. Bull. 1971, 19, 959. 2,6-naphthalenedicarboxaldehyde: Miyaji, T.; Azuma, C.; Asaoka, E.; Nakamura, S. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 1064; 2,7-diformyl-9,9-di-n-propylfluorene: Kauffman, J. M.; Khalaj, A.; Litak, P. T. ; Novinski, J. A.; Bajwa, G. S. J. Heterocycl. Chem. 1994, 31, 957; 9, 10-anthracenedicarboxaldehyde: Ferraris, J. P.; Barashkov, N. N.; Novikova, T. S. Synth. Met. 1996, 83, 39; 2,5-dimethoxyterephthaldicarboxaldehyde: Hörhold, H.-H.; Tillmann, H.; Bader, C.; Stockmann, R.; Nowotny, J.; Klemm, E.; Holzer, W.; Penzkofer, A. Synth. Met. 2001, 119, 199; 8 : Kane, J. J.; Gao, F.; Reinhardt, B. A.; Evers, R. C. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1992, 33, 192; 18 : Neidlein, R.; Winter, M. Synthesis 1998, 1362; 19; Heasley, V. L.; Titterington, D. R.; Rold, T. L. Heasley, G. E. J. Org. Chem. 1976, 41, 1285.
25. The following dialdehydes and 1,1-dibromo-1-alkenes have been reported previously. 4, 4′-diformylbiphenyl: Parrish, J. P.; Flanders, V. L.; Floyd, R. J.; Jung, K. W. Tetrahedron Lett. 2001, 42, 7729; 2-nitroterephthaldicarboxaldehyde: Saikachi, H.; Muto, H. Chem. Pharm. Bull. 1971, 19, 959. 2,6-naphthalenedicarboxaldehyde: Miyaji, T.; Azuma, C.; Asaoka, E.; Nakamura, S. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 1064; 2,7-diformyl-9,9-di-n-propylfluorene: Kauffman, J. M.; Khalaj, A.; Litak, P. T. ; Novinski, J. A.; Bajwa, G. S. J. Heterocycl. Chem. 1994, 31, 957; 9, 10-anthracenedicarboxaldehyde: Ferraris, J. P.; Barashkov, N. N.; Novikova, T. S. Synth. Met. 1996, 83, 39; 2,5-dimethoxyterephthaldicarboxaldehyde: Hörhold, H.-H.; Tillmann, H.; Bader, C.; Stockmann, R.; Nowotny, J.; Klemm, E.; Holzer, W.; Penzkofer, A. Synth. Met. 2001, 119, 199; 8 : Kane, J. J.; Gao, F.; Reinhardt, B. A.; Evers, R. C. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1992, 33, 192; 18 : Neidlein, R.; Winter, M. Synthesis 1998, 1362; 19; Heasley, V. L.; Titterington, D. R.; Rold, T. L. Heasley, G. E. J. Org. Chem. 1976, 41, 1285.
26. The following dialdehydes and 1,1-dibromo-1-alkenes have been reported previously. 4, 4′-diformylbiphenyl: Parrish, J. P.; Flanders, V. L.; Floyd, R. J.; Jung, K. W. Tetrahedron Lett. 2001, 42, 7729; 2-nitroterephthaldicarboxaldehyde: Saikachi, H.; Muto, H. Chem. Pharm. Bull. 1971, 19, 959. 2,6-naphthalenedicarboxaldehyde: Miyaji, T.; Azuma, C.; Asaoka, E.; Nakamura, S. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 1064; 2,7-diformyl-9,9-di-n-propylfluorene: Kauffman, J. M.; Khalaj, A.; Litak, P. T. ; Novinski, J. A.; Bajwa, G. S. J. Heterocycl. Chem. 1994, 31, 957; 9, 10-anthracenedicarboxaldehyde: Ferraris, J. P.; Barashkov, N. N.; Novikova, T. S. Synth. Met. 1996, 83, 39; 2,5-dimethoxyterephthaldicarboxaldehyde: Hörhold, H.-H.; Tillmann, H.; Bader, C.; Stockmann, R.; Nowotny, J.; Klemm, E.; Holzer, W.; Penzkofer, A. Synth. Met. 2001, 119, 199; 8 : Kane, J. J.; Gao, F.; Reinhardt, B. A.; Evers, R. C. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1992, 33, 192; 18 : Neidlein, R.; Winter, M. Synthesis 1998, 1362; 19; Heasley, V. L.; Titterington, D. R.; Rold, T. L. Heasley, G. E. J. Org. Chem. 1976, 41, 1285.
27. The following dialdehydes and 1,1-dibromo-1-alkenes have been reported previously. 4, 4′-diformylbiphenyl: Parrish, J. P.; Flanders, V. L.; Floyd, R. J.; Jung, K. W. Tetrahedron Lett. 2001, 42, 7729; 2-nitroterephthaldicarboxaldehyde: Saikachi, H.; Muto, H. Chem. Pharm. Bull. 1971, 19, 959. 2,6-naphthalenedicarboxaldehyde: Miyaji, T.; Azuma, C.; Asaoka, E.; Nakamura, S. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 1064; 2,7-diformyl-9,9-di-n-propylfluorene: Kauffman, J. M.; Khalaj, A.; Litak, P. T. ; Novinski, J. A.; Bajwa, G. S. J. Heterocycl. Chem. 1994, 31, 957; 9, 10-anthracenedicarboxaldehyde: Ferraris, J. P.; Barashkov, N. N.; Novikova, T. S. Synth. Met. 1996, 83, 39; 2,5-dimethoxyterephthaldicarboxaldehyde: Hörhold, H.-H.; Tillmann, H.; Bader, C.; Stockmann, R.; Nowotny, J.; Klemm, E.; Holzer, W.; Penzkofer, A. Synth. Met. 2001, 119, 199; 8 : Kane, J. J.; Gao, F.; Reinhardt, B. A.; Evers, R. C. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1992, 33, 192; 18 : Neidlein, R.; Winter, M. Synthesis 1998, 1362; 19; Heasley, V. L.; Titterington, D. R.; Rold, T. L. Heasley, G. E. J. Org. Chem. 1976, 41, 1285.
28. The following dialdehydes and 1,1-dibromo-1-alkenes have been reported previously. 4, 4′-diformylbiphenyl: Parrish, J. P.; Flanders, V. L.; Floyd, R. J.; Jung, K. W. Tetrahedron Lett. 2001, 42, 7729; 2-nitroterephthaldicarboxaldehyde: Saikachi, H.; Muto, H. Chem. Pharm. Bull. 1971, 19, 959. 2,6-naphthalenedicarboxaldehyde: Miyaji, T.; Azuma, C.; Asaoka, E.; Nakamura, S. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 1064; 2,7-diformyl-9,9-di-n-propylfluorene: Kauffman, J. M.; Khalaj, A.; Litak, P. T. ; Novinski, J. A.; Bajwa, G. S. J. Heterocycl. Chem. 1994, 31, 957; 9, 10-anthracenedicarboxaldehyde: Ferraris, J. P.; Barashkov, N. N.; Novikova, T. S. Synth. Met. 1996, 83, 39; 2,5-dimethoxyterephthaldicarboxaldehyde: Hörhold, H.-H.; Tillmann, H.; Bader, C.; Stockmann, R.; Nowotny, J.; Klemm, E.; Holzer, W.; Penzkofer, A. Synth. Met. 2001, 119, 199; 8 : Kane, J. J.; Gao, F.; Reinhardt, B. A.; Evers, R. C. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1992, 33, 192; 18 : Neidlein, R.; Winter, M. Synthesis 1998, 1362; 19; Heasley, V. L.; Titterington, D. R.; Rold, T. L. Heasley, G. E. J. Org. Chem. 1976, 41, 1285.
29. The following dialdehydes and 1,1-dibromo-1-alkenes have been reported previously. 4, 4′-diformylbiphenyl: Parrish, J. P.; Flanders, V. L.; Floyd, R. J.; Jung, K. W. Tetrahedron Lett. 2001, 42, 7729; 2-nitroterephthaldicarboxaldehyde: Saikachi, H.; Muto, H. Chem. Pharm. Bull. 1971, 19, 959. 2,6-naphthalenedicarboxaldehyde: Miyaji, T.; Azuma, C.; Asaoka, E.; Nakamura, S. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 1064; 2,7-diformyl-9,9-di-n-propylfluorene: Kauffman, J. M.; Khalaj, A.; Litak, P. T. ; Novinski, J. A.; Bajwa, G. S. J. Heterocycl. Chem. 1994, 31, 957; 9, 10-anthracenedicarboxaldehyde: Ferraris, J. P.; Barashkov, N. N.; Novikova, T. S. Synth. Met. 1996, 83, 39; 2,5-dimethoxyterephthaldicarboxaldehyde: Hörhold, H.-H.; Tillmann, H.; Bader, C.; Stockmann, R.; Nowotny, J.; Klemm, E.; Holzer, W.; Penzkofer, A. Synth. Met. 2001, 119, 199; 8 : Kane, J. J.; Gao, F.; Reinhardt, B. A.; Evers, R. C. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1992, 33, 192; 18 : Neidlein, R.; Winter, M. Synthesis 1998, 1362; 19; Heasley, V. L.; Titterington, D. R.; Rold, T. L. Heasley, G. E. J. Org. Chem. 1976, 41, 1285.
30. The following dialdehydes and 1,1-dibromo-1-alkenes have been reported previously. 4, 4′-diformylbiphenyl: Parrish, J. P.; Flanders, V. L.; Floyd, R. J.; Jung, K. W. Tetrahedron Lett. 2001, 42, 7729; 2-nitroterephthaldicarboxaldehyde: Saikachi, H.; Muto, H. Chem. Pharm. Bull. 1971, 19, 959. 2,6-naphthalenedicarboxaldehyde: Miyaji, T.; Azuma, C.; Asaoka, E.; Nakamura, S. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 1064; 2,7-diformyl-9,9-di-n-propylfluorene: Kauffman, J. M.; Khalaj, A.; Litak, P. T. ; Novinski, J. A.; Bajwa, G. S. J. Heterocycl. Chem. 1994, 31, 957; 9, 10-anthracenedicarboxaldehyde: Ferraris, J. P.; Barashkov, N. N.; Novikova, T. S. Synth. Met. 1996, 83, 39; 2,5-dimethoxyterephthaldicarboxaldehyde: Hörhold, H.-H.; Tillmann, H.; Bader, C.; Stockmann, R.; Nowotny, J.; Klemm, E.; Holzer, W.; Penzkofer, A. Synth. Met. 2001, 119, 199; 8 : Kane, J. J.; Gao, F.; Reinhardt, B. A.; Evers, R. C. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1992, 33, 192; 18 : Neidlein, R.; Winter, M. Synthesis 1998, 1362; 19; Heasley, V. L.; Titterington, D. R.; Rold, T. L. Heasley, G. E. J. Org. Chem. 1976, 41, 1285.
31. The following dialdehydes and 1,1-dibromo-1-alkenes have been reported previously. 4, 4′-diformylbiphenyl: Parrish, J. P.; Flanders, V. L.; Floyd, R. J.; Jung, K. W. Tetrahedron Lett. 2001, 42, 7729; 2-nitroterephthaldicarboxaldehyde: Saikachi, H.; Muto, H. Chem. Pharm. Bull. 1971, 19, 959. 2,6-naphthalenedicarboxaldehyde: Miyaji, T.; Azuma, C.; Asaoka, E.; Nakamura, S. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 1064; 2,7-diformyl-9,9-di-n-propylfluorene: Kauffman, J. M.; Khalaj, A.; Litak, P. T. ; Novinski, J. A.; Bajwa, G. S. J. Heterocycl. Chem. 1994, 31, 957; 9, 10-anthracenedicarboxaldehyde: Ferraris, J. P.; Barashkov, N. N.; Novikova, T. S. Synth. Met. 1996, 83, 39; 2,5-dimethoxyterephthaldicarboxaldehyde: Hörhold, H.-H.; Tillmann, H.; Bader, C.; Stockmann, R.; Nowotny, J.; Klemm, E.; Holzer, W.; Penzkofer, A. Synth. Met. 2001, 119, 199; 8 : Kane, J. J.; Gao, F.; Reinhardt, B. A.; Evers, R. C. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1992, 33, 192; 18 : Neidlein, R.; Winter, M. Synthesis 1998, 1362; 19; Heasley, V. L.; Titterington, D. R.; Rold, T. L. Heasley, G. E. J. Org. Chem. 1976, 41, 1285.
32. The following dialdehydes and 1,1-dibromo-1-alkenes have been reported previously. 4, 4′-diformylbiphenyl: Parrish, J. P.; Flanders, V. L.; Floyd, R. J.; Jung, K. W. Tetrahedron Lett. 2001, 42, 7729; 2-nitroterephthaldicarboxaldehyde: Saikachi, H.; Muto, H. Chem. Pharm. Bull. 1971, 19, 959. 2,6-naphthalenedicarboxaldehyde: Miyaji, T.; Azuma, C.; Asaoka, E.; Nakamura, S. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 1064; 2,7-diformyl-9,9-di-n-propylfluorene: Kauffman, J. M.; Khalaj, A.; Litak, P. T. ; Novinski, J. A.; Bajwa, G. S. J. Heterocycl. Chem. 1994, 31, 957; 9, 10-anthracenedicarboxaldehyde: Ferraris, J. P.; Barashkov, N. N.; Novikova, T. S. Synth. Met. 1996, 83, 39; 2,5-dimethoxyterephthaldicarboxaldehyde: Hörhold, H.-H.; Tillmann, H.; Bader, C.; Stockmann, R.; Nowotny, J.; Klemm, E.; Holzer, W.; Penzkofer, A. Synth. Met. 2001, 119, 199; 8 : Kane, J. J.; Gao, F.; Reinhardt, B. A.; Evers, R. C. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1992, 33, 192; 18 : Neidlein, R.; Winter, M. Synthesis 1998, 1362; 19; Heasley, V. L.; Titterington, D. R.; Rold, T. L. Heasley, G. E. J. Org. Chem. 1976, 41, 1285.