An exceptional red shift of emission maxima upon fluorine substitution

Journal of Organic Chemistry

Volumn 67, Issue 21, 2002, Pages 7185-7192

  Krebs, Frederik C ^a   Spanggaard, Holger ^a  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORINATION; PHOTOPHYSICAL PROPERTIES;

ALDEHYDES; BENZENE; CONDENSATION; DYES; FLUORESCENCE; HALOGENATION; INFRARED RADIATION; ORGANIC SOLVENTS; SYNTHESIS (CHEMICAL); ULTRAVIOLET SPECTROSCOPY;

SUBSTITUTION REACTIONS;

BENZENE DERIVATIVE; BORONIC ACID DERIVATIVE; FLUORINE; FUNCTIONAL GROUP; GOLD; OCTANE; PHENYL GROUP;

ARTICLE; ELECTRIC POTENTIAL; FLUORESCENCE SPECTROSCOPY; FLUORINATION; IONIZATION; LIGHT; PHYSICS; QUANTUM YIELD; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY; X RAY ANALYSIS;

EID: 0037131379     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo025592d     Document Type: Article

References (31)

1. (a) Krieg, B.; Manecke, G. Z. Naturforsch, B: Anorg. Chem. Org. Chem. Biochem. Biophys. Biol. 1967, 22, 132.
2. (b) Neunhoeffer, O.; Krieg, B. Z. Naturforsch., B: Anorg. Chem. Org. Chem. Biochem. Biophys. Biol. 1966, 21, 536.
3. (c) Cook, A. H.; Jones, D. G. J. Chem. Soc. 1941, 278.
4. (d) Steck, E. A.; Day, A. R. J. Am. Chem. Soc. 1943, 65, 452.
5. Krebs, F. C.; Jørgensen, M. J. Org. Chem. 2001, 66, 6169-6173.
6. Krebs, F. C.; Lindvold, L. R.; Jørgensen, M. Tett. Lett. 2001, 42, 6753-6757.
7. McLoughlin, V. C. R.; Thrower, J. Tetrahedron 1969, 25, 5921-5940.
8. Knunyants, I. L.; Yakobsen, G. G. Synthesis of Fluoroorganic Compounds; Springer-Verlag: Berlin, Heidelberg, New York, Tokyo, 1985.
9. Attempts to isolate the product at this point gave mainly the monobrominated species; in our hands it was not possible obtain a pure sample free from 1 and 2.
10. Kromm, P.; Allouchi, H.; Bideau, J.-P.; Cotrait, M. Mol. Cryst. Liq. Cryst. Sci. Technol., Sect. A 1994, 257, 9. Kromm, P.; Bideau, J.-P.; Cotrait, M.; Destrade, C.; Nguyen, H. Acta Crystallogr. 1994, C50, 112.
11. Kromm, P.; Allouchi, H.; Bideau, J.-P.; Cotrait, M. Mol. Cryst. Liq. Cryst. Sci. Technol., Sect. A 1994, 257, 9. Kromm, P.; Bideau, J.-P.; Cotrait, M.; Destrade, C.; Nguyen, H. Acta Crystallogr. 1994, C50, 112.
12. (a) Isikdag, I.; Ucucu, U.; Ozdemir, A.; Meric, A.; Ozturk, Y.; Aydin, S.; Ergun, B. Boll. Chim. Farm. 1999, 138, 453-456.
13. (b) Purushothaman, E.; Rajasekharan-Pillai, V. N. Indian J. Chem. B. 1989, 28, 290-293.
14. (c) Oda, K.; Sakai, M.; Tsujita, H.; Machida M. Synth. Commun. 1997, 27, 1183-1189.
15. Padwa, A.; Ku, H.; Mazzu, A. J. Org. Chem. 1978, 43, 381-387.
16. Baumann, W.; Bischof, H.; Fröhling, J. C.; Brittinger, C, Rettig, W.; Rotkiewicz, K. J. Photochem. Photobiol., A 1992, 64, 49.
17. Strehmel, B.; Sarker, A. M.; Malpert, J. H.; Strehmel, V.; Seifert, H.; Neckers, D. C. J. Am. Chem. Soc. 1999, 121, 1226-1236.
18. Jager, W. F.; Volkers, A. A.; Neckers, D. C. Macromolecules 1995, 28, 8153.
19. Insight II User Guide, October 1995. Biosym/MSI: San Diego, 1995.
20. Röcker, C.; Heilemann, A.; Fromherz, P. J. Phys. Chem. 1996, 100, 12172.
21. Rettig, W. Top. Cur. Chem. 1994, 69, 253.
22. Rehahn, M.; Schlueter, A.-D.; Feast, J. W. Synthesis 1988, 5, 386-388.
23. Park, P. C.; Yoshino, K.; Tomiyasu, H. Synthesis 1999, 12, 2041-2044.
24. SMART and SAINT; Area-Detector Control and Integration Software; Siemens Analytical X-ray Instruments Inc.: Madison, WI, 1995.
25. Sheldrick, G. M. Empirical absorption program (SADABS) written for the Siemens SMART platform.
26. Sheldrick, G. M. SHELX-97; Program for structure solution and refinement. 1997.
27. Sheldrick, G. M. SHELXTL95; Siemens Analytical X-ray Instruments Inc.: Madison, WI, 1995.
28. Spek, A. L. Acta Crystallogr. 1990, A46, C-31.
29. Ware, W. R.; Rothman, W. Chem. Phys. Lett. 1976, 39, 449-453.
30. Straume, M.; Fraiser-Cadoret, S. G.; Johnson, M. L. In Topics in Fluorescence Spectroscopy; Lakowicz. J. R., Ed.; Plenum Press: New York, 1991; Vol. 2, pp 177-240.
31. Salaneck, W. R.; Lögdlund, M.; Fahlman, M.; Greczynski, G.; Kugler, Th. Mater. Sci. Eng. 2001, R34, 121-146.