Synthesis and photophysical properties of dihydroheptacenes: New blue-emitting materials

Journal of Organic Chemistry

Volumn 71, Issue 11, 2006, Pages 4085-4091

  Mondal, Rajib ^a   Shah, Bipin K ^a   Neckers, Douglas C ^a  

^a BOWLING GREEN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CRYSTAL STRUCTURE; LIGHT EMISSION; LIGHT EMITTING DIODES; SOLID STATE DEVICES; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

BLUE EMITTERS; DIHYDROHEPTACENES; PHOTOPHYSICAL PROPERTIES; X-RAY CRYSTAL STRUCTURES;

OLEFINS;

ALKENE DERIVATIVE; DIHYDROHEPTACENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BLUE LIGHT; CHEMICAL PROCEDURES; CRYSTAL STRUCTURE; LIGHT EMITTING DIODE; SOLID STATE; SUBSTITUTION REACTION; SYNTHESIS;

EID: 33646910771     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0601314     Document Type: Article

References (28)

1. Contribution no. 576 from the Center for Photochemical Sciences.
2. Mitschke, U.; Bäuerle, P. J. Mater. Chem. 2002, 10, 1471.
3. Friend, R. H.; Gymer, R. W.; Holmes, A. B.; Burroughes, J. H.; Marks, R. N.; Taliani, C.; Bradley, D. D. C.; Dos Santos, D. A.; Brédas, J. L.; Lögdlund, M.; Salaneck, W. R. Nature 1999, 397, 121.
4. Segura, J. L.; Martin, N. J. Mater. Chem. 2000, 10, 2403.
5. Li, Z. H.; Wong, M. S.; Tao, Y.; Lu, J. Chem. Eur. J. 2005, 11, 3285.
6. Zheng, S.; Shi, J. Chem. Mater. 2001, 13, 4405.
7. Service, R. F. Science 2005, 310, 1762.
8. Kim, D. Y.; Cho, H. M.; Kim, C. Y. Prog. Polym. Sci. 2000, 25, 1089.
9. Shi, J.; Tang, C. W. Appl Phys. Lett. 2002, 80, 3201.
10. Cava, M. P.; VanMeter, J. P. J. Org. Chem. 1969, 34, 538-545.
11. Miller, G. P.; Briggs, J. Tetrahedron Lett. 2004, 45, 477-481.
12. Miller, G. P.; Briggs, J. Org. Lett. 2003, 5, 4203-4206.
13. Sciano, J. C. Handbook of Organic Photochemistry; CRC Press: Boca Raton, Florida, 1989; Vol. 1, p 231.
14. Birks, J. B. Photophysics of Aromatic Molecules; Wiley Interscience: New York, 1970; p 178.
15. Shah, B. K.; Neckers, D. C.; Shi, J.; Forsythe, E. W.; Morton, D. J. Phys. Chem. A 2005, 109, 7677.
16. Turro, N. J. Modern Molecular Photochemistry; University Science Books: Sausalito, CA, 1991; pp 186-187.
17. de Mello, J. C.; Wittmann, H. F.; Friend, R. H. Adv. Mater. 1997, 9, 230.
18. The solid-state emission was recorded by dispersing a very low amount of emitters in thin PMMA films. This may be the reason there were no differences in the solid state and solution emissions of 1-3. We did not record the solid-state emission from films composed of only the emitters. Nevertheless, given that there was no significant π-stacking observed in the crystal structure, it is unlikely that solid-state emission of 1-3 would differ from what was observed in the PMMA matrix.
19. Shah, B. K.; Neckers, D. C.; Shi, J.; Forsythe, E. W.; Morton, D. Chem. Mater. 2006, 18, 603.
20. Schwob, H. P.; Williams, D. F. J. Chem. Phys. 1973, 58, 1542.
21. List, E. J. W.; Guentner, R.; de Freitas, P. S.; Scherf, U. Adv. Mater. 2002, 14, 374.
22. Chan, K. L.; McKiernan, M. J.; Towns, C. R.; Holmes, A. B. J. Am. Chem. Soc. 2005, 127, 7662.
23. Carlson, R. G.; Srinivasachar, K.; Givens, R. S.; Matuszewski, B. K. J. Org. Chem. 1986, 51, 3978.
24. Hauser, C. R.; Tetenbaum, M. T.; Hoffenberg, D. S. J. Org. Chem. 1958, 23, 861.
25. Hawkins, R. T.; Lennarz, W. J.; Snyder, H. R. J. Am. Chem. Soc. 1960, 82, 3053.
26. Bruker SMART (Ver. 5.05) and SAINT-Plus (Ver. 7.08); Bruker AXS Inc.: Madison, WI, 1999.
27. Sheldrick, G. M. SADABS, Program for the Empirical Absorption Correction of Area Detector Data; University of Göttingen: Göttingen, Germany, 1996.
28. Sheldrick, G. M. SHELXTL (ver. 6.12); Bruker AXS, Inc.: Madison, WI, 2000.