Synthesis of two-photon absorbing unsymmetrical branched chromophores through direct tris(bromomethylation) of fluorene

Journal of Organic Chemistry

Volumn 70, Issue 13, 2005, Pages 5126-5132

  Yao, Sheng ^a   Belfield, Kevin D ^a  

^a UNIVERSITY OF CENTRAL FLORIDA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; ANISOTROPY; DERIVATIVES; ELECTRIC EXCITATION; ELECTRONS; FLUORESCENCE; FLUORINE; LASER APPLICATIONS; PHOTONS; SPECTROSCOPIC ANALYSIS; SYNTHESIS (CHEMICAL); ULTRAVIOLET RADIATION;

BROMOMETHYLATION; CARBOXYALDEHYDE MOIETIES; FEMTOSECOND LASER EXCITATIONS; FLUORENYL SYSTEMS;

CHROMOPHORES;

2,4,7 TRIS(BROMOMETHYL) 9,9 DIETHYLFLUORENE; 4,4,4{[9,9 BIS (ETHYL) 9H FLUORENE 2,4,7, TRIYL]TRI 2,1 ETHENEDIYL}TRIS(N,N DIPHENYL)BENZENEAMINE; 9,9 DIETHYL 2,4,7 TRIS[2 (4 NITROPHENYL) VINYL] 9H FLUORENE; ALDEHYDE; FLUORENE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANISOTROPY; ARTICLE; CHROMATOPHORE; FLUORESCENCE; LIGHT ABSORPTION; QUANTUM YIELD; STEADY STATE; SYNTHESIS; ULTRAVIOLET RADIATION;

EID: 20844441793     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0503512     Document Type: Article

References (47)

1. Numerous papers have been published in this area, e.g., see: (a) Belfield, K. D.; Bondar, M. V.; Morales, A. R.; Yavuz, O.; Przhonska, O. V. J. Phys. Org. Chem. 2003, 16, 194-201.
2. (b) Geng, Y.; Chen, A. C. A.; Ou, J. J.; Chen, S. H. Chem. Mater. 2003, 15, 4352-4360.
3. (c) Geng, Y.; Chen, A. C. A.; Ou, J. J.; Chen, S. H.; Klubek, K.; Vaeth, K. M.; Tang, C. W. Chem. Mater. 2003, 15, 4352-4360.
4. (d) Son, S. W.; Jung, S. H.; Cho, H. N. Synth. Metal. 2003, 137, 1065-1066.
5. (e) Zheng, M.; Lin, Z.; Ding, L.; Karasz, F. E. Macromolecules 2002, 35, 9939-9946.
6. (f) Cho, H. N.; Kim, D. Y.; Kim, Y. C.; Lee, J. Y.; Kim, C. Y. Adv. Mater. 1997, 9, 326-328.
7. (a) Perepichka, D. F.; Bryce, M. R.; Perepichka, I. F.; Lyubchik, S. B.; Christensen, C. A.; Godbert, N.; Batsanov, A. S.; Levillain, E.; McInnes, E. J. L.; Zhao, J. P. J. Am. Chem. Soc. 2002, 124, 14227-14238.
8. (b) Omercq, B.; Grasso, C.; Maldonado, J.-L.; Halik, M.; Barlow, S.; Marder, S. R.; Kippelen, B. J. Phys. Chem. B 2004, 108, 8647-8651.
9. (c) Perepichka, D. F.; Perepichka, I. F.; Bryce, M. R.; Moore, A. J.; Sokolov, N. I. Synth. Metal. 2001, 121 (1-3), 1487-1488.
10. (a) Burgi, L.; Richards, T. J.; Friend, R. H.; Sirringhaus, H. J. Appl. Phys. 2003, 94, 6129-6137.
11. (b) Paul, K. E.; Wong, W. S.; Ready, S. E.; Street, R. A. Appl. Phys. Lett. 2003, 83, 2070-2072.
12. (c) McCulloch, I.; Bailey, C.; Giles, M.; Heeney, M.; Sparrowe, D.; Shkunov, M.; Tierney, S. Polym. Prepr. 2003, 44, 325-326.
13. (a) Gaylord, B. S.; Heeger, A. J.; Bazan, G. C. J. Am. Chem. Soc. 2003, 125, 896-900.
14. (b) Zhang, M.; Lu, P.; Ma, Y.; Shen, J. J. Phys. Chem. B 2003, 107, 6535-6538.
15. (c) Yang, N. C.; Lee, S. M.; Suh, D. H. Polym. Bull. 2003, 49, 371-377.
16. (d) Yang, N. C.; Chang, S.; Suh, D. H. Polymer 2003, 44, 2143-2148.
17. For some examples, see: (a) Belfield, K. D.; Hagan, D. J.; Van Stryland, E. W.; Schafer, K. J.; Negres, R. A. Org. Lett. 1999, 1, 1575-1578.
18. (b) Baur, J. W.; Alexander, M. D., Jr.; Banach, M.; Denny, L. R.; Reinhardt, B. A.; Vaia, R. A.; Fleitz, P. A.; Kirkpatrick, S. M. Chem. Mater. 1999, 11, 2899-2906.
19. (c) Reinhardt, B. A.; Brott, L. L.; Clarson, S. J.; Dillard, A. G.; Bhatt, J. C.; Kannan, R.; Yuan, L.; He, G. S.; Prasad, P. N. Chem. Mater. 1998, 10, 1863-1874.
20. (d) Kannan, R.; He, G. S.; Yuan, L.; Xu, F.; Prasad, P. N.; Dombroskie, A. G.; Reinhardt, B. A.; Baur, J. W.; Vaia, R. A.; Tan, L.-S. Chem. Mater. 2001, 13, 1896-1904.
21. For reviews, see: (a) Moore, J. S. Acc. Chem. Res. 1997, 30, 402-413.
22. (b) Berresheim, A. J.; Muellen, K. Chem. Rev. 1999, 99, 1747-1785.
23. (c) Grayson, S. M.; Frechet, J. M. J. Chem. Rev. 2001, 101, 3819-3868.
24. (a) Peng, Z.; Pan, Y.; Xu, B.; Zhang, J. J. Am. Chem. Soc. 2000, 122, 6619-6623.
25. (b) Melinger, J. S.; Pan, Y.; Kleiman, V. D.; Peng, Z.; Davis, B. L.; McMorrow, D.; Lu, M. J. Am. Chem. Soc. 2002, 124, 12002-12012.
26. (c) Wang, J.; Lu, M.; Pan, Y.; Peng, Z. J. Org. Chem. 2002, 67, 7781-7786.
27. Pan, Y.; Peng, Z.; Melinger, J. S. Tetrahedron 2003, 59, 5495-5506.
28. (a) Mongin, O.; Porres, L.; Katan, C.; Pons, T.; Mertz, J.; Blanchard-Desce, M. Tetrahedron Lett. 2003, 44, 8121-8125.
29. (b) Kannan, R.; He, G. S.; Lin, T.-C.; Prasad, P. N.; Vaia, R. A.; Tan, L.-S. Chem. Mater. 2004, 16, 185-194.
30. (c) Chung, S.-J.; Kim, K-S.; Lin, T.-C.; He, G. S.; Swiatkiewicz, J.; Prasad, P. N. J. Phys. Chem. B 1999, 103, 10741-10745.
31. Belfield, K. D.; Morales, A. R.; Kang, B.-S.; Hales, J. M.; Hagan, D. J.; Van Stryland, E. W.; Chapela, V. M.; Percino, J. Chem. Mater. 2004, 16, 2267-2273.
32. An analogue of compound 1 was previously synthesized by the Heck coupling reaction, see: Lee, K.-S.; Lee, J. H.; Choi, H.; Cha, M.; Chung, M.-A.; Kim, Y. J.; Jung, S. Mol. Cryst. Liq. Cryst. Sci. Technol., Sect. A: Mole. Cryst. Liq. Cryst. 2001, 370, 155-159. The disadvantage of this method is the use of expensive tributyl(vinyl)tin and Pd catalysts under demanding conditions.
33. (a) Ahn, T.; Song, S.-Y.; Shim, H.-K. Macromolecules 2000, 33, 6764-6771.
34. (b) Liu, B.; Yu, W.-L.; Pei, J.; Liu, S.-Y.; Lai, Y.-H.; Huang, W. Macromolecules 2001, 34, 7932-7940.
35. 1H NMR.
36. 1H NMR; efforts to further characterize these are on going.
37. Belfield, K. D.; Morales, A. R.; Rang, B.-S.; Hales, J. M.; Hagan, D. J.; Van Stryland, E. W.; Chapela, V. M.; Percino, J. Chem. Mater. 2004, 16, 4634-4641.
38. (a) Negres, R. A.; Van Stryland, E. W.; Hagan, D. J.; Belfield, K. D.; Schafer, K. J.; Przhonska, O. V.; Reinhardt, B. A. Proc. SPIE Int. Soc. Opt. Eng. 1999, 3796, 88-97.
39. (b) Negres, R. A.; Hales, J. M.; Kobyakov, A.; Hagan, D. J.; Van Stryland, E. W. Opt. Lett. 2002, 27, 270-272.
40. (a) Chung, S.; Kim, K.-S.; Lin, T.-C.; He, C. S.; Swiatkiewicz, J.; Prasad, P. N. J. Phys. Chem. B 1999, 103, 10741-10745.
41. (b) Drobizhev, M.; Karotki, A.; Rebane, A.; Spangler, C. W. Opt. Lett. 2001, 26, 1081-1083.
42. (c) Abbotto, A.; Beverina, L.; Bozio, R.; Facchetti, A.; Ferrante, C.; Pagani, G. A.; Pedron, D.; Signorini, R. Chem. Commun. 2003, 17, 2144-2145.
43. McMonagh, A. M.; Humphrey, M. G.; Samoc, M.; Luther-Davies, B. Organometallics 1999, 18, 5195-5197.
44. Sheik-Bahea M.; Said A. A.; Wei T.; Hagan D. J.; Van Stryland E. IEEE J. Quantum Electron. 1990, 26, 760-769.
45. Kannan, R.; He, G. S.; Yuan, L.; Xu, F.; Prasad, P. N.; Dombroskie, A. G.; Reinhardt, B. A.; Baur, J. W.; Vaia, R. A.; Tan, L.-S. Chem. Mater. 2001, 13, 1896-1904.
46. Lai, G.; Bu, X. R.; Santos, J.; Mintz, E. A. Synlett 1997, 1275-1276.
47. Armarego, W. L. F.; Perrin, D. D. Purification of Laboratory Chemicals, 4th ed.; Butterworth-Heinemann: Oxford, UK, 2000; pp 192-193.