Synthesis and photophysics of ambipolar fluoren-9-ylidene malononitrile derivatives

Journal of Organic Chemistry

Volumn 74, Issue 21, 2009, Pages 8484-8487

  Estrada, Leandro A ^a   Neckers, Douglas C ^a  

^a BOWLING GREEN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMBIPOLAR; CHARGE TRANSFER STATE; EFFICIENT SYNTHESIS; MALONONITRILES; PHOTOPHYSICS; POLAR SOLVENTS; STRUCTURE ACTIVITY RELATIONSHIPS; UV-VIS ABSORPTIONS;

CHARGE TRANSFER; EXCITED STATES; FLUORESCENCE SPECTROSCOPY; ION EXCHANGE; SYNTHESIS (CHEMICAL);

EMISSION SPECTROSCOPY;

FLUORENE DERIVATIVE; MALONONITRILE;

ARTICLE; FLAME PHOTOMETRY; FLUORESCENCE SPECTROSCOPY; ISOMERIZATION; PHYSICS; PURIFICATION; SOXHLET EXTRACTION; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 70350733534     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901869g     Document Type: Article

References (56)

1. (a) Shirota, Y.; Kageyama, H. Chem. Rev. 2007, 107, 953.
2. (b) Kulkarni, A. P.; Tonzola, C. J.; Babel, A.; Jenekhe, S. A. Chem. Mater. 2004, 16, 4556.
3. (c) Coropceanu, V.; Cornil, J.; da Silva Filho, D. A.; Olivier, Y.; Silbey, R.; Brédas, J. L. Chem. Rev. 2007, 107, 926.
4. (d) Zaumseil, J.; Sirringhaus, H. Chem. Rev. 2007, 107, 1296.
5. (e) He, G. H.; Tan, L.-T.; Zheng, Q.; Prasad, P. N. Chem. Rev. 2008, 108, 1245.
6. For recent representative references on multiphoton absorbing materials based on fluorene, see: (a) Belfield, K. D.; Bondar, M. V.; Hernández, F. E.; Masunov, A. E.; Mikhailov, I. A.; Morales, A. R.; Przhonska, O. V.; Yao, S. J. Phys. Chem. C 2009, 113, 4706.
7. (b) Sun, M.; Ding, Y.; Zhao, L.; Ma, F. Chem. Phys. 2009, 359, 166.
8. (c) Zheng, Q.; Gupta, S. K.; He, G. S.; Tan, L.-S.; Prasad, P. N. Adv. Funct. Mater. 2008, 18, 2770.
9. (d) Belfield, K. D.; Bondar, M. V.; Hernández, F. E.; Przhonska, O. V.; Yai, S. J. Phys. Chem. B 2007, 111, 12723.
10. Hoegl, H.; Barchietto, G.; Tar, D. Photochem. Photobiol. 1972, 16, 335.
11. Perepichka, I. F.; Mysyk, D. D.; Sokolov, N. I. In Current Trends in Polymer Photochemistry; Allen, N. S., Edge, M., Bellobono, I. R., Selli, E., Eds.; Ellis Harwood: New York, London, 1995.
12. Perepichka's work in "Electron Acceptors of the Fluorene Series" involves a total of 13 parts published in different scientific journals. Among the ones involving FMs, see: (a) Part 5. Perepichka, I. F.; Popov, A. F.; Orekhova, T. V.; Bryce, M. R.; Vdovichenko, A. N.; Batsanov, A. S.; Goldenberg, L. M.; Howard, J. A. K.; Sokolov, N. I.; Megson, J. L. J. Chem. Soc., Perkin Trans. 2 1996, 2453.
13. (b) Part 6. Mysyk, D. D.; Perepichka, I. F.; Sokolov, N. I. J. Chem. Soc., Perin Trans. 2 1997, 537.
14. (c) Part 7. Perepichka, I. F.; Kuz'mina, L. G.; Perepichka, D. F.; Bryce, M. R.; Goldenberg, L. M.; Popov, A. F.; Howard, J. A. K. J. Org. Chem. 1998, 63, 6484.
15. (d) Part 10. Perepichka, I. F.; Popov, A. F.; Orekhova, T. V.; Bryce, M. R.; Andrievskii, A. M.; Batsanov, A. S.; Howard, J. A. K.; Sokolov, N. I. J. Org. Chem. 2000, 65, 3053.
16. (a) Bendikov, M.; Wudl, F.; Perepichka, D. F. Chem. Rev. 2004, 104, 4891.
17. (b) Perepichka, D. F.; Bryce, M. R. Angew. Chem., Int. Ed. 2005, 44, 5370 and references therein.
18. (a) Hasharoni, K.; Lebanon, H.; Greenfield, S. R.; Gosztola, D. J.; Svec, W. A.; Wasielewski, M. R. J. Am. Chem. Soc. 1995, 117, 8055.
19. (b) Greenfield, S. R.; Svec, W. A.; Gosztola, D.; Wasielewski, M. R. J. Am. Chem. Soc. 1996, 118, 6767.
20. (c) Sinks, L. E.; Wasielewski, M. R. J. Phys. Chem. A 2003, 107, 611.
21. (d) Weiss, E. A.; Ratner, M. A.; Wasielewski, M. R. J. Phys. Chem. A 2003, 107, 3639.
22. (a) Weiss, E. A.; Ahrens, M. J.; Sinks, L. E.; Gusev, A. V.; Ratner, M. A.; Wasielewski, M. R. J. Am. Chem. Soc. 2004, 126, 5577.
23. (b) Weiss, E. A.; Tauber, M. J.; Kelley, R. F.; Ahrens, M. J.; Ratner, M. A.; Wasielewski, M. R. J. Am. Chem. Soc. 2005, 127, 11842.
24. For interesting reviews in the subject, see: (a) Chinchilla, R.; Nájera, C. Chem. Rev. 2007, 107, 294.
25. (b) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
26. (c) Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644.
27. (d) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
28. (a) Brunner, K.; van Dijken, A.; Brner, H.; Bastiaansen, J. J. A. M.; Kiggen, N. M. M.; Langeveld, B. M. W. J. Am. Chem. Soc. 2004, 126, 6035.
29. (b) Wu, Z.; Xiong, Y.; Zou, J.; Wang, L.; Liu, J.; Chen, Q.; Yang, W.; Peng, J.; Cao, Y. Adv. Mater. 2008, 20, 2359.
30. (c) Yeh, H.-C.; Chien, C.-H.; Shih, P.-I.; Yuan, M.-C.; Shu, C.-F. Macromolecules 2008, 41, 3801.
31. Fomina, N.; Hogen-Esch, T. E. Macromolecules 2008, 41, 3765.
32. (a) Ipaktschi, J.; Hosseinzadeh, R.; Schlaf, P.; Dreiseidler, E.; Goddard, R. Helv. Chim. Acta 1998, 81, 1821.
33. (b) Ipaktschi, J.; Hosseinzadeh, R.; Schlaf, P.; Eckert, T. Helv. Chim. Acta 2000, 83, 1224.
34. Lo, S.-C.; Burn, P. L. Chem. Rev. 2007, 107, 1097.
35. Bunz, U. H. Chem. Rev. 2000, 100, 1605.
36. Liu, Y.; Nishiura, M.; Wang, Y.; Hou, Z. J. Am. Chem. Soc. 2006, 128, 5592.
37. Albaugh, P. A.; Dominguez-Manzanares, E.; Hong, J. E.; Hornback, W. J.; Jiang, D.; Ornstein, P. L.; Thompson, M. L.; Tromiczak, E. G.; Wu, Z.; Zarrinmayeh, H.; Zimmerman, D. M.; Castaño-Mansanet, A. M.; Huffman, L. G.; Miller, W. D. U.S. Patent Application Pub. No. US/20070066573.
38. Bhatt, M. V. Tetrahedron 1964, 20, 803.
39. Ciszek, J. W.; Tour, J. M. Tetrahedron Lett. 2004, 45, 2801.
40. Shirai, Y.; Osgood, A., J.; Zhao, Y.; Yao, Y.; Saudan, L.; Yang, H.; Hung, C.-Y.; Alemany, L. B.; Sasaki, T.; Morin, J.-F.; Guerrero, J. M.; Kelly, K. F.; Tour, J. M. J. Am. Chem. Soc. 2006, 128, 4854.
41. Qin, T.; Zhou, G.; Scheiber, H.; Bauer, R. E.; Baumgarten, M.; Anson, C. E.; List, E. J. W.; Müllen, K. Angew. Chem., Int. Ed. 2008, 47, 8292.
42. Wang, C.; Pålson, L.-O.; Batsanov, A. S.; Bryce, M. R. J. Am. Chem. Soc. 2006, 128, 3789.
43. Wong, W.-Y.; Lu, G.-L.; Choi, K.-H.; Lin, Z. Eur. J. Org. Chem. 2003, 365.
44. Birckner, E.; Grummt, U.-W.; Göller, A. H.; Pautzch, T.; Egbe, D. A. M.; Al-Higari, M.; Klemm, E. J. Phys. Chem. A 2001, 105, 10307.
45. Rault-Berthelot, J.; Rozé, C.; Granger, M. M. J. Electroanal. Chem. 1997, 436, 85.
46. Kim, S.; Lee, J. K.; Kang, S. O.; Ko, J.; Yum, J.-H.; Fantacci, S.; De Angelis, F.; Di Censo, D.; Nazeeruddin, M. K.; Grätzel, M. J. Am. Chem. Soc. 2006, 128, 16701.
47. Ferrante, C.; Kensy, U.; Dick, B. J. Phys. Chem. 1993, 97, 13457.
48. Katritzky, A. R.; Zhu, D.-W.; Schanze, K. S. J. Phys. Chem. 1991, 95, 5737.
49. See that pyrene excimer formation is achieved at concentrations higher than 1 μM.
50. Modern Molecular Photochemistry; Turro, N. J., Ed.; University Science Books: Sausalito, CA, 1991.
51. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
52. Lee, C.; Yang, W.; Parr, G. Phys. Rev. B 1988, 37, 785.
53. (a) Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213.
54. (b) Francl, M. M.; Petro, W. J.; Hehre, W. J.; Binkley, J. S.; Gordon, M. S.; DeFrees, D. J.; Pople, J. A. J. Chem. Phys. 1982, 77, 3654.
55. (c) Rassolov, V.; Pople, J. A.; Ratner, M. A.; Windus, T. L. J. Chem. Phys. 1998, 109, 1223.
56. Dreuw, A.; Head-Gordon, M. Chem. Rev. 2005, 105, 4009.