Synthesis, optical characterization, and electrochemical properties of isomeric tetraphenylbenzodifurans containing electron acceptor groups

Journal of Physical Chemistry A

Volumn 115, Issue 17, 2011, Pages 4157-4168

  Santos Pérez, Javier ^a   Crespo Hernández, Carlos E ^b   Reichardt, Christian ^b   Cabrera, Carlos R ^c   Feliciano Ramos, Ileana ^c   Arroyo Ramírez, Lisandra ^c   Meador, Michael A ^a  

^a NASA GLENN RESEARCH CENTER   (United States)

^b CASE WESTERN RESERVE UNIVERSITY   (United States)

^c UNIVERSITY OF PUERTO RICO   (Puerto Rico)

Author keywords

[No Author keywords available]

Indexed keywords

CONJUGATED SYSTEMS; DUAL FLUORESCENCE; ELECTRON ACCEPTOR GROUPS; ELECTRONIC ABSORPTION; EMISSION MAXIMA; ENERGY RANGES; HOMO-LUMO ENERGY GAP; LOW-TEMPERATURE EMISSION; OPTICAL CHARACTERIZATION; RED-SHIFTED; TWISTED INTRA-MOLECULAR CHARGE TRANSFERS; TWO-PHOTON ABSORPTION CROSS SECTION;

ABSORPTION; CHARGE TRANSFER; FLUORESCENCE; ION EXCHANGE; ORGANIC POLYMERS; TWO PHOTON PROCESSES;

ELECTROCHEMICAL PROPERTIES;

BENZOFURAN DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROCHEMISTRY; FLUORESCENCE; QUANTUM THEORY; STEREOISOMERISM; SYNTHESIS;

BENZOFURANS; ELECTROCHEMISTRY; FLUORESCENCE; MOLECULAR STRUCTURE; QUANTUM THEORY; STEREOISOMERISM;

EID: 79955534383     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp111174p     Document Type: Article

References (58)

1. Belfield, K. D.; Schafer, K. J. Chem. Mater. 2002, 14, 3656
2. Lee, J. B.; Heeney, M.; Tierney, S.; McCulloch, I.; Murphy, A.; Liu, J.; Fréchet, J. M. J. Mater. Res. Soc. Symp. Proc. 2005, 871E, I1.5.1
3. Shen, Z.; Burrows, P. E.; Bulovic, V.; Forrest, S. R.; Thompson, M. E. Science 1997, 276, 2009
4. Coropceanu, V.; Cornil, J.; da Silva Filho, D. A.; Olivier, Y.; Silbey, R.; Brédas, J.-l. Chem. Rev. 2007, 107, 926
5. Hoeben, F. J. M.; Jonkheijm, P.; Meijer, E. W.; Schenning, A. P. H. Chem. Rev. 2005, 105, 1491
6. Yang, J.; Dass, A.; Rawashdeh, A.-M. M.; Sotirious-Leventis, C.; Panzner, M. J.; Tyson, D. S.; Kinder, J. D.; Leventis, N. Chem. Mater. 2004, 16, 3457
7. Grabowski, Z. R.; Dobkowski, J. Pure Appl. Chem. 1983, 55, 245
8. Rettig, W. Angew. Chem., Int. Ed. Engl. 1986, 25, 971
9. Rettig, W. J. Phys. Chem. 1982, 86, 1970
10. Hrnjez, B. J.; Yazdi, P. T.; Fox, M. A.; Johnston, K. P. J. Am. Chem. Soc. 1989, 111, 1915
11. Rettig, W. Top. Curr. Chem. 1994, 169, 253
12. Cornelissen-Gude, C.; Rettig, W. J. Phys. Chem. A 1998, 102, 7754
13. Ait-Lyazidi, S.; Dkaki, M.; Bitit, N.; Meziane, D.; Cazeau-Dubroca, C.; Cazeau, Ph. Spectrochim. Acta, Part A 1999, 55, 89
14. Catalán, J.; Díaz, C.; López, V.; Claramunt, R. M. J. Phys. Chem. 1996, 100, 18392
15. Shukla, R.; Wadumethringe, S. H.; Lindeman, S. V.; Rathore, R. Org. Lett. 2008, 10, 3587
16. Abdul-Aziz, M.; Auping, J. V.; Meador, M. A. J. Org. Chem. 1995, 60, 1303
17. Tsuji, H.; Mitsui, C.; Llies, L.; Sato, Y.; Nakamura, E. J. Am. Chem. Soc. 2007, 129, 11902
18. Hayashi, N.; Saito, Y.; Higuchi, H.; Suzuki, K. J. Phys. Chem. A 2009, 113, 5342
19. Tsuji, H.; Mitsui, C.; Sato, Y.; Nakamura, E. Adv. Mater. 2009, 21, 3776
20. Chambers, J. J.; Kurrasch-Orbaugh, D. M.; Parker, M. A.; Nichol, D. E. J. Med. Chem. 2001, 44, 1003
21. Chawla, H. P. S.; Grover, P. K.; Anand, N. J. Med. Chem. 1970, 13, 54
22. Kacegi, T. B.; Kormány, A. G.; Lüthi, B. C. U.S. Patent 4,222,739, 1980.
23. Hartmann, C.-S. P.; Theidel, L. H. U.S. Patent 3,993,670, 1976.
24. Leaver, I. H.; Milligan, B. Dyes Pigm. 1984, 5, 109
25. Dawson, W. R.; Windsor, M. W. J. Phys. Chem. 1968, 72, 3251
26. Lippert, E.; Bunsenges, B. Phys. Chem. 1957, 61, 962
27. Baruah, M.; Qin, W.; Flors, C.; Hofkens, J.; Vallée, R. A. L.; Beljonne, D.; Auweraer, M. V. D.; Borggraeve, W. M. D.; Boens, N. J. Phys. Chem. A 2006, 110, 5998
28. Reichardt, C. Solvents and Solvent Effects in Organic Chemistry, 2 nd ed.; VCH: New York, N.Y., 1998; p 408.
29. Etaiw, S. E.-D. H.; Fayed, T. A.; Saleh, N. Z. J. Photochem. Photobiol., A 2006, 177, 238
30. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, K. N.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 03, Revision D.01; Gaussian, Inc.: Wallingford, CT; Pittsburgh, PA, 2004.
31. Becke, A. D. J. Chem. Phys. 1993, 98, 1372-1377
32. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, B37, 785-789
33. Momany, E. A.; Willett, J. L. J. Comput. Chem. 2000, 21, 1204-1219
34. Cramer, C. J. Essentials of Computational Chemistry: Theories and Models; John Wiley & Sons: New York, 2002.
35. Barone, V.; Cossi, M.; Tomasi, J. J. Chem. Phys. 1997, 107, 3210-3221
36. Cancès, M. T.; Mennucci, V.; Tomasi, J. J. Chem. Phys. 1997, 107, 3032-3041
37. Reichardt, C.; Vogt, R. A.; Crespo-Hernández, C. E. J. Chem. Phys. 2009, 131, 224518
38. Oulianov, D. A.; Tomov, I. V.; Dvornikov, A. S.; Rentzepis, P. M. Opt. Commun. 2001, 191, 235-243
39. Xu, C.; Webb, W. W. J. Opt. Soc. Am. B 1996, 13, 481-491
40. Thelakkat, M.; Schmidt, H.-W. Adv. Mater. 1998, 10, 219
41. Chaubal, N. S.; Sawant, M. R. J. Mol. Catal., A 2007, 261, 232
42. March, J. Advanced Organic Chemistry, 4 th ed.; Wiley Interscience: New York, 1992; p 672.
43. Lakowicz, J. R. Principles of Fluorescence Spectroscopy, 2 nd ed.; Kluwer Academic/Plenum Publishers: New York, 1999.
44. Zander, M.; Rettig, W. Chem. Phys. Lett. 1984, 110, 602
45. Crespo-Hernández, C. E.; Burdzinski, G.; Arce, R. J. Phys. Chem. A 2008, 112, 6313
46. Goerner, H.; Doepp, D. J. Chem. Soc., Perkin Trans. 2002, 120
47. Fournier, T.; Thomsen, C. L.; Thogersen, J.; Keiding, S. R. J. Phys. Chem. A 1998, 102, 1062
48. Tavender, S. M.; Parker, A. W.; Scholes, G. D.; Phillips, D. J. Phys. Chem. A 1997, 101, 5320
49. Hurley, R.; Testa, A. C. J. Am. Chem. Soc. 1968, 90, 1949
50. Farztdinov, V. M.; Schanz, R.; Kovalenko, S. A.; Ernsting, N. P. J. Phys. Chem. A 2000, 104, 11486
51. Kovalenko, S. A.; Schanz, R.; Farztdinov, V. M.; Hennig, H.; Ernsting, N. P. Chem. Phys. Lett. 2000, 323, 312
52. Takezaki, M.; Hirota, N.; Terazima, M. J. Phys. Chem. A 1997, 101, 3443
53. Lippert, E.; Rettig, W.; Bonacic-Koutecky, V.; Heisel, F.; Miehé, J. A. Adv. Chem. Phys. 1987, 68, 1
54. Graboswski, Z. R.; Rotkiewicz, K.; Rubaszewska, W.; Kirkor-Kaminska, E. Acta Phys. Pol., A 1978, 54, 767
55. Wang, Y.; He, G. S.; Prasad, P. N.; Goodson, T., III J. Am. Chem. Soc. 2005, 127, 10128
56. Lin, T.-C.; He, G. S.; Prasad, P. N.; Tan, L.-S. J. Mater. Chem. 2004, 14, 982
57. Bieri, G.; Asbrink, L. J. Electron Spectrosc. Relat. Phenom. 1980, 20, 149
58. Crespo-Hernández, C. E.; Arce, R.; Ishikawa, Y.; Gorb, L.; Leszczynski, J.; Close, D. M. J. Phys. Chem. A 2004, 108, 6373