Versatile strategy to access fully functionalized benzodifurans: Redox-active chromophores for the construction of extended φ-conjugated materials

Journal of Organic Chemistry

Volumn 75, Issue 10, 2010, Pages 3350-3357

  Yi, Chenyi ^a   Blum, Carmen ^a   Lehmann, Mario ^a   Keller, Stephan ^a   Liu, Shi Xia ^a   Frei, Gabriela ^a   Neels, Antonia ^b   Hauser, Jürg ^a   Schürch, Stefan ^a   Decurtins, Silvio ^a  

^a UNIVERSITY OF BERN   (Switzerland)

^b CSEM   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CONJUGATED MATERIALS; DOUBLE ANNULATION; FLUORESCENCE SWITCH; FUNCTIONALIZED; GOOD YIELD; LUMINESCENT MATERIAL; ONE-ELECTRON OXIDATION; PH-DEPENDENT; PHOTOPHYSICAL; REDOX-ACTIVE; SONOGASHIRA COUPLING REACTIONS; SYNTHETIC APPROACH;

CHEMICAL BONDS; CHEMICAL REACTIONS; CHROMOPHORES; ELECTROCHEMICAL PROPERTIES; ELECTRONIC PROPERTIES; ORGANIC POLYMERS;

DENSITY FUNCTIONAL THEORY;

FURAN DERIVATIVE; PYRIDINE;

ARTICLE; CHROMATOPHORE; ELECTRON; FLUORESCENCE; HECK REACTION; METHYLATION; OXIDATION REDUCTION REACTION; PH; SONOGASHIRA REACTION; SUZUKI REACTION;

BENZOFURANS; COMPUTER SIMULATION; HYDROGEN-ION CONCENTRATION; LUMINESCENCE; LUMINESCENT MEASUREMENTS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PYRIDINES;

EID: 77952495091     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100323s     Document Type: Article

References (45)

1. Chambers, J. J.; Kurrasch-Orbaugh, D. M.; Parker, M. A.; Nichols, D. E. J. Med. Chem. 2001, 44, 1003
2. Chambers, J. J.; Kurrasch-Orbaugh, D. M.; Nichols, D. E. Bioorg. Med. Chem. Lett. 2002, 12, 1997
3. Verghese, J.; Liang, A.; Sidhu, P. P. S.; Hindle, M.; Zhou, Q.; Desai, U. R. Bioorg. Med. Chem. Lett. 2009, 19, 4126
4. Kim, I.; Choi, J. Org. Biomol. Chem. 2009, 7, 2788
5. Manna, K.; Agrawal, Y. K. Bioorg. Med. Chem. Lett. 2009, 19, 2688
6. De Luca, L; Nieddu, G.; Porcheddu, A.; Giacomelli, G. Curr. Med. Chem. 2009, 16, 1
7. Liang, Z.; Ma, S.; Yu, J.; Xu, R. Tetrahedron 2007, 63, 12877
8. Tsuji, H.; Mitsui, C.; Ilies, L.; Sato, Y.; Nakamura, E. J. Am. Chem. Soc. 2007, 129, 11902
9. Hayashi, N; Saito, Y.; Higuchi, H.; Suzuki, K. J. Phys. Chem. A 2009, 113, 5342
10. Baraldi, I.; Benassi, E.; Ciorba, S.; Sindler-Kulyk, M.; Skoric, I.; Spalletti, A. Chem. Phys. 2009, 361, 61
11. Liang, Z.; Ma, S.; Yu, J.; Xu, R. J. Org. Chem. 2007, 72, 9219
12. Quezada, E.; Delogu, G.; Vina, D.; Santana, L.; Podda, G.; Matos, M. J.; Picciau, C. Helv. Chim. Acta 2009, 92, 1309
13. Caruso, U.; Panunzi, B.; Roviello, G. N.; Roviello, G.; Tingoli, M.; Tuzi, A. C. R. Chimie 2009, 12, 622
14. Davarani, S. S. H.; Fakhari, A. R.; Fumani, N. S.; Kalate-bojdi, M. Electrochem. Commun. 2008, 10, 1765
15. Peltzmann, R.; Unterweger, B.; Junek, H. Monatsh. Chem. 1979, 110, 739
16. Dalton, G. T.; Cifuentes, M. P.; Watson, L. A.; Petrie, S.; Stranger, R.; Samoc, M.; Humphrey, M. G. Inorg. Chem. 2009, 48, 6534
17. Tang, Y.; Zhou, Z.; Ogawa, K.; Lopez, G. P.; Schanze, K. S.; Whitten, D. G. Langmuir 2009, 25, 21
18. Shi, Z.-F.; Wang, L.-J.; Wang, H.; Cao, X.-P.; Zhang, H.-L. Org. Lett. 2007, 9, 595
19. Wang, C.; Batsanov, A. S.; Bryce, M. R.; Sage, I. Org. Lett. 2004, 6, 2181
20. Hundt, N.; Palaniappan, K.; Servello, J.; Dei, D. K.; Stefan, M. C.; Biewer, M. C. Org. Lett. 2009, 11, 4422
21. Chantean, S. H.; Tour, J. M. Tetrahedron Lett. 2001, 42, 3057
22. Zaman, M. B.; Tomura, M.; Yamashita, Y. J. Org. Chem. 2001, 66, 5987
23. Biradha, K.; Hongo, Y.; Fujita, M. Angew. Chem., Int. Ed. 2000, 39, 3843
24. Belanger, S.; Hupp, J. T.; Stern, C. L.; Slone, R. V.; Wastone, D. F.; Carrel, T. G. J. Am. Chem. Soc. 1999, 121, 557
25. Miller, J. S.; Epstein, A. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 385
26. Bockman, M. T.; Kochi, K. J. J. Org. Chem. 1990, 55, 4127
27. Barltrop, A. J.; Jackson, C. A. J. Chem. Soc., Perkin Trans. 2 1984, 367
28. Monk, P. M. S. The viologens: Physicochemical Properties, Synthesis and Applications of the Salts of 4,4′-Bipyridine; John Wiley & Sons Ltd.: Chichester, 1998.
29. Vermeulen, A. L.; Thompson, E. M. Nature 1992, 358, 656
30. Yi, C.; Blum, C.; Liu, S.-X.; Frei, G.; Neels, A.; Renaud, P.; Leutwyler, S.; Decurtins, S. J. Org. Chem. 2008, 73, 3596
31. Yi, C.; Blum, C.; Liu, S.-X.; Frei, G.; Neels, A.; Stoeckli-Evans, H.; Leutwyler, S.; Decurtins, S. Tetrahedron 2008, 64, 9437
32. Yi, C.; Blum, C.; Liu, S.-X.; Ran, Y.-F.; Frei, G.; Neels, A.; Stoeckli-Evans, H.; Calzaferri, G.; Leutwyler, S.; Decurtins, S. Cryst. Growth Des. 2008, 8, 3004
33. Obushak, M. D.; Martyak, R. L.; Matiychuk, V. S. Pol. J. Chem. 2002, 76, 1419
34. Shukla, R.; Wadumethrige, S. H.; Lindeman, S. V.; Rathore, R. Org. Lett. 2008, 10, 3587
35. Choi, H. D.; Seo, P. J.; Son, B. W.; Lee, U. Acta Crystallogr. 2007, E63, o2920
36. Takahashi, K.; Nihira, T.; Akiyama, K.; Ikegami, Y.; Fukuyo, E. J. Chem. Soc., Chem. Commun. 1992, 620
37. Chen, C. P.; Chan, S. H.; Chao, T. C.; Ting, C.; Ko, B. T. J. Am. Chem. Soc. 2008, 130, 12828
38. Brannon, J. H.; Magde, D. J. Phys. Chem. 1978, 82, 705
39. Hamai, S.; Hirayama, F. J. Phys. Chem. 1983, 87, 83
40. Ahlrich, R.; Bär, M.; Häser, M.; Horn, H.; Kölmel, C. Chem. Phys. Lett. 1989, 162, 165
41. Bauernschmitt, R.; Ahlrich, R. Chem. Phys. Lett. 1996, 256, 454
42. Bauernschmitt, R.; Häser, M.; Treutler, O.; Ahlrich, R. Chem. Phys. Lett. 1997, 264, 573
43. Zhang, J.; Cui, Y.; Wang, M.; Liu, J. Chem. Commun. 2002, 2526
44. López-Alvarado, P.; Avendaño, C.; Menéndez, J. C. Synth. Commun. 2002, 32, 3233
45. Dirk, S. M.; Price, D. W.; Chanteau, S.; Kosynkin, D. V.; Tour, J. M. Tetrahedron 2001, 57, 5109