Synthesis of new intramolecular charge transfer A-D-A tetrathiafulvalene- fused triads exhibiting large solvent sensitive emission behavior

Tetrahedron Letters

Volumn 52, Issue 19, 2011, Pages 2496-2500

  Bolligarla, Ramababu ^a   Das, Samar K ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

A D A TTF triads; Cyclic voltammetry; Emission; Large Stokes shifts; Solvatocromic effects

Indexed keywords

DIPYRIDO[3,2 ALPHA:2',3' C]PHENAZINE; PHENAZINE DERIVATIVE; QUINOXALINE; SILVER CHLORIDE; TETRATHIAFULVALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ELECTROCHEMISTRY; FIELD EMISSION; OXIDATION; SYNTHESIS;

EID: 79953708184     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.03.016     Document Type: Article

References (52)

1. F. Wudl, D. Wobschall, and E. Hufnagel J. Am. Chem. Soc. 94 1972 670 672
2. M. Bendikov, F. Wudl, and D.F. Perepichka Chem. Rev. 104 2004 4891 4945
3. M.C. Diaz, B.M. Illescas, N. Martin, I.F. Perepichka, M.R. Bryce, E. Levillain, R. Viruela, and E. Orti Chem. Eur. J. 12 2006 2709 2721
4. M. González, N. Martín, J.L. Segura, J. Garín, and J. Orduna Tetrahedron Lett. 39 1998 3269 3272
5. C.-G. Liu, W. Guan, P. Song, L.-K. Yan, and Z.-M. Su Inorg. Chem. 48 2009 6548 6554
6. J.L. Segura, and N. Martín Angew. Chem., Int. Ed. 40 2001 1372 1409
7. J. Yamada, and T. Sugimoto TTF Chemistry: Fundamentals and Application of Tetrathiafulvalene 2004 Springer Berlin
8. T. Otsubo, and K. Takimiya Bull. Chem. Soc. Jpn. 77 2004 43 58
9. R.M. Metzger, B. Chen, U. Höpfner, M.V. Lakshmikantham, D. Vuillaume, T. Kawai, X. Wu, H. Tachibana, T.V. Hughes, H. Sakurai, J.W. Baldwin, C. Hosch, M.P. Cava, L. Brehmer, and G.J. Ashwell J. Am. Chem. Soc. 119 1997 10455 10466
10. T. Iimori, T. Naito, and N. Ohta J. Phys. Chem. C 113 2009 4654 4661
11. H. Kim, W.A. Goddard, S.S. Jang, W.R. Dichtel, J.R. Heath, and J.F. Stoddart J. Phys. Chem. A 113 2009 2136 2143
12. M.A. Fox, M. Chanon, Photoinduced Electron Transfer 1988 Elsevier Amsterdam
13. H. Kurreck, and M. Huber Angew. Chem., Int. Ed. 34 1995 849 866
14. T. Michinobu, J.C. May, J.H. Lim, C. Bouden, J.P. Gisselbrecht, P. Seiler, M. Gross, I. Biaggio, and F. Diederich Chem. Commun. 2005 737 739
15. A.L. Thompson, T.S. Ahn, K.R.J. Thomas, S. Thayumanavam, T.J. Martinez, and C.J. Bardeen J. Am. Chem. Soc. 127 2005 16348 16349
16. P. Miguel, M.R. Bryce, L.M. Goldenberg, A. Beeby, V. Khodorkovsky, L. Shapiro, A. Niemz, A.O. Cuello, and V. Rotello J. Mater. Chem. 8 1998 71 76
17. J.L. Segura, N. Martín, C. Seoane, and M. Hanack Tetrahedron Lett. 37 1996 2503 2506
18. M. González, B. Illescas, N. Martín, J.L. Segura, C. Seoane, and M. Hanack Tetrahedron 54 1998 2853 2866
19. E. Tsiperman, T. Regev, J.Y. Becker, J. Bernstein, A. Ellern, V. Khodorkovsky, A. Shames, and L. Shapiro J. Chem. Soc., Chem. Commun. 1999 1125 1126
20. F. Dumur, N. Gautier, N. Gallego-Planas, Y. Sahin, E. Levillain, N. Mercier, and P. Hudhomme J. Org. Chem. 69 2004 2164 2177
21. H. Wu, D. Zhang, L. Su, K. Ohkubo, C. Zhang, S. Yin, L. Mao, Z. Shuai, S. Fukuzumi, and D. Zhu J. Am. Chem. Soc. 129 2007 6839 6846
22. M.P. Le Paillard, A. Robert, C. Garrigou-Lagrange, P. Delhas, P.L. Maguers, L. Ouahab, and L. Toupet Synth. Met. 58 1993 223 232
23. J.G. Hansen, K.S. Bang, N. Thorup, and J. Becher Eur. J. Org. Chem. 2000 2135 2144
24. T. Murata, Y. Morita, Y. Yakiyama, K. Fukui, H. Yamochi, G. Saito, and K. Nakasuji J. Am. Chem. Soc. 129 2007 10837 10846
25. J. Wu, N. Dupont, S.-X. Liu, A. Neels, A. Hauser, and S. Decurtins Chem. Asian J. 4 2009 392 399
26. L.M. Goldenberg, J.Y. Becker, O.P.-T. Levi, V.Y. Khodorkovsky, M.R. Bryce, and M.C. Petty J. Chem. Soc., Chem. Commun. 1995 475 476
27. L.M. Goldenberg, J.Y. Becker, O.P.-T. Levi, V.Y. Khodorkovsky, L.M. Shapiro, M.R. Bryce, J.P. Cresswell, and M.C. Petty J. Mater. Chem. 7 1997 901 907
28. K.B. Simonsen, K. Zong, R.D. Rogers, M.P. Cava, and J. Becher J. Org. Chem. 62 1997 679 686
29. K.B. Simonsen, N. Thorup, M.P. Cava, and J. Becher Chem. Commun. 1998 901 902
30. M.B. Nielsen, S.B. Nielsen, and J. Becher Chem. Commun. 1998 475 476
31. W. Devonport, M.A. Blower, M.R. Bryce, and L.M. Goldenberg J. Org. Chem. 62 1997 885 887
32. O.P.-T. Levi, J.Y. Becker, A. Ellern, and V. Khodorkovsky Tetrahedron Lett. 42 2001 1571 1573
33. A.J. Moore, A.S. Batsanov, M.R. Bryce, J.A.K. Howard, V. Khodorkovsky, L. Shapiro, and A. Shames Eur. J. Org. Chem. 2001 73 78
34. W. Xu, D. Zhang, H. Li, and D. Zhu J. Mater. Chem. 9 1999 1245 1249
35. S. Frenzel, and K. Müllen Synth. Met. 80 1996 175 182
36. X. Guo, D. Zhang, W. Xu, and D. Zhu Synth. Met. 137 2003 981 982
37. X. Guo, D. Zhang, H. Zhang, Q. Fan, W. Xu, X. Ai, L. Fan, and D. Zhu Tetrahedron 59 2003 4843 4850
38. W.H. Watson, E.E. Eduok, R.P. Kashyap, and M. Krawiec Tetrahedron 49 1993 3035 3042
39. N. Gautier, F. Dumur, V. Lloveras, J. Vidal-Gancedo, J. Veciana, C. Rovira, and P. Hudhomme Angew. Chem., Int. Ed. 42 2003 2765 2768
40. Q.-Y. Zhu, L.-B. Huo, Y.-R. Qin, Y.-P. Zhang, Z.-J. Lu, J.-P. Wang, and J. Dai J. Phys. Chem. B 114 2010 361 367
41. C. Jia, S.-X. Liu, C. Tanner, C. Leiggener, A. Neels, L. Sanguinet, E. Levillain, S. Leutwyler, A. Hauser, and S. Decurtins Chem. Eur. J. 13 2007 3804 3812
42. J. Rusanova, S. Decurtins, E. Rusanov, H. Stoeckli-Evans, S. Delahaye, and A. Hauser J. Chem. Soc., Dalton Trans. 2002 4318 4320
43. S. Ott, and R. Faust Synthesis 2005 3135 3139
44. -6 M concentration).
45. 2/C, 67.72; H, 3.25; N, 7.52. Found: C, 67.46; H, 3.59; N, 7.68.
46. J.L. Brusso, O.P. Clements, R.C. Haddon, M.E. Itkis, A.A. Leitch, R.T. Oakley, R.W. Reed, and J.F. Richardson J. Am. Chem. Soc. 126 2004 8256 8265
47. A. Unciti-Broceta, M.J. Pineda-de-las-Infantas, J.J. Díaz- Mochón, R. Romagnoli, P.G. Baraldi, M.A. Gallo, and A. Espinosa J. Org. Chem. 70 2005 2878 2880
48. S.V. More, M.N.V. Sastry, C.-C. Wang, and C.-F. Yao Tetrahedron Lett. 46 2005 6345 6348
49. 3/C, 64.92; H, 3.11; N, 7.21. Found: C, 65.23; H, 3.40; N, 6.96.
50. W. Paw, and R. Eisenberg Inorg. Chem. 36 1997 2287 2293
51. G.F. Smith, and F.W. Cagle Jr. J. Org. Chem. 12 1947 781 784
52. W. Guo, and S.O. Obare Tetrahedron Lett. 49 2008 4933 4936