Methylenepyran based dipolar and quadrupolar dyes: Synthesis, electrochemical and photochemical properties

Tetrahedron

Volumn 69, Issue 39, 2013, Pages 8392-8399

  Gauthier, Sébastien ^a   Vologdin, Nikolay ^a   Achelle, Sylvain ^a   Barsella, Alberto ^b   Caro, Bertrand ^a   Robin Le Guen, Françoise ^a  

^a INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

^b INSTITUT DE PHYSIQUE ET CHIMIE DES MATÉRIAUX DE STRASBOURG   (France)

Author keywords

Diazines; Dyes; Methylenepyran; Nonlinear optics; Push pull

Indexed keywords

PYRAN DERIVATIVE;

ARTICLE; CYCLIC POTENTIOMETRY; DRUG SYNTHESIS; ELECTROCHEMISTRY; ELECTRON; OPTICS; ORGANISMS BY ELECTRON DONOR; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY; PRIORITY JOURNAL;

EID: 84882284302     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.07.066     Document Type: Article

References (71)

1. Y. Lin, Y. Li, and X. Zhan Chem. Soc. Rev. 41 2012 4245
2. A. Hagfeldt, G. Boschloo, L. Sun, L. Kloo, and H. Pettersson Chem. Rev. 110 2010 6595
3. S. Günes, H. Neugebauer, and N.S. Sariciftci Chem. Rev. 107 2007 1324
4. A. Kraft, A.C. Grimsdale, and A.B. Holmes Angew. Chem., Int. Ed. 37 1998 402
5. U. Mitshke, and P. Bäuerle J. Mater. Chem. 10 2000 1471
6. S.-C. Lo, and P.L. Burn Chem. Rev. 107 2007 1097
7. Y. Ooyama, T. Okamoto, Y. Yamagushi, T. Suzuki, A. Hayashi, and K. Yoshida Chem. - Eur. J. 12 2006 7827
8. L. Xue, C. Liu, and H. Jiang Chem. Commun. 2009 1061
9. S. Achelle, A. Barsella, C. Baudequin, B. Caro, and F. Robin-Le Guen J. Org. Chem. 77 2012 4087
10. R. Gulliev, A. Coskun, and E.U. Akkaya J. Am. Chem. Soc. 131 2009 9007
11. R.L. Liu, H.Y. Lu, M. Li, S.Z. Hu, and C.F. Chen RSC Adv. 2 2012 4415
12. A.M. Costero, M. Parra, S. Gil, R. Gotor, P.M.E. Mancini, R. Martinez-Manez, F. Sancenon, and S. Royo Chem. - Asian J. 5 2010 1573
13. C.Z. Zhang, C.G. Lu, J. Zhu, G.Y. Lu, X. Wang, Z.W. Shi, F. Liu, and Y.P. Cui Chem. Mater. 18 2006 6091
14. J.D. Luo, J.L. Hua, J.G. Qin, J.Q. Cheng, Y.C. Shen, Z.H. Lu, P. Wang, and C. Ye Chem. Commun. 2001 171
15. T. Verbiest, S. Houbrechts, M. Kauranen, K. Clays, and A. Persoons J. Mater. Chem. 7 1997 2175
16. C. Wang, T. Zhang, and W. Lin Chem. Rev. 112 2012 1084
17. H.M. Kim, and B.R. Cho Chem. Commun. 2009 153
18. T. Taniuchi, S. Okada, and H. Nakanishi Appl. Phys. Lett. 95 2004 5984
19. T. Taniuchi, S. Ikeda, S. Okada, and H. Nakanishi Jpn. J. Appl. Phys. 44 2005 L652
20. A. Schneider, M. Neis, M. Stillhart, B. Ruiz, R.U.A. Khan, and P. Günter J. Opt. Soc. Am. B 23 2006 1822
21. A. Schneider, M. Stillhart, and P. Günter Opt. Express 14 2006 5376
22. Z. Yang, L. Mutter, M. Stillhart, B. Ruiz, S. Aravazhi, M. Jazbinšek, A. Schneider, V. Gramlich, and P. Günter Adv. Funct. Mater. 17 2007 2018
23. Z. Li, Q. Li, and J. Qin Polym. Chem. 2 2011 2723
24. G.S. He, L.S. Tan, Q. Zheng, and P.N. Prasad Chem. Rev. 108 2008 1245
25. H.N. Kim, Z. Guo, W. Zhu, J. Yoon, and H. Tian Chem. Soc. Rev. 40 2011 79
26. R.J. Xia, J.P. Malval, M. Jin, A. Spangenberg, D.C. Wan, H.T. Pu, T. Vergote, F. Morlet-Savary, H. Chaumeil, P. Baldeck, O. Poizat, and O. Soppera Chem. Mater. 24 2012 237
27. B.G. Tiemann, L.-T. Cheng, and S.-R. Marder J. Chem. Soc., Chem. Commun. 1993 735
28. N. Faux, B. Caro, F. Robin-le Guen, P. le Poul, K. Nakatani, and E. Ishow J. Organomet. Chem. 690 2005 4982
29. N. Faux, F. Robin-le Guen, P. le Poul, B. Caro, K. Nakatani, E. Ishow, and S. Golhen Eur. J. Inorg. Chem. 2006 3489
30. I. Millan, M. Fuentealba, C. Manzur, D. Carrillo, N. Faux, B. Caro, F. Robin-le Guen, S. Sinbandhit, I. Ledoux-Rak, and J.R. Hamon Eur. J. Inorg. Chem. 2006 1131
31. R. Andreu, L. Carrasquer, S. Franco, J. Garín, J. Orduna, N. Martínez de Baroja, R. Alicante, B. Villacampa, and M. Allain J. Org. Chem. 74 2009 6647
32. R. Andreu, E. Galán, J. Garín, V. Herrero, E. Lacarra, J. Orduna, R. Alicante, and B. Villacampa J. Org. Chem. 75 2010 1684
33. R. Andreu, E. Galán, J. Orduna, B. Villacampa, R. Alicante, J.T. López Navarrete, J. Casado, and J. Garín Chem. - Eur. J. 17 2011 826
34. E. Galán, R. Andreu, J. Garín, J. Orduna, B. Villacampa, and B. Diosdado Org. Biomol. Chem. 10 2012 8684
35. A.B. Marco, R. Andreu, S. Franco, J. Garín, J. Orduna, B. Villacampa, and R. Alicante Tetrahedron 69 2013 3919
36. Y.M. Porotnik, V. Hugues, M. Blanchard-Desce, and D.T. Gryko Chem. - Eur. J. 18 2012 9258
37. N. Faux, F. Robin-Le Guen, P. Le Poul, B. Caro, N. Le Poul, Y. Le Mest, S.J. Green, S. Le Roux, S. Kahlal, and J.Y. Saillard Tetrahedron 63 2007 7142
38. F. Ba, N. Cabon, F. Robin-Le Guen, P. Le Poul, N. Le Poul, Y. Le Mest, S. Golhen, and B. Caro Organometallics 27 2008 6396
39. F. Ba, N. Cabon, P. Le Poul, S. Kahlal, J.-Y. Saillard, N. Le Poul, S. Golhen, B. Caro, and F. Robin-Le Guen New J. Chem. 2013 10.1039/C3NJ41126E
40. S. Achelle, and N. Plé Curr. Org. Synth. 9 2012 163 and articles cited herein
41. D. Chen, C. Zhong, X. Dong, Z. Liu, and J. Qin J. Mater. Chem. 22 2012 4343
42. C. Hadad, S. Achelle, J. García-Martinez, and J. Rodríguez-López J. Org. Chem. 76 2011 3837
43. A.I. Aranda, S. Achelle, F. Hammerer, F. Mahuteau-Betzer, and M.P. Teulade-Fichou Dyes Pigm. 95 2012 400
44. S. Achelle, N. Plé, and A. Turck RSC Adv. 1 2011 364 and articles cited herein
45. H.H. Cho, T.E. Kang, K.-H. Kim, H. Kang, H.J. Kim, and B.J. Kim Macromolecules 45 2012 6415
46. For pyrazine, S. Achelle, C. Baudequin, and N. Plé Dyes Pigm. 98 2013 575 and articles cited herein
47. S. Achelle, J.P. Malval, S. Aloise, A. Barsella, A. Spangenberg, L. Mager, H. Akdas-Kilig, J.L. Fillaut, B. Caro, and F. Robin-Le Guen ChemPhysChem 2013 10.1002/cphc.201300419
48. G.A. Reynolds, and C.H. Chen J. Org. Chem. 45 1980 2453
49. F. Ba, F. Robin-Le Guen, N. Cabon, P. Le Poul, S. Golhen, N. Le Poul, and B. Caro J. Organomet. Chem. 695 2010 235
50. R. Chinchilla, and C. Nájera Chem. Rev. 107 2007 874
51. E.i Negishi, and L. Anastasia Chem. Rev. 103 2003 1979
52. B.U.W. Maes, P. Tapolcsányi, C. Meyers, and P. Mátyus Curr. Org. Chem. 10 2006 377
53. S. Achelle, N. Plé, D. Kreher, F. Mathevet, A. Turck, and A.-J. Attias Heterocycles 75 2008 357
54. S. Achelle, Y. Ramondenc, G. Dupas, and N. Plé Tetrahedron 64 2008 2783
55. S. Achelle, N. Saettel, P. Baldeck, M.-P. Teulade-Fichou, and P. Maillard J. Porphyrins Phthalocyanines 14 2010 877
56. E.M. Priego, L. Sánchez, M.A. Herranz, N. Martín, R. Viruela, and E. Ortí Org. Biomol. Chem. 5 2007 1201
57. D. Lorcy, R. Cartlier, A. Robert, A. Tallec, P. Le Meguerès, and L. Ouahab J. Org. Chem. 60 1995 2443
58. P. Frère, and P.J. Skabara Chem. Soc. Rev. 34 2005 69
59. G. Cheng, I. Mahmud, L.N. Dawe, L.M. Daniels, and Y. Zhao J. Org. Chem. 76 2011 2701
60. C.H. Chen, J.J. Doney, G.A. Reynolds, and F.D. Saeva J. Org. Chem. 48 1983 2757
61. G.A. Reynolds, F.D. Saeva, J. Doney, and C.H. Chen J. Org. Chem. 49 1984 4843
62. K.D. Singer, and A.F. Garito J. Phys. Chem. 75 1981 3572
63. B.F. Levine, and C.G. Bethea Appl. Phys. Lett. 24 1974 445
64. I. Ledoux, and J. Zyss Chem. Phys. 73 1982 203
65. T. Thami, P. Bassoul, M.A. Petit, J. Simon, A. Fort, M. Barzoukas, and A. Villaeys J. Am. Chem. Soc. 114 1992 915
66. L.-T. Cheng, W. Tam, S.H. Stevenson, G.R. Meredith, G. Rikken, and S.R. Marder J. Phys. Chem. 95 1991 10631
67. N. Hebbar, C. Fiol-Petit, Y. Ramondenc, G. Plé, and N. Plé Tetrahedron 67 2011 2287
68. Y.L. Wu, P.D. Jarowski, W.B. Schweizer, and F. Diederich Chem. - Eur. J. 16 2010 202
69. A.R. Morales, A. Frazer, A.W. Woodward, H.Y. Ahn-White, A. Forani, P. Tongwa, T. Timofeeva, and K.D. Belfield J. Org. Chem. 78 2013 1014
70. H.-J. Deussen, C. Boutton, N. Thorup, T. Geisler, E. Hendrickx, K. Bechgaard, A. Persoons, and T. Bjørnholm Chem. - Eur. J. 4 1998 240
71. X. Wang, V. Ervithayasuporn, Y. Zhang, and Y. Kawajkami Chem. Commun. 2011 1282