Cubic nonlinear optical properties of new zinc tetraphenyl porphyrins peripherally functionalized with electron-rich Ru(II) alkynyl substituents

Tetrahedron

Volumn 68, Issue 50, 2012, Pages 10351-10359

  Drouet, Samuel ^a   Merhi, Areej ^b   Yao, Dandan ^b   Cifuentes, Marie P ^c   Humphrey, Mark G ^c   Wielgus, Malgorzata ^d   Olesiak Banska, Joanna ^d   Matczyszyn, Katarzyna ^d   Samoc, Marek ^c,d   Paul, Frédéric ^a   Paul Roth, Christine O ^a,b  

^a INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

^b UNIVERSITÉ EUROPÉENNE DE BRETAGNE   (France)

^c AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

^d WROCLAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Acetylide complex; Nonlinear optics; Organometallics; Pi conjugation; Porphyrin

Indexed keywords

ACETYLENE DERIVATIVE; ALKYNYL GROUP; ORGANOMETALLIC COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RUTHENIUM DERIVATIVE; TETRAPHENYLPORPHYRIN DERIVATIVE; ZINC DERIVATIVE;

ARTICLE; CHEMICAL REACTION; COMPLEX FORMATION; FLUORESCENCE MICROSCOPY; NEAR INFRARED SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

TETRA;

EID: 84869090821     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.09.108     Document Type: Article

References (58)

1. S.R. Marder Chem. Commun. 2006 131 134
2. J.L. Brédas, C. Adant, P. Tackx, and A. Persoons Chem. Rev. 94 1994 243 278
3. G.S. He, L.S. Tan, Q. Zheng, and P.N. Prasad Chem. Rev. 108 2008 1245 1330
4. P.N. Prasad, and D.J. Williams Introduction to Nonlinear Optical Effects in Molecules and Polymers 1991 John Wiley & Sons New York, NY
5. B. Luther-Davies, and M. Samoc Curr. Opin. Solid State Mater. Sci. 2 1997 213 219
6. M. Samoc J. Mol. Model. 17 2011 2183 2189
7. S. di Bella, C. Dragonetti, M. Pizzotti, D. Roberto, F. Tessore, and R. Ugo Top. Organomet. Chem. 28 2010 1 55
8. O. Maury, and H. Le Bozec Acc. Chem. Res. 38 2005 691 703
9. J.P. Morrall, G.T. Dalton, M.G. Humphrey, and M. Samoc Adv. Organomet. Chem. 55 2008 61 136
10. M.G. Humphrey, M.P. Cifuentes, and M. Samoc Top. Organomet. Chem. 28 2011 57 73
11. T. Schwich, M.P. Cifuentes, P.A. Gugger, M. Samoc, and M.G. Humphrey Adv. Mater. 23 2011 1433 1435
12. A. Trujillo, R. Veillard, G. Argouarch, T. Roisnel, A. Singh, I. Ledoux, and F. Paul Dalton Trans. 41 2012 7454 7456
13. M.P. Cifuentes, C.E. Powell, M.G. Humphrey, G.A. Heath, M. Samoc, and B. Luther-Davies J. Phys. Chem. A 105 2001 9625 9627
14. C.E. Powell, M.P. Cifuentes, J.P. Morrall, R. Stranger, M.G. Humphrey, M. Samoc, B. Luther-Davies, and G.A. Heath J. Am. Chem. Soc. 125 2003 602 610
15. M. Pawlicki, H.A. Collins, R.G. Denning, and H.L. Anderson Angew. Chem., Int. Ed. 48 2009 3244 3266
16. M. Ravikanth, and K.G. Ravindra Curr. Sci. 68 1995 1010 1017
17. G. de la Torre, P. Vazquez, F. Agullo-Lopez, and T. Torres Chem. Rev. 104 2004 3723 3750
18. S.V. Rao, N.K.M.N. Srinivas, D.N. Rao, L. Giribabu, B.G. Mayia, R. Philip, and G.R. Kumar Opt. Commun. 182 2000 255 264
19. S.A. Odom, S. Webster, L.A. Padilha, D. Peceli, H. Hu, G. Nootz, S.-J. Chung, S. Ohira, J.D. Matichak, O.V. Przhonska, A.D. Kachkovski, S. Barlow, J.-L. Brédas, H.L. Anderson, D.J. Hagan, E.W. Van Stryland, and S.R. Marder J. Am. Chem. Soc. 131 2009 7510 7511
20. M. Drobizhev, Y. Stepanenko, Y. Dzenis, A. Karotki, A. Rebane, P.N. Taylor, and H.L. Anderson J. Am. Chem. Soc. 126 2004 15352 15353
21. M. Drobizhev, Y. Stepanenko, Y. Dzenis, A. Karotki, A. Rebane, P.N. Taylor, and H.L. Anderson J. Phys. Chem. B 109 2005 7223 7236
22. A. Karotki, M. Drobizhev, Y. Dzenis, P.N. Taylor, H.L. Anderson, and A. Rebane Phys. Chem. Chem. Phys. 6 2004 7 10
23. J.L. Humphrey, and D. Kuciauskas J. Phys. Chem. C 128 2006 3902 3903
24. J.L. Humphrey, and D. Kuciauskas J. Phys. Chem. B 108 2004 12016 12023
25. D.V.G.L.N. Rao, F.J. Aranda, J.F. Roach, and D.E. Remy Appl. Phys. Lett. 58 1991 1241 1243
26. N. Gauthier, G. Argouarch, F. Paul, L. Toupet, A. Ladjarafi, K. Costuas, J.-F. Halet, M. Samoc, M.P. Cifuentes, T.C. Corkery, and M.G. Humphrey Chem. - Eur. J. 17 2011 5561 5577 and refs therein
27. C.O. Paul-Roth, J. Rault-Berthelot, and G. Simonneaux Tetrahedron 60 2004 12169 12175
28. C.O. Paul-Roth, J. Rault-Berthelot, J. Letessier, G. Simonneaux, and J.-F. Bergamini J. Electroanal. Chem. 606 2007 103 116
29. C.O. Paul-Roth, and G. Simonneaux Tetrahedron Lett. 47 2006 3275 3278
30. C.O. Paul-Roth, and G. Simonneaux C. R. Acad. Sci., Ser. IIb: Chim. 9 2006 1277 1286
31. C.O. Paul-Roth, J.A.G. Williams, J. Letessier, and G. Simonneaux Tetrahedron Lett. 48 2007 4317 4322
32. S. Drouet, C.O. Paul-Roth, V. Fattori, M. Cocchi, and J.A.G. Williams New J. Chem. 35 2011 438 444
33. S. Drouet, and C.O. Paul-Roth Tetrahedron 65 2009 10693 10700
34. S. Drouet, A. Merhi, G. Argouarch, F. Paul, O. Mongin, M. Blanchard-Desce, and C.O. Paul-Roth Tetrahedron 68 2012 98 105
35. D. Bellows, S.M. Ali, C.P. Gros, M.E. Ojaimi, J.-M. Barbe, R. Guillard, and P.D. Harvey Inorg. Chem. 48 2009 7613 7629
36. Y.-J. Chen, S.-S. Chen, S.-S. Lo, T.-H. Huang, C.-C. Wu, G.-H. Lee, S.-M. Peng, and C.-Y. Yeh Chem. Commun. 2006 1015 1017
37. K. Onitsuka, H. Kitajima, M. Fujimoto, A. Iuchi, F. Takei, and S. Takahashi Chem. Commun. 2002 2576 2577
38. N. Gauthier, C. Olivier, S. Rigaut, D. Touchard, T. Roisnel, M.G. Humphrey, and F. Paul Organometallics 27 2008 1063 1072
39. See, for instance: S.K. Hurst, M.P. Cifuentes, and M.G. Humphrey Organometallics 21 2002 2353 2355
40. M.A. Fox, J.E. Harris, S. Heider, V. Pérez-Gregorio, M.E. Zakrzewska, J.D. Farmer, D.S. Yufit, J.A.K. Howard, and P.J. Low J. Organomet. Chem. 694 2009 2350 2358
41. K.A. Green, M.P. Cifuentes, T.C. Corkery, M. Samoc, and M.G. Humphrey Angew. Chem., Int. Ed. 48 2009 7867 7870
42. J.J. Bonnet, S.S. Eaton, G.R. Eaton, R.H. Holm, and J.A. Ibers J. Am. Chem. Soc. 95 1973 2141 2149
43. J.S. Lindsey, H.C. Hsu, and I.C. Schreiman Tetrahedron Lett. 27 1986 4969 4970
44. D. Touchard, P. Haquette, S. Guesmi, L. Le Pichon, A. Daridor, L. Toupet, and P.H. Dixneuf Organometallics 16 1997 3640 3648
45. A.M. McDonagh, C.E. Powell, J.P. Morrall, M.P. Cifuentes, and M.G. Humphrey Organometallics 22 2003 1402 1413
46. N. Gauthier, N. Tchouar, F. Justaud, G. Argouarch, M.P. Cifuentes, L. Toupet, D. Touchard, J.-F. Halet, S. Rigaut, M.G. Humphrey, K. Costuas, and F. Paul Organometallics 28 2009 2253 2266
47. F. Paul, J.-Y. Mevellec, and C. Lapinte J. Chem. Soc., Dalton Trans. 2002 1783 1790
48. C.O. Paul-Roth, J. Rault-Berthelot, G. Simonneaux, C. Pohriel, M. Abdalilah, and J. Letessier J. Electroanal. Chem. 597 2006 19 27
49. F. Paul, B.J. Ellis, M.I. Bruce, L. Toupet, T. Roisnel, K. Costuas, J.-F. Halet, and C. Lapinte Organometallics 25 2006 649 665
50. M.I. Bruce, A. Burgun, F. Gendron, G. Grelaud, J.-F. Halet, and B.W. Skelton Organometallics 30 2011 2861 2868
51. B. Babgi, L. Rigamonti, M.P. Cifuentes, T.C. Corkery, M.D. Randles, T. Schwich, S. Petrie, R. Stranger, A. Teshome, I. Asselberghs, K. Clays, M. Samoc, and M.G. Humphrey J. Am. Chem. Soc. 131 2009 10293 10307
52. G.T. Dalton, M.P. Cifuentes, L.A. Watson, S. Petrie, R. Stranger, M. Samoc, and M.G. Humphrey Inorg. Chem. 48 2009 6534 6547
53. G.T. Rohde, J.R. Sabin, C.D. Barrett, and V.N. Nemykin New J. Chem. 35 2011 1440 1448
54. E.S. Schmidt, T.S. Calderwood, and T.C. Bruice Inorg. Chem. 25 1986 3718 3720
55. R. Denis, L. Toupet, F. Paul, and C. Lapinte Organometallics 19 2000 4240 4251
56. M.P. Cifuentes, C.E. Powell, J.P.L. Morrall, A.M. McDonagh, N.T. Lucas, M.G. Humphrey, M. Samoc, S. Houbrechts, I. Asselberghs, K. Clays, A. Persoons, and T. Isoshima J. Am. Chem. Soc. 128 2006 10819 10832
57. X. Zhou, A.-M. Ren, J.-K. Feng, X.-J. Liu, and Y.-D. Zhang ChemPhysChem 4 2004 991 997
58. M. Samoc, A. Samoc, G.T. Dalton, M.P. Cifuentes, M.G. Humphrey, and P.A. Fleitz Two-photon Absorption Spectra and Dispersion of the Complex Cubic Hyperpolarizability γ in Organic and Organometallic Chromophores I. Rau, F. Kajzar, Multiphoton Processes in Organics and their Application 2011 Old City Philadelphia, PA 341 355