Symmetry loss of heptamethine cyanines: An example of dipole generation by ion-pairing effect

Proceedings of SPIE - The International Society for Optical Engineering

Volumn 8622, Issue , 2013, Pages

  Pascal, Simon ^a   Bouit, Pierre Antoine ^a   Le Guennic, Boris ^b   Parola, Stéphane ^a   Maury, Olivier ^a   Andraud, Chantal ^a  

^a UNIVERSITÉ LYON 1   (France)

^b INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

Author keywords

Cyanine; ion pairing; optical power limiting; spectroscopy

Indexed keywords

CLOSE RELATIONSHIPS; CYANINE; ION-PAIRING; NEAR-INFRARED DYES; NUMBER OF CARBON ATOMS; OPTICAL LIMITING APPLICATIONS; OPTICAL POWER LIMITING; THIRD-ORDER NONLINEAR OPTICAL;

AZO DYES; ELECTRONIC STRUCTURE; IONS; OPTICAL PROPERTIES; SPECTROSCOPY;

PHOTONIC DEVICES;

EID: 84878125772     PISSN: 0277786X     EISSN: None     Source Type: Conference Proceeding    
DOI: 10.1117/12.2008220     Document Type: Conference Paper

References (21)

1. A. Mishra, R. K. Behera, P. K. Behera, B. K. Mishra and G. B. Behera, "Cyanines during the 1990s: A Review," Chem. Rev. 100(6), 1973-2012 (2000)
2. A. V. Kulinich and A. I. Aleksandr, "Merocyanine dyes: synthesis, structure, properties and applications," Russian Chemical Reviews 78(2), 141 (2009)
3. G. Qian and Z. Y. Wang, "Near-Infrared Organic Compounds and Emerging Applications," Chem. Asian J. 5(5), 1006-1029 (2010)
4. L. Yuan, W. Lin, K. Zheng, L. He and W. Huang, "Far-red to near infrared analyte-responsive fluorescent probes based on organic fluorophore platforms for fluorescence imaging," Chemical Society Reviews 42(2), 622-661 (2013)
5. J. M. Hales, J. Matichak, S. Barlow, S. Ohira, K. Yesudas, J.-L. Bredas, J. W. Perry and S. R. Marder, "Design of Polymethine Dyes with Large Third-Order Optical Nonlinearities and Loss Figures of Merit," Science 327(5972), 1485-1488 (2010)
6. J. D. Matichak, J. M. Hales, S. Barlow, J. W. Perry and S. R. Marder, "Dioxaborine- and Indole-Terminated Polymethines: Effects of Bridge Substitution on Absorption Spectra and Third-Order Polarizabilities," J. Phys. Chem. A 115(11), 2160-2168 (2011)
7. P.-A. Bouit, G. Wetzel, G. Berginc, B. Loiseaux, L. Toupet, P. Feneyrou, Y. Bretonniere, K. Kamada, O. Maury and C. Andraud, "Near IR Nonlinear Absorbing Chromophores with Optical Limiting Properties at Telecommunication Wavelengths," Chem. Mater. 19(22), 5325-5335 (2007)
8. Q. Bellier, N. S. Makarov, P.-A. Bouit, S. Rigaut, K. Kamada, P. Feneyrou, G. Berginc, O. Maury, J. W. Perry and C. Andraud, "Excited state absorption: a key phenomenon for the improvement of biphotonic based optical limiting at telecommunication wavelengths," Phys. Chem. Chem. Phys. 14(44), 15299-15307 (2012)
9. J. M. Hales, S. Zheng, S. Barlow, S. R. Marder and J. W. Perry, "Bisdioxaborine Polymethines with Large Third-Order Nonlinearities for All-Optical Signal Processing," J. Am. Chem. Soc. 128(35), 11362-11363 (2006)
10. P.-A. Bouit, R. Westlund, P. Feneyrou, O. Maury, M. Malkoch, E. Malmstrom and C. Andraud, "Dendron decorated cyanine dyes for optical limiting applications in the range of telecommunication wavelengths," New J. Chem. 33(5), 964-968 (2009)
11. A. Scarpaci, A. Nantalaksakul, J. M. Hales, J. D. Matichak, S. Barlow, M. Rumi, J. W. Perry and S. R. Marder, "Effects of Dendronization on the Linear and Third-Order Nonlinear Optical Properties of Bis(thiopyrylium) Polymethine Dyes in Solution and the Solid State," Chem. Mater. 24(9), 1606-1618 (2012)
12. F. Wurthner, G. Archetti, R. Schmidt and H.-G. Kuball, "Solvent Effect on Color, Band Shape, and Charge-Density Distribution for Merocyanine Dyes Close to the Cyanine Limit," Angew. Chem. Int. Ed. 47(24), 4529-4532 (2008)
13. L. G. S. Brooker, R. H. Sprague, C. P. Smyth and G. L. Lewis, "Color and Constitution. I. Halochromism of Anhydronium Bases Related to the Cyanine Dyes1," J. Am. Chem. Soc. 62(5), 1116-1125 (1940)
14. L. M. Tolbert and X. Zhao, "Beyond the Cyanine Limit: Peierls Distortion and Symmetry Collapse in a Polymethine Dye," J. Am. Chem. Soc. 119(14), 3253-3258 (1997)
15. P.-A. Bouit, E. Di Piazza, S. p. Rigaut, B. Le Guennic, C. Aronica, L. Toupet, C. Andraud and O. Maury, "Stable Near-Infrared Anionic Polymethine Dyes: Structure, Photophysical, and Redox Properties," Org. Lett. 10(19), 4159-4162 (2008)
16. C. Cabanetos, W. Bentoumi, V. Silvestre, E. Blart, Y. Pellegrin, V. Montembault, A. Barsella, K. Dorkenoo, Y. Bretonniere, C. Andraud, L. Mager, L. Fontaine and F. Odobel, "New Cross-Linkable Polymers with Huisgen Reaction Incorporating High fÊfÀ Chromophores for Second-Order Nonlinear Optical Applications," Chem. Mater. 24(6), 1143-1157 (2012)
17. D.J. Owen, D. VanDerveer, G.B. Schuster. J.Am.Chem.Soc. 120,1705-1717 (1998).
18. P.-A. Bouit, C. Aronica, L. c. Toupet, B. Le Guennic, C. Andraud and O. Maury, "Continuous Symmetry Breaking Induced by Ion Pairing Effect in Heptamethine Cyanine Dyes: Beyond the Cyanine Limit," J. Am. Chem. Soc. 132(12), 4328-4335 (2010)
19. P.-A. Bouit, C. Aronica, L. Guy, A. Martinez, C. Andraud and O. Maury, "Diastereoselective supramolecular ion-pairing between the TRISPHAT anion and pro-chiral heptamethine cyanine dyes," Org. Biomol. Chem. 7(15), 3086-3090 (2009)
20. P.-A. Bouit, D. Rauh, S. Neugebauer, J. L. Delgado, E. D. Piazza, S. P. Rigaut, O. Maury, C. Andraud, V. Dyakonov and N. Martin, " A Cyanine-Cyanine" Salt Exhibiting Photovoltaic Properties," Org. Lett. 11(21), 4806-4809 (2009)
21. Z. A. Li, Y. Liu, H. Kim, J. M. Hales, S.-H. Jang, J. Luo, T. Baehr-Jones, M. Hochberg, S. R. Marder, J. W. Perry and A. K. Y. Jen, "High-Optical-Quality Blends of Anionic Polymethine Salts and Polycarbonate withEnhanced Third-Order Non-linearities for Silicon-Organic Hybrid Devices," Adv. Mater. 24(44), OP326-OP330 (2012)