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Optics Express

Optics Express

  • Editor: C. Martijn de Sterke
  • Vol. 20, Iss. 23 — Nov. 5, 2012
  • pp: 25311–25316
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Nonlinear absorption reversing between an electroactive ligand and its metal complexes

Konstantinos Iliopoulos, Abdelkrim El-Ghayoury, Hasnaa El Ouazzani, Mindaugas Pranaitis, Esmah Belhadj, Emilie Ripaud, Miloud Mazari, Marc Sallé, Denis Gindre, and Bouchta Sahraoui  »View Author Affiliations


Optics Express, Vol. 20, Issue 23, pp. 25311-25316 (2012)
http://dx.doi.org/10.1364/OE.20.025311


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Abstract

We present the nonlinear absorption investigation of an electroactive ligand and two ruthenium and iron metal complexes under 532 nm, 30 ps laser excitation, by the “open aperture” Z-scan technique. Significant nonlinear optical parameters have in all cases been measured, while the nonlinear attribute has been found to change from saturable to reverse saturable absorption between the initial ligand and its complexes.

© 2012 OSA

1. Introduction

Recently the possibility to employ the tetrathiafulvalene (TTF) unit in photonic applications has been widely investigated [1

1. I. Fuks-Janczarek, J. Luc, B. Sahraoui, F. Dumur, P. Hudhomme, J. Berdowski, and I. V. Kityk, “Third-order nonlinear optical figure of merits for conjugated TTF-quinone molecules,” J. Phys. Chem. B 109(20), 10179–10183 (2005). [CrossRef] [PubMed]

6

6. B. Insuasty, C. Atienza, C. Seoane, N. Martín, J. Garín, J. Orduna, R. Alcalá, and B. Villacampa, “Electronic and structural effects on the nonlinear optical behavior in push-pull TTF/tricarbonyl chromiun arene complexes,” J. Org. Chem. 69(21), 6986–6995 (2004). [CrossRef] [PubMed]

]. This is due to the enhanced charge transfer resulting from the electron donating ability of the TTF moiety, when it is properly connected to an electron accepting group [7

7. M. Bendikov, F. Wudl, and D. F. Perepichka, “Tetrathiafulvalenes, oligoacenenes, and their buckminsterfullerene derivatives: The brick and mortar of organic electronics,” Chem. Rev. 104(11), 4891–4946 (2004). [CrossRef] [PubMed]

,8

8. M. González, J. L. Segura, C. Seoane, N. Martín, J. Garín, J. Orduna, R. Alcalá, B. Villacampa, V. Hernández, and J. T. López Navarrete, “Tetrathiafulvalene derivatives as NLO-phores: Synthesis, electrochemistry, Raman spectroscopy, theoretical calculations, and NLO properties of novel TTF-derived donor-π-acceptor dyads,” J. Org. Chem. 66(26), 8872–8882 (2001). [CrossRef] [PubMed]

]. The TTF unit has also been combined with different coordinating heteroatom based ligands leading to transition metal complexes with specific electronic properties [9

9. D. Lorcy, N. Bellec, M. Fourmigue, and N. Avarvari, “Tetrathiafulvalene-based group XV ligands: Synthesis, coordination chemistry and radical cation salts,” Coord. Chem. Rev. 253(9–10), 1398–1438 (2009) (and references therein). [CrossRef]

]. Pyridine and 2,2’-bipyridine based ligands have been extensively used for the preparation of such metal complexes [10

10. Q. Wang, P. Day, J.-P. Griffiths, H. Nie, and J. D. Wallis, “Synthetic strategies for preparing BEDT-TTF derivatives functionalised with metal ion binding groups,” New J. Chem. 30(12), 1790–1800 (2006). [CrossRef]

,11

11. B. J. Coe, T. J. Meyer, and P. S. White, “Control of axial ligand substitution in trans-bis(2,2'-bipyridine)ruthenium(II) complexes. Crystal and molecular structure of trans-(4-ethylpyridine)(dimethyl sulfoxide)bis(2,2'-bipyridine)ruthenium(II) hexafluorophosphate, trans-[Ru(bpy)2(4-Etpy)(DMSO)](PF6)2,” Inorg. Chem. 32(19), 4012–4020 (1993). [CrossRef]

]. In addition to these ligands, the 2,2':6',2”-Terpyridine is also known to coordinate a large series of metal ions and to form very stable metal complexes [12

12. H. Hofmeier and U. S. Schubert, “Recent developments in the supramolecular chemistry of terpyridine-metal complexes,” Chem. Soc. Rev. 33(6), 373–399 (2004). [CrossRef] [PubMed]

], however only one system where this ligand is associated with an electroactive TTF moiety has been published so far [10

10. Q. Wang, P. Day, J.-P. Griffiths, H. Nie, and J. D. Wallis, “Synthetic strategies for preparing BEDT-TTF derivatives functionalised with metal ion binding groups,” New J. Chem. 30(12), 1790–1800 (2006). [CrossRef]

].

2. Synthesis/preparation of samples

3. Results and discussion

For the determination of the nonlinear absorption of the samples the “open aperture” Z-scan has been employed using the frequency doubled exit (532 nm) of a 30 ps diode pumpedpassively mode-locked Nd:YVO4 laser with a repetition rate of 10 Hz. In this way the imaginary part of the third order nonlinear susceptibility (Imχ(3)), as well as of the second hyperpolarizability (Imγ) have been determined. The details concerning the “open aperture” Z-scan technique as well as the equations in order to determine the nonlinear optical parameters from the experimental data will not be given here, as detailed information can be found in the literature [17

17. M. Sheik-Bahae, A. A. Said, T. H. Wei, D. J. Hagan, and E. W. Van Stryland, “Sensitive measurement of optical nonlinearities using a single beam,” IEEE J. Quantum Electron. 26(4), 760–769 (1990). [CrossRef]

]. For the needs of the measurements, solutions of different concentrations of all three systems have been prepared. For solubility reasons, ligand S1 was dissolved in chloroform, while the ruthenium metal complex S2 and the iron complex S3 were dissolved in dimethylformamide (DMF) and acetonitrile respectively. The utilized range of concentrations for all investigated molecules has been carefully chosen to allow high NLO signals, without formation of molecular aggregations in the solutions. The samples have been introduced into 1 mm thick cells in order to be studied by the “open aperture” Z-scan technique. In all cases for the laser energies used the contribution of the solvents has been found to be negligible, so the total response can be attributed to the metal complexes.

The transmittance of the samples has been measured by moving them along the transmission axis of the laser beam and the normalized curves (i.e. the “open aperture” Z-scans) have been obtained. In Fig. 3
Fig. 3 “Open-aperture” Z-scans obtained for the S1 system for different sample concentrations.
, characteristic curves for the ligand S1, which correspond to different concentrations in chloroform and under the same experimental conditions, can be seen. It is obvious that around the focal plane of the lens (z = 0), where the laser intensity is maximum, there is a strong transmittance minimum for all investigated concentrations indicating RSA type behaviour, which is associated with optical limiting action. It can be also seen that the dip increases by increasing the concentration of the ligand S1, as expected for third order nonlinearity. “Open aperture” Z-scans have been also measured for the ruthenium and iron metal complexes (S2, S3). The fact that the normalized transmittance exhibited maximum around the focal plane, as it can be seen in Fig. 4(a)
Fig. 4 “Open-aperture” Z-scans obtained for the (a) S2 and (b) S3 systems.
, 4(b) for the two compounds respectively, indicates Saturable Absorption (S.A.) behaviour, opposing the nonlinear absorption attribute of the initial ligand S1.

From a plethora of “open-aperture” Z-scan curves, obtained under several different laser excitation intensities in order to verify that no saturation of the nonlinearity takes place, thenonlinear optical parameters of the systems have been determined and can be seen in Table 1

Table 1. Nonlinear optical parameters determined from the Z-scan measurements (30 ps, 532 nm).

table-icon
View This Table
. More specifically the nonlinear absorption coefficient (β), as well as the Imχ(3) are tabulated for similar concentrations of the S1-S3 molecules. Also the concentration independent Imγ value, which is characteristic of each molecule has been obtained and is shown in the same table. The negative sign in the nonlinear optical parameters of the systems S2, S3 indicates an S.A. behavior. In all cases, high Imγ values have been found reaching 0.57 × 10−30 esu and ‒0.33 × 10−30 esu for the R.S.A. and S.A. respectively. Comparison between the complexes S2, S3 shows that the imaginary part of the second hyperpolarizability is larger in the case of S3 by about 16 times. This significant enhancement can be attributed to the presence of the additional TTF group in S3 and also to the different nature of the metal ion.

The reversing of the nonlinear absorption character of the molecular systems studied here reflects that the introduction of the metal cations can drastically change the energy levels of the systems, and this includes also the introduction of the metal to ligand charge transfer states. So the S.A. character of the systems S2, S3 can be attributed to the fact that the excited-state absorption cross-section in these Ru, Fe complexes is lower compared with that of the ground state absorption cross-section, while the inverse is taking place in the case of the S1 system. Consequently the higher, positive γ value of the S1 molecule can be attributed to excited state enhancement of the third order nonlinear absorption, which is well known to affect the third order nonlinearities under the ps regime and has been described in details elsewhere [18

18. B. Gu, K. Lou, J. Chen, Y. Li, H.-T. Wang, and W. Ji, “Excited-state enhancement of third-order optical nonlinearities: photodynamics and characterization,” Opt. Express 18(26), 26843–26853 (2010). [CrossRef] [PubMed]

].

The SA character found for the systems S2, S3 is in very good agreement with the results of Konstantaki et al. [19

19. M. Konstantaki, E. Koudoumas, S. Couris, P. Laine, E. Amouyal, and S. Leach, “Substantial non-linear optical response of new polyads based on Ru and Os complexes of modified terpyridines,” J. Phys. Chem. B 105(44), 10797–10804 (2001). [CrossRef]

]. In their work, the authors have shown that Ru and Os complexes exhibit S.A. character under 0.5 ps laser pulses at 497 nm, while they attribute this behaviour to the fact that the duration of the pulse is much shorter than the lifetime of the triplet state.

The reversing of the nonlinear absorption attribute has been previously investigated in the literature, while the origins of the effect can be various depending on the nature of the system. Cassano et al [20

20. T. Cassano, R. Tommasi, M. Arca, and F. A. Devillanova, “Investigation of the nonlinear absorption of [M(Et2timdt)2 ] (M = Pd, Pt) in the pico- and nanosecond timescales using the Z-scan technique,” J. Phys. Condens. Matter 18(23), 5279–5290 (2006). [CrossRef]

] for example have observed such an effect using the Z-scan technique with nanosecond laser pulses. Actually they studied two metal dithiolenes (Pt and Pd) and they have found S.A and R.S.A. for the Pd-based and the Pt-based system respectively. Such switching behaviour has been also found to be dependent upon the pulse duration and the laser excitation wavelength [21

21. W. F. Guo, X. B. Sun, J. Sun, X. Q. Wang, G. H. Zhang, Q. Ren, and D. Xu, “Nonlinear optical absorption of a metal dithiolene complex irradiated by different laser pulses at near-infrared wavelengths,” Chem. Phys. Lett. 435(1–3), 65–68 (2007). [CrossRef]

,22

22. K. P. Unnikrishnan, J. Thomas, V. P. N. Nampoori, and C. P. G. Vallabhan, “Wavelength dependence of nonlinear absorption in a bis-phthalocyanine studied using the Z-scan technique,” Appl. Phys. B 75(8), 871–874 (2002). [CrossRef]

].

4. Conclusion

In conclusion, the nonlinear absorption properties of an electroactive ligand, as well as of a ruthenium and iron metal complexes have been investigated. It has been found that although the initial ligand S1 exhibits RSA attribute, the S2 and S3 complexes exhibit exactly the opposite response (i.e. SA). The γ values have been found to be 0.57 × 10−30 esu, −0.021 × 10−30 esu and −0.33 × 10−30 esu for the systems S1, S2, S3 respectively. This reversing of the nonlinear absorption found in our work is highly desirable for nonlinear optics, as the combination of the S.A. and R.S.A. action of the systems can be employed in several different ways, covering a large field of photonic applications.

Acknowledgment

The authors gratefully acknowledge the CMEP for financial support to E. B. (PHC Tassili 08MDU730).

References and links

1.

I. Fuks-Janczarek, J. Luc, B. Sahraoui, F. Dumur, P. Hudhomme, J. Berdowski, and I. V. Kityk, “Third-order nonlinear optical figure of merits for conjugated TTF-quinone molecules,” J. Phys. Chem. B 109(20), 10179–10183 (2005). [CrossRef] [PubMed]

2.

N. Terkia-Derdra, R. Andreu, M. Salle, E. Levillain, J. Orduna, J. Garin, E. Orti, R. Viruela, R. Pou-Amerigo, B. Sahraoui, A. Gorgues, J. F. Favard, and A. Riou, “π Conjugation across the tetrathiafulvalene core: synthesis of extended tetrathiafulvalene derivatives and theoretical analysis of their unusual electrochemical properties,” Chemistry 6(7), 1199–1213 (2000). [CrossRef] [PubMed]

3.

K. Iliopoulos, R. Czaplicki, H. El Ouazzani, J. Y. Balandier, M. Chas, S. Goeb, M. Salle, D. Gindre, and B. Sahraoui, “Physical origin of the third order nonlinear optical response of orthogonal pyrrolo-tetrathiafulvalene derivatives,” Appl. Phys. Lett. 97(10), 101104 (2010). [CrossRef]

4.

B. Sahraoui, X. N. Phu, M. Sallé, and A. Gorgues, “Electronic and nuclear contributions to the third-order nonlinear optical susceptibilities of new p-N, N’-dimethylaniline tetrathiafulvalene derivatives,” Opt. Lett. 23(23), 1811–1813 (1998). [CrossRef] [PubMed]

5.

J. F. Lamère, I. Malfant, A. Sournia-Saquet, P. G. Lacroix, J. M. Fabre, L. Kaboub, T. Abbaz, A. Gouasmia, I. Asselberghs, and K. Clays, “Quadratic nonlinear optical response in partially charged donor-substituted tetrathiafulvalene: From a computational investigation to a rational synthetic feasibility,” Chem. Mater. 19(4), 805–815 (2007). [CrossRef]

6.

B. Insuasty, C. Atienza, C. Seoane, N. Martín, J. Garín, J. Orduna, R. Alcalá, and B. Villacampa, “Electronic and structural effects on the nonlinear optical behavior in push-pull TTF/tricarbonyl chromiun arene complexes,” J. Org. Chem. 69(21), 6986–6995 (2004). [CrossRef] [PubMed]

7.

M. Bendikov, F. Wudl, and D. F. Perepichka, “Tetrathiafulvalenes, oligoacenenes, and their buckminsterfullerene derivatives: The brick and mortar of organic electronics,” Chem. Rev. 104(11), 4891–4946 (2004). [CrossRef] [PubMed]

8.

M. González, J. L. Segura, C. Seoane, N. Martín, J. Garín, J. Orduna, R. Alcalá, B. Villacampa, V. Hernández, and J. T. López Navarrete, “Tetrathiafulvalene derivatives as NLO-phores: Synthesis, electrochemistry, Raman spectroscopy, theoretical calculations, and NLO properties of novel TTF-derived donor-π-acceptor dyads,” J. Org. Chem. 66(26), 8872–8882 (2001). [CrossRef] [PubMed]

9.

D. Lorcy, N. Bellec, M. Fourmigue, and N. Avarvari, “Tetrathiafulvalene-based group XV ligands: Synthesis, coordination chemistry and radical cation salts,” Coord. Chem. Rev. 253(9–10), 1398–1438 (2009) (and references therein). [CrossRef]

10.

Q. Wang, P. Day, J.-P. Griffiths, H. Nie, and J. D. Wallis, “Synthetic strategies for preparing BEDT-TTF derivatives functionalised with metal ion binding groups,” New J. Chem. 30(12), 1790–1800 (2006). [CrossRef]

11.

B. J. Coe, T. J. Meyer, and P. S. White, “Control of axial ligand substitution in trans-bis(2,2'-bipyridine)ruthenium(II) complexes. Crystal and molecular structure of trans-(4-ethylpyridine)(dimethyl sulfoxide)bis(2,2'-bipyridine)ruthenium(II) hexafluorophosphate, trans-[Ru(bpy)2(4-Etpy)(DMSO)](PF6)2,” Inorg. Chem. 32(19), 4012–4020 (1993). [CrossRef]

12.

H. Hofmeier and U. S. Schubert, “Recent developments in the supramolecular chemistry of terpyridine-metal complexes,” Chem. Soc. Rev. 33(6), 373–399 (2004). [CrossRef] [PubMed]

13.

E. Ripaud, A. El-Ghayoury, E. Belhadj, M. Mazari, and M. Sallé, Manuscript in preparation.

14.

K. Heuzé, M. Fourmigué, and P. Batail, “The crystal chemistry of amide-functionalized ethylenedithiotetrathiafulvalenes: EDT-TTF-CONRR′ (R, R′ = H, Me),” J. Mater. Chem. 9(10), 2373–2379 (1999). [CrossRef]

15.

T. Mutai, J.-D. Cheon, S. Arita, and K. Araki, “Phenyl-substituted 2,2′:6′,2″-terpyridines as highly fluorescent compounds—effect of the number of pyridine rings on fluorescence properties,” J.Chem.Soc., Perkin Trans. 2(5), 862–865 (2002). [CrossRef]

16.

T. Mutai, J.-D. Cheon, G. Tsuchiya, and K. Araki, “6-Amino-2,2′:6′,2″-terpyridines as highly fluorescent compounds—effect of the number of pyridine rings on fluorescence properties,” J. Chem. Soc. Perkin Trans. 2(5), 862–865 (2002).

17.

M. Sheik-Bahae, A. A. Said, T. H. Wei, D. J. Hagan, and E. W. Van Stryland, “Sensitive measurement of optical nonlinearities using a single beam,” IEEE J. Quantum Electron. 26(4), 760–769 (1990). [CrossRef]

18.

B. Gu, K. Lou, J. Chen, Y. Li, H.-T. Wang, and W. Ji, “Excited-state enhancement of third-order optical nonlinearities: photodynamics and characterization,” Opt. Express 18(26), 26843–26853 (2010). [CrossRef] [PubMed]

19.

M. Konstantaki, E. Koudoumas, S. Couris, P. Laine, E. Amouyal, and S. Leach, “Substantial non-linear optical response of new polyads based on Ru and Os complexes of modified terpyridines,” J. Phys. Chem. B 105(44), 10797–10804 (2001). [CrossRef]

20.

T. Cassano, R. Tommasi, M. Arca, and F. A. Devillanova, “Investigation of the nonlinear absorption of [M(Et2timdt)2 ] (M = Pd, Pt) in the pico- and nanosecond timescales using the Z-scan technique,” J. Phys. Condens. Matter 18(23), 5279–5290 (2006). [CrossRef]

21.

W. F. Guo, X. B. Sun, J. Sun, X. Q. Wang, G. H. Zhang, Q. Ren, and D. Xu, “Nonlinear optical absorption of a metal dithiolene complex irradiated by different laser pulses at near-infrared wavelengths,” Chem. Phys. Lett. 435(1–3), 65–68 (2007). [CrossRef]

22.

K. P. Unnikrishnan, J. Thomas, V. P. N. Nampoori, and C. P. G. Vallabhan, “Wavelength dependence of nonlinear absorption in a bis-phthalocyanine studied using the Z-scan technique,” Appl. Phys. B 75(8), 871–874 (2002). [CrossRef]

OCIS Codes
(160.4330) Materials : Nonlinear optical materials
(190.4400) Nonlinear optics : Nonlinear optics, materials
(190.4710) Nonlinear optics : Optical nonlinearities in organic materials

ToC Category:
Nonlinear Optics

History
Original Manuscript: June 28, 2012
Revised Manuscript: August 22, 2012
Manuscript Accepted: August 22, 2012
Published: October 23, 2012

Citation
Konstantinos Iliopoulos, Abdelkrim El-Ghayoury, Hasnaa El Ouazzani, Mindaugas Pranaitis, Esmah Belhadj, Emilie Ripaud, Miloud Mazari, Marc Sallé, Denis Gindre, and Bouchta Sahraoui, "Nonlinear absorption reversing between an electroactive ligand and its metal complexes," Opt. Express 20, 25311-25316 (2012)
http://www.opticsinfobase.org/oe/abstract.cfm?URI=oe-20-23-25311


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References

  1. I. Fuks-Janczarek, J. Luc, B. Sahraoui, F. Dumur, P. Hudhomme, J. Berdowski, and I. V. Kityk, “Third-order nonlinear optical figure of merits for conjugated TTF-quinone molecules,” J. Phys. Chem. B109(20), 10179–10183 (2005). [CrossRef] [PubMed]
  2. N. Terkia-Derdra, R. Andreu, M. Salle, E. Levillain, J. Orduna, J. Garin, E. Orti, R. Viruela, R. Pou-Amerigo, B. Sahraoui, A. Gorgues, J. F. Favard, and A. Riou, “π Conjugation across the tetrathiafulvalene core: synthesis of extended tetrathiafulvalene derivatives and theoretical analysis of their unusual electrochemical properties,” Chemistry6(7), 1199–1213 (2000). [CrossRef] [PubMed]
  3. K. Iliopoulos, R. Czaplicki, H. El Ouazzani, J. Y. Balandier, M. Chas, S. Goeb, M. Salle, D. Gindre, and B. Sahraoui, “Physical origin of the third order nonlinear optical response of orthogonal pyrrolo-tetrathiafulvalene derivatives,” Appl. Phys. Lett.97(10), 101104 (2010). [CrossRef]
  4. B. Sahraoui, X. N. Phu, M. Sallé, and A. Gorgues, “Electronic and nuclear contributions to the third-order nonlinear optical susceptibilities of new p-N, N’-dimethylaniline tetrathiafulvalene derivatives,” Opt. Lett.23(23), 1811–1813 (1998). [CrossRef] [PubMed]
  5. J. F. Lamère, I. Malfant, A. Sournia-Saquet, P. G. Lacroix, J. M. Fabre, L. Kaboub, T. Abbaz, A. Gouasmia, I. Asselberghs, and K. Clays, “Quadratic nonlinear optical response in partially charged donor-substituted tetrathiafulvalene: From a computational investigation to a rational synthetic feasibility,” Chem. Mater.19(4), 805–815 (2007). [CrossRef]
  6. B. Insuasty, C. Atienza, C. Seoane, N. Martín, J. Garín, J. Orduna, R. Alcalá, and B. Villacampa, “Electronic and structural effects on the nonlinear optical behavior in push-pull TTF/tricarbonyl chromiun arene complexes,” J. Org. Chem.69(21), 6986–6995 (2004). [CrossRef] [PubMed]
  7. M. Bendikov, F. Wudl, and D. F. Perepichka, “Tetrathiafulvalenes, oligoacenenes, and their buckminsterfullerene derivatives: The brick and mortar of organic electronics,” Chem. Rev.104(11), 4891–4946 (2004). [CrossRef] [PubMed]
  8. M. González, J. L. Segura, C. Seoane, N. Martín, J. Garín, J. Orduna, R. Alcalá, B. Villacampa, V. Hernández, and J. T. López Navarrete, “Tetrathiafulvalene derivatives as NLO-phores: Synthesis, electrochemistry, Raman spectroscopy, theoretical calculations, and NLO properties of novel TTF-derived donor-π-acceptor dyads,” J. Org. Chem.66(26), 8872–8882 (2001). [CrossRef] [PubMed]
  9. D. Lorcy, N. Bellec, M. Fourmigue, and N. Avarvari, “Tetrathiafulvalene-based group XV ligands: Synthesis, coordination chemistry and radical cation salts,” Coord. Chem. Rev.253(9–10), 1398–1438 (2009) (and references therein). [CrossRef]
  10. Q. Wang, P. Day, J.-P. Griffiths, H. Nie, and J. D. Wallis, “Synthetic strategies for preparing BEDT-TTF derivatives functionalised with metal ion binding groups,” New J. Chem.30(12), 1790–1800 (2006). [CrossRef]
  11. B. J. Coe, T. J. Meyer, and P. S. White, “Control of axial ligand substitution in trans-bis(2,2'-bipyridine)ruthenium(II) complexes. Crystal and molecular structure of trans-(4-ethylpyridine)(dimethyl sulfoxide)bis(2,2'-bipyridine)ruthenium(II) hexafluorophosphate, trans-[Ru(bpy)2(4-Etpy)(DMSO)](PF6)2,” Inorg. Chem.32(19), 4012–4020 (1993). [CrossRef]
  12. H. Hofmeier and U. S. Schubert, “Recent developments in the supramolecular chemistry of terpyridine-metal complexes,” Chem. Soc. Rev.33(6), 373–399 (2004). [CrossRef] [PubMed]
  13. E. Ripaud, A. El-Ghayoury, E. Belhadj, M. Mazari, and M. Sallé, Manuscript in preparation.
  14. K. Heuzé, M. Fourmigué, and P. Batail, “The crystal chemistry of amide-functionalized ethylenedithiotetrathiafulvalenes: EDT-TTF-CONRR′ (R, R′ = H, Me),” J. Mater. Chem.9(10), 2373–2379 (1999). [CrossRef]
  15. T. Mutai, J.-D. Cheon, S. Arita, and K. Araki, “Phenyl-substituted 2,2′:6′,2″-terpyridines as highly fluorescent compounds—effect of the number of pyridine rings on fluorescence properties,” J.Chem.Soc., Perkin Trans.2(5), 862–865 (2002). [CrossRef]
  16. T. Mutai, J.-D. Cheon, G. Tsuchiya, and K. Araki, “6-Amino-2,2′:6′,2″-terpyridines as highly fluorescent compounds—effect of the number of pyridine rings on fluorescence properties,” J. Chem. Soc. Perkin Trans.2(5), 862–865 (2002).
  17. M. Sheik-Bahae, A. A. Said, T. H. Wei, D. J. Hagan, and E. W. Van Stryland, “Sensitive measurement of optical nonlinearities using a single beam,” IEEE J. Quantum Electron.26(4), 760–769 (1990). [CrossRef]
  18. B. Gu, K. Lou, J. Chen, Y. Li, H.-T. Wang, and W. Ji, “Excited-state enhancement of third-order optical nonlinearities: photodynamics and characterization,” Opt. Express18(26), 26843–26853 (2010). [CrossRef] [PubMed]
  19. M. Konstantaki, E. Koudoumas, S. Couris, P. Laine, E. Amouyal, and S. Leach, “Substantial non-linear optical response of new polyads based on Ru and Os complexes of modified terpyridines,” J. Phys. Chem. B105(44), 10797–10804 (2001). [CrossRef]
  20. T. Cassano, R. Tommasi, M. Arca, and F. A. Devillanova, “Investigation of the nonlinear absorption of [M(Et2timdt)2 ] (M = Pd, Pt) in the pico- and nanosecond timescales using the Z-scan technique,” J. Phys. Condens. Matter18(23), 5279–5290 (2006). [CrossRef]
  21. W. F. Guo, X. B. Sun, J. Sun, X. Q. Wang, G. H. Zhang, Q. Ren, and D. Xu, “Nonlinear optical absorption of a metal dithiolene complex irradiated by different laser pulses at near-infrared wavelengths,” Chem. Phys. Lett.435(1–3), 65–68 (2007). [CrossRef]
  22. K. P. Unnikrishnan, J. Thomas, V. P. N. Nampoori, and C. P. G. Vallabhan, “Wavelength dependence of nonlinear absorption in a bis-phthalocyanine studied using the Z-scan technique,” Appl. Phys. B75(8), 871–874 (2002). [CrossRef]

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