Nonlinear Optical Properties Tuning in Meso-Tetraphenylporphyrin Derivatives Substituted with Donor/Acceptor Groups in Picosecond and Nanosecond Regimes
Abstract
:1. Introduction
2. Results and Discussion
2.1. Linear Absorption Characterization
2.2. Picosecond Z-Scan Measurements
2.3. Nanosecond Z-Scan Measurements
2.4. Second-Order Molecular Hyperpolarizabilities
3. Experimental Section
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
- Hales, J.M.; Matichak, J.; Barlow, S.; Ohira, S.; Yesudas, K.; Bredas, J.L.; Perry, J.W.; Marder, S.R. Design of Polymethine Dyes with Large Third-Order Optical Nonlinearities and Loss Figures of Merit. Science 2010, 327, 1485–1488. [Google Scholar] [CrossRef] [PubMed]
- Bouit, P.A.; Wetzel, G.; Berginc, G.; Loiseaux, B.; Toupet, L.; Feneyrou, P.; Bretonnière, Y.; Kamada, K.; Maury, O.; Andraud, C. Near IR Nonlinear Absorbing Chromophores with Optical Limiting Properties at Telecommunication Wavelengths. Chem. Mater. 2007, 19, 5325–5335. [Google Scholar] [CrossRef]
- Wei, T.H.; Hagan, D.J.; Sence, M.J.; Vanstryland, E.W.; Perry, J.W.; Coulter, D.R. Direct Measurements of Nonlinear Absorption and Refraction in Solutions of Phthalocyanines. Appl. Phys. B 1992, 54, 46–51. [Google Scholar] [CrossRef]
- Thomas, S.; Pati, Y.A.; Ramasesha, S. Linear and Nonlinear Optical Properties of Expanded Porphyrins: A DMRG Study. J. Phys. Chem. A 2013, 117, 7804–7809. [Google Scholar] [CrossRef] [PubMed]
- De la Torre, G.; Vaquez, P.; Agullo-Lopez, F.; Torres, T. Role of structural factors in the nonlinear optical properties of phthalocyanines and related compounds. Chem. Rev. 2004, 104, 3723–3750. [Google Scholar] [CrossRef] [PubMed]
- Humphrey, J.; Kuciauskas, D. Charge-transfer states determine iron porphyrin film third-order nonlinear optical properties in the near-IR spectral region. J. Phys. Chem. B 2004, 108, 12016–12023. [Google Scholar] [CrossRef]
- Bessho, T.; Zakeeruddin, S.M.; Yeh, C.Y.; Diau, E.W.G.; Gratzel, M. Highly Efficient Mesoscopic Dye-Sensitized Solar Cells Based on Donor-Acceptor-Substituted Porphyrins. Angew. Chem. Int. Edit. 2010, 49, 6646–6649. [Google Scholar] [CrossRef]
- Calvete, M.; Yang, G.Y.; Hanack, M. Porphyrins and phthalocyanines as materials for optical limiting. Synth. Metals 2004, 141, 231–243. [Google Scholar] [CrossRef]
- Drouet, S.; Merhi, A.; Grelaud, G.; Cifuentes, M.P.; Humphrey, M.G.; Matczyszyn, K.; Samoc, M.; Toupet, L.; Paul-Roth, C.O.; Paul, F. Enhanced two-photon absorption cross-sections of zinc(II) tetraphenylporphyrins peripherally substituted with d(6)-metal alkynyl complexes. New J. Chem. 2012, 36, 2192–2195. [Google Scholar] [CrossRef] [Green Version]
- Zawadzka, M.; Wang, J.; Blau, W.J.; Senge, M.O. Modeling of Nonlinear Absorption of 5,10-A(2)B(2) Porphyrins in the Nanosecond Regime. J. Phys. Chem. A 2013, 117, 15–26. [Google Scholar] [CrossRef] [PubMed]
- Zhang, X.L.; Liu, Z.B.; Zhao, X.; Yan, X.Q.; Li, X.C.; Tian, J.G. Optical limiting effect and ultrafast saturable absorption in a solid PMMA composite containing porphyrin-covalently functionalized multi-walled carbon nanotubes. Opt. Express 2013, 21, 25277–25284. [Google Scholar] [CrossRef] [PubMed]
- Swain, D.; Rana, A.; Panda, P.K.; Rao, S.V. Strong two-photon absorption properties and ultrafast pump-probe studies of novel porphyrin derivatives. Chem. Phys. Lett. 2014, 610, 310–315. [Google Scholar] [CrossRef]
- Huang, C.S.; Li, Y.L.; Song, Y.L.; Li, Y.J.; Liu, H.B.; Zhu, D.B. Ordered Nanosphere Alignment of Porphyrin for the Improvement of Nonlinear Optical Properties. Adv. Mater. 2010, 22, 3532–3536. [Google Scholar] [CrossRef] [PubMed]
- Quiroz-Segoviano, R.I.Y.; Serratos, I.N.; Rojas-Gonzalez, F.; Tello-Solis, S.R.; Sosa-Fonseca, R.; Medina-Juarez, O.; Menchaca-Campos, C.; Garcia-Sanchez, M.A. On Tuning the Fluorescence Emission of Porphyrin Free Bases Bonded to the Pore Walls of Organo-Modified Silica. Molecules 2014, 19, 2261–2285. [Google Scholar] [CrossRef] [PubMed]
- Rao, D.N. Excited state dynamics in porphyrins in relevance to third-order nonlinearity and optical limiting. Opt. Mater. 2003, 21, 45–49. [Google Scholar] [CrossRef]
- Hales, J.M.; Cozzuol, M.; Screen, T.E.O.; Anderson, H.L.; Perry, J.W. Metalloporphyrin polymer with temporally agile, broadband nonlinear absorption for optical limiting in the near infrared. Opt. Express 2009, 17, 18478–18488. [Google Scholar] [CrossRef] [PubMed]
- Mishra, S.R.; Rawat, H.S.; Laghate, M. Nonlinear absorption and optical limiting IN metalloporphyrins. Opt. Commun. 1998, 147, 328–332. [Google Scholar] [CrossRef]
- Zhang, X.L.; Chen, X.D.; Li, X.C.; Ying, C.F.; Liu, Z.B.; Tian, J.G. Enhanced reverse saturable absorption and optical limiting properties in a protonated water-soluble porphyrin. J. Opt. 2013, 15. [Google Scholar] [CrossRef]
- Wang, A.J.; Long, L.L.; Zhao, W.; Song, Y.L.; Humphrey, M.G.; Cifuentes, M.P.; Wu, X.Z.; Fu, Y.S.; Zhang, D.D.; Li, X.F.; et al. Increased optical nonlinearities of graphene nanohybrids covalently functionalized by axially-coordinated porphyrins. Carbon 2013, 53, 327–338. [Google Scholar]
- Krishna, M.B.M.; Kumar, V.P.; Venkatramaiah, N.; Venkatesan, R.; Rao, D.N. Nonlinear optical properties of covalently linked graphene-metal porphyrin composite materials. Appl. Phys. Lett. 2011, 98, 081106:1–081106:4. [Google Scholar] [CrossRef]
- Jiang, X.; Du, Y.L.; Liu, C.; Huo, P.F.; Geng, Z.; Zhang, S.L.; Wang, G.B. Synthesis and optical properties of hyperbranched PAEKs containing porphyrin and its metal derivatives. Chin. J. Polym. Sci. 2014, 32, 73–83. [Google Scholar] [CrossRef]
- Liu, Y.L.; Liu, Z.B.; Tian, J.G.; Zhu, Y.; Zheng, J.Y. Effects of metallization and bromination on nonlinear optical properties of diphenylporphyrins. Opt. Commun. 2008, 281, 776–781. [Google Scholar] [CrossRef]
- Ahn, H.; Lee, M.T.; Chang, Y.M. Spectral dependence of third-order nonlinear optical properties in InN. Appl. Phys. Lett. 2014, 104, 201904:1–201904:5. [Google Scholar]
- Roy, S.; Yadav, C. Femtosecond all-optical parallel logic gates based on tunable saturable to reverse saturable absorption in graphene-oxide thin films. Appl. Phys. Lett. 2013, 103, 241113:1–241113:5. [Google Scholar]
- Srinivas, N.K.M.N.; Rao, S.V.; Rao, D.N. Saturable and reverse saturable absorption of rhodamine B in methanol and water. J. Opt. Soc. Am. B Opt. Phys. 2003, 20, 2470–2479. [Google Scholar] [CrossRef]
- Boyd, R.W. Nonlinear Optics, 3rd ed.; Academic Press: New York, NY, USA, 2007; p. 243. [Google Scholar]
- Sheikbahae, M.; Hutchings, D.C.; Hagan, D.J.; Vanstryland, E.W. Dispersion of Bound Electronic Nonlinear Refraction in Solids. IEEE J. Quantum Electron. 1991, 27, 1296–1309. [Google Scholar] [CrossRef]
- Tsang, H.K.; Wong, C.S.; Liang, T.K.; Day, I.E.; Roberts, S.W.; Harpin, A.; Drake, J.; Asghari, M. Optical dispersion, two-photon absorption and self-phase modulation in silicon waveguides at 1.5 µm wavelength. Appl. Phys. Lett. 2002, 80, 416–418. [Google Scholar] [CrossRef]
- Jiang, L.; Jiu, T.G.; Li, Y.L.; Li, Y.B.; Yang, J.Y.; Li, J.B.; Li, C.H.; Liu, H.B.; Song, Y.L. Excited-state absorption and sign tuning of nonlinear refraction in porphyrin derivatives. J. Phys. Chem. B 2008, 112, 756–759. [Google Scholar] [CrossRef] [PubMed]
- Shi, Z.H.; Zhou, Y.S.; Zhang, L.J.; Hassan, S.U.; Qu, N.N. Solution Properties and Effect of Anions on Third-Order Optical Nonlinearity of Porphyrin-Heteropolyoxometalate Hybrid System. J. Phys. Chem. C 2014, 118, 6413–6422. [Google Scholar] [CrossRef]
- Wang, L.; Chen, Y.L.; Jiang, J.Z. Controlling the growth of porphyrin based nanostructures for tuning third-order NLO properties. Nanoscale 2014, 6, 1871–1878. [Google Scholar] [CrossRef] [PubMed]
- Du, Y.L.; Zhang, S.L.; Jiang, X.; Zhu, K.; Geng, Z.; Fang, Y.; Huo, P.F.; Liu, C.; Song, Y.L.; Wang, G.B. Synthesis and Optical Properties of Poly(aryl ether ketone)s Incorporating Porphyrins in the Backbones. J. Polym. Sci. Part A Polym. Chem. 2014, 52, 1282–1290. [Google Scholar] [CrossRef]
- Sendhil, K.; Vijayan, C.; Kothiyal, M.P. Nonlinear optical properties of a porphyrin derivative incorporated in Nafion polymer. Opt. Mater. 2005, 27, 1606–1609. [Google Scholar] [CrossRef]
- Bezerra, A.G.; Borissevitch, I.E.; de Araujo, R.E.; Gomes, A.S.L.; de Araujo, C.B. Investigation of picosecond optical nonlinearity in porphyrin metal complexes derivatives. Chem. Phys. Lett. 2000, 318, 511–516. [Google Scholar] [CrossRef]
- Jiang, L.; Lu, F.S.; Li, H.M.; Chang, Q.; Li, Y.L.; Liu, H.B.; Wang, S.; Song, Y.L.; Cui, G.L.; Wang, N.; et al. Third-order nonlinear optical properties of an ultrathin film containing a porphyrin derivative. J. Phys. Chem. B 2005, 109, 6311–6315. [Google Scholar]
- Sheikbahae, M.; Said, A.A.; Wei, T.H.; Hagan, D.J.; Vanstryland, E.W. Sensitive Measurement of Optical Nonlinearities Using a Single Beam. IEEE J. Quantum Electron. 1990, 26, 760–769. [Google Scholar] [CrossRef]
- Capitosti, G.J.; Guerrero, C.D.; Binkley, D.E.; Rajesh, C.S.; Modarelli, D.A. Efficient synthesis of porphyrin-containing, benzoquinone-terminated, rigid polyphenylene dendrimers. J. Org. Chem. 2003, 68, 247–261. [Google Scholar] [CrossRef] [PubMed]
- Yang, J.Y.; Wang, Y.X.; Zhang, X.R.; Li, C.W.; Jin, X.; Shui, M.; Song, Y.L. Characterization of the transient thermal-lens effect using top-hat beam Z-scan. J. Phys. B At. Mol. Opt. Phys. 2009, 42, 225404:1–225404:5. [Google Scholar]
- Anusha, P.T.; Swain, D.; Hamad, S.; Giribabu, L.; Prashant, T.S.; Tewari, S.P.; Rao, S.V. Ultrafast Excited-State Dynamics and Dispersion Studies of Third-Order Optical Nonlinearities in Novel Corroles. J. Phys. Chem. C 2012, 116, 17828–17837. [Google Scholar] [CrossRef]
- Yang, J.Y.; Song, Y.L. Direct observation of the transient thermal-lensing effect using the phase-object Z-scan technique. Opt. Lett. 2009, 34, 157–159. [Google Scholar] [CrossRef]
- Brochard, P.; Grolier-Mazza, V.; Cabanel, R. Thermal nonlinear refraction in dye solutions: A study of the transient regime. J. Opt. Soc. Am. B Opt. Phys. 1997, 14, 405–414. [Google Scholar] [CrossRef]
- Kovsh, D.I.; Hagan, D.J.; van Stryland, E.W. Numerical modeling of thermal refraction in liquids in the transient regime. Opt. Express 1999, 4, 315–327. [Google Scholar] [CrossRef] [PubMed]
- Chen, Z.H.; Zhong, C.; Zhang, Z.; Li, Z.Y.; Niu, L.H.; Bin, Y.J.; Zhang, F.S. Photoresponsive J-aggregation behavior of a novel azobenzene-phthalocyanine dyad and its third-order optical nonlinearity. J. Phys. Chem. B 2008, 112, 7387–7394. [Google Scholar] [CrossRef] [PubMed]
- Rao, S.V.; Srinivas, N.K.M.N.; Rao, D.N.; Giribabu, L.; Maiya, B.G.; Philip, R.; Kumar, G.R. Studies of third-order optical nonlinearity and nonlinear absorption in tetra tolyl porphyrins using degenerate four wave mixing and Z-scan. Opt. Commun. 2000, 182, 255–264. [Google Scholar] [CrossRef]
- Senge, M.O.; Fazekas, M.; Notaras, E.G.A.; Blau, W.J.; Zawadzka, M.; Locos, O.B.; Mhuircheartaigh, E.M.N. Nonlinear optical properties of porphyrins. Adv. Mater. 2007, 19, 2737–2774. [Google Scholar] [CrossRef]
- Sample Availability: Samples of the compounds investigated here are available from the authors.
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Ao, G.; Xiao, Z.; Qian, X.; Li, Z.; Wang, Y.; Zhang, X.; Song, Y. Nonlinear Optical Properties Tuning in Meso-Tetraphenylporphyrin Derivatives Substituted with Donor/Acceptor Groups in Picosecond and Nanosecond Regimes. Molecules 2015, 20, 5554-5565. https://doi.org/10.3390/molecules20045554
Ao G, Xiao Z, Qian X, Li Z, Wang Y, Zhang X, Song Y. Nonlinear Optical Properties Tuning in Meso-Tetraphenylporphyrin Derivatives Substituted with Donor/Acceptor Groups in Picosecond and Nanosecond Regimes. Molecules. 2015; 20(4):5554-5565. https://doi.org/10.3390/molecules20045554
Chicago/Turabian StyleAo, Guanghong, Zhengguo Xiao, Xuemin Qian, Zhongguo Li, Yuxiao Wang, Xueru Zhang, and Yinglin Song. 2015. "Nonlinear Optical Properties Tuning in Meso-Tetraphenylporphyrin Derivatives Substituted with Donor/Acceptor Groups in Picosecond and Nanosecond Regimes" Molecules 20, no. 4: 5554-5565. https://doi.org/10.3390/molecules20045554