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Optics Express

Optics Express

  • Editor: C. Martijn de Sterke
  • Vol. 17, Iss. 15 — Jul. 20, 2009
  • pp: 12777–12784
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Enhanced laser action of Perylene-Red doped polymeric materials

I. García-Moreno, A. Costela, M. Pintado-Sierra, V. Martín, and R. Sastre  »View Author Affiliations


Optics Express, Vol. 17, Issue 15, pp. 12777-12784 (2009)
http://dx.doi.org/10.1364/OE.17.012777


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Abstract

The laser action of Perylene-Red doped in linear, crosslinked, fluorinated and sililated polymeric materials is reported. The purity of dye was found to be a key factor to enhance its solid-state laser behaviour. The samples were transversely pumped at 532 nm, with 5.5 mJ/pulse and 10 Hz repetition rate. Perylene-Red doped copolymers of methyl methacrylate with a 10 vol% proportion of 2,2,2-trifluoroethyl-methacrylate exhibited a lasing efficiency of 26% with a high photostability since the dye laser output remained at the same level after 100,000 pump pulses in the same position of the sample. This lasing behaviour is, to the best of our knowledge, the highest achieved to date for organic, inorganic, and hybrid materials doped with Perylene-Red.

© 2009 OSA

1. Introduction

Solid-state dye lasers with tunable emission at the red-edge spectral region could replace their liquid phase counterparts finding a niche in optical and optoelectronic applications provided the laser behaviour of the as yet reported systems is improved. Dyes derived from perylene di-imides have particularly attractive optical properties [1

1. K. Petritsch, J. J. Dittmer, E. A. Marseglia, R. H. Friend, A. Lux, G. G. Rozenberg, S. C. Moratti, and A. B. Holmes, “Dye-based donor/acceptor solar cells,” Sol. Energy Mater. Sol. Cells 61(1), 63–72 (2000). [CrossRef]

3

3. Z. J. Chen, M. G. Debije, T. Debaerdemaeker, P. Osswald, and F. Würthner, “Tetrachloro-substituted perylene bisimide dyes as promising n-type organic semiconductors: studies on structural, electrochemical and charge transport properties,” ChemPhysChem 5(1), 137–140 (2004). [CrossRef] [PubMed]

] due to an exceptional chemical, thermal, and photochemical stability with high fluorescence quantum yield close to unity [4

4. R. P. Haugland, Handbook of Fluorescent Probes and Research Chemicals, (Molecular Probes Inc., Eugene, 1989).

6

6. A. Rademacher, S. Märkle, and H. Langhals, “Soluble perylene fluorescent dyes with high photostability,” Chem. Ber. 115(8), 2927–2934 (1982). [CrossRef]

]. One of these red-emitting dyes which has been adapted to solid-state hosts is the non-ionic and nonpolar dye commercially named Perylene-Red (Per-Red, Fig. 1
Fig. 1 Molecular structures of Perylene-Red (Per-Red) dye as well as the monomers selected in this work: methyl methacrylate (MMA), 3-(trimethoxysilyl)propyl methacrylate (TMSPMA), 2,2,2-trifluoroethyl-methacrylate (TFMA), ethylene glycol dimethacrylate (EGDMA), pentaerythritol triacrylate (PETA), and pentaerythritol tetraacrylate (PETRA).
) [7

7. M. Schneider and K. Müllen, “Hybrid materials doped with covalently bound perylene dyes through the sol-gel process,” Chem. Mater. 12(2), 352–362 (2000). [CrossRef]

10

10. R. O. Al-Kaysi, T. Sang Ahn, A. M. Müller, and C. J. Bardeen, “The photophysical properties of chromophores at high (100 mM and above) concentrations in polymers and as neat solids,” Phys. Chem. Chem. Phys. 8(29), 3453–3459 (2006). [CrossRef] [PubMed]

]. Surprisingly, in spite of its good photophysical and photochemical properties, few reports have appeared on the lasing behaviour Per-Red doped solid-state materials [11

11. M. Canva, P. Georges, J.-F. Perelgritz, A. Brum, F. Chaput, and J.-P. Boilot, “Perylene- and pyrromethene-doped xerogel for a pulsed laser,” Appl. Opt. 34(3), 428–431 (1995). [CrossRef] [PubMed]

18

18. N. Tanaka, N. Barashkov, J. Heath, and W. N. Sisk, “Photodegradation of polymer-dispersed perylene di-imide dyes,” Appl. Opt. 45(16), 3846–3851 (2006). [CrossRef] [PubMed]

]. A number of reasons could justify this scarcity of studies, mainly the insolubility of this dye in common organic solvents, which probably led to Per-Red dye being one of the first dyes to be incorporated into sol-gel hybrid materials [19

19. R. Reisfeld, D. Brusilovsky, M. Eyal, E. Miron, Z. Burstein, and J. Ivri, “A new solid-state tunable laser in the visible,” Chem. Phys. Lett. 160(1), 43–44 (1989). [CrossRef]

,20

20. J. Ivri, Z. Burshtein, E. Miron, R. Reisfeld, and M. Eyal, “The perylene derivative BASF-241 solution as a new tunable dye laser in the visible,” IEEE J. Quantum Electron. 26(9), 1516–1520 (1990). [CrossRef]

], in spite of some serious limitations exhibited by these materials (complex and lengthy synthesis process, fragility which results in difficult mechanization of the final material, and most important, frequent optical inhomogeneity caused by refractive index mismatch between organic and inorganic parts). These early experimental studies revealed that this dye lases in the 610-640 nm range with a photostability much higher than that of the rhodamine family dyes, which are well known to be fairly stable [21

21. A. Dubois, M. Canva, A. Brun, F. Chaput, and J. P. Boilot, “Photostability of dye molecules trapped in solid matrices,” Appl. Opt. 35(18), 3193–3199 (1996). [CrossRef] [PubMed]

], albeit with a much lower lasing efficiency [13

13. A. Costela, I. García-Moreno, and R. Sastre, Handbook of Advanced Electronic and Photonic Materials and Devices (Academic Press, New York, 2001), Vol. 7, Chap. 4.

].

2. Experimental

2.1 Materials

Perylene-Red (BASF Lumogen Red 305) was first used as received with a purity of only 90% (checked by spectroscopic and chromatographic methods). Thus, the dye purity was improved up to a 99% through a flash column chromatography based on silica with hexane/ethyl acetate 95/5 v/v proportion as eluent, to remove the N-methyl-2-pyrrolidone, identified by NMR-1H as the principal impurity. Solvents for laser studies were of spectroscopic grade (Merck, Aldrich or Sigma) and were used without purification. Linear copolymers were obtained by copolymerization of methyl methacrylate (MMA) with different volumetric proportions of the sililated monomer 3-(trimethoxysilyl)propyl methacrylate (TMSPMA) as well as the fluorinated monomer 2,2,2-trifluoroethyl methacrylate (TFMA). Crosslinked matrices were obtained by copolymerization of MMA with di-, tri- and tetra-functionalizated comonomers, such as ethylenglycol dimethacrylate (EGDMA), pentaerythritol triacrylate (PETA) and pentaerythritol tetraacrylate (PETRA), respectively. All monomers were purchased from Aldrich and were used as received. Figure 1 shows the molecular structures of these monomers.

2.2 Preparation of solid polymeric samples

Per-Red was incorporated into the different solid matrices following the procedure previously described [23

23. A. Costela, I. García-Moreno, J. Barroso, and R. Sastre, “Laser performance of pyrromethene 567 dye in solid matrices of methyl methacrylate with different comonomers,” Appl. Phys. B 70, 367–373 (2000). [CrossRef]

], and rendering materials named as COP(MMA/monomer). The solid monolith laser samples were cast in a cylindrical shape, forming rods of 10 mm diameter and 10 mm length. A cut was made parallel to the axis of cylinder to obtain a lateral flat surface of ≈6 × 10 mm. This surface as well as the ends of the laser rods were prepared for lasing experiments by using a grinding and polishing machine (Phoenix Beta 4000, Buehler) until optical-grade finished.

2.3 Methods

Liquid solutions of dyes were contained in 1 cm optical-path quartz cells that were carefully sealed to avoid solvent evaporation during experiments. Both the liquid cells and the solid samples were transversely pumped at 532 nm with 5.5 mJ, 6 ns FWHM pulses from a frequency-doubled Q-switched Nd:YAG laser (Monocrom OPL-10) at a repetition rate of up to 10 Hz. Details of the experimental system can be found elsewhere [23

23. A. Costela, I. García-Moreno, J. Barroso, and R. Sastre, “Laser performance of pyrromethene 567 dye in solid matrices of methyl methacrylate with different comonomers,” Appl. Phys. B 70, 367–373 (2000). [CrossRef]

,25

25. A. Costela, I. García-Moreno, D. del Agua, O. García, and R. Sastre, “Silicon-containing organic matrices as hosts for highly photostable solid-state dye lasers,” Appl. Phys. Lett. 85(12), 2160–2162 (2004). [CrossRef]

,26

26. O. García, R. Sastre, D. del Agua, A. Costela, and I. García-Moreno, “New fluorinated polymers doped with BODIPY chromophore as highly efficient and photostable optical materials,” Chem. Mater. 18(3), 601–602 (2006). [CrossRef]

].

Narrow-line-width laser emission and tuning ranges of dye solutions were obtained by placing the samples in a home-made Shoshan-type oscillator [28

28. I. Shoshan, N. N. Danon, and U. P. Oppenheim, “Narrowband operation of a pulsed dye laser without intracavity beam expansion,” J. Appl. Phys. 48(11), 4495–4497 (1977). [CrossRef]

], consisting of full-reflecting aluminium back and tuning mirrors and a 2400-lines mm−1 holographic grating in grazing incidence, with outcoupling via the grating zero order. Wavelength tuning was accomplished by rotation of the tuning mirror. Tuning mirror and grating (both from Optometrics) were 5 cm wide and the angle of incidence on the grating was 88.5°. Laser line width was measured with a Fabry-Perot etalon (IC Optical Systems) with a free spectral range of 15.9 GHz.

Absorption and fluorescence (after excitation at 532 nm) spectra of the dyes were recorded on a fibre optic spectrophotometer (Ocean Optics USB2000) and on a spectrofluorimeter (Perkin Elmer LS-50B), respectively, for diluted (5x10−4 M) and concentrated (1x10−3 M) dye solutions in ethyl acetate contained in 0.01 cm optical path length quartz cuvettes.

3. Results and discussion

A systematic analysis of the laser behaviour of the dye in liquid phase was previously carried out as a guide to develop polymeric materials enhancing its laser action in solid-state. Under the selected experimental conditions, a concentration of 5 × 10−4 M, corresponding to an optical density (for a 1 cm path length at 532 nm) of 16, in ethyl acetate optimized the lasing efficiency (21%) of the dye when used as received. The purification process of the dye increased this conversion efficiency up to 26% although, when compared with other laser dyes pumped under the same experimental conditions, Per-Red is the least efficient because of its high excited-state absorption impairing the conversion efficiency [29

29. M. D. Rahn and T. A. King, “Comparison of laser performance of dye molecules in sol-gel, polycom, ormosil, and poly(methyl methacrylate) host media,” Appl. Opt. 34(36), 8260–8271 (1995). [CrossRef] [PubMed]

]. In order to analyze the influence of the dye purity on the laser photostability, solutions of both pure and non-purified Per-Red were irradiated under experimental conditions identical to those selected to irradiate the fluorophores when doped into solid polymeric matrices. Because the irradiated volume in solid samples was estimated to be 8 μL, capillary tubes into which ethyl acetate solutions (5 × 10−4 M) of dyes were incorporated offer the best geometry to reproduce the area irradiated in the solid samples, thus maintaining the same laser pump conditions in both cases. Although the low optical quality of the capillary prevents laser emission from the dyes, information about photostabilities can be obtained by monitoring the decrease in laser-induced fluorescence intensity, excited transversally to the capillary, as a function of the number of pump pulses. The fluorescence emission was monitored perpendicular to the exciting beam, and its collection and analysis was carried out with the same set-up selected to characterize the laser emission from dyes incorporated into solid samples. From the results obtained (Fig. 2
Fig. 2 Normalized laser-induced fluorescence emission as a function of the number of pump pulses at 10 Hz repetition rate for (a) pure and (b) impure Perylene-Red dye in ethyl acetate solutions.
) it can be concluded, for the first time to the best of our knowledge that the Per-Red photostability depends strongly on the purity of the chromophore since the presence of impurities in the commercial dye impairs drastically its laser action.

The influence of both composition and structure of solid matrix on the laser action of Per-Red was analyzed, in a systematic way, for the purified dye dissolved at a 5x10−4 M concentration in a number of copolymeric formulations with different compositions and/or degree of crosslinked based on MMA, since this is the monomer which mimics the ethyl acetate solvent.

Broad-line-width laser emission in a simple plane-plane non-tunable resonator with a single peak centred at the wavelength of ≈620 nm, beam divergence of ≈5 mrad, and pulse duration of ≈5 ns FWHM, was obtained from all the materials under study. The tuning capability of the dye-doped solid matrices, one of the most important features of dye lasers, was determined placing the samples in a grazing-incidence grating cavity in Shoshan configuration. Tunable laser emission with line width of the order of 0.15 cm−1 was obtained, with a tuning range of 50 nm, from 605 to 655 nm.

A summary of the results obtained is shown in Table 1

Table 1. Laser parametersa for Perylene-Red dye in linear, crosslinked, fluorinated and silicon-containing organic matrices. Nd:YAG laser (second harmonic) pump energy and repetition rate: 5.5 mJ/pulse and 10 Hz, respectively. Dye concentration: 5x10−4 M.

table-icon
View This Table
, where data on lasing efficiency, peak of the laser emission and intensity of the laser output (referred to initial intensity) after 100,000 pump pulses in the same position of the sample are included. For the sake of clarity, the evolution of the lasing photostability with the number of pump pulses is shown in Fig. 3
Fig. 3 Normalized laser output as a function of the number of pump pulses for Perylene-Red dye dissolved in (a) COP(MMA/TFMA 7/3), (b) silicon-containing copolymer COP(MMA/TMSPMA 9/1) and (c) crosslinked copolymer COP(MMA/PETRA 7/3). Dye concentration: 5x10−4 M. Pump energy and repetition rate: 5.5 mJ/pulse and 10 Hz, respectively.
for some of these optical materials. Lasing efficiencies up to 21% were obtained depending on the matrix composition, which are only slightly lower than those registered in liquid phase, in spite of the polishing surface of the solid samples relevant to laser operation not being laser grade, which results in higher losses in the optical cavity.

Lasing efficiency and photostability optimizes in the matrix with fluorinated composition. Polymers that contain atomic fluorine in or along the backbone possess many desirable physical properties, mainly due to high thermal stability, high optical damage threshold, and enhanced chemical resistance when compared to their non-fluorinated analogues [31

31. J. J. Reisinger and M. A. Hillmyer, “Synthesis of fluorinated polymers by chemical modification,” Prog. Polym. Sci. 27(5), 971–1005 (2002). [CrossRef]

]. In addition, the fluoropolymers increase the rigidity of the matrix enhancing, at the same time, the fractional free volume (FFV) that, estimated from the polymer specific volume and the specific van der Walls volume [32

32. J. Espeso, A. E. Lozano, J. G. de la Campa, and J. de Abajo, “Effect of substituents on the permeation properties of polyamide membranes,” J. Membr. Sci. 280(1-2), 659–665 (2006). [CrossRef]

], can be up to 1.87 times higher than that obtained in sililated matrices with the same monomer proportion. As was discussed for the crosslinked matrices, the free volume available within the polymeric matrix could control, at least to some extension, the photodegradation process of the dye. Consequently, and taking into account the molecular size of Per-Red, the fluorinated matrices could be defining a protecting “polymer cage” so that the free volume is completely occupied by the dye reducing the photobleaching rate. In order to lend support to this tentative conclusion, a more detailed study of free volume holes and their distribution inside the matrix is currently in progress.

To the best of our knowledge, this laser action is the highest achieved up to date for solid-state dye laser based on Perylene-Red doped organic, inorganic and hybrid matrices under less efficient and more demanding transversal pumping selected in the present work, without rotating or translating the sample to distribute the thermal load over a large volume, even as our resonator cavity was non-optimized.

In conclusion, the results presented in this work indicate that the laser action of the nonpolar and non-ionic Perylene-Red dye is greatly enhanced in polymeric matrices by properly incorporating fluorine atoms into the structure of the organic monomers. Reasonable lasing efficiencies for laser operation under transversal pumping in non-optimized cavities were recorded with a long stable lifetime operation, with only a slight degradation in the laser output after 100,000 pump pulses in a static sample at 10 Hz repetition rate. These new laser materials that exhibit important advantages with respect to the sol-gel hybrid matrices since they remain organic, have the potential to be used as active media in highly processible, reproducible, versatile, and easy to handle solid-state dye lasers and to substitute existing commercially available dye lasers in liquid phase impelling the applications of this new technology into optoelectronic fields.

The materials described in this work and their utilization in solid-state dye lasers are coverted by Spanish Patent No. P200802558 filed on September 2008.

Acknowledgements

This work was supported by Project MAT2007-65778-C02-C01 of the Spanish CICYT. V. Martín thanks CSIC for her JAE-postdoctoral contract. M. Pintado-Sierra acknowledges a research grant for MICINN (cofinanced by Fondo Social Europeo).

References and links

1.

K. Petritsch, J. J. Dittmer, E. A. Marseglia, R. H. Friend, A. Lux, G. G. Rozenberg, S. C. Moratti, and A. B. Holmes, “Dye-based donor/acceptor solar cells,” Sol. Energy Mater. Sol. Cells 61(1), 63–72 (2000). [CrossRef]

2.

P. R. L. Malenfant, C. D. Dimitrakopoulos, J. D. Gelorme, L. L. Kosbar, T. O. Graham, A. Curioni, and W. Andreoni, “N-type organic thin-film transistor with high field-effect mobility based on a N,N-dialkyl-3,4,9,10-perylene tetracarboxylic diimide derivative,” Appl. Phys. Lett. 80(14), 2517–2519 (2002). [CrossRef]

3.

Z. J. Chen, M. G. Debije, T. Debaerdemaeker, P. Osswald, and F. Würthner, “Tetrachloro-substituted perylene bisimide dyes as promising n-type organic semiconductors: studies on structural, electrochemical and charge transport properties,” ChemPhysChem 5(1), 137–140 (2004). [CrossRef] [PubMed]

4.

R. P. Haugland, Handbook of Fluorescent Probes and Research Chemicals, (Molecular Probes Inc., Eugene, 1989).

5.

Y. Nagao and T. Misono, “Synthesis and properties of N-alkyl-N’-aryl-3,4:9,10-perylene bys(dicarboximide),” Dyes Pigm. 5(3), 171–188 (1984). [CrossRef]

6.

A. Rademacher, S. Märkle, and H. Langhals, “Soluble perylene fluorescent dyes with high photostability,” Chem. Ber. 115(8), 2927–2934 (1982). [CrossRef]

7.

M. Schneider and K. Müllen, “Hybrid materials doped with covalently bound perylene dyes through the sol-gel process,” Chem. Mater. 12(2), 352–362 (2000). [CrossRef]

8.

T. Vosch, J. Hofkens, M. Cotlet, F. Köhn, H. Fujiwara, R. Gronheid, K. Van Der Biest, T. Weil, A. Herrmann, K. Müllen, S. Mukamel, M. Van der Auweraer, and F. C. De Schryver, “Influence of structural and rotational isomerism on the triplet blinking of individual dendrimer molecules,” Angew. Chem. 40(24), 4643–4648 (2001). [CrossRef]

9.

R. Gronheid, J. Hofkens, F. Köhn, T. Weil, E. Reuther, K. Müllen, and F. C. De Schryver, “Intramolecular Förster energy transfer in a dendritic system at the single molecule level,” J. Am. Chem. Soc. 124(11), 2418–2419 (2002). [CrossRef] [PubMed]

10.

R. O. Al-Kaysi, T. Sang Ahn, A. M. Müller, and C. J. Bardeen, “The photophysical properties of chromophores at high (100 mM and above) concentrations in polymers and as neat solids,” Phys. Chem. Chem. Phys. 8(29), 3453–3459 (2006). [CrossRef] [PubMed]

11.

M. Canva, P. Georges, J.-F. Perelgritz, A. Brum, F. Chaput, and J.-P. Boilot, “Perylene- and pyrromethene-doped xerogel for a pulsed laser,” Appl. Opt. 34(3), 428–431 (1995). [CrossRef] [PubMed]

12.

M. Faloss, M. Canva, P. Georges, A. Brun, F. Chaput, and J. P. Boilot, “Toward millions of laser pulses with pyrromethene- and perylene-doped xerogels,” Appl. Opt. 36(27), 6760–6763 (1997). [CrossRef]

13.

A. Costela, I. García-Moreno, and R. Sastre, Handbook of Advanced Electronic and Photonic Materials and Devices (Academic Press, New York, 2001), Vol. 7, Chap. 4.

14.

Y. Yang, G. Qian, Z. Wang, and M. Wang, “Influence of the thickness and composition of the solid-state dye laser media on the laser properties,” Opt. Commun. 204, 277–282 (2002).

15.

G. Qian, Y. Yang, Z. Wang, Ch. Yang, Z. Yang, and M. Wang, “Pathways for folding and re-unfolding transitions in denatured conformations of anhydrous proteins,” Chem. Phys. Lett. 368, 555–562 (2003). [CrossRef]

16.

Y. Yang, M. Wang, G. Qian, Z. Wang, and X. Fan, “Laser properties and photostabilities of laser dyes doped in ORMOSILs,” Opt. Mater. 24(4), 621–628 (2004). [CrossRef]

17.

T. H. Nhung, M. Canva, F. Chaput, H. Goudket, G. Roger, A. Brun, D. D. Manh, N. D. Hung, and J. Boilot, “Dye energy transfer in xerogel matrices and application to solid-state dye lasers,” Opt. Commun. 232(1-6), 343–351 (2004). [CrossRef]

18.

N. Tanaka, N. Barashkov, J. Heath, and W. N. Sisk, “Photodegradation of polymer-dispersed perylene di-imide dyes,” Appl. Opt. 45(16), 3846–3851 (2006). [CrossRef] [PubMed]

19.

R. Reisfeld, D. Brusilovsky, M. Eyal, E. Miron, Z. Burstein, and J. Ivri, “A new solid-state tunable laser in the visible,” Chem. Phys. Lett. 160(1), 43–44 (1989). [CrossRef]

20.

J. Ivri, Z. Burshtein, E. Miron, R. Reisfeld, and M. Eyal, “The perylene derivative BASF-241 solution as a new tunable dye laser in the visible,” IEEE J. Quantum Electron. 26(9), 1516–1520 (1990). [CrossRef]

21.

A. Dubois, M. Canva, A. Brun, F. Chaput, and J. P. Boilot, “Photostability of dye molecules trapped in solid matrices,” Appl. Opt. 35(18), 3193–3199 (1996). [CrossRef] [PubMed]

22.

M. Álvarez, F. Amat-Guerri, A. Costela, I. García-Moreno, C. Gómez, M. Liras, and R. Sastre, “Linear and cross-linked polymeric solid-state dye lasers based on 8-substituted alkyl analogues of pyrromethene 567,” Appl. Phys. B 80(8), 993–1006 (2005). [CrossRef]

23.

A. Costela, I. García-Moreno, J. Barroso, and R. Sastre, “Laser performance of pyrromethene 567 dye in solid matrices of methyl methacrylate with different comonomers,” Appl. Phys. B 70, 367–373 (2000). [CrossRef]

24.

A. Costela, I. García-Moreno, C. Gómez, O. García, and R. Sastre, “Laser performance of pyrromethene 567 dye in solid polymeric matrices with different cross-linking degrees,” J. Appl. Phys. 90(7), 3159 (2001). [CrossRef]

25.

A. Costela, I. García-Moreno, D. del Agua, O. García, and R. Sastre, “Silicon-containing organic matrices as hosts for highly photostable solid-state dye lasers,” Appl. Phys. Lett. 85(12), 2160–2162 (2004). [CrossRef]

26.

O. García, R. Sastre, D. del Agua, A. Costela, and I. García-Moreno, “New fluorinated polymers doped with BODIPY chromophore as highly efficient and photostable optical materials,” Chem. Mater. 18(3), 601–602 (2006). [CrossRef]

27.

Y. Yang, J. Zou, H. Rong, G. D. Qian, Z. Y. Wang, and M. Q. Wang, “Influence of various coumarin dyes on the laser performance of laser dyes co-doped into ORMOSILs,” Appl. Phys. B 86(2), 309–313 (2007). [CrossRef]

28.

I. Shoshan, N. N. Danon, and U. P. Oppenheim, “Narrowband operation of a pulsed dye laser without intracavity beam expansion,” J. Appl. Phys. 48(11), 4495–4497 (1977). [CrossRef]

29.

M. D. Rahn and T. A. King, “Comparison of laser performance of dye molecules in sol-gel, polycom, ormosil, and poly(methyl methacrylate) host media,” Appl. Opt. 34(36), 8260–8271 (1995). [CrossRef] [PubMed]

30.

A. Tyagi, D. del Agua, A. Penzkofer, O. García, R. Sastre, A. Costela, and I. García-Moreno, “Photophysical characterization of pyrromethene 597 laser dye in cross-linked silicon containing organic copolymers,” Chem. Phys. 342, 201–214 (2007). [CrossRef]

31.

J. J. Reisinger and M. A. Hillmyer, “Synthesis of fluorinated polymers by chemical modification,” Prog. Polym. Sci. 27(5), 971–1005 (2002). [CrossRef]

32.

J. Espeso, A. E. Lozano, J. G. de la Campa, and J. de Abajo, “Effect of substituents on the permeation properties of polyamide membranes,” J. Membr. Sci. 280(1-2), 659–665 (2006). [CrossRef]

OCIS Codes
(140.2050) Lasers and laser optics : Dye lasers
(140.3580) Lasers and laser optics : Lasers, solid-state
(160.3380) Materials : Laser materials
(160.5470) Materials : Polymers

ToC Category:
Lasers and Laser Optics

History
Original Manuscript: April 8, 2009
Revised Manuscript: June 17, 2009
Manuscript Accepted: June 19, 2009
Published: July 13, 2009

Citation
I. García-Moreno, A. Costela, M. Pintado-Sierra, V. Martín, and R. Sastre, "Enhanced laser action of Perylene-Red doped polymeric materials," Opt. Express 17, 12777-12784 (2009)
http://www.opticsinfobase.org/oe/abstract.cfm?URI=oe-17-15-12777


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References

  1. K. Petritsch, J. J. Dittmer, E. A. Marseglia, R. H. Friend, A. Lux, G. G. Rozenberg, S. C. Moratti, and A. B. Holmes, “Dye-based donor/acceptor solar cells,” Sol. Energy Mater. Sol. Cells 61(1), 63–72 (2000). [CrossRef]
  2. P. R. L. Malenfant, C. D. Dimitrakopoulos, J. D. Gelorme, L. L. Kosbar, T. O. Graham, A. Curioni, and W. Andreoni, “N-type organic thin-film transistor with high field-effect mobility based on a N,N’-dialkyl-3,4,9,10-perylene tetracarboxylic diimide derivative,” Appl. Phys. Lett. 80(14), 2517–2519 (2002). [CrossRef]
  3. Z. J. Chen, M. G. Debije, T. Debaerdemaeker, P. Osswald, and F. Würthner, “Tetrachloro-substituted perylene bisimide dyes as promising n-type organic semiconductors: studies on structural, electrochemical and charge transport properties,” ChemPhysChem 5(1), 137–140 (2004). [CrossRef] [PubMed]
  4. R. P. Haugland, Handbook of Fluorescent Probes and Research Chemicals, (Molecular Probes Inc., Eugene, 1989).
  5. Y. Nagao and T. Misono, “Synthesis and properties of N-alkyl-N’-aryl-3,4:9,10-perylene bys(dicarboximide),” Dyes Pigm. 5(3), 171–188 (1984). [CrossRef]
  6. A. Rademacher, S. Märkle, and H. Langhals, “Soluble perylene fluorescent dyes with high photostability,” Chem. Ber. 115(8), 2927–2934 (1982). [CrossRef]
  7. M. Schneider and K. Müllen, “Hybrid materials doped with covalently bound perylene dyes through the sol-gel process,” Chem. Mater. 12(2), 352–362 (2000). [CrossRef]
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