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Virtual Journal for Biomedical Optics

Virtual Journal for Biomedical Optics

| EXPLORING THE INTERFACE OF LIGHT AND BIOMEDICINE

  • Editors: Andrew Dunn and Anthony Durkin
  • Vol. 8, Iss. 6 — Jun. 27, 2013
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Solvent-free fluidic organic dye lasers

Eun Young Choi, Loic Mager, Tran Thi Cham, Kokou D. Dorkenoo, Alain Fort, Jeong Weon Wu, Alberto Barsella, and Jean-Charles Ribierre  »View Author Affiliations


Optics Express, Vol. 21, Issue 9, pp. 11368-11375 (2013)
http://dx.doi.org/10.1364/OE.21.011368


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Abstract

We report on the demonstration of liquid organic dye lasers based on 9-(2-ethylhexyl)carbazole (EHCz), so-called liquid carbazole, doped with green- and red-emitting laser dyes. Both waveguide and Fabry-Perot type microcavity fluidic organic dye lasers were prepared by capillary action under solvent-free conditions. Cascade Förster-type energy transfer processes from liquid carbazole to laser dyes were employed to achieve color-variable amplified spontaneous emission and lasing. Overall, this study provides the first step towards the development of solvent-free fluidic organic semiconducting lasers and demonstrates a new kind of optoelectronic applications for liquid organic semiconductors.

© 2013 OSA

1. Introduction

In recent years, liquid organic semiconductors have emerged as a promising class of materials for organic optoelectronics [1

1. J. C. Ribierre, T. Aoyama, T. Muto, Y. Imase, and T. Wada, “Charge transport properties in liquid carbazole,” Org. Electron. 9(3), 396–400 (2008). [CrossRef]

3

3. S. Santhosh Babu, J. Aimi, H. Ozawa, N. Shirahata, A. Saeki, S. Seki, A. Ajayaghosh, H. Möhwald, and T. Nakanishi, “Solvent-free luminescent organic liquids,” Angew. Chem. Int. Ed. Engl. 51(14), 3391–3395 (2012). [CrossRef] [PubMed]

]. These soft optoelectronic functional materials present several advantages over conventional organic semiconductors, including solvent-free device processing, ultimate mechanical flexibility and tunable optoelectronic responses. Organic conjugated molecules which are liquid at room temperature have been successfully used in a variety of organic optoelectronic applications such as photorefractive devices [4

4. J. C. Ribierre, T. Aoyama, T. Kobayashi, T. Sassa, T. Muto, and T. Wada, “Influence of the liquid carbazole concentration on charge trapping in C60 sensitized photorefractive polymers,” J. Appl. Phys. 102(3), 033106 (2007). [CrossRef]

], organic light-emitting diodes (OLEDs) [5

5. D. Xu and C. Adachi, “Organic light-emitting diode with liquid emitting layer,” Appl. Phys. Lett. 95(5), 053304 (2009). [CrossRef]

7

7. C. H. Shim, S. Hirata, J. Oshima, T. Edura, R. Hattori, and C. Adachi, “Uniform and refreshable liquid electroluminescent device with a back side reservoir,” Appl. Phys. Lett. 101(11), 113302 (2012). [CrossRef]

], dye-sensitized solar cells [8

8. H. J. Snaith, S. M. Zakeeruddin, Q. Wang, P. Péchy, and M. Grätzel, “Dye-sensitized solar cells incorporating a “liquid” hole-transporting material,” Nano Lett. 6(9), 2000–2003 (2006). [CrossRef] [PubMed]

] and bistable memories [9

9. J. C. Ribierre, T. Aoyama, T. Muto, and P. André, “Hybrid organic-inorganic liquid bistable memory devices,” Org. Electron. 12(11), 1800–1805 (2011). [CrossRef]

]. Microfluidic OLEDs were recently reported in which fresh liquid organic semiconductors could be continuously supplied to the emitting layer [7

7. C. H. Shim, S. Hirata, J. Oshima, T. Edura, R. Hattori, and C. Adachi, “Uniform and refreshable liquid electroluminescent device with a back side reservoir,” Appl. Phys. Lett. 101(11), 113302 (2012). [CrossRef]

]. Such a convectional circulation of a liquid organic semiconducting material can be applied to the development of degradation-free organic optoelectronic devices. In that context, the demonstration of solvent-free optofluidic semiconducting organic lasers would be an important step towards the development of liquid organic optoelectronic applications.

Over the past few years, optofluidic dye lasers have gained interest as miniature coherent light sources for integrated optics and lab-on-a-chip applications [10

10. H. Schmidt and A. R. Hawkins, “The photonic integration of non-solid media using optofluidics,” Nat. Photonics 5(10), 598–604 (2011). [CrossRef]

]. In particular, these devices have been shown to be very promising for high sensitivity chemical and biosensing [11

11. Y. Chen, L. Lei, K. Zhang, J. Shi, L. Wang, H. Li, X. M. Zhang, Y. Wang, and H. L. W. Chan, “Optofluidic microcavities: Dye-lasers and biosensors,” Biomicrofluidics 4(4), 043002 (2010). [CrossRef]

]. To date, a variety of optical resonator structures have been used for these microfabricated laser sources including Fabry-Perot cavities, distributed feedback gratings, microdroplets and microring cavities [12

12. B. Helbo, A. Kristensen, and A. Menon, “A micro-cavity fluidic dye laser,” J. Micromech. Microeng. 13(2), 307–311 (2003). [CrossRef]

15

15. Y. Sun, S. I. Shopova, C. S. Wu, S. Arnold, and X. Fan, “Bioinspired optofluidic FRET lasers via DNA scaffolds,” Proc. Natl. Acad. Sci. U.S.A. 107(37), 16039–16042 (2010). [CrossRef] [PubMed]

]. The solution of organic dye molecules injected into the optofluidic dye lasers provides the optical gain and thus plays a critical role on the optical properties of the laser emission. However, up to now, these liquid dye solutions have been always prepared in a solvent and thus do not show any semiconducting properties. Here, we demonstrate that liquid organic semiconducting materials can be used as gain medium in solvent-free optofluidic organic lasers [16

16. D. Psaltis, S. R. Quake, and C. H. Yang, “Developing optofluidic technology through the fusion of microfluidics and optics,” Nature 442(7101), 381–386 (2006). [CrossRef] [PubMed]

18

18. A. E. Vasdekis, G. E. Town, G. A. Turnbull, and I. D. W. Samuel, “Fluidic fibre dye lasers,” Opt. Express 15(7), 3962–3967 (2007). [CrossRef] [PubMed]

] allying the nonvolatility and the high concentration of electronically active π-conjugated moieties typically obtained in organic semiconducting films [19

19. I. D. W. Samuel and G. A. Turnbull, “Organic semiconductor lasers,” Chem. Rev. 107(4), 1272–1295 (2007). [CrossRef] [PubMed]

] with the versatility and tunability of liquid dye lasers [20

20. C. Monat, P. Domachuk, and B. J. Eggleton, “Integrated optofluidics: a new river of light,” Nat. Photonics 1(2), 106–114 (2007). [CrossRef]

].

2. Experimental methods

The chemical structures of EHCz, C153 and DCM are shown in Fig. 1(a)
Fig. 1 (a) Chemical structure of liquid carbazole (EHCz), coumarin 153 (C153) and DCM. (b) Photographs of waveguiding capillary tubes filled with (1) EHCz:C153:DCM (95; 3.1; 1.9 wt.%), (2) EHCz:DCM (97.5:2.5 wt.%) and (3) EHCz:C153 (96.5: 3.5 wt.%). (c) Photograph of interference fringes observed on a screen from a Fabry-Perot type microcavity solvent-free liquid organic green dye laser filled with EHCz:C153 (96.5; 3.5 wt.%). The device was optically pumped at 355 nm by the third harmonic of a nanosecond Nd:YAG laser.
. These organic materials were purchased from Sigma-Aldrich and used without further purification. The laser dyes were mixed with liquid carbazole at various concentrations in chloroform solution. After the full evaporation of the residual solvent, the liquid composite materials were incorporated into optofluidic devices by capillarity. Figures 1(b) and 1(c) show photographs of waveguiding and Fabry-Perot type microcavity devices filled with the liquid carbazole blends.

Absorption and fluorescence spectra were recorded using an absorption spectrophotometer (Hitachi U-3310) and a steady-state fluorimeter (PTI QuantaMaster 40) respectively. For the fluorescence spectra measurements, the liquid emitting material was sandwiched between two identical precleaned fused silica substrates. For the absorption spectra measurements in solution, the molecules were dissolved in chloroform and the solutions were placed in a 1cm quartz cuvette.

Single core capillary glass tubes used in this work for making waveguide liquid organic light-emitting devices had a core diameter and a glass cladding thickness of 500 ± 100 and 10 μm respectively. Due to the low viscosity of liquid carbazole at room temperature, the infilling process of these tubes by capillary action was carried out by directly dipping them in the liquid organic composite materials. The other type of optofluidic organic laser devices was based on Fabry-Perot type microcavities. The liquid blends were placed between two identical dielectric mirrors with a high reflectance at the emission wavelengths of the green and red organic lasers (Melles Griot, model AR1-1025-C-0 with a reflectance R > 98% between 470 and 550 nm, model HN-1025-C-0 with a reflectance R > 98% between 600 and 680 nm). The thickness of the Fabry-Perot cavities was controlled using silica spheres with a diameter of 5 μm dispersed into a silicon paste.

The fluidic organic devices were optically pumped at 355 nm using the third harmonic of a Nd:YAG laser (Continuum SureLite II) with a repetition rate and pulse duration of 10 Hz and 6-8 ns, respectively. The waveguiding structures were excited perpendicularly to the long axis of the capillary tubes by a stripe of dimension 0.15 mm x 1 cm. The axial emission from the liquid organic materials was collected at one end of the capillary tubes using an optical fiber coupled to a CCD spectrometer (Avantes Avaspec 2048). For the characterization of the microcavity devices, the diameter of the excitation laser beam illuminating the samples was 3 mm and the incidence angle was around 10°. The laser output was collected perpendicularly to the microcavities also using the optical fiber coupled to the CCD spectrometer. Note that all the preparation and characterization of the devices were performed in this work under ambient atmosphere conditions.

3. Energy transfer from liquid carbazole to laser dyes

The absorption and fluorescence spectra of a neat liquid EHCz layer sandwiched between two fused silica substrates are shown in Fig. 2(a)
Fig. 2 (a) Normalized absorbance and photoluminescence spectra of the liquid host material and the laser dyes. The spectra from EHCz are measured from a solvent-free neat layer whereas the other spectra are from solutions in chloroform. Note that the spectra measured in C153 and DCM are vertically shifted for clarity reasons. (b) Photoluminescence spectra measured in solvent-free liquid carbazole blends. The excitation wavelength was 350 nm.
. It can be seen that liquid carbazole is fully transparent in the visible and strongly absorbs light in the ultraviolet. The two peaks observed at 335 and 348 nm are assigned to the absorption from the carbazole monomer unit [1

1. J. C. Ribierre, T. Aoyama, T. Muto, Y. Imase, and T. Wada, “Charge transport properties in liquid carbazole,” Org. Electron. 9(3), 396–400 (2008). [CrossRef]

]. The fluorescence spectrum of EHCz shows a blue emission with a maximum at 410 nm. Figure 2(a) also shows the absorption and emission spectra of C153 and DCM in chloroform. The maximum in the fluorescence spectrum of these dyes is observed at 533 and 609 nm respectively. It is well-known that Förster-type energy transfer depends on the overlap between the emission spectrum of the donor molecule and the absorption spectrum of the acceptor [23

23. A. Dodabalapur, M. Berggren, R. E. Slusher, and Z. Bao, “Light amplification in organic thin films using cascade energy transfer,” Nature 389(6650), 466–469 (1997). [CrossRef]

26

26. A. Ruseckas, J. C. Ribierre, P. E. Shaw, S. V. Staton, P. L. Burn, and I. D. W. Samuel, “Singlet energy transfer and singlet-singlet annihilation in light-emitting blends of organic semiconductors,” Appl. Phys. Lett. 95(18), 183305 (2009). [CrossRef]

]. The overlaps observed between the optical spectra shown in Fig. 2(a) suggest that energy transfer can take place from EHCz to C153 and DCM as well as from C153 to DCM. Note that energy transfer from carbazole derivatives to coumarin dyes have been successfully used in OLEDs and organic solid-state lasers [27

27. E. Gautier-Thianche, C. Sentein, A. Lorin, C. Denis, P. Raimond, and J. M. Nunzi, “Effect of coumarin on blue light-emitting diodes based on carbazole polymers,” J. Appl. Phys. 83(8), 4236 (1998). [CrossRef]

,28

28. V. G. Kozlov, G. Parthasarathy, P. E. Burrows, S. R. Forrest, Y. You, and M. E. Thompson, “Optically pumped blue organic semiconductor lasers,” Appl. Phys. Lett. 72(2), 144 (1998). [CrossRef]

].

We prepared three different solvent-free liquid blends: EHCz:C153 (96.5:3.5 wt.%), EHCz:DCM (97.5:2.5 wt.%) and EHCz:C153:DCM (95:3.1:1.9 wt.%) and placed them between two fused silica substrates. The two laser dyes were well dissolved in the liquid carbazole host and our samples presented an excellent optical homogeneity. The fluorescence spectra of the three blends, which are displayed in Fig. 2(b), were measured using an excitation wavelength of 350 nm. At such a wavelength, the absorption of the blends is dominated by the contribution from the liquid carbazole host. The emission spectra provide evidence that energy transfer takes place from the liquid carbazole matrix to the C153 and DCM dyes in good consistency with the resonance energy transfer theory [29

29. T. Förster, “Transfer mechanisms of electronic excitation,” Discuss. Faraday Soc. 27, 7 (1959). [CrossRef]

]. We also found that the ternary blend (EHCz:C153:DCM) shows a similar fluorescence spectrum as the binary blend (EHCz:DCM). However, the fluorescence efficiency from the DCM dyes is significantly increased by the incorporation of C153, which can be attributed to cascade energy transfer from EHCz to DCM through C153 [23

23. A. Dodabalapur, M. Berggren, R. E. Slusher, and Z. Bao, “Light amplification in organic thin films using cascade energy transfer,” Nature 389(6650), 466–469 (1997). [CrossRef]

].

4. Amplified spontaneous emission and lasing in solvent-free dye-doped liquid carbazole

Figure 4(a)
Fig. 4 (a) Schematic representation of a Fabry-Perot type microcavity solvent-free fluidic organic dye laser. (b) An example of transmission spectrum measured in a microcavity filled with EHCz:C153 (96.8:3.2 wt.%) using unpolarized white light at normal incidence. For this sample, four cavity modes were clearly observed at 533, 548, 564 and 580 nm.
displays a schematic representation of Fabry-Perot type microcavity organic dye lasers used in this study. The green- and red-light-emitting devices were filled with EHCz:C153 (96.8:3.2 wt.%) and EHCz:C153:DCM (95:3.1:1.9 wt.%) respectively. The transmission spectrum of a EHCz:C153 microcavity is shown in Fig. 4(b) and was obtained using an unpolarized white light at normal incidence. For this specific sample, four cavity modes were observed in the spectrum at 533, 548, 564 and 580 nm with a FWHM varying between 3 and 4 nm. This leads to a quality factor Q ranging from 130 to 160. From the position of the modes in the transmission spectrum of Fig. 4(b), the physical thickness of the microcavity is found to be around 5.8 ± 0.2 μm.

As shown in Fig. 5(a)
Fig. 5 (a) Laser emission spectra from Fabry-Perot type solvent-free liquid organic microcavities based on EHCz:C153 (96.8:3.2 wt.%) and EHCz:C153:DCM (95:3.1:1.9 wt.%). (b) Temporal decay of the laser emission intensity from the EHCz:C153 microcavity for pulse repetition rate of 10 Hz and a pumping energy density of about 0.13 mJ/cm2. The solid line corresponds to a fit by a single exponential decay function. (c) Output intensity as a function of the input energy density showing a laser emission with a lasing threshold for wavelengths of 512 and 526 nm from the EHCz:C153 microcavity laser.
, above the laser threshold, dual wavelength laser emission was observed in both devices. Green laser emission at 512 and 526 nm was observed in the emission spectrum of EHCz:C153 (96.8:3.2 wt.%). In the case of EHCz:C153:DCM (95:3.1:1.9 wt.%), the red laser emission peaks were located at 625 and 647 nm. The FWHM of the laser modes was found to be around 1 nm, which is the resolution limit of our spectrometer. This dual wavelength laser emission is presumably due to the large pump spot size area used in this work. Such a pumping configuration can lead to resonance conditions changing over the excited area and thus to multi-mode operation [34

34. B. Schütte, H. Gothe, S. I. Hintschich, M. Sudzius, H. Fröb, V. G. Lyssenko, and K. Leo, “Continuously tunable laser emission from a wedge-shaped organic microcavity,” Appl. Phys. Lett. 92(16), 163309 (2008). [CrossRef]

]. However, degradation of the organic layer is reduced and the device stability during our measurements was improved. As displayed in Fig. 5(b), we monitored the decay of the laser emission from the EHCz:C153 microcavity for a 355 nm pumping energy density of about 0.13 mJ/cm2 at a repetition rate of 10 Hz. The decay can be fitted by a single exponential function with an average characteristic response time of about 10 minutes. This response time was found to decrease as the pumping beam spot size is reduced or the pumping energy density is increased. Note that an extinction of the laser emission was typically observed after 30-60 minutes of continuous operation depending on the pump power. This decay can be explained by bleaching of the light-emitting molecules. Because the viscosity of EHCz is higher than solvents commonly used in optofluidics, the bleached molecules cannot be replaced by diffusion only [35

35. T. Wienhold, F. Breithaupt, C. Vannahme, M. B. Christiansen, W. Dörfler, A. Kristensen, and T. Mappes, “Diffusion driven optofluidic dye lasers encapsulated into polymer chips,” Lab Chip 12(19), 3734–3739 (2012). [CrossRef] [PubMed]

] and the bleaching should be compensated by externally pumping the liquid medium for more stable continuous operation of the devices.

Overall, this work demonstrates solvent-free liquid organic semiconducting dye lasers and the performances of these devices are already comparable with those typically obtained in organic solid-state dye lasers.

4. Conclusions

In summary, we examined the amplified spontaneous emission and lasing properties of the liquid carbazole EHCz blended with the laser dyes Coumarin 153 and DCM. Waveguide and Fabry-Perot type microcavity organic dye laser devices were prepared by capillary action under solvent-free conditions. The practicality of these laser sources is enhanced by the possibility of tuning effectively their emission via a cascade energy transfer scheme. This study demonstrates that liquid organic conjugated light-emitting materials can be used as gain medium for the realization of tunable solvent-free fluidic organic lasers and paves the way for the development of novel optofluidic systems with semiconducting functionalities.

Acknowledgments

This work has been carried out in the framework of the French-Korean International Laboratory “CNRS-EWHA Research Center for Ultrafast Optics and Nanoelectronics of Functional Nanostructures”. The authors would like to acknowledge funding from “Campus France” (STAR program). JCR also acknowledges the support by the Basic Science Researcher Program and the Quantum Metamaterials Research Center (QMMRC) through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (grants 2011-0008650, 2012-0000543).

References and links

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S. Santhosh Babu, J. Aimi, H. Ozawa, N. Shirahata, A. Saeki, S. Seki, A. Ajayaghosh, H. Möhwald, and T. Nakanishi, “Solvent-free luminescent organic liquids,” Angew. Chem. Int. Ed. Engl. 51(14), 3391–3395 (2012). [CrossRef] [PubMed]

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J. C. Ribierre, T. Aoyama, T. Kobayashi, T. Sassa, T. Muto, and T. Wada, “Influence of the liquid carbazole concentration on charge trapping in C60 sensitized photorefractive polymers,” J. Appl. Phys. 102(3), 033106 (2007). [CrossRef]

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D. Xu and C. Adachi, “Organic light-emitting diode with liquid emitting layer,” Appl. Phys. Lett. 95(5), 053304 (2009). [CrossRef]

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S. Hirata, K. Kubota, H. H. Jung, O. Hirata, K. Goushi, M. Yahiro, and C. Adachi, “Improvement of electroluminescence performance of organic light-emitting diodes with a liquid-emitting layer by introduction of electrolyte and a hole-blocking layer,” Adv. Mater. 23(7), 889–893 (2011). [CrossRef] [PubMed]

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C. H. Shim, S. Hirata, J. Oshima, T. Edura, R. Hattori, and C. Adachi, “Uniform and refreshable liquid electroluminescent device with a back side reservoir,” Appl. Phys. Lett. 101(11), 113302 (2012). [CrossRef]

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H. J. Snaith, S. M. Zakeeruddin, Q. Wang, P. Péchy, and M. Grätzel, “Dye-sensitized solar cells incorporating a “liquid” hole-transporting material,” Nano Lett. 6(9), 2000–2003 (2006). [CrossRef] [PubMed]

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J. C. Ribierre, T. Aoyama, T. Muto, and P. André, “Hybrid organic-inorganic liquid bistable memory devices,” Org. Electron. 12(11), 1800–1805 (2011). [CrossRef]

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H. Schmidt and A. R. Hawkins, “The photonic integration of non-solid media using optofluidics,” Nat. Photonics 5(10), 598–604 (2011). [CrossRef]

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Y. Chen, L. Lei, K. Zhang, J. Shi, L. Wang, H. Li, X. M. Zhang, Y. Wang, and H. L. W. Chan, “Optofluidic microcavities: Dye-lasers and biosensors,” Biomicrofluidics 4(4), 043002 (2010). [CrossRef]

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B. Helbo, A. Kristensen, and A. Menon, “A micro-cavity fluidic dye laser,” J. Micromech. Microeng. 13(2), 307–311 (2003). [CrossRef]

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W. Song, A. E. Vasdekis, Z. Li, and D. Psaltis, “Optofluidic evanescent dye laser based on a distributed feedback circular grating,” Appl. Phys. Lett. 94(16), 161110 (2009). [CrossRef]

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S. K. Y. Tang, Z. Li, A. R. Abate, J. J. Agresti, D. A. Weitz, D. Psaltis, and G. M. Whitesides, “A multi-color fast-switching microfluidic droplet dye laser,” Lab Chip 9(19), 2767–2771 (2009). [CrossRef] [PubMed]

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Y. Sun, S. I. Shopova, C. S. Wu, S. Arnold, and X. Fan, “Bioinspired optofluidic FRET lasers via DNA scaffolds,” Proc. Natl. Acad. Sci. U.S.A. 107(37), 16039–16042 (2010). [CrossRef] [PubMed]

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D. Psaltis, S. R. Quake, and C. H. Yang, “Developing optofluidic technology through the fusion of microfluidics and optics,” Nature 442(7101), 381–386 (2006). [CrossRef] [PubMed]

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Z. Li and D. Psaltis, “Optofluidic dye lasers,” Microfluid. Nanofluid. 4(1-2), 145–158 (2008). [CrossRef]

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35.

T. Wienhold, F. Breithaupt, C. Vannahme, M. B. Christiansen, W. Dörfler, A. Kristensen, and T. Mappes, “Diffusion driven optofluidic dye lasers encapsulated into polymer chips,” Lab Chip 12(19), 3734–3739 (2012). [CrossRef] [PubMed]

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OCIS Codes
(140.3380) Lasers and laser optics : Laser materials
(140.3510) Lasers and laser optics : Lasers, fiber
(160.4890) Materials : Organic materials
(230.7370) Optical devices : Waveguides
(140.3948) Lasers and laser optics : Microcavity devices

ToC Category:
Lasers and Laser Optics

History
Original Manuscript: March 14, 2013
Revised Manuscript: April 25, 2013
Manuscript Accepted: April 28, 2013
Published: May 2, 2013

Virtual Issues
Vol. 8, Iss. 6 Virtual Journal for Biomedical Optics

Citation
Eun Young Choi, Loic Mager, Tran Thi Cham, Kokou D. Dorkenoo, Alain Fort, Jeong Weon Wu, Alberto Barsella, and Jean-Charles Ribierre, "Solvent-free fluidic organic dye lasers," Opt. Express 21, 11368-11375 (2013)
http://www.opticsinfobase.org/vjbo/abstract.cfm?URI=oe-21-9-11368


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References

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