Low-Threshold Organic Lasers Based on Single-Crystalline

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Chemical and Dynamical Processes in Solution; Polymers, Glasses, and Soft Matter

Low-Threshold Organic Lasers Based on Single-Crystalline Microribbons of Aggregation-Induced Emission Luminogens Guoqing Wei, Yichen Tao, Junjie Wu, Zhizhou Li, Ming-Peng Zhuo, Xue-Dong Wang, and Liang-Sheng Liao J. Phys. Chem. Lett., Just Accepted Manuscript • Publication Date (Web): 25 Jan 2019 Downloaded from http://pubs.acs.org on January 25, 2019

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The Journal of Physical Chemistry Letters

Low-Threshold Organic Lasers Based on SingleCrystalline Microribbons of Aggregation-Induced Emission Luminogens Guo-Qing Wei,

1

Yi-Chen Tao,

1

Jun-Jie Wu,

1

Zhi-Zhou Li,

1

Ming-Peng Zhuo,

1

Xue-Dong

Wang,*1 and Liang-Sheng Liao*1,2 1. Institute of Functional Nano & Soft Materials (FUNSOM), Jiangsu Key Laboratory for Carbon-Based Functional Materials & Devices, Joint International Research Laboratory of Carbon-Based Functional Materials and Devices, Soochow University, 199 Ren'ai Road, Suzhou, 215123, Jiangsu, PR China 2. Institute of Organic Optoelectronics, Jiangsu Industrial Technology Research Institute (JITRI), Wujiang, Suzhou, Jiangsu 215211, P. R. China Corresponding Author email: *E-mail: [email protected] (Xue-Dong Wang); *Email: [email protected] (Liang-Sheng Liao).

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The Journal of Physical Chemistry Letters 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60

ABSTRACT Solid-state lasers (SSLs) play an important role in developing optoelectronic devices, optical communication, and modern medicine fields. As compared with inorganic SSLs, the electricallypumped organic SSLs (OSSLs) still remain unrealized because of the high lasing threshold and low carrier mobility. Herein, we firstly demonstrate the laser action at ~520 nm based on the self-assembled single-crystalline organic microribbons of the aggregation-induced emission (AIE) molecules of 1,4-bis((E)-4-(1,2,2-triphenylvinyl)styryl)-2,5-dimethoxybenzene (TPDSB). Moreover, these as-prepared organic microribbons exhibit effective optical waveguide with low optical loss of 0.012 dB μm-1, indicating good light confinement for laser resonator feedback. Impressively, the multiple mode and the single mode lasing are both achieved from individual organic microribbon, whose lasing threshold is as low as 653 nJ cm-2. These “bottom-up” synthesized organic microribbons based on AIE-active molecules offer a new strategy for the realization of the ultralow threshold OSSLs, which would eventually contribute to the realization of electrically-pumped OSSLs. TOC GRAPHICS

KEYWORDS: Aggregation-induced emission, Self-assembly, Solid-state lasers, Organic Semiconductor, Nanophotonics 2 Environment ACS Paragon Plus

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Organic semiconductor materials have received a great deal of interests over the past decades owing to their inherent merits, such as tunable optical/electrical properties, versatile compatibility to substrates, solution-processing approach.[1-3] Accordingly, various kinds of organic semiconductor materials promisingly serve in optoelectronic devices such as organic light-emitting diodes (OLEDs),[4,5] organic solar cells,[6] organic field effect transistors (OFETs),[7] organic solid-state lasers (OSSLs),[8] and many others.[9-12] Particularly, among these optoelectronic devices, OSSLs have made great progress during the past decade while just are in the early stage of development. As we all know, electrically pumped OSSLs have not been indeed realized, and a variety of organic small molecules and polymers have been adopted as the active gain medium for the realization of optically pumped OSSLs.[13-15] More recently, it is reported that the near-infrared (NIR) lasing at 720 nm is achieved based on the single-crystalline nanowires of small organic molecules of (E)-3-(4-(dimethylamino)-2-methoxyphenyl)-1-(1hydroxynaphthalen-2-yl)prop-2-en-1-one.[16] Nonetheless, the study of the OSSLs still needs further investigation from the material aspect. Nevertheless, organic semiconductor materials are suffering from aggregation-caused quenching (ACQ) in optoelectronic applications.[17-19] Prof. Benzhong Tang’s team firstly reported the concept of aggregation-induced emission (AIE) in 2001,[20] which has provided a new approach to avoid the impact from ACQ. The high solid-state PL efficiency of AIE materials has made them promising to be applied in various optoelectronic devices, such as OLED[21], bioimaging,[22] sensing[23], and many others.[24,25] To illustrate, the AIE-active tetraphenylethene (TPE)-PNPB was adopted as light emitter and hole transporter simultaneously in a bilayer OLED device, the EL efficiencies were measured as high as 16.2 cd A-1, 14.4 lm W1,

and 5.35% in air.[26] Furthermore, for the OSSLs, ACQ effect increases the lasing threshold or



forbids the laser action’ is revised as ‘ACQ effect increases the lasing threshold or forbids the laser action due to the excited electron loss from non-radiative path. In contrast, the high solid state PLQY of AIE luminogens suggests less non-radiative process, for which the population inversion is easier to form[27]. Therefore, AIE-active organic materials can act as the excelllent active laser medium for the realization of the ultralow threshold OSSLs, which can further contribute to the electrically-pumped OSSLs. However, up to date, laser action based on AIE organic materials has not been demonstrated. Herein, the green laser action of ~520 nm with an ultralow threshold of 653 nJ cm-2 is observed in the self-assembled single-crystalline organic microribbons of 1,4-bis((E)-4-(1,2,2triphenylvinyl)styryl)-2,5-dimethoxybenzene (TPDSB), which displays the pronounced AIE behavior of as high as ~2500 times enhanced. Besides, the individual TPDSB organic microribbon exhibits the optical loss of as low as 0.012 dBμm-1, which indicates the fine photon confinement and the microcavity effect. Impressively, we achieved multi-mode laser emission from the microribbons (l = 60 um) at room temperature. More significantly, the single mode lasing is observed above the threshold of 1053 nJ cm-2 in the microribbon with the length of 10 μm, which acts as the high-quality factor Q of ~2565 for the Fabry-Perot (FP) cavity. Therefore, our demonstration provides the insight for the realization of AIE-based high performance OSSLs.


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Figure 1. (a) Synthetic routine of TPDSB organic molecule and the photograph of TPDSB powder under the 365 nm ultra-violet lamp. (b) Water fraction resolved PL spectra of the TPDSB solutions or suspensions or nano-aggregates in THF/water mixture with different volumertic fraction of water (fw, vol %). Inset: The corresponding PL photographs of TPDSB solutions or suspensions or nano-aggregates in THF/water mixture with different volumertic fraction of water exposed under 365 nm UV lamp. (c) The integrated intensities of the PL spectra shown in (b) versus water fraction. Figure 1(a) shows the chemical structure and the synthetic routine of TPDSB organic molecules. The benzene rings labeled with green color on the TPDSB molecule are bonded to the etheny with σ bond, which enables them to stretch along three dimensions and rotate around the etheny. Impressively, the TPDSB dry powder exhibits bright green light under a 365 nm UV lamp. The PL spectra of TPDSB in THF under 77 K and 298 K (Figure S2) exhibit the enhancement of PL intensity from the solution state to the aggregate state. To investigate its AIE property, TPDSB powder was placed in six bottles by the equal mass of 3.4 mg, and 4 ml



mixture of DCM/water with different water fraction (fw, vol%) was added into the bottles respectively. Water is poor solvent for TPDSB, as a result, TPDSB molecules aggregate in varying degrees according to different water fraction fw. As is seen, pure TPDSB in DCM is nearly non-luminescent under 365 nm UV lamp. In contrast, as fw increases, TPDSB molecules aggregate and induce the enhancement of emission. At fw = 60 vol%, the emission is “turned on” with a significant enhancement. Bright green light is observed afterwards, which is a typical behavior of AIE phenomena.[28] The inset of Figure 1b demonstrates the fluorescence images of the as-prepared samples (A-F), and the corresponded water fraction resolved PL spectra of A-F is shown in Figure 1(b). The spectra exhibits nearly flat line parallel to the abscissa for A and rapidly risen intensities for B-F. The emission spectra curves were integrated and the resulted intensities were plotted versus the fraction of water content as shown in Figure 1(c). A tremendous PL enhancement of 2500 times from fw = 0% to fw = 90% suggests the good AIE property of TPDSB molecules.

Figure 2. (a) Scanning electron microscopy (SEM) image of TPDSB microribbons with a scale bar of 30 μm. Inset: the simulated growth morphology of TPDSB microribbon based on the 6 Environment ACS Paragon Plus

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attachment energy. (b) The selected area electron diffraction (SAED) pattern of one typical TPDSB microribbon with a scale bar of 5 1/nm. Inset: the corresponding transmission electron microscopy (TEM) image with a scale bar of 100 μm. (c) Fluorescence microscopy image of the TPSDB organic microribbons with a scale bar of 100 μm. (d) The PL images by exciting the identical TPDSB microribbon at different points with 375 nm laser. (e) The spatial resolved PL spectra from the tip of the microribbon for different separation distances between the exciting point and the right tip of the microribbon shown in (d). Inset: The fitted curve of the ratio between the PL intensity at the tip and exciting point versus the distance D between tip and exciting point. The curve is fitted with an exponential decay function Itip/Ibody = Aexp(-αD), where α is the loss coefficient. The scale bar is 20 μm. Table 1. The photophysical properties of TPDSB solution and microribbons. TPDSB

Φ (%)

τ (ns)

kr (ns-1)

Solution

6.5

2.80

0.023

Microribbons

85.6

1.70

0.504

The microstructures of TPDSB were prepared based on the facile solution-drying method at room temperature.[29] As is known to us, the unit cell of TPDSB has the lattice parameters of a = 5.62 Å, b = 9.35 Å, c = 28.24 Å, α = 95.9°, β = 93.6°, γ = 102.8° (Figure S3 and Table S1). As shown in Figure 2(a), these as-prepared organic microstructures exhibit ribbon-like morphology. The inset gives the growth morphology of TPDSB, which is simulated based on the attachment energy using Material Studio Package (Table S2), and the simulated equilibrium morphology of TPDSB molecules is shown in Figure S4. According to the result, the TPDSB molecules are prone to form the rectangular ribbon-like structure, which is consistent with the as-prepared



microstructure. The selected area electron diffraction pattern (SAED) is shown in Figure 2(b). The spots marked by the green triangle and red square were found representing the (011) and (111) crystal planes respectively by comparing the calculated interplanar distance with the SAED pattern. This proclaims that the single-crystalline microribbons grow along the [1-11] crystal direction. Besides, the bright clear spots on the SAED pattern suggest the good crystallinity of the TPDSB organic microribbons. Moreover, Figure 2(c) demonstrates the PL image of TPDSB microribbons, these microribbons emit bright green light from the edges and relatively dark green light from the body part, which suggests that TPDSB microribbons have potential performance on optical waveguide. Additionally, Table 1 shows the photophysical properties of TPDSB solution and organic microribbons, the photoluminescence quantum yield (PLQY) Φ of TPDSB solution is only 6.5% in contrast to as high as 85.6% of TPDSB microribbons, the photoluminescence lifetime τ is measured as 2.8 ns for TPDSB solution and 1.7 ns for microribbons, and thus the corresponding radiative decay rate kr is calculated to be as 0.023 and 0.504 ns-1 relatively for solution and crystals according to kr = Φ/τ. The tremendous rises of Φ and kr from solution state to aggregation state further confirm the excellent AIE property of TPDSB molecules. Besides, the high solid state PLQY suggests TPDSB can be potentially applied in low threshold OSSLs as gain medium. Spatial resolved PL spectra was performed to study the optical waveguide property of the TPDSB microribbons. The micro-area PL images of are shown in Figure. 2(d). The generated photons are confined within the microribbon and propagate along the axis of it. The optical loss can be evaluated by the luminance change at the right tip on the microribbon marked with yellow circle (labeled with 1, 2, 3, 4, 5 and 6) when accurately shifting the exciting spot. The corresponding spatial resolved PL spectra are shown in Figure 2(e). The PL intensity rises as the


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exciting spot approaching the right tip. The PL intensity at the exciting spots Ibody and the intensity at the tip Itip were recorded. The out-coupled intensity Itip /Ibody performs an exponential decay with the increase of the distance between the exciting spot and the right tip (The inset of Figure 2e). The optical loss coefficient α at 526 nm can be estimated by fitting with Itip /Ibody = Aexp(-αD), where D is the distance between the exciting spot and right emitting tip. The optical loss coefficient for the typical microribbon in figure 2(d) is estimated as 0.0175 dB μm-1. Figure S5 illustrates the optical loss coefficients of eight different microribbons estimated in the same way. The resulted α values distribute from 0.012 to 0.020 dB μm-1, which suggests TPDSB microribbon has attractive optical waveguide property. Two reasons are supposed to be responsible for the low optical loss coefficient. First, smooth surface resulted from good crystallinity inhibits the light leakage and confine the photons within the microribbon. Besides, the aggregation induced red shift of the emission spectrum (Figure S1) decreases the overlap area with absorption spectrum, consequently, recombination from self-absorption is suppressed.[30]

Figure 3. (a) Schematic of one microribbon on SiO2 substrate excited by the 355 nm nanosecond pulse laser. (b) The PL spectra of multi-mode laser emission from one individual TPDSB 9 Environment ACS Paragon Plus


microribbon with the length of 60 μm under different pump densities. Inset: The fluorescence microscopy image the typical TPDSB microribbon. (c) The integrated PL intensity (green circles) and the full width at half maximum (FWHM, blue squares) as a function of the pump density. The lasing threshold Pth is identified as the intersection between the linear and superlinear region. (d) PL spectra of the laser emission from different TPDSB microribbons with length l = 40, 60 and 100 μm, respectively.(e) Mode spacing Δλ at λ = 526 nm versus 1/L of the microribbons. Top inset: schematic of a TPDSB microribbon functioning as an optical waveguide and with two ends defining a FP cavity. Bottom inset: The optical mode simulation for a single microribbon with length l = 40 μm. The 355 nm nanosecond pulse laser is focused to a spot to uniformly to excite the individual TPDSB microribbon (Figure 3(a)). Figure S6 demonstrates the PL spectra of one bulk TPDSB single crystal excited by the 355 nm nanosecond pulse laser with different pump energy. The PL spectra exhibit an evolution from the spontaneous emission to the amplified spontaneous emission (ASE), which indicates that TPDSB is an excellent active medium for laser action. Figure 3(b) demonstrate the PL spectra one TPDSB microribbon with length l = 60 μm under different pump energy density. At low pump density of 510 nJ cm-2, the nearly flat line of spontaneous emission dominates the PL spectra. When the pump density exceeds the threshold in the range between 510 nJ cm-2 and 840 nJ cm-2, a set of sharp peaks merge around 527 nm on the top of spontaneous emission spectrum. The intensity increases dramatically as further increasing the pump density, which refers to the multi-mode laser emission. The inset illustrates the image of the microribbon with l = 60 μm when it is pumped under 3750 nJ cm-2. Spatial interference pattern can be found at both terminus, which suggests the formation of the FP microcavity within the microribbon. Besides, the plot of the corresponding integrated PL intensities and FWHM


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versus pump density is shown in Figure 3(c). The threshold Pth = 653 nJ cm-2 is identified as the intersection between the linear and superlinear region. The length dependent lasing modes of TPDSB microribbons are shown in Figure 3(d). The mode spacing Δλ decreases with the increase of the length l. For instance, Δλ = 0.66, 0.48 and 0.30 nm for length l = 40, 60 and 100 μm, respectively. This evolution corresponds to the characteristics of FP cavity. To further understand the resonant mode and the relationship 2 between the cavity and mode spacing, the   2l  [n   (dn / d )] mode spacing is given by (1) where l is the length of the microribbon, λ is the wavelength of light, n is the refractive index of the crystal, and dn/dλ is the dispersion relation.[31] Figure 3(e) reveals the relation between Δλ and 1/L, where L = 2l. It is clear that Δλ exhibits a linear increase with the increase of 1/L, which is consistent with the relation shown in the equation (1). the bottom inset gives the simulated 2D electric field distributions for the typical TPDSB microribbon with l = 40 μm, the interference patterns can be found at the terminus, which confirms that FP cavity is formed along the length direction in TPDSB microribbon.



Figure 4. (a) PL spectra of the spontaneous emission and amplified spontaneous emission of TPDSB microribbons. The blue region represents the potential lasing region. (b) PL spectra of single mode laser emission for one typical microribbon with length l = 10 μm. Inset: the localized PL spectrum. (c) The integrated PL intensity as a function of pump density. The lasing threshold Pth is identified as the intersection between the linear and superlinear region. In contrast, single mode lasing is more desirable due to its inherent merits compared with the multi-mode lasing. According to equation (1), smaller resonators give PL spectra with broader mode spacing Δλ, which suggests less existing lasing modes. Therefore, small resonator size is required to achieve single mode lasing. Figure 4(a) shows the spectra of PL emission and ASE for TPDSB microribbons. The blue region represents the possible optical gain area. In the experiment, we indeed obtained the single mode laser emission around 513 nm from a small TPDSB microribbon with length l = 10 μm (Figure 4(b)). When the pump density exceeds the threshold between 840 nJ cm-2 and 1640 nJ cm-2, the sharp lasing peak rises rapidly at 513 nm. Moreover, the quality factor Q can be measured according to the definition Q = λ/Δλ, where λ is


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the lasing wavelength and Δλ is the full width at half maximum (FWHM), which is fitted to be 0.20 nm (inset of Figure 4(b)) using a Gaussian function. In this case, Q is calculated to be 2565, which suggests the high quality laser with good monochromaticity. In addition, according to the relationship of the integrated intensities versus pump density shown in Figure 4(c), the threshold Pth is found as low as 1053 nJ cm-2. Therefore, single mode lasing with excellent monochromaticity is achieved in the AIE-active organic microribbons. In summary, we have demonstrated the new organic molecule TPDSB with excellent AIE performance. We have identified that the individual self-assembled TPDSB organic microribbon exhibits effective optical waveguide with a optical loss of as low as 0.012 dB μm-1, which suggests the good photon confinement and the microcavity effect. Significantly, we firstly achieve the multi-mode and the single-mode laser emission based on the AIE-active microribbon FP resonator with a high Q of ~2565, whose lasing threshold is as low as 653 nJ cm-2. Our work has provided an approach for the ultra-low threshold OSSLs based on AIE materials, which would eventually contribute to the realization of electrically-pumped OSSLs.

ASSOCIATED CONTENT Supporting Information. The Supporting Information is available free of charge on the ACS Publications website at DOI: Notes The authors declare no competing financial interest. ACKNOWLEDGMENT 13 Environment ACS Paragon Plus


The authors acknowledge financial support from the National Natural Science Foundation of China (No. 21703148), the National Key Research and Development Plan of China (Grant No. 2016YFB0400700), and the Natural Science Foundation of Jiangsu Province (BK20170330), and This project is also funded by the Collaborative Innovation Center of Suzhou Nano Science and Technology (CIC-Nano), by the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD), and by the “111” Project of The State Administration of Foreign Experts Affairs of China

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Table of Contents Graphic

The organic microcrystals of AIE-active molecules are fabricated through the facile solutionevaporation method, which perform the effective optical waveguiding with a low loss coefficient of 0.012 dB μm-1. Both multi-mode and single mode green lasing with an untralow threshold of 653 nJ cm-2 are successfully achieved in these AIE-active organic microribbons, which can serve as the coherent light in micro/nanoscale.


Low-Threshold Organic Lasers Based on Single-Crystalline

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