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Optik
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Growth and characterization of an efcient nonlinear optical single crystal: Urea p-nitrophenol
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A. Rathika 1 , R. Ganapathi Raman

Department of Physics, Noorul Islam Centre for Higher Education, Kumaracoil, Thuckalay, Kanyakumari 629 175, India

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a r t i c l e

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a b s t r a c t
An organic nonlinear optical single crystal of urea p-nitrophenol has been synthesized and grown by slow evaporation solution growth technique. The grown crystals were characterized by single crystal and powder X-ray diffraction analysis and it was found to be the structure of the crystal belongs to triclinic system. The various functional groups were identied by FT-IR and Raman spectral analysis. Thermal stability of the grown crystal was studied by TGA/DTA. The optical properties of the grown crystals were analyzed by UVvis. The mechanical properties of the grown crystal were studied by Vickers microhardness measurements. Nonlinear optical property of the crystal was conrmed using the Kurtz and Perry powder technique and a study of its SHG efciency in comparison with KDP has made. 2014 Published by Elsevier GmbH.

Article history: Received 17 June 2013 Accepted 5 December 2013 Available online xxx Keywords: Crystal growth from solution Vibrational analysis Thermal analysis SHG PACS: 81.10.Dn 63.70.+h 81.70.Pg 42.65.Ky

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1. Introduction During the decade of crystal research, second order nonlinear optical properties has attracted the attention of many researchers to search for a variety of new types of nonlinear optical (NLO) materials because of the potential application in various engineering technological elds [13]. In the search for NLO crystals, conjugated structure compounds with electron donor and acceptor substituents are extensively studied. Due to their delocalised electrons, they generally have a high second harmonic generation (SHG) efciency. Single crystals are the backbone of the modern technological revolution. The impact of single crystals is clearly visible in industries like semiconductors, optics etc. Most of the high performance optoelectronic devices are made from crystalline materials [4]. Organic compounds are often formed by weak van der Waals and hydrogen bonds and hence possess high degree of delocalization. Urea, a promising organic crystal exhibits large nonlinear optical coefcients, high degree of birefringence and relatively high laser damage threshold [58]. Urea has some undesirable

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Corresponding author. Tel.: +91 9976715576. E-mail addresses: rathidhanu@gmail.com (A. Rathika), ganapathiraman83@gmail.com (R. Ganapathi Raman). 1 Tel.: +91 9626840787. http://dx.doi.org/10.1016/j.ijleo.2013.12.032 0030-4026/ 2014 Published by Elsevier GmbH.

mechanical and chemical properties, i.e., mechanically soft and hygroscopic nature. As a result of hygroscopic nature, urea cannot be exposed to normal atmosphere, and for practical applications it is being used by immersing it in an index-matching uid with compatible chemical and optical characteristics. Amongst them, the nonlinearity of urea is comparable with that of another important commercial NLO material potassium dihydrogen phosphate (KDP) [9,10]. In the title compound, C6 H5 NO3 CH4 N2 O, p-nitrophenol molecules are linked to urea molecules by O H O and N H O hydrogen bonds forming network structure [11]. Urea crystals attract the attention of both theoretical and experimental scientists due to their nonlinear optical piezoelectric properties. Urea is highly soluble in water and the corresponding solution has some important features: Urea is representative of one class of materials, which are applicable to photonics and reference material in the diffusive mixing of organic solutions (DMOS) experiment in micro cavity carried out by NASA [12]. They are potentially useful materials for frequency doubling of near IR laser radiation single crystal of the material which have high laser damage threshold [13]. During the past decade researchers have shown much interest in p-nitrophenol family of crystals due to their high laser damage threshold, transparency window, extended thermal stability and high NLO coefcient [1418]. p-Nitrophenol totally matches this criterion with its electron donor substituents OH and electron acceptor substituents NO2 and phenyl group form a

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Please cite this article in press as: A. Rathika, R. Ganapathi Raman, Growth and characterization of an efcient nonlinear optical single crystal: Urea p-nitrophenol, Optik - Int. J. Light Electron Opt. (2014), http://dx.doi.org/10.1016/j.ijleo.2013.12.032

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Fig. 1. Reaction scheme of UPN crystal.

Fig. 3. Powder XRD prole of UPN crystal.

Fig. 2. Grown UPN crystal.

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conjugated molecular conguration. p-Nitrophenol derivatives are interesting candidates as they are a typical one-dimensional (1D) donor-acceptor system, and the presence of phenolic OH favors the formation of salts with various organic and inorganic bases. In this paper, we report the growth and characterization studies of urea p-nitrophenol (UPN) single crystal. 2. Experimental 2.1. Synthesis and crystal growth In the present investigation, Analar reagent (AR) grade of urea (CH4 N2 O) and p-nitrophenol (C6 H5 NO3 ) were taken in the optimized ratio 1:1 as per the reaction. The reaction scheme of the title compound is depicted in Fig. 1. The mixture was stirred well to avoid co-precipitation of multiple phases and which yields the UPN. The solution was ltered and transferred to crystal growth vessels and crystallization was allowed to take place by slow evaporation solution growth technique at room temperature. Supersaturated solution was prepared in the known amount of methanol and kept at room temperature for controlled evaporation. After the growth period of 25 days, yellow coloured single crystals were harvested with the dimension of 22 25 5 mm3 . The photographs of as grown crystals are shown in Fig. 2. 2.2. Characterization studies The grown UPN single crystals have been subjected to various characterization studies. The Bruker Kappa APEXII single crystal X-ray diffractometer, used to estimate the cell parameters and the powder X-ray diffraction pattern was checked by XPERT-PRO X-ray diffractometer of UPN crystal. The FTIR spectrum of UPN was recorded using a 8400S Shimadzu infrared spectrophotometer using KBr pellet technique in the region 4500500 cm1 . The FT-Raman spectrum was recorded using a BRUKER: RFS 27: standalone FT-Raman spectrometer in the region 40000 cm1 . The TGA/DTA studies showed the thermal properties of grown crystal carried using TA instruments, model: Q600 SDT and Q20 DSC thermal analyzer. The UVvis transmission spectrum of UPN crystal was studied in the range 400900 nm by PerkinElmer Lambda 35 UVvis spectrometer. >Microhardness measurement was carried out using LeitzWetzlar Vickers microhardness tester tted with a diamond pyramidal indenter attached to an optical microscope.

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Fig. 4. (a) FTIR spectrum of UPN crystal. (b) FT-Raman spectrum of UPN crystal.

Nonlinear optical property of the crystal was conrmed using the Kurtz and Perry powder technique and a study of its SHG efciency in comparison with KDP has made. 3. Results and discussion The single crystal X-ray diffraction study was carried out to conrm the cell parameter values of UPN crystal. The esti b = 10.2300 A, c = 11.8100 A, mated cell parameters are a = 3.7619 A, 3 it belongs to triclinic sys = / = / = / 90 and volume V = 442 A tem with the space group of P1. The unit cell parameters are in good agreement with the reported values [11]. The crystalline nature of the grown crystal was checked by taking the X-ray diffraction pat radiation. The tern of powder samples with Cu K ( = 0.71073 A) sample was scanned 2 in the range of 1080 at the rate of 2 /min. The indexed powder XRD pattern is shown in Fig. 3. The appearance of sharp and strong peaks conrmed the good crystallinity nature of the grown sample. Fig. 4a and b shows the FTIR and Raman spectrum of UPN crystal and the vibrational band assignments are summarized in Table 1. Normally stretching, bending and wagging deformation of NH band appears around 35003000, 17001600,

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Please cite this article in press as: A. Rathika, R. Ganapathi Raman, Growth and characterization of an efcient nonlinear optical single crystal: Urea p-nitrophenol, Optik - Int. J. Light Electron Opt. (2014), http://dx.doi.org/10.1016/j.ijleo.2013.12.032

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A. Rathika, R. Ganapathi Raman / Optik xxx (2014) xxxxxx 3 Assignments Raman 3089 (w) 1602 (m) 1570 (w) 1497 (vw) 1324 (vs) 1165 (vw) 1103 (m) 1006 (w) 866 (m) 640 (w) 605 (vw) 369 (w) 259 (w); 111 (s) C H stretching vibration C C asymmetric stretching COO asymmetric stretching NH3 + bending CH in-plane bending CH wagging C C N asymmetric bending CN stretching C H out- of- plane bending CN deformation COO bending C OH in-plane bending Lattice vibrations

Table 1 Observed vibrational wavenumber and their assignments of UPN. Wavenumber (cm1 ) IR 3040 (m) 1645 (w) 1581 (w) 1491 (m) 1338 (s) 1159 (w) 1109 (s) 997 (vw) 846 (s) 630 (m) 607 (s) 493 (w)

Q4 Vs very strong, vw very weak, s strong, m medium, w weak.

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1150900 cm1 respectively in vibrational spectrum [19]. Aromatic compounds commonly exhibit multiple weak bands in the region 31003000 cm1 due to aromatic C H stretching vibration. There are six equivalent C C bonds in benzene and consequently there will be six C C stretching vibrations in the region 16451602 cm1 . Two overlapped bands at around 1581 cm1 and 1570 cm1 in FTIR and Raman spectra were attributed to the asymmetric stretch mode of the COO group. The bands due to C H in-plane bending vibrations are observed as a number of strong intensity sharp bands in the region 13001200 cm1 . When there is in-plane interaction above 1200 cm1 , a carbon and its hydrogen usually move in the opposite direction while below 1200 cm1 , they move in the same direction. Silverstein et al. [20] assigned C N stretching vibration in the region 1000900 cm1 . The medium intensity peak related to C C N asymmetric bending became weak in the spectra. The C H out-of plane bending and stretching vibrations are strongly coupled vibrations and occur in the region 900866 cm1 . Other bands of COO bending and CN deformation mode were observed at 640600 cm1 . In Raman spectra the bands observed at lower Q3 wave number (259 and 119 cm1 ) are assign to lattice vibrations of UPN crystal. The TGDTA curves of title compound were shown in Fig. 5. The material stable up to 132 C illustrating the absence of solvent in the crystal lattice was observed in TG curve. In DTA curve two weight loss starts around 122 C and weight loss corresponding to decomposition of title compound was observed at 234 C, which takes place over large temperature range (122234 C) where almost all the compounds decomposed as its gaseous products. The second endothermic peak in the DTA curve shows that the material is fully decomposed at 234 C. Though the TG curve indicates one stage decomposition, the DTA curve certainly conrms the two stage decomposition. Hence the one stage decomposition observed in the TGA can be split into two stages according to DTA observations.

Fig. 6. (a) UVvis transmittance spectrum of UPN crystal. (b) Plot of (h)2 vs. photon energy.

Hence both the studies conrmed application of the crystal for NLO applications up to 122 C. UVvisible transmission spectrum of UPN crystal was recorded in the range of 400900 nm using 1.58 mm thickness crystal sample Fig. 6a. The UPN crystal is active in the UVvis region and the compound material could be viable alternative for optical materials in that entire region. It has good transparency of about 80% with lower cut-off wavelength 482 nm. The dependence of optical absorption coefcient with the photon energy helps to study the band structure and the type of transition of the electron. The absorption coefcient () and the optical parameters such as refractive index (n), reectance (R) and extinction coefcient (K) have been determined from the transmission (T) spectrum based on the following relations, 2.3026 log = t 1 T (1)

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where T is the transmittance and t is the thickness of the crystal. The absorption coefcient is related to the extinction coefcient K by, K= 4 (2)

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The reectance (R) in terms of the absorption coefcient and refractive index (n) can be derived from the relations, R= n= exp(t ) exp(t )T exp(3t )T + exp(2t )T 2 exp(t ) + exp(2t )T (3) (4)

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(R + 1) 2 R (R 1)

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In the high photon energy region, the energy dependence of absorption coefcient suggests the occurrence of direct band gap of the crystal obeying the following equation for high photon energies (h) [21], (h ) = A(Eg h )
Fig. 5. TGA/DTA spectrum of UPN crystal.
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(5)

where Eg is the optical band gap of the crystal and A is a constant. The variation of (h)1/2 with h [22] in the fundamental

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Fig. 7. (a) Plot of refractive index vs. wavelength. (b) Plot of extinction coefcient vs. wavelength. Fig. 8. (a) Plot of Vickers hardness (Hv ) against load (P) of UPN crystal. (b) Plot of log P vs. log d.
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absorption region is plotted in Fig. 6b. The band gap of the crystal was evaluated by extrapolation of the linear part of the graph and found to be 2.42 eV. The wide band gap of the UPN crystals conrms the large transmittance in the visible region. Fig. 7a and b represents the variation of refractive index and extinction coefcient with respect to photon energy (1.26.5 eV) respectively. It is importantly noticed that the crystal has positive refractive index (n = 1.2 at 4 eV) with respect to energy and this indicated the focusing nature of the crystal. From the graph, it is cleared that the extinction coefcient depends on the photon energy. Since the internal energy of the device also depends on the photon energy, by tailoring the photon energy one can achieve the desired material to fabricate the optoelectronic devices. From Fig. 8a, Vickers hardness (Hv ) number increases initially with load up to 75 g and cracks were observed beyond 75 g. This type of load variation of hardness is termed as reverse indentation size effect [23]. At low loads, the indenter penetrates only the top surface layers generating dislocations, which results in the increase of hardness in this region. The load independence of hardness at higher loads can be attributed to the mutual interaction or rearrangement of dislocations. The relation between load and the size of indentation can be correlated using Meyers law, P = k1 dm , where k1 is a constant and m is the Meyers index. The slope of log P versus log d gives the work hardening coefcient (m) and it was calculated to be 2.1 (Fig. 8b) which indicates that UPN crystal belongs to soft material category [24]. The most widely used technique for conrming the SHG efciency of grown crystal is determined using the Kurtz and Perry powder technique [25]. In this experiment Q-switched Nd:YAG laser (1064 nm, Quanta ray series, USA) emitting a fundamental wavelength of 1064 nm was used. The grown single crystal is powdered with a uniform particle size of 125150 m, and then packed in a microcapillary of uniform bore and exposed to the laser radiation. The SHG was conrmed by the emission of green radiation (532 nm). The input laser energy incident on the sample was 0.68 J, an energy level optimized to cause any chemical decomposition of the sample. KDP is used as a reference material for the present

measurement [26]. The SHG efciency of UPN is 8.3 mJ with reference to KDP 8.8 mJ. 4. Conclusions Single crystals of urea p-nitrophenol were grown by slow evaporation solution growth technique from using methanol as solvent. The grown crystals were characterized by single crystal and powder X-ray diffraction analysis and it was found to be the structure of the crystal belongs to triclinic system. Vibrational nature of the functional groups presented in the grown crystal was studied. Optical band gap and electric susceptibility have been calculated through UVvis spectrum. It is observed from TGA/DTA studies that there is no phase transition in the grown material and is stable up to 122 C. From the mechanical measurements, it was observed that the hardness increases with increase of load. The SHG efciency of UPN is 8.3 mJ with reference to KDP 8.8 mJ. Acknowledgements One of the authors A. R would like to acknowledge Noorul Islam Centre for Higher Educational Trust for providing the nancial assistance. The authors are thankful to M.K University, Madurai, SAIF, IIT Madras, B. S. Abdur Rahman University, Chennai for the Instrumentation facilities. References
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Please cite this article in press as: A. Rathika, R. Ganapathi Raman, Growth and characterization of an efcient nonlinear optical single crystal: Urea p-nitrophenol, Optik - Int. J. Light Electron Opt. (2014), http://dx.doi.org/10.1016/j.ijleo.2013.12.032