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  • ISSN (Print): 2328-3777, ISSN (Online): 2328-3785, ISSN (CD-ROM): 2328-3793 American International Journal of Research in Formal, Applied & Natural Sciences AIJRFANS 14-294; © 2014, AIJRFANS All Rights Reserved Page 161 AIJRFANS is a refereed, indexed, peer-reviewed, multidisciplinary and open access journal published by International Association of Scientific Innovation and Research (IASIR), USA (An Association Unifying the Sciences, Engineering, and Applied Research) Available online at http://www.iasir.net Synthesis, Characterization and Study of Optical Constant of 4-(4-N,N-Dimethylaminobenzylideneamino)Phenyltellurium Tribromide Adil Ali Al-Fregi1 , Ghufran Mohammad Shabeeb2 1 Chemistry Department, College of Science, University of Basrah, Basrah, IRAQ 2 Physics Department, College of Education for Pure Sciences , University of Basrah, Basrah, IRAQ I. Introduction Tellurium is one of members of group 16 in the periodic table. Tellurium lies between selenium and polonium and have electronic configuration [Kr]4d10 5s2 5p4 , it bears resemblance to this group especially to selenium in many of its properties and reactions [1]. Tellurium and its compounds have several applications in different fields. Organotellurium compounds have been mainly used as antioxidant agents [2,3], polymerization catalysts [4,5], antitumors and pharmaceutical agents [6-8], organic super conductors [9,10], synthetic intermediate [11-13] and as ligands with many transition metal ions [14,15]. In recent years there has been a growing interest in studing the organotellurium compounds which have N→Te intramolecular interaction [16,17]. There are several types of organotellurium compounds containing nitro, amino and azomethine groups which show such intramolecular interaction [18-29]. One of these compounds represent in organotellurium compounds which contain azomethine groups [20,30,31]. Organyltellurium trihalides (RTeX3 where X= Cl, Br, I; R = alkyl, aryl) constitute a large and a well studied class of compounds [5,10]. Generally, the stability of alkyltellurium trihalides are lower than aryltellurium trihalides, thus, methyltellurium trihalides (CH3TeX3 ; X = Cl, Br and I) are very sensitive to light and moisture, and decomposed in solutions while the corresponding phenyltellurium trihalides are stable under the same conditions [32]. Generally, the structures of organyltellurium trihalides are connected into infinite chains [32- 34] or dimeric structures by halogene bridges [32-35]. The important methods for preparing organyltellurium trihalides are reaction of tellurium tetrahalides (TeX4; X = Cl, Br) with several compounds such as alkenes [36], alkynes [37], ketones [38] and activated aromatic compounds [33]. In some cases, the direct substitution of tellurium tetrahalides with aromatic compounds is not feasible or give low yield. The substitution reaction of arylmercuric chloride with tellurium tetrahalides gave the corresponding aryltellurium trihalide in good yield [39,40]. Several attempts to prepare tellurated Schiff bases by reacting Schiff bases with tellurium tetrabromide were failed and leading to ionic products [41,42]. Singh and McWhinnie [43] prepared {4-substituted-2-(phenyliminomethyl) phenyl}tellurium tribromide by reacting 4-substituted-2-(phenyliminomethyl) phenyl mercuric chloride with tellurium tetrabromide, Scheme1. Al-Rubaie et al [30] reported the synthesis of a new series of tellurated Schiff bases compounds of formula ArTeBr3 (Ar =5-RC6H3N=CHC6H5, R=Cl, Br, CH3O and NO2) by reaction of tellurium tetrabromide with the corresponding arylmercuric chloride in 1:1 mole ratio, Scheme 2 . Abstract: 4-(4-N,N-dimethylaminobenzylideneamino) phenyltellurium tribromide synthesed by reaction of ehtanolic solutons of 4- aminophenylmercuric chloride with 4-N,N-dimethylaminobenzaldehyde then with tellurium tetrabromide. The prepared compund 4-(4-N,N-dimethylaminobenzylideneamino)phenyltellurium tribromide was charecterized by several techniques such as elemental analysis ; FTIR, UV-Visible, 1 H and 13 C- NMR spectroscopies ; X-Ray diffraction and molar conductivity. Optical absorption of 4-(4-N,N- dimethylaminobenzylideneamino)phenyltellurium tribromide was measured. The X-ray analysis revealed that these films are amorphous nature. Then films were deposited using cast method. Transmittance measurements in the wavelength range(190-900)nm are used to calculate the refractive index(n), the absorption index(k) and the optical energy gap. Keywords: optical absorption; refractive index; optical energy gap; organotellurium compounds; azomethine group; Schiff base.
  • Adil Ali Al-Fregi et al., American International Journal of Research in Formal, Applied & Natural Sciences, 6(2), March-May, 2014, pp. 161-171 AIJRFANS 14-294; © 2014, AIJRFANS All Rights Reserved Page 162 In the present work, attempts will be made to prepare and characterization a new organyltellurium tribromide compound containing azomethine group (-CH=N) namely 4-(4-N,N- dimethylaminobenzylideamino)phenyltellurium tribromide and study of optical constant of it by using thin films technique. Both of the optical constant, n(refractive index) and k (extinction coefficient), represent fundamental properties of a material not only because of their relation to the electronic structure but also due to their applications in many integrated optical devices. Thus, calculating n and k, of material are the key parameters for a device design [44]. The refractive index provides the information about the chemical bonding and electronic structure of the material [45]. The evaluation of refractive indices of optical material is of considerable importance for application in integrated optical devices such as switches, filters and modulators [46]. II. Experimental Section A. Chemicals All chemicals used in this study were supplied from the commercial sources by famous chemical companies . Bromine, 4-N,N-dimethylaminobenzaldehyde, p-toluenesulfonic acid and mercuric acetate were supplied by British Drug House (BDH). Absolute ethanol, aniline, benzene and tellurium 99.5% were supplied from Fluka company. Diethyl ether, dioxane, hexane and sodium chloride were supplied by Reidal de Hean company. Argon gas 99.995% was purchased from Jordan Gases company. Tellurium tetrabromide which used in the present work was prepared by a literature method [47] 4- aminophenylmercuric chloride was prepared by the literature methods [48]. All the prepared compounds gave the correct melting points and infrared spectra. B. Purification of Solvents The solvents were obtained from commercial sources and are analytically pure solvents. Some solvents such as dioxane and ethanol were cautiously purified and drying according to literature methods and were kept over molecular sieve type A4 and stored in clean dark containers [49,50]. C. Physical Measurements Melting points of all solid compounds were determined by using a Gallenkamp Thermo point apparatus. Elemental analysis for carbon, hydrogen, nitrogen and sullphur were performed at AL al-Bayt Univrsity, Al- Mafraq, Jordan using a Euro vector EA 3000A Elemental Analysis (Italy). Infrared spectra for the synthesed compounds were recorded as KBr disk or thin film supported on KBr disk using a FT-IR spectrophotometer Shimadzu model 8400S in range 4000-400 cm-1 at Department of Chemistry, College of Science, University of Basrah. UV-Vis spectra for the synthesized compounds were recorded at Department of Chemistry, College of Science, University of Basrah by using Scan 80D (England) at range 200-800 nm using ethanol or chloroform as a solvents and 1cm3 pathway quartz cells. 1 H-and 13 C NMR spectra were recorded at Al al-Bayt University, Jordan by using a Bruker 300 MHz (Germany). Chemical shift of all 1 H-and 13 C NMR spectra were recorded in δ(ppm) unit downfield from the internal reference tetramethylsilane (TMS), using DMSO-d6 solvent. The molar conductivity for synthesized compounds were measured in 1x10-3 M solutions of dimethylsulfoxide solvent at room temperature using a Konduktoskop model 365B using standard conductivity cell with constant equal to 0.81 cm-1 . D. Synthesis of 4-(4-N,N-dimethylaminobenzylideneamino)phenylmercuric chloride A mixture of 4-aminophenylmercuric chloride (2.43 g , 8.00 mmol) in 50 mL of ethanol and 4-N,N- dimethylaminobenzaldehyde (1.19 g,8.00 mmol) in 50 mL of ethanol containing 0.1 g of p-toluenesulfonic acid was refluxed with stirring for 5h. After cooling, the precipitate was collected by filtration and washed several times with ethanol. The solid product was twice recrystallized from a mixture of ethanol and benzene (3:2) to give a pale yellow solid. Yields 88%, melting point 191-193 0 C , Table 1. E. Synthesis of 4-(4-N,N-dimethylaminobenzylideneamino)phenyltellurium tribromide A mixture of tellurium tetrabromide (1.78 g, 4.00 mmol) in 35 mL of dry dioxane and 4-(4-N,N- dimethylaminobenzylideamino)phenyl mercuric chloride (1.83 g, 4.00 mmol) in 30 mL of dry dioxane was refluxed with stirring for 6h under argon atmosphere. The resulting solution was filtered hot and on cooling deposited 2:1 complex of dioxane and mercuric chloride as white plates, which was filtered off. The filtrate was evaporated by a rotary evaporator to give a yellow precipitate. Recrystallization of the crude product from a mixture of diethyl ether and hexane (7:3) gave a yellow solid. Yield 60% and melting point 155 – 156 0 C , Table 1.
  • Adil Ali Al-Fregi et al., American International Journal of Research in Formal, Applied & Natural Sciences, 6(2), March-May, 2014, pp. 161-171 AIJRFANS 14-294; © 2014, AIJRFANS All Rights Reserved Page 163 Comp. No. Compound Stracture Colour Melting Point(o C) Yield% Molar conductiv- ity Elemental analysis Found (calculated) C% H% N% 1 Pale yellow 191-193 88 33.05 40.01 (39.22) 3.26 (3.29) 6.08 (6.10) 2 Yellow 155-156 60 28.99 30.44 (30.50) 2.52 (2.56) 4.73 (4.74) Table 1 : Some physical properties and elemental analysis of new organometallic compounds containing azomethine groups 1 and 2 in cm-1 unit. III. Results and Discussion X-ray diffraction (XRD) studies were carried out to get an idea about the structural changes produced in the investigated 4-(4-N,N-dimethylaminobenzylideneamino)phenyltellurium tribromide thin films. The diffracted intensity as a function of the reflection angle was, measured automatically by the X-ray diffractopmeter. The absence of a peak in X-ray spectra confirmed the amorphous nature of 4-(4-N,N- dimethylaminobenzylideneamino)phenyltellurium tribromide samples. Fig. (1): (XRD) of4-(4-N,N-dimethylaminobenzylideneamino)phenyltellurium tribromide thin film. The elemental analysis (CHN) of compounds 1 and 2 are in good agreement with the calculated values ,Table 1. The IR spectra of the two new synthesized compounds 1 and 2 display common feature in certain region and characteristic bands in the fingerprint and other regions. Table 2 shows the important functional groups vibration bands and some representive IR spectra are shown in Fig. 2 and 3. The IR spectra of compounds 1 and 2 show a strong band at 1668 and 1618 cm-1 respectively, can be attributed to CH=N stretching . These values are in good agreement with previous works [51-53]. The IR spectra of mercurated Schiff bases 1 shows no stretching bands vibration of carbonyl groups of at 1715 cm-1 and stretching band of amino groups of mercurated anilines (i.e 4-aminophenylmercuric chloride at 3450-3100 cm-1 range [51,53,54] this indicates the complete condensation between carbonyl and amino groups. The IR spectra of aryltellurium tribromides 2 is quite similar to those of the mercurated Schiff base 1. This means that telluration has occurred at the point of mercuration. The IR spectra of compounds 1 and 2 show a weak bands in the range 3110-3060 cm-1 due to aromatic C-H stretching while weak bands were appeared at 2921- 2817 cm-1 range due to stretching of aliphatic C-H bands [53,54]. Also, compounds 1 show two strong bands appeared in 1598 and 1365 cm-1 , while compound 2 at 1541 and 1325 cm-1 can be attributed to asymmetrical and symmetrical stretching of aromatic (C=C) [53,54].
  • Adil Ali Al-Fregi et al., American International Journal of Research in Formal, Applied & Natural Sciences, 6(2), March-May, 2014, pp. 161-171 AIJRFANS 14-294; © 2014, AIJRFANS All Rights Reserved Page 164 Furthermore, several variable bands between 815 – 700 cm-1 range can be assigned to aromatic C-H bending while the band at 1365-1317 cm-1 due to aliphatic C-H bending [53,54]. The IR spectra of compounds 1 and 2 show a strong band at 1232 and 1200 cm-1 respectively, attributed to ν(C-N) [53,54]. Comp.No. Aromatic ν(C-H) Aliphatic νas (C-H) νs (C-H) ν(C=N) νas(C=C) νs (C=C) Bending νara(C-H) ν(C-N) 1 3110 w 2912 w 2817 w 1668 s 1598 s 1365 s 815 s 721 m 1232 s 2 3066 w 2921 w 1618 s 1541 s 1325 s 813 m 840 m 7500 m 1200 s Table 2 : Selected infrared bonds vibration of new organometallic compounds containing azomethine groups in cm-1 unit. Fig. (2): showed the FtIR- spectrum of 4-(4-N,N-dimethylaminobenzylideneamino)phenylmercuric chlorid . Fig. (3): showed the FTIR spectrum of 4-(4-N,N-dimethylaminobenzylideneamino)phenyltellurium tribromide. .
  • Adil Ali Al-Fregi et al., American International Journal of Research in Formal, Applied & Natural Sciences, 6(2), March-May, 2014, pp. 161-171 AIJRFANS 14-294; © 2014, AIJRFANS All Rights Reserved Page 165 The 1 H NMR spectra of compounds 1 and 2 were measured in DMSO-d6 solvent and are represented in Fig. 4 and 5 respectively and summarized in Table 3. In general, 1 H NMR spectra of the 1 and 2 show the expected signals in proper intensity ratio, Table 3. Fig. (4): 1 H NMR spectrum of compound 1. Fig. (5): 1 H NMR spectrum of compound 2. The 1 H NMR spectra of compounds 1and 2, Fig.3 and 4, respectively gave another evidences for forming azomethine group (-CH=N-) by showing a singlet signal at 8.33 and 8.32 ppm respectively, Table 3. These values are in agreement with previously reported data [53,56]. The 1 H NMR spectrum of compound 1 and 2, Fig. 6 and 7, respectively, show a multple signals at between 7.44 - 6.18 ppm can be assigned to aromatic protons of phenyl groups [53-55]. Furthermore, these spectra show a singlet signal at 2.27 ppm can be attributed to methyl groups [53-55]. Comp. No. Compound Structure Chemical Shift (ppm) TMS = 0 ppm 1 8.33 ( s , 1H , CH=N) 7.43 – 6.18 ( m, 8H, Ar-H) 2.27 ( s, 6H, 2 CH3)
  • Adil Ali Al-Fregi et al., American International Journal of Research in Formal, Applied & Natural Sciences, 6(2), March-May, 2014, pp. 161-171 AIJRFANS 14-294; © 2014, AIJRFANS All Rights Reserved Page 166 2 8.32 (s , 1H , CH=N) 7.44 – 6.18 ( m, 8H, Ar-H) 2.27 ( s, 6H, 2 CH3) Table 3 : 1 H NMR data for organometallic compounds containing azomethine groups 1 and 2. The 13 C NMR spectra of some synthesized compounds 1 and 2 were recorded using DMSO-d6 solvent. Fig. 5 and 6 represented 13 C NMR spectra of synthesized compounds while 13 C NMR data were summarized in Table 4. Fig. (6): 13 C NMR spectra of compound1. Fig. (7): 13 C NMR spectra of compound 2. 13 C- NMR spectra proved further evidences about characterization of synthesized compounds . The 13 C- NMR spectra of 1 and 2 show the signal of methine carbon atoms (C7) at 169.12 and 169.44 ppm, respectively which are in agreement with previous reported works [53-56],Table 4. 13 C NMR spectra of compounds 1 and 2 show a lowfield signal at (155.69 and 155.62) ppm and ( 145.56 and 145. 60) ppm, respectively can be assigned to aromatic carbon atoms which attached with nitrogen atom (C4) and (C11) , Table 4 . The high chemical shifts for these carbon signals attributed to presence of high electronegativity of nitrogen atom [53-56]. The 13 C NMR spectra of 1 and 2 show a high field signal at 113.18 and 113.19 ppm respectively can be assigned to tellurated carbon atoms (Te-C) (C1) [53-56]. The low chemical shift, comparatively, for carbon atoms bearing tellurium atom compared with other aromatic carbon atoms may be attributed to the polarity of Te-C bond [56]. Generally, the other signals between 145.60 - 120.09 ppm in 13 C NMR spectra of 1 and 2 can be assigned to aromatic carbon atoms, Table 4. The high field signals at 47.43 and 47.84 ppm in both 13 C- NMR spectra of compounds 1 and 2, respectively are due to methyl groups (C14 and C15) [53-56].
  • Adil Ali Al-Fregi et al., American International Journal of Research in Formal, Applied & Natural Sciences, 6(2), March-May, 2014, pp. 161-171 AIJRFANS 14-294; © 2014, AIJRFANS All Rights Reserved Page 167 Comp. No. Compound structure Chemical shift (ppm) TMS = 0 ppm 1 169.12 (C7) , 155.69 (C4) 145.56 (C11) , 130.55 (C2, C6) 130.16 (C9,C13 ) , 127.74 (C3,C5) 122.08 (C8) , 120.09 (C10,C12) 113.18 (C1) , 47.43 (C14, C15) 2 169.44 (C7) , 155.62 (C4) 145. 60 (C11) , 130.16 (C2, C6) 129.12 (C9,C13 ) , 128.30 (C3,C5) 122.31 (C8) , 120.10 (C10,C12) 113.19 (C1) , 47.84 (C14, C15) Table 4 : 13 C -NMR data for organometallic compounds containing azomethine groups 1 and 2. The UV-Vis spectra of compounds 1 and 2 were measured at 1 x 10-4 M using chloroform as a solvent. Fig. 8 and 9 have shown the UV-Vis spectra for the synthesized compounds Table 5. Fig. (8): UV-Vis. spectrum of compound 1. Fig. (9): UV-Vis. spectrum of compound 2.
  • Adil Ali Al-Fregi et al., American International Journal of Research in Formal, Applied & Natural Sciences, 6(2), March-May, 2014, pp. 161-171 AIJRFANS 14-294; © 2014, AIJRFANS All Rights Reserved Page 168 In general, the UV-Vis spectra of compounds 1 and 2 showed two strong bands , The first band at 245 nm with molar extraction (Є) ranged 13000 and 11500 M-1 .cm-1 , respectively is attributed to π→π* transitions of the aromatic rings [53,54]. The second band observed at 295 nm (molar extinction Є = 12250 and 10100 M-1 .cm-1 , respectively) which may attributed to π→π* transitions of azomethine groups [53,54]. Comp.No. Wavelength nm (molar extinction M-1 .cm-1 ) 1 245 (13000) , 295 (12250) 2 245 (11500) , 295 (10100) Table 5 : UV-Vis data of compounds 1 and 2 The molar conductivities were determined for compounds 1 and 2 in 1 x 10-3 M of DMSO solvent at room temperature, Table 1. The molar conductances of 1 and 2 were found at 33.05 and 28.99 ohm-1 cm2 mol-1 respectively, Table 1. This indicates that these compounds behave as 1:1 electrolyte which are in agree well with previous work in DMSO solution [57-59]. This observation may be due to ionic character of one Te-Br bond in these compounds. IV. Optical Constant The optical parameters for 4 -(4-N,N-dimethylaminobenzylideneamino)phenyltellurium tribromide films deposited on glass substrate have been investigated . The analysis of the absorption coefficient has been carried out to obtain the optical energy gapand also, the analysis of the refractive index n with the help of the absorption index k has been carried out to obtain the optical conductivity. The values of n and k are determined from the transmittance and reflectance spectra of the thin films. The reflectance and refractive index of any solid certain wavelength are expressed as [60]. K= (1) R= (2) The spectral distributions of the mean values of n and k versus wavelength for the investigated-(4-N,N- dimethylaminobenzylideneamino)phenyltellurium tribromide are shown in Fig.10. Fig. (10): Dependence of the mean values of the refractive index n on the wavelength. Fig. (11): Dependence of the mean values of the absorption index k on the wavelength. The absorption coefficient have been estimated after correction for the reflection losses. The absorption coefficient is given by [61]:
  • Adil Ali Al-Fregi et al., American International Journal of Research in Formal, Applied & Natural Sciences, 6(2), March-May, 2014, pp. 161-171 AIJRFANS 14-294; © 2014, AIJRFANS All Rights Reserved Page 169 =( )*A (3) Where d is the thickness of the sample and Ais the absorption after correction. The absorption edge can be divided into two regions depending on the value of absorption coefficient . For <104 cm-1 , there is usually an Urbach tail [62] in which depends exponentially on photon energy, h .Fig.(22) shows a plot of log( ) as a function of photon energy h . Fig. (22): Dependence of the absorption coefficient α on the photon energy. For 104 106 cm-1 in the high-absorption region( where absorption is associated with inter-band transitions). The following relation [63,64] is obeyed: h = (h -Eopt)n (4) Where is the band tailing parameter, Eopt is the optical band gap and n is an index which can assume values 1,2,3,1/2 and 3/2 depending on the nature of the electronic transition responsible for the absorption [65]. The relation between ( h )1/2 and photon energy shown in Fig. (23). Fig. (13): Dependence of the ( h )1/2 on the photon energy. The absorption coefficient can be used to calculate the optical conductivity opt as follows [66]. opt= (5) Where c the velocity of the light. Fig.(14) shows the variation of optical conductivity opt as a function of photon energy. Fig. (24): Dependence of the opt on the photon energy. The increased of optical conductivity at high photon energy is due to the high absorbance of 4-(4-N,N- dimethylaminobenzylideneamino)phenyltellurium tribromide thin films and also may be due to the electron excited by photon energy [67].
  • Adil Ali Al-Fregi et al., American International Journal of Research in Formal, Applied & Natural Sciences, 6(2), March-May, 2014, pp. 161-171 AIJRFANS 14-294; © 2014, AIJRFANS All Rights Reserved Page 170 V. Conclusions 4-(4-N,N-dimethylaminobenzylideneamino)phenyltellurium tribromide thin films have been deposited on glass substrate by cast method, and X-ray diffraction shows that it is structure. The optical constant of A1 was calculated from the transmittance spectra. The estimation of the corresponding band gap Eg is 2 eV. References [1] F. A. Cotton and G.Wilkinson, Advanced Inorganic Chemistry, A Comperehensive Text, Willey-Interscience Publisher, New York, 6th Ed, 1999. [2] M. McNaughton, L.Engman, A.Birminghan, G.Powis and I.A.Cotgreave, J.Mid. Chem., 47, 233 (2004). [3] C.W. Nogueira , G. Zeni and J. B. T. Rocha, Chem. Rev, 104, 6255 (2004) . [4] A. Goto, Y. Kwak, T. Fukuda , S. Yamago , K. Iida, M. Nakajima and J.I. Yoshida, J.Am. Chem. Soc., 125 , 2720 (2003). [5] S. 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