Journal of Applied Chemical Research (Indexed by Ministry of Science and ISC) Editor-in-Chief Ali Mahmoudi, Ph.D (Associate Prof., Islamic Azad University, Karaj Branch, Iran) Managing Editor Abbas Ahmadi, Ph.D (Associate Prof., Islamic Azad University, Karaj Branch, Iran) Regional Editor Bita Mohtat, Ph.D (Associate Prof., Islamic Azad University, Karaj Branch, Iran) Editorial Board Saeed Dehghanpour, Ph.D (Associate Prof., Alzahra University, Tehran, Iran) Lida Fotouhi, Ph.D (Prof., Alzahra University, Tehran, Iran) Nader Zabarjad, Ph.D (Associate Prof., Islamic Azad University, Central branch, Iran) Mahmoud Sharifimoghadam, Ph.D (Prof., Tarbiatemoalem University, Tehran, Iran) Khodadad Nazari, Ph.D (Associate Prof., Petroleum Research Institute, Tehran, Iran) Mohsen Daneshtalab, Ph.D (Prof., Memorial University, Canada) Masayuki Sato, Ph.D (Prof., Shizoka University, Japan) R.K.Agarwall, Ph.D (Prof., Singh University, India) Surendra Prasad, Ph.D (Prof., South Pacific University, Fiji) Literal Editor Natasha Pourdana, Ph.D (Assistant Prof.) Volume 7, No.4, 2013 Address Faculty of Science, Islamic Azad University, Karaj branch P.O Box: 31485-313, Karaj, Iran (www.jacr.kiau.ac.ir ) Journal of Applied Chemical Research, 7, (2013) Content of issue Pages Probing the Nature of Annealing Silicon Carbide Samples for Solar Cell Ahmad Zatirostami*1, Khikmat Muminov2, A.Kholov3 Department of Science and Engineering, Sari Branch, Islamic Azad University, Sari, Iran Academy of Science of the Republic of Tajikistan, S.U.Umarov, Physical Technical Institute, Tajikistan 2,3 Determination of Saturates, Aromatics, Resins and Asphaltenes (SARA) Fractions 15 in Iran Crude oil Sample by Means of Chromatography Methods:Study of the Geochemical Parameters Elham Keshmirizadeh*, Somayeh Shobeirian1, Mahmoud Memariani2 Department of Applied Chemistry, Islamic Azad University, Karaj Branch, Iran Chemistry Research Institute of Petroleum Industry-Geosciences Research Division, Tehran, Iran A Study on Peel Volatile Constituents and Juice Quality Parameters of Four 25 Tangerine (Citrus reticulata) Cultivars from Ramsar, Iran Behzad Babazadeh Darjazi Department of Horticulture, Faculty of Agriculture, Roudehen Branch, Islamic Azad University, Roudehen, Iran A Novel Method for the Synthesis of CaO Nanoparticle for the Decomposition of 39 Sulfurous Pollutant Meysam Sadeghi*1, Mir Hassan Husseini2 Department of Chemistry, Faculty of Sciences, Imam Hussein Comprehensive University, Tehran, Iran Nano Center Research, Imam Hussein Comprehensive University, Tehran, Iran 1,2 Removal of Basic Blue 159 from Aqueous Solution Using Banana Peel as a Low- 51 Cost Adsorbent Maral Pishgar1*, Mohammad Esmaeil Yazdanshenas2, Mohammad Hosein Ghorbani1, Khosro Farizadeh3 Islamic Azad University South Tehran Branch, Tehran, Iran Islamic Azad University Yazd Branch, Textile Department, Yazd, Iran Islamic Azad University Shahre Rey Branch, Textile Department, Tehran, Iran Development of a Mild Hydrothermal Method toward Preparation of ZnS 63 Spherical Nanoparticles Leila Vafayi1, Soodabe Gharibe1, Shahrara Afshar2 Department of Science, Islamic Azad University, Firoozkooh Branch, Iran Department of Chemistry, Iran University of Science and Technology, 16846-13114 Tehran, Iran Quantum Chemical Investigations of the Photovoltaic Properties of Conjugated 71 Molecules Based Oligothiophene and Carbazole N Belghiti1, M N Bennani1, Si Mohamed Bouzzine2, Mohamed Hamidi2, Mohamed Bouachrine3* Laboratoire de Recherche «Chimie-Biologie appliquées l’environnement», Faculté des Sciences, Université Moulay Ismail Meknès, Maroc URMM/UCTA, Faculté des Sciences et Techniques d’Errachidia, Université Moulay Ismaïl, Maroc ESTM, Université Moulay Ismail, Meknes, Maroc New Benzimidazoles Derivatives: Synthesis, Characterization and Antifungal Activities 85 Abbas Ahmadi*, Babak Nahri-Niknafs Pharmaceutical Sciences Branch, Islamic Azad University, Tehran, Iran Journal of Applied Chemical 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should be addressed to: Journal of Applied Chemical Research office, Department of Chemistry, Islamic Azad University, Karaj branch, P.O Box 31485-313, Karaj, Iran Journal of Applied Chemical Research, 7, 4, 7-13 (2013) Journal of Applied Chemical Research w w w j a c r k i a u a c i r Probing the Nature of Annealing Silicon Carbide Samples for Solar Cell Ahmad Zatirostami*1, Khikmat Muminov2, A.Kholov3 Department of Science and Engineering, Sari branch, Islamic Azad University, Sari, Iran 2,3 Academy of Science of the Republic of Tajikistan, S.U.Umarov, Physical Technical Institute, Tajikistan Received 12 Jun 2013; Final version received 24 Aug 2013 Abstract SiC powder preparation using Sol-Gel method The size of nano-particles grows as the temperature exceeds 900° C Size of probable agglomerations produced, is approximately less than 50nm The surface is suitable to be used for dye solar cells SiC emission occurs at wavelength area of 11.3μm or wave number area of 884.95 cm-1 In this paper probing the nature of annealed SiC samples in mixture, sintered, burned, and washed with Si, being removed We can conclude that the efficiency in trapping solar energy increases Key words: Amorphous, Mixture, Nanostructure, Thin film, XRD Introduction A Losses due to reflection Today, nano-materials and nanostructures are B Recombination dissipation, not only the forefront of the hot researches C Loss due to series and parallel resistance on the fundamental material, but also have Three approaches to curb the first two loss entered slowly and intrusively into our daily mechanisms: [3] lives In recent years, the dye –sensitized A Increased number of energy levels, B nano-structured solar cells (DNSC) based trapping hot carriers before normalization, on nanostructure metal oxide films have C generating pairs of electron - hole per high attracted much attention to themselves The energy photons or producing a higher energy electrons and holes produced by light need to carrier pair with more than a low-energy move on a shorter path to prevent the charge photon recombination greatly [1,2] Infrared spectroscopy is carried out, based * Corresponding author: Ahmad Zatirostami, Department of Science and Engineering, Islamic Azad University, Sari branch, Sari, Iran.Email: Ahmad.zati@mail.ru A Zatirostami et al., J Appl Chem Res., 7, 4, 7-13 (2013) on the radiation absorption and probing the conventional IR methods In brief, the vibration mutations of molecules and ions qualitative and quantitative identification of This method is employed as a powerful and organic compounds containing Nanoparticles, advanced method in determining structures determination of functional group types and and measuring chemical species Interaction of infrared radiation would result its molecular bonds, are FTIR objectives [4] in modification of vibration energy of bonding Experimental in molecules in the sample, which nominates Material it as an appropriate method in identification The reason why Sol-Gel Method is employed of functional groups and the molecular in the production of SiC Nano-powder, refers structure If the molecular dipole moment is to factors such as : achieving high purity, changed during the vibration, Infrared energy increasing chemical activity, being needless of absorption would occur In electromagnetic applying complex equipments, enhancing the spectrum, the region between 0.8 and 400 functionality in Sintering materials, attaining micrometers belong to infrared, but the region high production capability, enabling control used for chemical analysis, is between 0.8 to over properties and morphology, enabling 50 micrometers synthesis at molecular level, enabling the In order to obtain qualitative identification production of very small particles with united of an unknown sample, infrared spectrum of diameter, enabling the production of particles the sample is drawn based on the functional with manageable and very high specific groups and existing molecular bonds, and by surface area, reducing the number of un- referring to relevant tables, which provides reacted materials in the final product [5] vibration position of different bonds or In sol-gel method, in order to synthesize IR spectra of objects, wavelength or wave SiC nanopowder, when drying procedure number of groups and bonds would be is complete, Samples are powdered and are identified One of the characteristics of FTIR annealed at a temperatures of 500, 700, 900 is that the entire wavelength of the considered and 1000° C the process of annealing samples spectral region is simultaneously emitted was done in Chemical vapor deposition (CVD) on the sample While in dispersive methods, furnace, in air atmosphere with a thermal only a small number of wavelengths reached gradient of 5° C per minute In order to probe the sample at one time Therefore, the speed, particle shapes and for surface analysis of resolution and signal-to-noise ratio in Fourier structures, Scanning Electron Microscope is transform method is significantly better than used [6] A Zatirostami et al., J Appl Chem Res., 7, 4, 7-13 (2013) Radiation-absorption analysis using FTIR of hydrolysis reactions and condensation of C-C bond has an absorption frequency of 1200 silicon alkoxide cm-1, double bond of C = C has an absorption B - SiC emission occurs at wavelength area of frequency of 1650 cm-1 and triple bond of C = C 11.3μm or wave number area of 884.95 cm-1 [3] has an absorption frequency of 2150 cm-1 The Comparing these spectra we’ll realize that in bending motion is easier than stretch motion K=λ-1=825.48 cm-1, there is a Si-C bonding For example, bending C-H is assigned to the which is a result of bonding among carbon area of 1340 cm-1 and stretching C-H is assigned atoms in acetic acid and ethanol with the Si to the area of 3000 cm-1 Hybridization type also bond in hydrolyzed and condensate Tetraethyl affects the absorption frequencies, so that the orthosilicate liquid (SiC8H20O4) Moreover, bonds power are respectively SP> SP2> SP3 by comparing spectra, we can conclude that In the Range of K = λ-1 = 600 cm-1 to 1400 as the temperature increases, the amount of cm-1 ,due to limited amount of absorbed absorption has increased due to SiC formation energy and the bending vibration of absorbed C–In K=λ-1=1087.78 cm-1, in a range of energy, most molecular Bonds are complex 500oC to 700oC due to the double bond of and crowded and therefore identification of C=O, absorption increases However in the entire absorption bonds in this region would range of 700oC to 1000oC as temperature be difficult In other words, there is a unique is increased, due to the formation of single pattern in this region [7] bond C-O, the absorption is promptly Absorption bonds in the region of K=λ-1=600 reduced In this absorption frequency, at all cm-1 to 1400 cm-1 , have more absorbed energy temperatures stated, Si-O bond is identifiable which is mostly because of stretching vibration which is because of hydrolysis reaction and in stronger bonds condensation of the silicon aloxides FTIR spectrum for SiC nanopowder, annealed D-In K = λ-1 = 2337.56 cm-1, absorption bonds at temperatures of 500oC, 700oC, 1000oC have more energy, which is generally because using (FTIR, SHIMADZU 8400S, JAPAN) of stretching vibration of strong bonds (Group suggests: frequency region) A – In the wave number K=λ-1=478.31 cm-1, as At K=λ-1=1380.94 cm-1 C-C and C-O bonds, the the temperature increases, absorption amount wave number of K=λ-1=1535.23 cm-1 double is reduced (From 90% in 500oC to 27% at bonds of C = C, in absorption frequency K=λ- 1000oC) On the other hand, in the absorption =2923.38 cm-1 C-H bonds are identifiable frequency or wave number, siloxane bond (SiO-Si) is observable This bond is the result Probing the nature of annealed SiC samples 10 A Zatirostami et al., J Appl Chem Res., 7, 4, 7-13 (2013) in different states are characterized by high efficiency in trapping A - Mixture: solar energy, as light collector and transmitter With a review on the mixture of Si and C CNTs have excellent electrical properties, using XRD we’d come to this conclusion that, and play different roles in nano-structured at lower temperatures the biggest proportion solar cells They could also be employed as of Si phase is restored However, at this transparent electrode in nano-structured solar temperature, CNT or carbon nano-tubes will cells also be restored (Figure1) These nano-tubes Figure1 X-Ray Diffraction –Mixture Figure X-Ray Diffraction - Mixture B - Sintered: reduced which means that according to Debye By sintering Si and C, and by placing the - Scherrer equation, particle size has increased sample at 1200 °C for minutes, we’ll realize The reduction in resulting peaks intensity that in addition to restoring Si and CNT, indicates rapid weakening in formation of Si, silicon carbide is also restored (Figure 2), But CNT due to the Sintering at 1200 ° C with reduction in their height, their width is M Bouachrine et al., J Appl Chem Res., 7, 4, 71-84 (2013) 77 On the other hand, it is interesting to study how ab-initio HF and DFT calculations performed the p-doped π-conjugated molecule becomes the byJ Casado et al [12] And S.M Bouzzine et ultimate responsible of chargetransport As said al [13] for substitutingoligothiophenes.The before, to obtain oxidized optimized structure, optimized geometry of the cationic compound we started from the optimized structure of the indicates the formation of the positive) polaron neutral form We can conclude that during the defect localized in the middle of the molecule doping process and for all studied compounds the and extending over the adjacent repeat units simple bonds become shorter, while the double The charged species are characterized by ones become longer (Table 2) The inter-rings a reversal of the single double C-C bond bonds are longer than normal double bonds A pattern; the geometry process thus induces the quinoid-like distortion emerges as a result of the appearance of a strong quinoid character within oxidation These results are consistent with the the molecule Table Comparison between di and i forms PCTPYPP neutral and doped d1(Å) d2(Å) d3(Å) d4(Å) d5(Å) 1(°) 2(°) 3(°) 4(°) 5(°) PCTPYPP neutral 1.489 1.473 1.436 1.440 1.480 PCTPYPP doped 1.482 1.443 1.403 1.411 1.456 59.01 -41.41 5.56 6.49 74.38 37.27 11.77 1.12 3.37 19.95 Electronic and photovoltaic properties in comparison with those of compound PCDT Electronic structures are fundamental to The HOMO and LUMO energies ofPCDT to the interpretation and understanding of the PCTPYPP change significantly, (respectively: absorption spectra The calculated frontier -4.96 eV and -1.67eV ; -5.00eV and -1.68eV ; orbital energies (fours occupied orbital and -4.97eV and -2.60eV ; -4.86eV and -1.86eV ; fours unoccupied orbital) and energy gaps -4.71eV and -2.63eV ; -4.64eV and -2.57eV) It between highest occupied molecular orbital can also be found that, the HOMO and LUMO (HOMO) and lowest unoccupied molecular energies of the studied compoundares lightly orbital (LUMO) are listed in Table As shown different This implies that different structures in Table 3, one remark that all studied molecules play key roleson electronic properties In (PCDT, PCDTB, PCDTBT, PCTTT, PCTPY, addition, the energies of Egap of differing PCTPYPP) exhibit stabilization HOMO levels slightly from 3.32eV to 2.07eV depending M Bouachrine et al., J Appl Chem Res., 7, 4, 71-84 (2013) 78 on the different structures They are studied PCDT with alower energy gap (3.00eV) This in the following order PCDTB>PCDT>PCT may be attributed to the presence of an additive TT>PCDTBT>PCTPY>PCTPYPP For the thiophene ring in PCTTT On the other hand comparison between PCDT (HOMO: -4.96eV, the comparison between PCTTT and PCDTB LUMO: -1.67eV) and PCTTT (HOMO: show that the replacement of thiophene -4.86eV, LUMO: -1.86 eV) compounds, ringbyphenylene causes a increase of band itcanbeseena net stabilization of LUMO Gap accompanying with a net stabilization energies and destabilization of the energies of of HOMO and destabilization LUMO levels HOMO.The energygap between HOMO and This is in agreement with what it was found in LUMO of PCTTT is also lower than that of experimental results [6] Table 3.Values of HOMO (eV), LUMO (eV) and Egap (eV) energies calculated for the studied compound obtained by B3LYP/6-31G(d) Compounds E(LUMO) (eV) E(HOMO) (eV) Egap (eV) PCDT -1.67 -4.96 3.29 PCDTB -1.68 -5.00 3.32 PCDTBT PCTTT PCTPY -2.60 -1.86 -2.63 -4.97 -4.86 -4.71 2.36 3.00 2.07 PCTPYPP -2.57 -4.64 2.07 The calculated band gap Egap of the studied the HOMO and LUMO levels were compared compound increases in the following orde As shown in Table 4, the change of molecular rPCDTB>PCDT>PCTTT>PCDTBT>PCT PY> PCTPYPP structure shows a great effect on the HOMO Figure shows detailed and on the LUMO levels The experiment data of absolute energy of the frontier orbitals phenomenon was quite consistent with for studying compounds, ITO, PCBM and previous literature [14], which reported aluminum (Al) is included for comparison that the increase of the HOMO levels may purposes It is deduced that substitution suggest a negative effect on organic solar cell pushes up/down the HOMO/LUMO energies performance due to the broader gap between in agreement with their electron acceptor the HOMO level of the organic molecules and character To evaluate the possibilities of the LUMO level of PCBM (Voc) As shown electron transfer from the excited studied in figure 3, both HOMO and LUMO levels molecules to the conductive band of PCBM, of the studied molecules agreed well with the M Bouachrine et al., J Appl Chem Res., 7, 4, 71-84 (2013) requirement for an efficient photosentizer On 79 HOMO of the studied molecules range from the one hand, the HOMO levels of the studied 1.42 eV to 1.78 eV ,these valuesare sufficient compoundswere higher than that of PCBM for a possible efficient electron injection Knowingthat in organicsolarcells, the open Therefore, all the studied molecules can circuit voltage isfound to belinearlydependent be used as sensitizers because the electron on the HOMO level of the donor and injection process from the excited molecule the LUMO level of the acceptor[15].The to the conduction band of PCBM and the difference between the energy of conduction subsequent regeneration is possible in an band (LUMO) of PCBM and the energy of organic sensitized solar cell -1 LUMO -2 Energy (eV) -3 -4 Al -5 ITO HOMO -6 PCBM PCDT PCDTB PCDTBT PCDTTT PCDTPY PCDTPYPP Figure 3.Data of the absolute energy of the frontier orbitals HOMO and LUMO for the studied molecules and ITO, PCBM and the aluminum (Al) Table Table4.Energyvalues of ELUMO (ev), EHOMO (ev) andtheopen circuit voltage Voc (ev) [16] Compounds PCDT PCDTB PCDTBT PCTTT PCTPY PCTPYPP PCBM E(LUMO) (ev) -1.67 -1.68 -2.60 -1.86 -2.63 -2.57 - 3.22 E(HOMO) (ev) -4.96 -5.00 -4.97 -4.86 -4.71 -4.64 - 5.98 i(ev) 1.55 1.53 0.62 1.36 0.59 0.65 Voc(ev) 1.74 1.78 1.74 1.63 1.48 1.42 80 M Bouachrine et al., J Appl Chem Res., 7, 4, 71-84 (2013) Finally, it is important to examine the HOMO the neutral form possess a π-bonding character and the LUMO for these compounds because within subunit and a π-antibonding character the relative ordering of occupied and virtual between the consecutive subunits while the orbital provides a reasonable qualitative LUMOs possess a π-antibonding character indication of excitations properties [17] within subunit and a π-bonding character In general, as shown in Figure (LUMO, between the subunits whereas it is the opposite HOMO), the HOMOs of these oligomers in in the case of doped forms HOMO LUMO (PCDT) (PCDTB) (PCDTBT) M Bouachrine et al., J Appl Chem Res., 7, 4, 71-84 (2013) 81 (PCTTT) (PCTPY) (PCTPYPP) Figure 4.The contour plots of HOMO and LUMO orbitals of study compounds PCDTtoPCTPYPP in neutral form Absorption and electronic properties PCTPY, PCTPYPPusing ZINDO/s method Based on the optimized molecular structures As illustrated in Table 5, we can find the values with B3LYP/6-31G(d) method We have of calculated wavelength λmax and oscillator calculated the UV-vis spectra of the studied strength (O.S) along with main excitation compounds PCDT, PCDTB, PCDTBT, PCTTT, configuration of the studied compounds M Bouachrine et al., J Appl Chem Res., 7, 4, 71-84 (2013) 82 Excitation to the S1 state corresponds almost give a good description of the absorption exclusively to the promotion of an electron properties of the studied compound and from the HOMO to the LUMO orbital The can be employed to predict the electronic absorption wavelengths arising from S0→S1 characteristics of other materials It should electronic transition increase progressively benoted that the difference between the oretical with the increasing of conjugation lengths It is and experimental value scan be explained reasonable, since HOMO→LUMO transition bythe factthat the calculations assume thatthe is predominant in S0→S1 electronic transition; moleculesin the vapor state the results are a decrease of the LUMO and an Another consider a point in that the position increase of the HOMO energy These values of λmax shows a bathochromic shift when are calculated by ZINDO method starting with passing from PCDT to PCTPYPP, which also optimized geometry obtained at B3LYP/6- can be seen respectively in PCDT(449.56nm), 31G(d) level However, we believe that the PCDTB (425.36nm), PCDTBT(622.68nm), bulk of intermolecular effect must be taken PCTTT(495.80nm), PCTPY(739.50nm) and into account This effect is the source of the PCTPYPP (732.62nm) due to the increasing deviation between the calculation and the of the extended conjugation through the We can remark for comparing calculated and system of aryl groups and multiple bonds experimental results [13] a linear relationship Those interesting pointsare seen both in the between calculated and experimental results theoretical and experimental results[6] Therefore, the DFT theoretical calculations Table 5.Absorption Compound PCDT PCDTB PCDTBT PCTTT PCTPY PCTPYPP abs (nm) obtained by the ZINDO/s method Transition S0 /S1 S0/ S2 S0/ S3 S0 /S1 S0/ S2 S0/ S3 S0 /S1 S0/ S2 S0/ S3 max (nm) 449.56 345.49 337.10 425.36 364.08 336.77 622.68 408.06 396.50 Eex(eV) 0.65178 0.48359 0.38868 0.60567 0.45522 0.37485 0.66374 0.49008 0.38713 O.S 1.5806 0.1405 0.0127 2.0874 0.1359 0.0122 0.9183 0.8340 0.3806 S0 /S1 S0/ S2 S0/ S3 S0 /S1 S0/ S2 S0/ S3 S0 /S1 S0/ S2 S0/ S3 495.80 376.04 337.54 739.50 448.01 412.19 732.62 453.21 432.21 0.64860 0.49076 0.38921 0.67882 0.43195 0.51179 0.67973 0.44252 0.49942 1.7891 0.0743 0.0272 0.9844 0.7645 0.0281 0.8140 0.6735 1.2279 MO/character HOMO LUMO HOMO LUMO+1 HOMO-2 LUMO+1 HOMO LUMO HOMO LUMO+1 HOMO-2 LUMO+1 HOMO LUMO HOMO HOMO-1 HOMO HOMO HOMO-1 HOMO HOMO HOMO-1 HOMO HOMO HOMO-1 LUMO+1 LUMO LUMO LUMO+1 LUMO LUMO LUMO+2 LUMO LUMO LUMO+1 LUMO M Bouachrine et al., J Appl Chem Res., 7, 4, 71-84 (2013) Conclusion 83 and also can be employed to explore their This study, is a theoretical analysis of the suitability in electroluminescent devices geometries and electronic properties of three and in related application Presumably, the various compoundsbased on theoligothiophene procedures of theoretical calculations can be and carbazole which displays the effect of employed to predict and assume the electronic substituted groups and on the structural and properties on yet prepared and efficiency opto-electronic properties of these materials proved the other materials, and further to The concluding remarks are: design novel materials for organic solar cells • The results of the optimized structures for all studied compounds so that they have similar Acknowledgements conformations (quasi planar conformation) We This work was supported by Volubilis found that the incorporation of several groups Program (N° MA/11/248), and the convention does not change the geometric parameters CNRST/CNRS (Project chimie1009) We • The calculated frontier orbital energies are grateful to the “Association Marocaine HOMO and LUMO and energy gaps showed des ChimistesThéoriciens” (AMCT) for its that the energy gaps of the studied molecules pertinent help concerning the programs differs lightly from2.07eV to 3.32eVdepending on the different structures The calculated band References gap Egap of the studied compound increases [1] P.C Hariharan, J.A Pople, Mol Phys., 27, in the following order PCDTB>PCDT>PCTT 209 (1974) T>PCDTBT>PCTPY>PCTPYPP [2] K Müllen, G Wegner (Eds.), Electronic • The replacement of thiophene ring with Materials,The oligomers Approach, Wiley- phenyl enecauses a decrease of band Gap VCH, Weinheim, New York, 1998, pp 105- and a net destabilization of both HOMO and 197 ; J Cornil, D Beljonne, J L Brédas, LUMO levels K Mûllen, G Wegner (Eds.) 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Final version received 04 Sep 2013 Abstract One of the most important goals in medicinal chemistry is the development of new heterocyclic compounds with pharmaceutical activity Thus, a novel series of the derivatives of benzimidazole were synthesized and the structures of all the synthesized compounds have been confirmed by IR, 1H- and 13C-NMR, Mass Spectroscopy and elemental analysis The title compounds have been evaluated for antifungal activities against Candida albicans, Candida glabrata, and Candida krusei Some of these compounds have been found to exhibit moderate to good antifungal activity when compared with commercially available fungicides Keywords: Benzimidazole, Spectroscopic techniques, Antifungal activity, Fungicides Introduction benzimidazoles.[1] Benzimidazole has Benzimidazole is a heterocyclic aromatic fungicidal properties [2-4] It acts by binding organic compound This bicyclic compound to the fungal microtubules and stopping consists of the fusion of benzene and imidazole hyphal growth It also binds to the spindle The usual synthesis involves condensation of microtubules and blocks nuclear division Due o-phenylenediamine with formic acid [1], or to great potential of the moiety, in this work, the equivalent trimethyl orthoformate: is reported a study on synthesis of some novel derivatives of 2-bromomethyl-benzimidazole C6H4(NH2)2+HC(OCH3)3→C6H4N(NH)CH+3 CH3OH (Structures of 5-10 in Figure 1) These derivatives were screened for antifungal By altering the carboxylic acid used, this activity against Candida albicans, Candida method is generally able to afford 2-substituted glabrata, and Candida krusei *Corresponding author: Dr Abbas Ahmadi, Associate Professor, Pharmaceutical Sciences Branch, Islamic Azad University, Tehran, Iran Email: ahmadikiau@yahoo.com, Tel: +98-912-1879707 A Ahmadi et al., J Appl Chem Res., 7, 4, 85-91 (2013) 86 R2 N R3 N R1 5) R1 = NO2 R2 = CH3 R3 = H 6) R1 = NO2 R2 = CH3 R3 = Br 7) R1 = NO2 R2 = R3 = Br 8) R1 = NH2 R2 = CH3 R3 = H 9) R1 = NH2 R2 = CH3 R3 = Br 10) R1 = NH2 R2 = R3 = Br Figure Chemical structures of chemical compound synthesized Experimental Synthesis of Compounds Material and Equipments General procedure for the preparation of the All chemicals and solvents were obtained from compounds (5-7) E-Merck and Sigma-Aldrich and used without 1-Bromo-2,4-dinitrobenzene (2 mmol, 0.5 further purification All melting points are gr) is mixed with DMF (5 ml) and methyl/ uncorrected and taken with an Electrothermal cyclobutylamine (2.2 mmol) The mixture is melting point apparatus (Electrothermal Eng heated at reflux for 12 hrs then cooled and Ltd, Essex, UK) IR spectra were determinate concentrated under vacuum (Intermediates 2a in KBr on a Shimadzu Dr-8031 instrument and 2b) The 2-nitro group of compounds 2a The and 2b was reduced to 2-amino (3a and 3b) by H and 13 C-NMR spectrums of the synthesized compounds were measured in using Na2S/NaHCO3 in methanol according to DMSO-d6 or CDCl3 solution and TMS as Willitzer et al method [5] To a mixture of the the internal standard using a Varian Mercury appropriate benzaldehyde derivative (4a and 400, 400MHz instrument All Chemical shifts 4b) (1.5 mmol) in mL of EtOH, then was were reported as δ (ppm) values The Mass added a solution of 0.01 mole of Na2S2O5 in Spectra were recorded on a LCQ ion trap mass ml of water in portions to the cooled spectrometer (Thermo Fisher San Jose.CA, ethanolic solution The precipitate formed was USA), equipped with an EI source Elemental filtered off and dried A total of 1.2 mmol of analyses were carried out using a Perkin- this precipitate and 1.2 mmol of compound 3a Elmer, CHN elemental analyzer or 3b in ml of DMF were heated under reflux A Ahmadi et al., J Appl Chem Res., 7, 4, 85-91 (2013) 87 for hr, and then it was concentrated At the ppm): 3.41 (t, 3H, CH3), 7.32-7.52 (4H, m, end of this period the reaction mixture was Ar-benzimidazole), 7.85 (d, 1H, Jo= 8.8 Hz), cooled and poured into water and the resulting 8.22 (dd, 1H, Jo =8.8 Hz, Jm= Hz), 8.71 solid was collected, washed with water The (d, 1H, Jm= Hz); 13C-NMR (δ/ppm): 39.1, precipitate re-crystallized from ethanol-water 115.6, 119, 123, 129.5, 131.5, 135.6, 137.0, mixture (Scheme 1) [6, 7] 138.5, 139.2, 146.5, 149.7 Anal Calcd for C14H10BrN3O2: C, 50.62; H, 3.03; N, 12.65 1-methyl-5-nitro-2-phenyl-1H-benzimidazole % Found: C, 50.65; H, 3.08; N, 12.61 % (5) MS (m/z, regulatory intensity, %): 331 (100), White powder; Yield 75%; m.p 125-127 oC; 332(16), 322 (98) IR (KBr, cm-1): 2965 (CH), 1655 (N=C), 1313 (C-N stretching), 889 (C-C bonding aromatic) 2-(4-Bromophenyl)-1-cyclobutyl-5-nitro H-NMR (δ/ppm): 3.68 (t, 3H, CH3, 7.24-7.63 1H-benzimidazol (7) (5H, m, Ar-benzimidazole), 7.95 (d, 1H, Jo= Light yellow powder; Yield 85%; m.p 1918.8 Hz), 8.25 (dd, 1H, Jo =8.8 Hz, Jm= Hz), 193 oC; IR (KBr, cm-1): 2952 (CH), 1672 8.69 (d, 1H, Jm= Hz) 13C-NMR (δ / ppm): (N=C), 1293 (C-N stretching), 918 (C-C 32.1, 115.1, 118, 129.5, 130.5, 133.5, 136.0, bonding aromatic), 681 (C-Br); 1H-NMR (δ/ 137.5, 137.9, 144.4, 148.7 Anal Calcd for ppm): 2.05 (m, 2H, CH2), 2.65 (4H,s,CH2, C14H11N3O2: C, 64.40; H, 4.38; N, 14.59 % Cylobutyl),5.2 (1H,s, CH,Cylobutyl) Found: C, 64.51; H, 4.30; N, 14.48 % MS 7.64 (4H, m, Ar-benzimidazole), 7.76 (d, 1H, (m/z, regulatory intensity, %): 253 (100), Jo= 8.8 Hz,), 8.42 (dd, 1H, Jo =8.8 Hz, Jm= 2254 (16) Hz), 8.75 (d, 1H, Jm= Hz); 13C-NMR (δ/ 7.41- ppm): 21.5, 29.5, 66.5, 117.5, 119.0, 123.5, 2-(4-Bromophenyl)-1-methyl-5-nitro-1H- 126, 128, 129.5, 134.5, 136.8, 143.3, 149.4 benzimidazol (6) Anal Calcd For C17H14BrN3O2: C, 54.86; H, Light yellow powder; Yield 70%, m.p 158- 3.79; N, 11.29 %, Found: C, 54.90; H, 3.76; N, 160 oC; IR (KBr, cm-1): 2975 (CH), 1671 11.33 % MS (m/z, regulatory intensity, %): (N=C), 1294 (C-N stretching), 885 (C-C 371 (100), 373 (97), 372 (25) bonding aromatic), 679 (C-Br); 1H-NMR (δ/ A Ahmadi et al., J Appl Chem Res., 7, 4, 85-91 (2013) 88 Br NHR1 + O2N R1NH2 NO2 NHR Na2S NaHCO3 O2N NO2 O2N a, R1 = methyl b, R1 = cyclobutyl NH2 a, R1 = methyl b, R1 = cyclobutyl R2 R1 N R2 N O2N CH NaO3S (5) , R1 = methyl; R2 = H (6) , R1 = methyl; R2 = Br (7) , R1 = cyclobutyl; R2 = Br OH a, R2 = H b, R2 = Br Scheme Schematic synthesis of intermediates and new compounds (5-7) General procedure for the preparation of the 6.98-7.71 (3H, m, Ar-Bbenzimidazole), 7.63 compounds (8-10) (d, 1H, Jo= 8.8 Hz), 8.14 (dd, 1H, Jo =8.8 Hz, Mixture of 5-Nitrobenzimidazole derivatives Jm= Hz), 8.49 (d, 1H, Jm= Hz); 13C-NMR 5-7 (1 mmol) in 10 mL of hot EtOH and 10 mL (δ/ppm): 38.1, 113.5, 115.5, 118.5, 119.5, of 6N HC1 were heated under reflux and then 129.7 ,132.8, 133.0,134.5, 137.5, 139.8, SnCl2.2H20 was added in portions until the 145.8 Anal Calcd for C14H13N3: C, 75.31; H, starting material was completely exhausted 5.87; N, 18.82 % Found: C, 75.35; H, 5.81; The ethanol was decanted; the residue was N, 18.72 % MS (m/z, regulatory intensity, made alkaline with KOH, then, extracted %): 223 (100), 224 (18) with EtOAc, and washed with water EtOAc was evaporated slowly and the precipitate re- - ( - B r o m o - p h e n y l ) - - m e t h y l - H crystallized from ethanol (Scheme 2) [5-7] benzimidazole-5-ylamine (9) Light yellow powder; Yield 81%, m p 147- 1-Methyl-2-phenyl-1H-benzimidazole-5- 149oC; IR (KBr, cm-1): 3335 (NH), 2955 ylamine (8) (CH), 1642 (N=C), 1281 (C-N stretching), White cream powder; Yield 79%; m p 181- 918 (C-C bonding aromatic), 695 (C-Br); 183 oC; IR (KBr, cm-1):3175 (NH), 2991 (CH), 1633 (N=C), 1289 (C-N stretching), 3H, CH3), 4.71 (s, 2H, NH2), 6.91-7.68 (3H, 892 (C-C bonding aromatic); 1H-NMR (δ/ m, Ar-Bbenzimidazole), 7.65 (d, 1H, Jo= 8.8 ppm): 1.48 (t, 3H, CH3), 4.75 (s, 2H, NH2), Hz), 8.21 (dd, 1H, Jo =8.8 Hz, Jm= Hz), H-NMR (δ/ppm): 1H-NMR (δ/ppm): 1.45 (t, A Ahmadi et al., J Appl Chem Res., 7, 4, 85-91 (2013) 8.52 (d, 1H, Jm= Hz); 13 C-NMR (δ/ppm): 89 915 (C-C bonding aromatic), 702 (C-Br); 31.2, 111.5, 116.5, 119.5, 123, 127.5, 133.8, H-NMR (δ/ppm): 2.20 (m, 2H, CH2), 3.25 (m, 135.3, 137.2, 138.2, 139.8, 148.3 Anal.Calcd 4H, CH2),4.5 (s, 1H, CH), 4.88 (s, 2H, NH2), for C14H12BrN3: C, 55.65; H, 4.00; N, 13.91 6.93-7.68 (3H, m, Ar-Bbenzimidazole), 7.75 % Found: C, 55.60; H, 4.05; N, 13.86 % MS (d, 1H, Jo= 8.8 Hz), 8.48 (dd, 1H, Jo =8.8 Hz, (m/z, regulatory intensity, %): 301 (100), 303 Jm= Hz), 8.67 (d, 1H, Jm= Hz) 13C-NMR (97), 302 (20) (δ/ppm): 19.7, 30.9, 118.5, 119.0,120, 122.5, 126.6, 129.8, 134.5, 139.5, 142.5, 146.1 Anal 2-(4-Bromo-phenyl)-1-cyclobutyl-1H- Calcd For C17H16BrN3: C, 59.66; H, 4.71; N, benzimidazole-5-ylamine (10) 12.28 % Found: C, 59.62; H, 4.69; N, 12.20 White yellow powder; Yield 86%, m p 166- % MS (m/z, regulatory intensity, %): 341 168 oC; IR (KBr, cm-1 ): 3158 (NH), 2997 (100), 343 (98), 344 (21) (CH), 1668 (N=C), 1301 (C-N stretching), R1 R1 R2 O2 N SnCl2 R2 O2 N (5) , R1 = methyl; R2 = H R2 = Br (6) , R1 = methyl; (7) , R1 = cyclobutyl; R2 = Br (8) , R1 = methyl; R2 = H R2 = Br (9) , R1 =methyl; (10) , R1 = cyclobutyl ; R2 = Br Scheme Schematic synthesis of new compounds (8 - 10) Antifungal activity assay concentration (MIC), expressed in µg/mL The yeasts Candida albicans, patient isolate Candida glabrata and Candida krusei were Results and discussion grown on Sabouraud Dextrose Broth (Difco); Chemistry the yeasts were incubated for 48 h at 25.91°C In continuation of our interest to investigate of The antifungal activity tests were carried new pharmaceutical potential compounds, the out at pH 7.4 in Sabouraud Dextrose Broth syntheses of biologically active benzimidazole and the 2-fold dilution was applied A set of derivatives were carried out in this study To tubes containing only inoculated broth was materialize the proposed project, initially, kept as controls After incubation for 48 h at intermediates were synthesized from 25.91°C, the last tube with no yeast growth 1-Bromo-2,4-dinitrobenzene by reaction with was recorded to represent minimum inhibitory methyl/cyclobutylamine in DMF according A Ahmadi et al., J Appl Chem Res., 7, 4, 85-91 (2013) 90 to the literature [5] The 2-nitro group of mL Further dilutions of the compounds and compounds was reduced to 2-amino by using standards in the test medium were prepared at Na2S/NaHCO3 in methanol [5] Condensation the required quantities of 50, 25, 12.5, 6.25, of o-phenylenediamines with the Na2S2O5 3.125, 1.5 and 0.75 µg/mL concentrations The adduct of appropriate benzaldehydes in DMF final inoculums size was 105 CFU/ml The [8] gave 5-7 Reduction of compounds 5-7 MICs were defined as the lowest concentrations with SnCl2.2H20 produced 8-10 The structures of the compounds that prevented visible of 5-10 were deduced from their elemental growth It was determined that the solvent analysis, mass spectrometric data, 1H-and had no antifungal activity against any of the C-NMR, and IR spectral data, given in test microorganisms All the compounds were 13 Experimental section tested for their in vitro growth inhibitory activity against C albicans, patient isolate C glabrata and C krusei (Table 1) Compounds Antifungal activity The in vitro antifungal activity of the compounds 5, 7, and 10 possessed comparable activity was tested by the tube dilution technique [9] Each to fluconazole and cotrimoxazole against C of the test compounds and standards Miconazole, albicans with a MIC of 12.5 µg/mL However Fluconazole and Cotrimoxazole were dissolved none of the compounds was superior to the in 10% DMSO, at concentrations of 100 µg/ standards used against any fungi Table Antifungal activities of the synthesized compounds (MIC, µg/ml ) Compound C.albicans C.glabrata C.krusei 12.5 6.25 6.25 25 25 12.5 12.5 25 6.25 12.5 25 12.5 25 25 6.25 10 12.5 12.5 12.5 Fluconazole 12.5 3.125 3.125 Miconazole 6.25 3.125 1.5 Cotrimoxazole 12.5 3.125 3.125 Conclusion mass spectroscopy and elemental analysis A series of some novel Benzimidazole Our studies clearly demonstrate that novel derivatives were successfully synthesized and Benzimidazole derivatives had significant characterized using IR, 1H- and 13 C-NMR, antifungal activity against different fungi A Ahmadi et al., J Appl Chem Res., 7, 4, 85-91 (2013) species As a consequence, we can conclude that newly synthesized Benzimidazole derivatives can be used for the development of new fungicide References [1] E C Wagner and W H Millett Org Synth Coll., 2, 65 (1943) [2] B Can-Eke, M.O Puskullu, E Buyukbingol, M Ican, Chemico-Biological Interactions, 113, 65 (1998) [3] C Kus, G Ayhan-Kilcigil, B Can-Eke, M Iscan, Arch Pharm Res., 27, 156 (2004) [4] G Ayhan-Kilcigil, C Ku, T Coban, B Can-Eke, M Lcan, J Enz Inhibit Med Chem., 19, 129 (2004) [5] H Willitzer, D Brauniger, D Engelmann, D Krebs, W Ozegowski, M Tonew, Pharmazie, 33(1), 30 (1978) [6] G Ayhan Kilcigil, N Altanlar, Turk J Chem., 30, 223 (2006) [7] A Ahmadi, B Nahri-Niknafs, E-Journal of Chemistry, (S1), S85-S90 (2011) [8] H.F Ridley, R.G.W Spickett, G.M.J Timmis, Heterocyclic Chem., 2, 453 (1965) [9] D.F Sahm, J.A Washington, Antibacterial Susceptibility Tests: Dilution Methods, in Manual of Clinical Microbiology, 5th ed., eds A Balowes, W.J Hausler, K.L Hermann, H.D Shadomy, American Society for Microbiology, Washington DC USA, ,p.1105(1991) 91 ... Branch, Islamic Azad University, Tehran, Iran Journal of Applied Chemical Research, 7, (2013) Journal of Applied Chemical Research (JACR) (Journal of Applied Chemistry, JAC, before) is published... addressed to: Journal of Applied Chemical Research office, Department of Chemistry, Islamic Azad University, Karaj branch, P.O Box 31485-313, Karaj, Iran Journal of Applied Chemical Research, 7,... only the Si and SiC phases Journal of Applied Chemical Research, 7, 4, 15-24 (2013) Journal of Applied Chemical Research w w w j a c r k i a u a c i r Determination of Saturates, Aromatics, Resins