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Item investigation on photophysical and third–order nonlinear optical properties of novel thermally–stable thiophene–imidazo [2,1-b][1,3,4] thiadiazole based azomethines(Elsevier, 2019) Kakekochi, Viprabha; Udayakumar, D.; Nikhil, P.P.; Keloth, ChandrasekharanThe use of π–conjugated semiconducting materials in flexible and large–area optoelectronic devices is proliferated worldwide owing to the easy structural modifications and solution processability possible, leading to the change in opto–electronic properties. In this context, new class of thiophene and imidazo [2,1-b][1,3,4] thiadiazole (ITD) based conjugated azomethines (TI1–TI3) were designed and synthesized. The photophysical and electrochemical properties of the synthesized azomethines (TI1–TI3) were investigated experimentally, which were further validated with the aid of theoretical calculations. Further, the azomethines TI1 and TI2 were subjected to Z–scan analysis to study the nonlinear optical (NLO) properties. The molecules exhibited effective two photon absorption (TPA) with the large nonlinear absorption coefficient (βeff) of the order of 10−10 m W−1. The planar structure of TI1 furnished a better interaction between donor and acceptor moieties and extended the π–conjugation, providing an improved βeff (0.81 × 10−10 m W−1) to TI1 compared to that of TI2 (0.55 × 10−10 m W−1). From the results it is inferred that the molecules could be of potential materials to be used in efficient photonic devices.Item Z-scan and degenerate four wave mixing studies on newly synthesized copolymers containing alternating substituted thiophene and 1,3,4-oxadiazole units(2006) Kiran, A.J.; Udayakumar, D.; Chandrasekharan, K.; Adhikari, A.V.; Shashikala, H.D.The third-order nonlinear optical properties of newly synthesized copolymers containing alternating substituted thiophene and 1,3,4-oxadiazole units have been studied in DMF solution at 532 nm by using single beam Z-scan and degenerate four wave mixing techniques with nanosecond laser pulses. The variation of nonlinear response among the copolymers clearly indicates the dependence of ?(3) on donor and acceptor type of units present in the copolymers. The nonlinear refractive index, n2, of the investigated copolymers is found to be negative and the magnitude is as high as 10-10 esu. All samples exhibit strong reverse saturation absorption at the wavelength used and show good optical limiting of nanosecond pulses. The concentration dependence of n2 and the two-photon absorption coefficient (?) has been studied. � 2006 IOP Publishing Ltd.Item Thiophene-based donor-acceptor conjugated polymer as potential optoelectronic and photonic material(2013) Murali, M.G.; Udayakumar, D.; Yadav, V.; Srivastava, R.; Safakath, K.In this paper, we report the synthesis, characterization and optical properties of a donor-acceptor conjugated polymer, PTh-CN, containing 3,4-didodecyloxythiophene and cyanovinylene units. The polymer possesses a low band gap of 1.75 eV as calculated from the onset absorption edge. From the electrochemical study, the HOMO and LUMO energy levels of the polymer are figured out to be -5.52 eV and -3.52 eV, respectively. Polymer light-emitting diodes are fabricated using PTh-CN as the emissive layer with a device configuration of ITO/PEDOT:PSS/PTh-CN/Al. The device showed stable saturated red electroluminescence with CIE coordinate values (0.65, 0.32) at 12 V, which are very close to the values for standard red demanded by the NTSC. In addition, the device showed good colour stability under different bias voltages and the threshold voltage of the PLED device is found to be as low as 3.1 V. Further, a nanocomposite of the polymer and TiO2 nanoparticles is prepared by the dispersion method. The nonlinear optical properties of PTh-CN and PTh-CN/TiO 2 nanocomposite are studied using z-scan technique. The polymer solution, polymer film and polymer/TiO2 nanocomposite film show a strong saturable absorption behaviour. The value of saturation intensity (I s) is found to be of the order 1011-1012 W/m2, indicating that the materials are useful candidates for photonic applications. [Figure not available: see fulltext.] 2013 Indian Academy of Sciences.Item The bioisosteric modification of pyrazinamide derivatives led to potent antitubercular agents: Synthesis via click approach and molecular docking of pyrazine-1,2,3-triazoles(2020) Reddyrajula, R.; Udayakumar, D.Tuberculosis remains as a major public health risk which causes the highest mortality rate globally and an improved regimen is required to treat the drug-resistant strains. Pyrazinamide is a first-line antitubercular drug used in combination therapy with other anti-TB drugs. Herein, we describe the modification of pyrazinamide structure using bioisosterism and rational approaches by incorporating the 1,2,3-triazole moiety. Three sets of pyrazine-1,2,3-triazoles (3a-o, 5a-o and 9a-l) are designed, synthesized and evaluated for their in vitro inhibitory potency against mycobacterium tuberculosis H37Rv. The pyrazine-1,2,3-triazoles synthesized through the bioisosteric modification displayed improved activity as compared to rationally modified pyrazine-1,2,3-triazoles. Among 42 title compounds, seven derivatives demonstrated significant anti-tubercular activity with the MIC of 1.56 ?g/mL, which are two-fold more potent than the parent compound pyrazinamide. Further, the synthesized pyrazinamide analogs demonstrated moderate inhibition activity against several bacterial strains and possessed an acceptable in vitro cytotoxicity profile as well. Additionally, the activity profile of pyrazine-1,2,3-triazoles was validated by performing the molecular docking studies against the Inh A enzyme. Furthermore, in silico ADME prediction revealed good oral bioavailability for the potent molecules. 2019 Elsevier LtdItem Synthesis of novel 5-[(1,2,3-triazol-4-yl)methyl]-1-methyl-3H-pyridazino[4,5-b]indol-4-one derivatives by click reaction and exploration of their anticancer activity(2016) Panathur, N.; Gokhale, N.; Udayakumar, D.; Koushik, P.V.; Yogeeswari, P.; Sriram, D.A series of pyridazino[4,5-b]indole derivatives containing alkyl-, benzyl- and phenacyl-substituted 1,2,3-triazolylmethyl units was synthesized using click chemistry approach. All 30 compounds of the series were screened in vitro against four cancer cell lines, viz. breast cancer cells MDA-MB-231 and MCF 7, human primary glioblastoma U-87 and human neuroblastoma IMR-32 cell lines. Most of the compounds exhibited potent cancer cell growth inhibition activity at very low micromolar concentrations. The IC50 value of compounds 7v and 7x against human neuroblastoma IMR-32 cell line is 0.07 and 0.04 ?M, respectively. Among the tested compounds, ten compounds showed IC50 value less than 1 ?M against MDA-MB-231 cells, whereas against IMR-32 cells, nine compounds and, against U-87 cells, six compounds showed similar inhibition activity. Further, these molecules exhibited prominent binding affinity and docking scores in the molecular simulation study with the target enzyme PI3 kinase. Graphical Abstract: This paper illustrates the synthesis of new fused indole-pyridazinone derivatives containing substituted 1,2,3-triazoles via click chemistry approach. Most of the compounds exhibited potent cancer cell growth inhibition activity at very low micromolar concentrations. [Figure not available: see fulltext.] 2015 Springer Science+Business Media New York.Item Synthesis of new pyrazole-triazole hybrids by click reaction using a green solvent and evaluation of their antitubercular and antibacterial activity(2016) Nayak, N.; Ramprasad, J.; Udayakumar, D.; Yogeeswari, P.; Sriram, D.; Kumar, H.S.S.; Peethambar, S.K.; Achur, R.A new series of pyrazole-based 1,2,3-triazole derivatives (6a-x) were synthesized by employing click reaction using a 2:1 mixture of PEG-400 and water as green solvent. The synthesized intermediate and final compounds were characterized by 1H NMR, 13C NMR, and mass spectra and elemental analysis techniques. The structure of one of the final compounds, 6a was evidenced by single crystal X-ray diffraction study. Among the twenty-four compounds, five compounds (6a, 6b, 6d, 6f, and 6g) showed significant antitubercular activity against Mycobacterium tuberculosis H37Rv with a minimum inhibitory concentration (MIC) ? 6.25 ?g/mL. The 4-(((5-(4-Chlorophenyl)-1-phenyl-1H-pyrazol-3-yl)methoxy)methyl)-1-cyclohexyl-1H-1,2,3-triazole (6g) was the most potent compound of the series, which showed a MIC of 3.13 ?g/mL. The cytotoxicity study of active anti-TB compounds on normal Vero cells revealed that the compounds are non-toxic with a high selectivity index (>37). Most of the pyrazole-1,2,3-triazole derivatives with a 4-chlorophenyl substitution at position-5 of the pyrazole ring showed a better anti-TB activity than the corresponding 4-bromophenyl or 4-methoxyphenyl substituted derivatives. The target compounds were also evaluated for their in vitro antibacterial activity and six compounds (6a, 6c, 6d, 6e, 6l, and 6w) showed promising inhibition activity against four tested strains. Springer Science+Business Media Dordrecht 2015.Item Synthesis and third order optical nonlinearity studies of the donor-acceptor conjugated polymer, poly(2-[3,4-didodecyloxy-5-(1,3,4-oxadiazol- 2-yl)thiophen-2-yl]-5-phenyl-1,3,4-oxadiazole) and a polymer/TiO2 nanocomposite(2010) Murali, M.G.; Ramya, M.G.; Udayakumar, D.; Lakshmi, N.B.; Philip, R.A donor-acceptor conjugated polymer (PDOThPOD) containing 3,4-didodecyloxythiophene and (1,3,4-oxadiazolyl)benzene units is synthesized by using precursor polyhydrazide route. Cyclic voltammetry studies reveal that the polymer possesses a low-lying LUMO energy level (-3.57 eV). A nanocomposite of polymer PDOThPOD and nano TiO2 is also prepared. The linear optical properties of PDOThPOD and the nanocomposite are studied using UV-vis absorption spectroscopy and fluorescence emission spectroscopy. z-scan technique is used to study the third order nonlinear optical properties of the polymer and nanocomposite films. Both polymer and nanocomposite films show a strong optical limiting behavior. The value of nonlinear absorption coefficient (?) is found to be of the order of 10-7 m/W, indicating that these materials are potentially suited for fabricating optical limiters. 2010 Elsevier B.V. All rights reserved.Item Synthesis and study of optical properties of linear and hyperbranched conjugated polymers containing thiophene and triphenylamine units(2014) Prashanth, Kumar, K.R.; Murali, M.G.; Udayakumar, D.We report the synthesis of solution processable donor-acceptor type conjugated monomer (M1) and polymers (P1 and P2) consisting of electron-accepting 1,3,4-oxadiazole unit and electron-donating 3,4-didecyloxythiophene, and triphenylamine units through Wittig polycondensation reaction. The linear polymer P1 is thermally stable up to 325 C whereas the hyperbranched polymer P2 showed better thermal stability with an onset of decomposition at 375 C. Polymer P2 showed lower band gap energy (1.96 eV) than that of P1 (2.09 eV). Polymers P1 and P2 emit yellow and orange light, respectively, under the irradiation of UV light. Electrochemical studies revealed that the polymers possess high-lying highest occupied molecular orbital and low-lying lowest unoccupied molecular orbital energy levels. Polymer light-emitting diodes are fabricated with the device configuration of ITO/PEDOT:PSS/polymer (P1 or P2)/Al. The device based on P2 showed a very low threshold voltage of 2 V. The third-order nonlinear optical properties of the polymers are studied using Z-scan technique. Both polymers showed a strong optical limiting behavior. The value of nonlinear absorption coefficient (?) of the polymers is of the order 10-10mW-1 which indicates that these materials may be accomplished for fabricating optical limiters. 2013 Taylor & Francis.Item Synthesis and antimycobacterial screening of new N-(4-(5-aryl-3-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-pyrazol-1-yl)phenyl)-4-amide derivatives(2016) Nayak, N.; Ramprasad, J.; Udayakumar, D.; Yogeeswari, P.; Sriram, D.This article demonstrates the synthesis, characterization and the study of in vitro antitubercular activities of twenty four new N-(4-(5-aryl-3-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-pyrazol-1-yl)phenyl)-4-amide derivatives (8a-x). The antitubercular activity of the compounds against Mycobacterium tuberculosis H37Rv (MTB) revealed that 2-chloro-N-(4-(5-(4-chlorophenyl)-3-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-pyrazol-1-yl)phenyl)benzamide (8n) is the most promising lead molecule with a MIC of 1.56 ?g/mL, while the corresponding unsubstituted benzamide derivative (8o) is the next most active molecule with a MIC of 3.13 ?g/mL. Interestingly, the pyrazole intermediate 5b containing chlorophenyl and N-acylcarbohydrazide substituents also showed significant activity (MIC = 3.13 ?g/mL). Further, the active molecules did not show toxicity against a normal NIH 3T3 cell line, signifying their suitability for further drug development. 2016 Udayakumar Dalimba.Item Synthesis and biological evaluation of new imidazo[2,1-b][1,3,4]thiadiazole-benzimidazole derivatives(2015) Ramprasad, J.; Nayak, N.; Udayakumar, D.; Yogeeswari, P.; Sriram, D.; Peethambar, S.K.; Achur, R.; Kumar, H.S.S.In this report, we describe the synthesis and biological evaluation of a new series of 2-(imidazo[2,1-b][1,3,4]thiadiazol-5-yl)-1H-benzimidazole derivatives (5a-ac). The molecules were analyzed by 1H NMR, 13C NMR, mass spectral and elemental data. The structure of one of the pre-final compounds, 6-(4-methoxyphenyl)-2-(4-methylphenyl)imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde (4d) and that of a target compound, 2-[2-methyl-6-(4-methyl phenyl) imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-1H-benzimidazole (5aa) were confirmed by single crystal XRD studies. All the target compounds were screened for in vitro anti-tuberculosis activity against Mycobacterium tuberculosis H37Rv strain. Seven (5c, 5d, 5l, 5p, 5r, 5z and 5aa) out of twenty nine compounds showed potent anti-tubercular activity with a MIC of 3.125 ?g/mL. A p-substituted phenyl group (p-tolyl or p-chlorophenyl) in the imidazo[2,1-b][1,3,4]thiadiazole ring and/or a chloro group in the benzimidazole ring enhance anti-tuberculosis activity whereas a nitro group in the benzimidazole ring reduces the activity. In the antibacterial screening, compounds 5i, 5w and 5ac showed promising activity against the tested bacterial strains. Further, antifungal and antioxidant activities of these molecules were also investigated. In the cytotoxicity study, the active antitubercular compounds exhibited very low toxicity against a normal cell line. 2015 Elsevier Masson SAS.