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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 Third-order nonlinear optical studies of newly synthesized polyoxadiazoles containing 3,4-dialkoxythiophenes(2006) Udayakumar, D.; John, Kiran, A.; Adhikari, A.V.; Chandrasekharan, K.; Umesh, G.; Shashikala, H.D.The third-order nonlinear optical properties of newly synthesized soluble polyoxadiazoles containing 3,4-dialkoxythiophenes were investigated by using Z-scan and degenerate four-wave mixing (DFWM) techniques. The measurements were performed at 532 nm with 7 ns pulses from a Nd:YAG laser. We found a good agreement between the values of ?(3) determined from both the experiments. Z-scan results indicate a negative nonlinear refractive index, n2, whose magnitude is of the order of 10-10 esu for all the copolymers. The variation of nonlinear response among the copolymers clearly indicates the dependence of ?(3) on donor and acceptor type of units present in these copolymers. The copolymers exhibit strong reverse saturable absorption and good optical limiting properties at 532 nm. 2006 Elsevier B.V. All rights reserved.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, characterization, and nonlinear optical properties of donor-acceptor conjugated polymers and polymer/Ag nanocomposites(2012) Murali, M.G.; Udayakumar, D.; Sridharan, K.Two new donor-acceptor (D-A) conjugated polymers P1 and P2 containing 3,4-didodecyloxythiophene and 1,3,4-oxadiazole units are synthesized via Wittig reaction methodology. Cyclic voltammetry studies reveal that the polymers are both p and n dopable, and possess low-lying LUMO energy levels (-3.34 eV for P1 and -3.46 eV for P2) and high-lying HOMO energy levels (-5.34 eV for P1 and -5.27 eV for P2). The optical band gap of the polymers is in the range of 2.25-2.29 eV, calculated from the onset absorption edge. The polymers emit orange to yellow light in the film state when irradiated with a UV light. The synthesized polymers are used to prepare polymer nanocomposites with different wt% of silver nanoparticles. The polymer nanocomposites are characterized by UV-Vis absorption spectroscopy, field emission scanning electron microscopy, and thermogravimetric analysis. Both polymers and polymer/ Ag nanocomposites show good thermal stability with onset decomposition temperature around 300 C under nitrogen atmosphere. The nonlinear optical properties of polymers and polymer/Ag nanocomposites are measured by Z-scan technique. Both polymers and polymer nanocomposites show a good optical limiting behavior. Nearly five times enhancement in the nonlinear optical properties is observed for polymer/Ag nanocomposites. The value of effective two-photon absorption coefficient (?) is in the order of 10 -10-10 -11 m/W. These results indicate that the synthesized polymers (P1 and P2) and their Ag nanocomposites are expected to be good candidates for application in photonic devices. Springer Science+Business Media, LLC 2012.Item 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 nonlinear optical characterization of copolymers containing alternating 3,4-dialkoxythiophene and 1,3,4-oxadiazolydbenzene units(2007) Udayakumar, D.; Kiran, A.J.; Adhikari, A.V.; Chandrasekharan, K.; Shashikala, H.D.We report the synthesis and linear and third-order nonlinear optical (NLP) characterization of two novel copolymers containing alternating 3,4-dialkoxythiophene and 1,4-bis(1,3,4-oxadiazolyl)benzene units. The copolymers were synthesized with a precursor polyhydrazide route. Both copolymers exhibited fluorescence around 430 nm under the irradiation of UV light. The NLO measurements were made with the single-beam Z-scan technique with Nd:YAG nanosecond laser pulses at 532 nm. The nonlinear refractive index of the investigated copolymers was negative, and the magnitude was as high as 10 -10 esu. The samples exhibited strong reverse saturation absorption and very good optical limiting properties at the wavelength used. The concentration dependence of third-order NLO parameters was studied. 2007 Wiley Periodicals, Inc.