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Item Trihydrazone functionalized cyanopyridine discoids: Synthesis, mesogenic and optical properties(2014) Ahipa, T.N.; Adhikari, A.V.A new series of trihydrazone functionalized cyanopyridine derivatives (CPTH-Dm) carrying 3,4-dialkoxyphenyl groups was designed and synthesized successfully as discotic columnar liquid crystals. These new discoid mesogens display hexagonal columnar phase with a wide mesophase range from ambient temperature to 110 C and the observed columnar assembly is due to the presence of intermolecular hydrogen bonds and ?-? interactions in them. Their optical studies reveal that the compounds are good blue light emitters and hence they are potential candidates for OLED device fabrication. � 2013 Elsevier Ltd. All rights reserved.Item Synthesis, structural analysis and solvatochromic behaviour of 4,6-bis (4-butoxyphenyl)-2-methoxynicotinonitrile mesogen(2013) Ahipa, T.N.; Kumar, V.; Adhikari, A.V.In this communication, we report the synthesis and characterisation of a new luminescent liquid crystalline material, 4,6-bis (4-butoxyphenyl)-2-methoxynicotinonitrile (3). We have confirmed its structure by Fourier transform infrared and 1H nuclear magnetic resonance spectroscopy, elemental analysis and X-ray single crystal diffraction studies. The newly synthesised compound crystallises in a monoclinic system with the space group C2/c and its cell parameters are found to be a = 25.181(4) , b = 15.651(4) , c = 12.703(19) , V = 4880.4 (16) , Z = 8. The results indicate that the presence of weak CH... O and CH... N hydrogen bonding as short-range intermolecular interactions are responsible for the formation of its crystal assembly. The measured torsion angle shows the existence of a distorted structure for the molecule wherein 4-butoxyphenylene ring substituent at the fourth position of the central pyridine ring forms a torsion angle ?[C(4), C(3), C(10), C(19)] of 40.55 . Its liquid crystalline behaviour was investigated with the aid of polarised optical microscopy and differential scanning calorimetry. The study reveals that the compound displays a broad nematic phase in the range of 78-112 C. Further, solution phase optical studies indicate that it is a blue light emitter in different non-polar and polar organic solvents at a concentration of 10-5M. 2013 Copyright Taylor and Francis Group, LLC.Item New luminescent 2-methoxy-6-(4-methoxy-phenyl)-4-p-tolyl-nicotinonitrile: Synthesis, crystal structure, DFT and photophysical studies(2014) Ahipa, T.N.; Kamath, P.R.; Kumar, V.; Adhikari, A.V.In the current communication, we report the synthesis, spectroscopic, crystal structure, DFT and photophysical studies of a new nicotinonitrile derivative, viz. 2-methoxy-6-(4-methoxy-phenyl)-4-p-tolyl-nicotinonitrile (2) as a potential blue light emitting material. The compound 2 was synthesized in good yield via a simple route. The acquired spectral and elemental analysis data were in consistent with the chemical structure of 2. The single crystal study further confirms its three dimensional structure, molecular shape, and nature of short contacts. Its DFT calculations reveal that compound 2 possesses a non-planar structure and its theoretical IR spectral data are found to be in accordance with experimental values. In addition, its UV-visible and fluorescence spectral measurements prove that the compound exhibits good absorption and fluorescence properties. Also, it shows positive solvatochromic effect when the solvent polarity was varied from non-polar to polar. 2014 Elsevier B.V. All rights reserved.Item New columnar liquid crystal materials based on luminescent 2-methoxy-3-cyanopyridines(2014) Ahipa, T.N.; Kumar, V.; Adhikari, A.V.A new series of donor-acceptor-donor (D-A-D) type luminescent mesogens carrying 2-methoxy-3-cyanopyridine as a central core linked with variable alkoxy chain lengths (m = 6 and 8) as terminal substituents was synthesized and characterized using spectral methods. The newly synthesized molecules were subjected to single-crystal X-ray diffraction (SCXRD), powder X-ray diffraction (PXRD), differential scanning calorimetric (DSC), polarizing optical microscopy (POM), and fluorescence emission studies in order to ascertain their mesogenic and photophysical properties. The SCXRD data on 4a and 4b reveal that the presence of short intermolecular contacts, viz. C-H N, C-H O, C-H ?, and ? ? interactions, is responsible for their crystal packing. The measured torsion angle values indicate that molecules possess distorted non-planar structure. The DSC, POM, and PXRD studies confirm that all the molecules show thermotropic liquid crystalline behaviour and exhibit rectangular columnar phase. Further, their UV-visible and fluorescence spectral studies reveal that the target molecules are luminescent displaying a strong absorption band in the range of 335-340 nm and a blue fluorescence emission band in the range of 395-425 nm (both in solution and film state) with good fluorescence quantum yields (10-49 %). 2014 Springer Science+Business Media New York.Item New cyanopyridone based luminescent liquid crystalline materials: Synthesis and characterization(2014) Ahipa, T.N.; Adhikari, A.V.A new series of 4-(3,4-bis(akyloxy)phenyl)-6-(4-((1-(4-cyano- or 4-nitro-benzyl)-1H-1,2,3-triazol-4-yl)-methoxy)phenyl)-2-oxo-1,2-dihydropyridine-3-carbonitriles carrying terminal di-alkoxy chain lengths (viz. octyloxy, decyloxy, dodecyloxy, tetradecyloxy and hexadodecyloxy) as well as terminal polar groups -CN or -NO2 have been designed and synthesized successfully as luminescent mesogens. Their thermotropic behaviors have been studied by means of differential scanning calorimetry and polarized optical microscopy. The supramolecular organizations in them were explored by the temperature dependent X-ray di ffraction method and their photophysical properties were investigated using UV-visible and fluorescence spectral methods. The mesogenic study reveals that the presence of hydrogen bonds, as well as dimerization between the molecules, is mainly responsible for the formation of the ambient temperature hexagonal columnar phase (Colh) in the new molecules. Their photophysical study indicates that the compounds exhibit a strong absorption band at ?370 nm and a blue emission band at ?466 nm with good quantum yields of ?0.62 when compared to quinine sulphate (?f = 0.54) in chloroform. Also, the compounds show a slightly red shift in the absorption band with increased solvent polarity. In liquid crystalline films, they display a bathochromic shift in the emission band because of the intimate overlap of molecular cores in the hexagonal columnar phase. The Royal Society of Chemistry and Owner Societies 2014.Item New 4-(2-(4-alkoxyphenyl)-6-methoxypyridin-4-yl)benzonitriles: Synthesis, liquid crystalline behavior and photo physical properties(2014) Ahipa, T.N.; Kumar, V.; Shankar, Rao, D.S.; Prasad, S.K.; Adhikari, A.V.A new series of luminescent 4-(2-(4-alkoxyphenyl)-6-methoxypyridin-4-yl) benzonitriles containing three ring systems, viz. methoxy pyridine, benzonitrile and alkoxy benzene with variable alkoxy chain length, with bent-core structures were synthesized as potential mesogens and characterized by spectral techniques. Their liquid crystalline behavior was investigated by polarizing optical microscopy (POM), differential scanning calorimetry (DSC) and variable temperature powder X-ray diffraction (PXRD) measurements. The study reveals that compounds with shorter chain lengths [i.e. m = 4] exclusively exhibit the nematic phase while compounds with longer chain lengths [i.e. m = 6-14 (only even)] show predominantly the orthorhombic columnar phase. Single crystal X-ray analysis of 4-(2-(4-butyloxy/octyloxyphenyl)-6-methoxypyridin-4-yl)benzonitriles reveals that they possess slightly non-planar unsymmetrical bent structures and their molecular packing consists of nonconventional H-bond interactions; it also explains the observed liquid crystalline phase. An optical study indicates that the title compounds are good blue emitting materials showing absorption and emission bands in the range 335-345 nm and 415-460 nm, respectively. An electrochemical study of 4-(2-(4-octyloxyphenyl)-6-methoxypyridin-4-yl) benzonitrile shows a band gap of 1.89 eV with HOMO and LUMO energy levels of -5.06 and -3.17 eV, respectively. Also, density functional theory (DFT) calculations confirm its optimized geometry, electronic absorption and frontier molecular orbital distributions. the Partner Organisations 2014.Item Blue emitting 1,8-naphthalimides with electron transport properties for organic light emitting diode applications(2017) Ulla, H.; Kiran, M.R.; Garudachari, B.; Ahipa, T.N.; Tarafder, K.; Adhikari, A.V.; Umesh, G.; Satyanarayan, M.N.In this article, the synthesis, characterization and use of two novel naphthalimides as electron-transporting emitter materials for organic light emitting diode (OLED) applications are reported. The molecules were obtained by substituting electron donating chloro-phenoxy group at the C-4 position. A detailed optical, thermal, electrochemical and related properties were systematically studied. Furthermore, theoretical calculations (DFT) were performed to get a better understanding of the electronic structures. The synthesized molecules were used as electron transporters and emitters in OLEDs with three different device configurations. The devices with the molecules showed blue emission with efficiencies of 1.89 cdA-1, 0.98 lmW?1, 0.71% at 100 cdm-2. The phosphorescent devices with naphthalimides as electron transport materials displayed better performance in comparison to the device without any electron transporting material and were analogous with the device using standard electron transporting material, Alq3. The results demonstrate that the naphthalimides could play a significant part in the progress of OLEDs. 2017 Elsevier B.V.Item 2-Methoxypyridine derivatives: Synthesis, liquid crystalline and photo-physical properties(2014) Ahipa, T.N.; Adhikari, A.V.We herein report the design and synthesis of fourteen new bent shaped luminescent mesogens carrying a pyridine core substituted with various polar groups. They possess a slightly non-planar bent conformation with various intermolecular interactions, as evidenced by their single crystal X-ray diffraction study, and exhibit an ambient to elevated temperature liquid crystalline phase (N or Colr), which has been confirmed by differential scanning calorimetry, polarized optical microscopy, and powder X-ray diffraction techniques. In these compounds, the nature of polar substituents influences significantly the formation of the mesophase over a wide thermal range. The appearance of the nematic phase is due to the presence of the lateral CN group attached to the pyridine core and the terminal F or Cl substituent. The formation of a rectangular columnar phase is attributed to the absence of the lateral CN group in the pyridine core and the presence of the terminal Br, NO2 or 4-pyridyl group. 2014 The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.Item Synthesis and mesomorphism of new 2-methoxy-3-cyanopyridine mesogens(2012) Ahipa, T.N.; Adhikari, A.V.In the present paper, we describe the synthesis and characterization of six new bent -shaped molecules carrying the 2-methoxy-3-cyanopyridine as a core possessing an outer phenylene unit at the lengthening arm with different alkoxy chain lengths (C-10 and C-12). Mesomorphic behaviors of the new compounds were investigated using optical polarizing microscope and DSC studies. Also, the effect of structural variables on mesogenic properties was studied. All the new cyanopyridine derivatives showed good liquid crystalline properties and exhibit smectic phase. � 2012 Copyright Society of Photo-Optical Instrumentation Engineers (SPIE).