757240-40-7Relevant academic research and scientific papers
Anticancer, antimicrobial activities of quinoline based hydrazone analogues: Synthesis, characterization and molecular docking
Katariya, Kanubhai D,Shah, Shailesh R.,Reddy, Dushyanth
, (2020)
Based on the biologically active heterocycle quinoline, a series (18a-p) of quinoline hydrazone analogues were prepared, starting from 6-bromo/6-chloro-2-methyl-quinolin-4-yl-hydrazines. For all the newly synthesized compounds cytotoxic activities were carried out at the National Cancer Institute (NCI), USA, against full NCI 60 human cancer cell lines. Amongst all the tested compounds, nine compounds (18b, 18d, 18e, 18f, 18g, 18h, 18i, 18j, 18l) exhibited important anti-proliferative activity at 10 μM concentration and were further screened at 10-fold dilutions of five different concentrations (0.01, 0.1, 1, 10 and 100 μM) with GI50 values ranging from 0.33 to 4.87 μM and LC50 values ranging from 4.67 μM to >100j μM. Further, the mean values of GI50, TGI and LC50 of the most potent compound 18j were compared with the clinically used anticancer agents bendamustine and chlorambucil, revealed that the quinolyl hydrazones holds promise as a potential anticancer agents. Further all the newly prepared compounds were screened for their antimicrobial activity. All the quinolyl hydrazones displayed good to excellent antimicrobial activity with MIC values ranging from 6.25 to 100 μg/mL against the tested pathogenic strains. Molecular docking of the synthesized compounds into the active binding site of human DNA topoisomerase I (htopoI) was carried out to predict the binding mode to the DNA topoisomerase I inhibitors. Hopefully in future, compounds based on quinoline core could be used as a lead compounds for designing new anticancer agents.
Synthesis, mesomorphism, photophysics and device performance of liquid-crystalline pincer complexes of gold(iii)
Parker, Rachel R.,Liu, Denghui,Yu, Xiankang,Whitwood, Adrian C.,Zhu, Weiguo,Williams,Wang, Yafei,Lynam, Jason M.,Bruce, Duncan W.
, p. 1287 - 1302 (2021/02/12)
Emissive gold(iii) complexes of pincer 2,6-diphenylpyridines also bearing a phenylacetylide ligand have been modified at both the pincer and phenylacetylide to confer liquid crystalline properties, with most complexes showing a columnar hexagonal phase in
Effect of regioisomerism on the self-assembly, photophysical and gelation behavior of aroylhydrazone based polycatenars: Synthesis and characterization
Kanth, Priyanka,Singh, Hemant Kumar,Kumar, Vijay,Singh, Sachin Kumar,Rao, D.S. Shankar,Prasad, S. Krishna,Singh, Bachcha
, (2019/07/02)
In this paper we report five series of aroylhydrazone based polycatenars differing from each other in number and position of alkoxy chains on one end of the core; keeping other end the same. A systematic variation in the structures was carried out to understand the effect of position and chain length on the mesophase behavior. In the case of single alkoxy chain at 4-position, there is a transition from Smectic C to Smectic A mesophase during cooling and Smectic A to Smectic C transition in heating cycle in all the homologues except n = 6 & n = 8. In the case of two alkoxy chains at 3-, 5-positions, the compounds are non-mesogenic in nature. On changing the position of alkoxy chains from 3-, 5-positions to 3-, 4-positions, intermolecular forces weaken and these compounds become liquid crystalline and show columnar rectangular mesophase resulting from the effect of regioisomerism. Moving on to the series with three alkoxy chains, it was observed that 2-, 3-, 4-trialkoxy substituted compounds exhibit columnar rectangular mesophase except lower chain length (n = 6 & 8) while 3-, 4-, 5-trialkoxy substituted aroylhydrazones show columnar rectangular mesophase; except n = 10 which shows columnar oblique mesophase. Thus it was established that on increasing density of alkoxy chains around one terminal, mesophase changes from smectic to columnar mesophase. Temperature dependent Raman studies confirm the presence of intermolecular hydrogen bonding. Further, effect of substitution pattern did not show much influence on the photophysical properties of the mesogenic series in solid and solution state. However, the non-mesogenic series showed a different absorption and emission transition from the mesogenic series in solid and solution state. Solid state fluorescence studies show almost similar emission maxima in all the series. However, it was also noticed that non-mesogenic series show maximum red shifted emission maxima in solid state as compared to that of solution. All the series showed good gelation properties with less than 1% CGC (wt%) suggesting the strong ability of molecules to form gel. These H-bonded liquid-crystalline gels have immense potential for applications in emissive displays.
Supramolecular columnar self-assembly of wedge-shaped rhodanine based dyes: Synthesis and optoelectronic properties
Vinayakumara,Kumar, Sandeep,Adhikari, Airody Vasudeva
, p. 215 - 222 (2018/11/20)
The development of small π-conjugated functional organic molecules capable of forming supramolecular columnar self-assembly, is a rapidly growing area of material research. In this context, the present work describes the design and synthesis of a new seri
Self-assembly of taper- and wedge-shaped maleimide derivatives: Synthesis and structure-property relationship
Vinayakumara,Kumar, Sandeep,Prasad, S. Krishna,Adhikari, Airody Vasudeva
, p. 765 - 772 (2019/04/25)
Herein, we describe design and synthesis of five new amphiphilic systems, viz. 10b-c and 11a-c composed of maleimide at the focal point and alkoxy phenyl ring at the periphery. Their self-assembling behaviour was examined systematically by varying the length of hydrophobic part and aromatic core segment. Evidently, on increasing the aromatic core length, maleimide based amphiphiles relatively emerge as two distinct molecular structures, i.e. wedge- and tapered-shaped. The mesomorphic studies of the two series reveal that, tapered-shaped maleimide derivatives assemble into a smectic A phase with an interesting phasmidic arrangement, whereas the wedge-shaped molecules exclusively form a prospective supramolecular hexagonal columnar mesophase through the intermolecular hydrogen-bonding via maleimide head group. These self-assembled materials could demonstrate high-sensitivity towards various external stimuli.
Synthesis and photophysical investigations of C3-triazine based star-like conjugated molecules
Duraimurugan, Kumaraguru,Dhanamoorthy, Vaithialingam,Madhavan, Jagannathan,Siva, Ayyanar
, p. 164 - 171 (2018/04/20)
Here, we reported two different C3-triazine based star-like D-π-A compounds with a very good yield by Wittig-Horner reaction. Photophysical, aggregation enhanced emission and electrochemical properties were systematically studied. These compoun
s-Triazine-Based Functional Discotic Liquid Crystals: Synthesis, Mesomorphism and Photoluminescence
Veerabhadraswamy, B. N.,Dambal, Hashambi K.,Rao, D. S. Shankar,Yelamaggad, C. V.
, p. 2225 - 2237 (2016/08/27)
A new series of C3-symmetric, π-conjugated molecules was designed, synthesized and characterized. The materials were derived from electron-accepting s-triazine, appended covalently to electron-donating styrylbenzene arms, and were readily prepared in excellent yield with high purity by means of three-fold condensation of triphosphonate with n-alkoxybenzaldehydes under Horner–Wadsworth–Emmons reaction conditions. Examination of the phase transitional properties by several complementary techniques evidenced self-assembly into a hexagonal columnar phase, occurring over wide and reasonable thermal ranges. The photophysical properties were studied both in solution and in the fluid/frozen columnar states by UV/Vis absorption and photoluminescence spectroscopy. The emission spectra obtained as a function of the temperature rule out the breaking-up of larger columns and a non-radiative, thermally activated process. A study carried out on thin films of the glassy columnar state, which accounts for conserved fluorescence, defect-free orientation, and freezing ionic species, with the help of atomic force microscopy (AFM) images, suggested a homogeneous granular morphology comprising fibrillar structures. Dissimilarities in the surface morphology and birefringence of thin films of the solid and frozen columnar states were clearly shown by Raman spectroscopy. An electrochemical investigation revealed a LUMO energy of ?4.0 eV. Thus, the discotic motifs presented herein meet certain criteria of organic materials, which are essential for developing electronic devices.
Piezoflurochromism and Aggregation Induced Emission Properties of 9, 10-bis (trisalkoxystyryl) Anthracene Derivatives
Duraimurugan, Kumaraguru,Sivamani, Jayaraman,Sathiyaraj, Munusamy,Thiagarajan, Viruthachalam,Siva, Ayyanar
, p. 1211 - 1218 (2016/07/30)
We report the synthesis of trisalkoxy substituted 9, 10-bis styrylanthracene derivatives (C8-ant and C12-ant) by Heck coupling with very good yield and their photophysical properties. Both C8-ant and C12-ant exhibit aggregation induced emission (AIE), mec
Tuning the thermotropic properties of liquid crystalline p-substituted aroylhydrazones
Singh, Hemant Kumar,Singh, Sachin Kumar,Nandi, Rajib,Singh, Madan Kumar,Kumar, Vijay,Singh, Ranjan K.,Rao, D. S. Shankar,Prasad, S. Krishna,Singh, Bachcha
, p. 44274 - 44281 (2015/06/02)
The synthesis and mesomorphic properties of forty substituted aroylhydrazones with peripheral mono-, di- and tri- alkoxy chains derived from a p-amino aroylhydrazone core are described. The compounds with two side chains exhibited a smectic A phase, while the compounds with six soft alkoxy side chains at symmetrical positions formed a rectangular columnar mesophase. The structures of these mesophases were confirmed by differential scanning calorimetry (DSC) analysis, polarized optical microscopy (POM) and powder X-ray diffraction (XRD) studies. Raman studies with the help of density functional theory on some of the mesogenic members have been performed to understand the changes in the intermolecular interactions during phase transitions. A structure-property relationship has been deduced, and mesogenic properties are found to be dependent on the chain length, density and position of the alkoxy chains around the molecular core.
Benzothiadiazole-based dyes that emit red light in solution, solid, and liquid state
Ishi-I, Tsutomu,Sakai, Miki,Shinoda, Chihiro
, p. 9475 - 9480 (2013/10/08)
In this paper, we report the preparation and red-light-emitting behavior of benzothiadiazole-tris(alkyloxy)phenylethene dyes. In solution, we observed an efficient red light emission with high fluorescence quantum yields (up to 0.78). With increase in solvent polarity, the emission bands shifted to longer wavelengths accompanied by a large Stokes shift of up to 152 nm. A moderate fluorescence quantum yield of 0.52 could be achieved even in the polar solvent dimethylformamide. Red light emission with good fluorescence quantum yields (up to 0.50) was also observed in the bulk solid, liquid, and film state.
