67707-09-9Relevant articles and documents
Human peripheral blood mononuclear cells targeted multidimensional switch for selective detection of HSO3? anion
Bhattacharyya, Maitree,Das, Partha Pratim,Das, Sangita,Ghoshal, Kakali,Mondal, Tapan Kumar,Patra, Lakshman,Thomas, Sabu,Walton, James W.
, (2021/12/13)
A new ratiometric π-conjugated luminophore with donor-acceptor (D- π- A) network CM {(E)-2-(4-(2-(9-butyl-9H-carbazol-3-yl)vinyl)benzylidine)malononitrile} has been synthesized by malononitrile conjugated carbazole dye with an intervening p-styryl spacer. Here, p-styryl conjugated malononitrile is used as a recognition site for the detection of HSO3? with a fast response time (within 50 s). In a mixed aqueous solution, CM reacts with HSO3? to give a new product 1-(9-butyl-9H-carbazol-3-yl)-2-(4-(2, 2-dicyanovinyl)phenyl)ethane-1-sulfonic acid. The probe exhibits positive solvatofluorochromism with solid state red fluorescence. The restriction of intermolecular rotation of p-styryl conjugated malononitrile unit enhances the typical solid state fluorescence properties. The probe (CM and its corresponding aldehyde CA) also demonstrates a strong solvent dependence yielding blue to green to pink and even red fluorescence in commonly used organic solvents like n-hexane, toluene, diethyl ether (DEE), THF, DCM, Dioxane, CH3CN and MeOH. The chemodosimetric approach of HSO3? selectively takes place at the olefinic carbon exhibiting a prominent chromogenic as well as ratiometric fluorescence change with a 147 nm blue-shift in the fluorescence spectrum. CM can detect HSO3? as low as 1.21 × 10?8 M. Moreover, the CM can be successfully applied to detect intrinsically generated intracellular HSO3? in human peripheral blood mononuclear cells (PBMCs). CM has shown sharp intensities (2628 ± 511.8) when the cells are HSO3? untreated. At green channel (at 486 nm) almost negligible fluorescence intensities are found (423 ± 127.5) for HSO3? untreated samples. However, the green fluorescence (2863 ± 427.5) increases significantly (p 3?. The CM has been effectively utilized for evaluating the bisulfite ions in food samples as well. The concentrations of HSO3? in diluted sugar samples have been determined with the recovery of 97.6–9.12%.
Carbazole-based π-conjugated 2,2′-Bipyridines, a new class of organic chromophores: Photophysical, ultrafast nonlinear optical and computational studies
Bodapati, Ramakrishna,Das, Samar K.,Dey, Gaurav Ranjan,Jose, K. V. Jovan,Krishnakanth, Katturi Naga,Ramteke, Gunjan R.,Rao, S. Venugopal
, (2020/11/03)
The developmen of donor-acceptor (D-A) architecture based organic chromophores with large two-photon absorption (2 PA) cross-sections are essential for myriad of applications, ranging from nonlinear microscopy to biomedical imaging. Here, we present the results from a comprehensive study of 2 PA cross-sections of a new series of carbazole mono substituted-π-conjugated-2,2′-bipyridine derivatives with D-π-A architecture, possessing carbazole as the donor moiety and bipyridine core as an acceptor. Further, we have extended the π-conjugation by introducing the phenyl and butoxy substituted phenyl linkers. The fluorescence properties of these D-A chromophores are highly sensitive to solvent polarity and alteration of electron donor functionalities. The relevant computation studies support our experimental results, e.g., a shift in emission maxima and band gaps of the molecules. The third-order nonlinear optical (NLO) properties of the title donor-acceptor (D-A) chromophores demonstrated that 2 PA cross-section values are in the range of 6–39 GM, obtained using ~50 fs (fs) laser pulses at a wavelength of 800 nm. Further, the nonlinear refractive indices (n2) of these chromophores were found to be ~10?14 cm2/W, rendering them potential optical switching candidates since the coefficients were obtained with kHz, fs pulses extracting pure electronic nonlinearities. Based on our experimental findings and theoretical calculations presented in this study, we believe that carbazole-based π-conjugated 2,2′-bipyridines, demonstrated in this work, would be potential ligands to obtain a series of transition metal coordination complexes of interesting physical properties (for example, superior NLO behaviour).
The aggregation induced fluorescence effect enhanced by a reasonable length of carbon chain
Zhang, Hanjun,Tao, Furong,Cui, Yuezhi,Xu, Zhen
, (2020/02/04)
Six different barbituric acid derivatives using ethyl, propyl, butyl, pentyl, hexyl and heptyl groups as hydrophobic substituents were prepared. Molecular dynamics simulation was carried out to study the effect of different carbon chain lengths on the aggregation-induced emission process. Among the compounds, the CB-5 containing a hexyl substituent exhibited the strongest Aggregation induced emission (AIE) effect, not the CB-6 with longest carbon chain. The aggregates of CB-5 was used to detect the 2, 4, 6-trinitrotoluene (TNT) in aqueous media, exhibiting a maximum quenching constant of 3.1 × 105 M? 1. The paper sensor based on CB-5 showed a superior sensitivity toward TNT both in vapor and solution. This provided a clear strategy for designing compounds that utilize the hydrophobic interaction of long-chain alkyl chains to enhance the AIE effect.
Hydrazide-integrated carbazoles: Synthesis, computational, anticancer and molecular docking studies
Krishnan, Kannan Gokula,Ashothai, Pathinettampadi,Padmavathy, Krishnaraj,Lim, Wei-Meng,Mai, Chun-Wai,Thanikachalam, Punniyakoti V.,Ramalingan, Chennan
, p. 12069 - 12077 (2019/08/07)
A new class of carbazole-based hydrazides 6a-c, synthesized from carbazole by employing a multistep synthetic strategy, has been described. Detailed insight into their structures (6a-c) has been elucidated by UV-Vis, FT-IR and NMR (1H and 13C) spectroscopic studies. Theoretical investigation of the molecules 6a-c has been accomplished utilizing DFT and TD-DFT techniques with the B3LYP/6-311++G(d,p) method. Theoretical findings such as optimized structural, vibrational, and electronic properties, and proton and carbon chemical shifts of the targets 6a-c are in harmony with their experimental results and/or structurally related reported ones. Cytotoxicity of the target hydrazides 6a-c has been evaluated using human pancreatic cancer cells (AsPC1 and SW1990). The hydrazides 6a-c displayed a significant in vitro cytotoxic effect against both the pancreatic cancer cells AsPC1 (concentration that inhibits 50% cell viability, IC50: 3.42 ± 0.41 μM for 6a) and SW1990 (IC50: 22.42 ± 1.40 μM for 6a). The superior binding energy resulting from the in silico molecular docking approach of the hydrazide 6a indicates its greater affinity towards the receptor (binding energy: -8.63 kcal mol-1 and IC50: 475.05 nM). Thus, the hydrazide 6a could serve as a new lead for the development of anticancer agents.
Novel acrylamide/acrylonitrile-tethered carbazoles: Synthesis, structural, biological, and density functional theory studies
Padmavathy, Krishnaraj,Krishnan, Kannan Gokula,Kumar, Chandran Udhaya,Sathiyaraj, Ethiraj,Sivaramakarthikeyan, Ramar,Lim, Wei-Meng,Mai, Chun-Wai,Ramalingan, Chennan
, p. 13418 - 13429 (2019/09/06)
A series of novel carbazolylacrylamides/acrylonitriles 6a-6h were synthesized and their structures were established using various analytical, spectroscopic, and single-crystal X-ray diffraction techniques. The antioxidant evaluation of the target chemical entities 6a-6h was conducted by the DPPH method. The carbazolylacrylonitrile 6h displayed 65.7% radical scavenging activity (IC50 value, 65.08 μM) with respect to standard ascorbic acid. The in vitro cytotoxic activity studies revealed 6e and 6h as promising anticancer molecules against a human pancreatic cancer cell line, i.e., AsPC1. Density functional theory studies of a model chemical entity 6g were performed and the results obtained were compared with those obtained experimentally. The appropriate structure, the corresponding bonding features and the vibrational frequencies for the molecule 6g were determined by employing the DFT-B3LYP method with the 6-311++G(d,p) basis set. The vibrational frequencies of the carbazolylacrylonitrile 6g calculated theoretically were found to be in good agreement with the corresponding experimental results. In addition, the chemical shifts of 1H and 13C of 6g were computed by the gauge independent atomic orbital (GIAO) method and compared with the experimental ones.
Density functional theory study of carbazole dyes: Potential application of carbazole dyes in dye-sensitized solar cells
Salimi Beni, Alireza,Zarandi, Maryam,Hosseinzadeh, Behzad,Najafi Chermahini
, p. 155 - 163 (2018/05/03)
Dyes applied in dye synthesized solar cells are an important class of organic compounds. In order to extension novel dyes, three organic dyes (TB-CH, TB-CB and DTB-CB) which contain hexyl and butyl moieties as a branch and thiobarbutiric acid moiety as an electron acceptor, connected by carbazole unit have been studied. We report the synthesis, molecular structures, and study of adsorption of dyes on TiO2 anatase by density functional theory (DFT). Molecular orbital analysis study indicated all dyes can give suitable electron injection from their LUMO orbitals to the TiO2 conduction band. Also, dyes were investigated by UV spectroscopy and cyclic voltammetry (CV). The synthesized dyes were characterized extensively by IR, 1HNMR, 13CNMR, mass spectroscopy and CHN analysis. Results of Photo physical, electrochemical properties and density functional theory investigation indicated TB-CH, TB-CB and DTB-CB have potential for application in dye sensitized solar cell. The adsorption energy of each dye/TiO2 complex was ?1.05, ?1.01 and ?1.00 eV for TB-CH, TB-CB and DTB-CB, respectively.
Preferential intermolecular interactions lead to chiral recognition: Enantioselective gel formation and collapse
Gambhir, Diksha,Kumar, Sunil,Dey, Gourab,Krishnan, Venkata,Koner, Rik Rani
supporting information, p. 11407 - 11410 (2018/10/20)
Interesting self-assembly of an amino acid based molecular material into a hydrogel in the presence of selective enantiomeric chiral amines leading to chiral recognition has been demonstrated. Moreover, collapse of a metallogel formed from the same material in the presence of selective enantiomers validated its enantioselective affinity. Importantly, in addition to relevant experimental techniques, DFT studies have been successfully explored to establish chiral recognition through enantioselective gelation.
p-TsOH-mediated, Versatile, and Efficient Approach for the Synthesis of Triazolyl-Carbazoles from Nitrovinylcarbazoles and Azide via 1, 3-Dipolar Cycloaddition
Avula, Vijay Kumar Reddy,Vallela, Swetha,Anireddy, Jaya Shree,Chamarthi, Naga Raju
, p. 1361 - 1368 (2017/03/27)
An efficient method for the synthesis of N-alkylated 3-(1-benzyl-1H-1,2,3-triazole-4-yl)-9H-carbazoles (5, 6, 7, 8, 9, 10) and 9-ethyl-3,6-di(1H-1,2,3-triazole-4-yl)-9H-carbazole (13) has been developed from nitroolefines. The effects of catalyst and solvent on these reactions have been investigated. p-TsOH-THF was found to be the best system for this reaction. Various triazolyl-carbazoles were prepared in good to excellent yields.
Carbazole-benzimidazole based dyes for acid responsive ratiometric emissive switches
Aich, Krishnendu,Das, Sangita,Goswami, Shyamaprosad,Quah, Ching Kheng,Sarkar, Deblina,Mondal, Tapan Kumar,Fun, Hoong-Kun
, p. 6907 - 6915 (2016/08/10)
Three carbazole based benzimidazole derivatives exhibiting the effect of intramolecular charge transfer (ICT) caused by the donor-acceptor interaction between their carbazole and benzimidazole units were synthesized. Their photophysical properties were systematically investigated in various solvents with different polarities. Positive solvatofluorochromic effects were observed with the change of solvent from non-polar to polar for all of the three dyes. The synthesized compounds presented proton-induced absorption as well as ratiometric emission changes, indicating that these compounds might be used as proton sensors. The dyes in their solid state are also able to detect acid vapours. The optimized structures of the dyes and their protonated forms were calculated by density functional theory calculations.
Molecular Design of Carbazole-based Dyes and the Influence of Alkyl Substituent on the Performance of Dye-Sensitized Solar Cells
Beni,Zarandi,Madram,Bayat,Chermahini,Ghahary
, p. 29 - 43 (2016/07/06)
Carbazole is an alternant polycyclic aromatic hydrocarbon consisting of three fused rings with a large, aromatic system, containing nitrogen atom showing extensive electron delocalization. In this work, carbazole applied as π-conjugated bridge to construct electron donor–π–electron acceptor (D–π–A) organic dyes, where barbutiric acid and thiazolidine-2,4-dione as electron acceptor. The effects of these three acceptors and length of alkyl on the performance of the DSSCs were investigated systematically along with their photophysical and photo electrochemical properties. These series of organic dyes include (B-CH, B-C B, DT-CB, DB-CB). Our investigation indicate among dyes containing butyl as same donor, DT-CB exhibited the maximum overall conversion efficiency of 1.44% and from dyes by deferent electron donor B-CH shows conversion efficiency of 1.47%.
