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%.
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.
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.
