- A bifunctional probe based on naphthalene derivative for absorbance-ratiometic detection of Ag+ and fluorescence “turn-on” sensing of Zn2+ and its practical application in water samples, walnut and living cells
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In this work, naphthalene with good biocompatibility was selected, and the probe NBOS was synthesized with 2-Amino-phenol and 2-Amino-benzenethiol. The structure of probe NBOS was confirmed by X-ray Crystallography. Furthermore, the probe showed absorbance-ratiometic sensing for Ag+ over a pH range from 6 to 7.5 and fluorescence “turn on” signal response towards Zn2+ in the pH range of 6–10 in EtOH/H2O (9/1, V/V, pH = 7.4) mixture. The detection limit was obtained to be 4.24 μM for Ag+ and 3.17 nM for Zn2+. Moreover, it could be efficiently recycled by treating Na2EDTA. The sensing mechanism of probe NBOS toward Ag+ and Zn2+ was investigated by FT-IR, HNMR, job'plot and ESI-MS. Typically, the coordination mode of NBOS with Zn2+ was confirmed by DFT calculation. Moreover, probe NBOS was successfully applied in the detection Ag+ and Zn2+ in real water samples. Importantly, probe NBOS could be used to detect Zn2+ in walnut and living cells. Based on the high throughput analysis strategy, absorbance and fluorescence signals of NBOS could be designed as a NOT and OR logic gate controlled by Ag+ (Input 1) and Zn2+ (Input 2).
- Li, Na-Na,Bi, Cai-Feng,Zhang, Xia,Xu, Cun-Gang,Fan, Chuan-Bin,Gao, Wei-Song,Zong, Zi-Ao,Zuo, Shan-Shan,Niu, Chuan-Feng,Fan, Yu-Hua
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- Fluorescent coumarin derivatives with viscosity sensitive emission - Synthesis, photophysical properties and computational studies
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New derivatives of (benzo[d]azolyl)-benzo[f]chromenone were synthesized from the intermediate 3-(1,3-benzazol-2-yl)naphthalen-2-ol, obtained from 3-hydroxynaphthalene-2-carboxylic acid and 2-amino phenol in the presence of PCl3 in chlorobenzene at 130-135°C. The compounds were characterized by FT-IR, 1 H NMR, mass spectroscopy and elemental analysis. The synthesized compounds are fluorescent which absorb in the range of 296 to 332 nm while emit in the range of 368 to 404 nm. The experimental absorption and emission wavelengths for the compounds 5 and 6 are in good agreement with those predicted using the Time-Dependent Density Functional Theory (TD-DFT) [B3LYP/6-31G(d)]. The largest wavelength difference between the experimental and computed absorption maxima was 29 nm (tetrahedrofuran) for compound 5 while for emission it was 61 nm (dichloromethane) for compound 7. The emission intensities of all the compounds decrease continuously as the viscosity of the microenvironment increases. The compounds are thermally stable up to a temperature range of 300 to 350°C.
- Phatangare, Kiran R.,Lanke, Sandip K.,Sekar, Nagaiyan
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- Palladium catalyzed Csp2-H activation for direct aryl hydroxylation: The unprecedented role of 1,4-dioxane as a source of hydroxyl radicals
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A novel strategy for direct aryl hydroxylation via Pd-catalysed Csp2-H activation through an unprecedented hydroxyl radical transfer from 1,4-dioxane, used as a solvent, is reported with bio relevant and sterically hindered heterocycles and various acyclic functionalities as versatile directing groups.
- Seth, Kapileswar,Nautiyal, Manesh,Purohit, Priyank,Parikh, Naisargee,Chakraborti, Asit K.
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p. 191 - 194
(2015/01/09)
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- Systematic color tuning of a family of luminescent azole-based organoboron compounds suitable for OLED applications
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A new tunable luminescent family of heterocyclic aromatic compounds containing boron has been prepared and characterized through NMR spectroscopy, mass spectrometry, absorption and fluorescence spectroscopy as well as structural study using single crystal X-ray crystallography. Spectroscopic properties of the new compounds were also studied using DFT and TDDFT computational models that showed very good agreement of the theoretical data with experimental results. Through introduction of auxochromic atoms such as sulfur and extension of the π system of the ligands it is possible to cover a large range of the visible spectrum. Activation and enhancement of the luminescence is achieved by condensation reactions that introduce the boron fragment forming stable, sublimable compounds suitable for OLED applications.
- Kiprof, Paul,Carlson, Jeffrey C.,Anderson, Derrick R.,Nemykin, Victor N.
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p. 15120 - 15132
(2013/10/22)
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- ESIPT inspired fluorescent 2-(4-benzo[d]oxazol-2-yl)naphtho[1,2-d]oxazol-2- yl)phenol: Experimental and DFT based approach to photophysical properties
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ESIPT inspired fluorescent 2-(4-benzo[d]oxazol-2-yl)naphtho[1,2-d]oxazol-2- yl)phenol was synthesized from 1-amino-3-(1,3-benzoxazol-2-yl)naphthalen-2-ol. Photophysical behavior of the synthesized compound was studied using UV-visible and fluorescence spectroscopy in polar and non-polar solvents. The synthesized naphthoxazolyl benzoxazole is fluorescent and very sensitive to the micro-environment. It shows a single absorption and dual emission in non-polar solvents with large Stokes shift originating from Excited State Intramolecular Proton Transfer while in polar solvents only a single short wavelength emission is observed. Experimental absorption and emission wavelengths are in good agreement with those predicted using the Time-Dependent Density Functional Theory (TD-DFT) [B3LYP/6-31G(d)]. The largest wavelength difference between the experimental and computed absorption maxima was 16 nm (acetonitrile) and 7 nm (ethyl acetate, THF, and 1,4-dioxane) in the short and long wavelength regions, respectively. A largest difference of 25 nm was observed for the short wavelength emission in DMF and 22 nm for the longer wavelength emission in chloroform.
- Phatangare, Kiran R.,Gupta, Vinod D.,Tathe, Abhinav B.,Padalkar, Vikas S.,Patil, Vikas S.,Ramasami, Ponnadurai,Sekar, Nagaiyan
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supporting information
p. 1767 - 1777
(2013/03/14)
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- Synthesis, photophysical property study of novel fluorescent 4-(1,3-benzoxazol-2-yl)-2-phenylnaphtho[1,2-d][1,3]oxazole derivatives and their antimicrobial activity
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A series of 4-(1,3-benzoxazol-2-yl)-2-phenylnaphtho[1,2-d][1,3]oxazole derivatives have been synthesized from intermediate 1-amino-3-(1,3-benzoxazol-2- yl)naphthalen-2-ol. This intermediate was obtained by coupling 3-(1,3-benzoxazol-2-yl)naphthalen-2-ol with 4-sulphobenzenediazonium chloride followed by reduction with sodium dithionate in water at pH 8-9. 3-(1,3-benzoxazol-2-yl)naphthalen-2-ol was synthesized from 3- hydroxynaphthalene-2-carboxylic acid and 2-amino phenol in the presence of PCl3 in chlorobenzene at 130-135 C. All these compounds were characterized by FT-IR, 1H NMR, mass spectral and elemental analysis. The synthesized compounds are fluorescent which absorbs in the range of 296 to 332 nm while emits in the ranges of 368 to 404 nm with excellent quantum yield. All compounds were evaluated for in vitro antibacterial activities against Escherichia coli and Staphylococcus aureus strains and in vitro antifungal activity against Candida albicans and Aspergillus niger strains by using serial dilution method.
- Phatangare, Kiran R.,Borse, Bhushan N.,Padalkar, Vikas S.,Patil, Vikas S.,Gupta, Vinod D.,Umape, Prashant G.,Sekar
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p. 141 - 151
(2013/04/24)
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