2218-96-4Relevant academic research and scientific papers
A Highly Selective and Sensitive Colorimetric Chemosensor for the Detection of Hydrogen Sulfide: A Real-time Application in Multiple platforms
Jothi, Dhanapal,Munusamy, Sathishkumar,Kulathu Iyer, Sathiyanarayanan
, p. 141 - 149 (2022)
Calorimetric chemosensors are found to be advantageous sensing systems due to their simplicity and favorable responsive properties. Although some colorimetric probes have been reported to detect hydrogen sulfide (H2S), the creation of rapid, highly selective and sensitive probes for the detection of H2S remains a challenging target. In this work, we established dinitrosulphonamide decorated phenanthridine and 2,4-dinitro-N-(4-(7,8,13,14-tetrahydrodibenzo[a, i]phenanthridin-5-yl)phenyl)benzenesulfonamide (PHSH), for the calorimetric detection of H2S. H2S-triggered thiolysis of PHSH resulted in a marked absorption enhancement alongside a visual color change from colorless to dark yellow. The result indicated that the chemosensor showed high sensitivity and selectivity with a fast response of less than 10?s with a detection limit as low as 6.5?nM. The chemosensor reaction mechanism with H2S was studied by UV-vis, 1H NMR, mass and HPLC analysis. In addition, the chemosensor has been used for the determination of H2S in many real-time samples.
A new near-infrared fluorescent chemodosimeter for discrimination of sulfide from disulfide
Xie, Puhui,Zhu, Yanru,Huang, Xuewei,Gao, Guangqin,Guo, Fengqi,Yang, Guoyu
, p. 2823 - 2837 (2018)
A new near-infrared fluorescent “turn-on” chemodosimeter (probe 1) based on dicyanomethylene-4H-chromene fluorophore for sulfide was developed. Probe 1 showed good fluorescence selectivity to sulfide over other anions and thiol-containing compounds. The d
A 2,5-diaryl-1,3,4-oxadiazole-based fluorescent probe for rapid and highly selective recognition of hydrogen sulfide with a large Stokes shift through switching on ESIPT
Tang, Lijun,Zheng, Zhuxuan,Zhong, Keli,Bian, Yanjiang
, p. 1361 - 1364 (2016)
A new 2,5-diaryl-1,3,4-oxadiazole derived ratiometric fluorescent probe (OXDNP) for hydrogen sulfide recognition has been developed. Probe OXDNP displays highly selective and sensitive detection to HS? over other anions and thiol-containing amino acids in DMSO solution with fast response and a large Stokes shift. Through HS? induced thiolysis of the dinitrophenyl ether, the excited state intramolecular proton transfer (ESIPT) featured precursor was released, which led to dual fluorescence emission ‘turn on’ and ratiometric emission behavior of the sensing system. The pseudo-first-order reaction rate constant was calculated to be 1.234 s?1. The HS? recognition mechanism was proved by HPLC–MS and 1H NMR comparison investigations.
Dual-functional multi-application probe: Rapid detection of H2S and colorimetric recognition of HSO3? in food and cell
Chen, Lin,Hou, Shuhua,Li, Xuepeng,Tang, Lijun,Tang, Yiwei,Yan, Xiaomei,Zhong, Keli
, (2020)
Since hydrogen sulfide (H2S) and bisulfite (HSO3?) are widely used in the biological environment and industrial production, many fluorescent probes have been developed to detect them individually. However, designing and sy
A fluorescence turn-on probe for hydrogen sulfide and biothiols based on PET & TICT and its imaging in HeLa cells
Jin, Xiaodong,Zhang, Caiting,Zhang, Xueqiong,Zhong, Hui,Zhu, Hongjun
supporting information, (2020/09/02)
In this paper, a photoinduced electron transfer (PET)& twisted intramolecular charge transfer (TICT)-based fluorescent probe (1) for detecting biothiols (GSH/Cys/Hcy) and hydrogen sulfide with fluorescence turn on was developed. The probe could recognize
A PET-based turn-on fluorescent probe for sensitive detection of thiols and H2S and its bioimaging application in living cells, tissues and zebrafish
Xu, Kaixin,He, Longwei,Yang, Yunzhen,Lin, Weiying
supporting information, p. 2865 - 2869 (2019/02/17)
A turn-on fluorescent probe, containing a naphthalimide platform and benzothiazole modified by the 2,4-dinitrobenzenesulfonyl (DNBS) group, was designed as an efficient fluorescent probe for sensitive detection of biological thiols and H2S spec
Fluorogenic protein labeling through photoinduced electron transfer-based BL-tag technology
Sadhu, Kalyan K.,Mizukami, Shin,Lanam, Carolyn R.,Kikuchi, Kazuya
supporting information; scheme or table, p. 272 - 276 (2012/05/20)
Keeping quenchers on a short leash: Shortening of the linker chain length combined with modification of the quencher moiety was found to improve fluorogenic probes useful for protein labeling by the mutant β-lactamase-tag (BL-tag) technology. The most eff
Selective reduction of nitroaromatic compounds on silver nanoparticles by visible light
Xia, Lixin,Hu, Xinhu,Sun, Mengtao,Li, Jushi,Yang, Donghui,Wang, Xiaofang,Xu, Hongxing
, p. 1024 - 1028 (2012/10/29)
For the first time, we report experimentally and theoretically that nitroaromatic compounds, 2,4-dinitrobenzenethiol and 4-chloro-2- nitrobenzenethiol, on silver sols can be selectively reduced to 2-amino-4-nitrobenzenethiol and 2-amino-4-chlorobenzenethiol simply by irradiating with a visible light in ambient conditions, and the selective photoreduction is a very facile process. The results of quantum chemical calculations are in good agreement with our experimental data. Copyright
Kinetics and mechanism of the reactions of S-2,4-dinitrophenyl 4-substituted thiobenzoates with secondary alicyclic amines
Castro, Enrique A.,Aguayo, Raul,Bessolo, Jorge,Santos, Jose G.
, p. 7788 - 7791 (2007/10/03)
The title reactions, in 44 wt % ethanol-water at 25.0 °C, exhibit slightly curved Bronsted-type plots (log kN versus pK a of amines) with slopes β1 = 0.1-0.44 (at high pKa) and β2 ca. 0.7 (at low pKa). The magnitude of some of these slopes, together with the fact that the curvature center (pKa0 = 9.5-10.8) does not change with the electronic effects of the benzoyl substituent, suggests that these reactions are not stepwise, but concerted.
Kinetics and Mechanism of the Benzenethiolysis of O-Ethyl S-(2,4-Dinitrophenyl) and O-Ethyl S-(2,4,6-Trinitrophenyl) Dithiocarbonates and O-Methyl O-(2,4-Dinitrophenyl) Thiocarbonate
Castro, Enrique A.,Pavez, Paulina,Santos, Jose G.
, p. 9034 - 9039 (2007/10/03)
Reactions of O-ethyl 2,4-dinitrophenyl dithiocarbonate (EDNPDTC), O-ethyl 2,4,6-trinitrophenyl dithiocarbonate (ETNPDTC), and O-methyl O-(2,4-dinitrophenyl) thiocarbonate (MDNPTOC) with a series of benzenethiolate anions in aqueous solution, at 25.0 °C and an ionic strength of 0.2 M (KCl), are subjected to a kinetic investigation. Under excess benzenethiolate, these reactions obey pseudo-first-order kinetics and are first order in benzenethiolate. Nonetheless, similar reactant concentrations were used in the reactions of 4-nitrobenzenethiolate anion with the ethyl trinitrophenyl ester (ETNPDTC), which showed overall second-order kinetics. The nucleophilic rate constants (kN) are pH independent, except those for the reactions of ETNPDTC with the X-benzenethiolates with X = H, 4-Cl, and 3-Cl, which increase as pH decreases. The Bronsted-type plots (log kN vs pK a of benzenethiols) are linear with slopes β = 0.66 for the reactions of both ethyl dinitrophenyl ester (EDNPDTC) and ethyl trinitrophenyl ester (ETNPDTC) and β = 0.58 for those of the thiocarbonate ester (MDNPTOC). For the benzenethiolysis of MDNPTOC and EDNPDTC, no breaks were found in the Bronsted-type plots at pKa 4.1 and 3.4, respectively, consistent with concerted mechanisms. Benzenethiolysis of the ethyl trinitrophenyl ester (ETNPDTC) should also be concerted in view of the even more unstable tetrahedral intermediate that would have been formed had this reaction been stepwise. ETNPDTC is more reactive toward benzenethiolate anions than EDNPDTC due to the better leaving group involved in the former substrate. The kN values found for the reactions of EDNPDTC with benzenethiolates are larger than those obtained for the concerted reactions of the same substrate with isobasic phenoxide anions. This is explained by Pearson's hard and soft acids and bases principle. The concerted mechanism for the benzenethiolysis of MDNPTOC, in contrast to the stepwise mechanism found for the phenolysis of this substrate, is attributed to the greater kinetic instability of the hypothetical tetrahedral intermediate formed in the former reaction, due to the greater nucleofugality of ArS- compared with an isobasic ArO-. Benzenethiolates are more reactive toward MDNPTOC and EDNPDTC than the corresponding carbonate and thiolcarbonate, respectively. This is also in accordance with the HSAB principle, since benzenthiolates are relatively soft bases that prefer to bind to a relatively soft thiocarbonyl center rather than a relatively hard carbonyl center.
