- Dual signaling of thallium(III) ions via oxidative cleavage of a sulfonhydrazide linkage
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The thallium is widely used in various research and industrial applications but is very toxic. In this work, we developed a novel reaction-based dual signaling probe for the selective and sensitive determination of Tl3+ via the oxidative cleavage of a rhodamine–dansylhydrazide conjugate. The designed probe showed pronounced colorimetric and fluorescence signaling behavior toward Tl3+ with a detection limit of 1.3 × 10–7 M (0.027 ppm), as well as selectivity over other common metal ions, anions, and oxidants. The Tl3+ signaling process required less than 2 min and was not influenced by the solution pH within the range of 4.0–5.5; however, the signal diminished significantly above pH 6.0. To demonstrate the practical applicability of the designed probe, a simple and convenient colorimetric assay for the determination of Tl3+ in commercial reagents was established using an office scanner as a readily available signal capturing device.
- Ahn, Sangdoo,Chang, Suk-Kyu,Choi, Myung Gil,Lee, Yu Jeong,Park, Tae Jung,Yoo, Jae Hoon
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- A mild method for synthesizing carboxylic acids by oxidation of aldoximes using hypervalent iodine reagents
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A mild oxidation method for the conversion of aldoximes to carboxylic acids was developed mediated by hypervalent iodine reagents. This method covers a wide range of functionalized aldoximes and proceeds under mild conditions, utilizing PhI(OH)OTs as an oxidant.
- Nakamura, Akira,Kanou, Hodaka,Tanaka, Junki,Imamiya, Akira,Maegawa, Tomohiro,Miki, Yasuyoshi
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supporting information
p. 541 - 544
(2018/02/07)
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- Activation of fluorescence of lactone forms of rhodamine dyes by photodehydrogenation of aryl(hetaryl)pyrazolines
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Aryl(hetaryl)pyrazolines are effective photogenerators of acid providing an irreversible photochemical activation of fluorescence of rhodamine group dyes. The effect of solvent on two consecutive reactions, photodehydrogenation of pyrazoline and lactone ring opening of the dye was studied. An increase in solvent polarity leads to an increase in the rate of both reactions by different degrees. The systems under study are believed to be promising for the formation of recording media for multilayer optical file type disks of ultrahigh data storage capacity with fluorescent readout.
- Traven,Dolotov,Ivanov
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p. 735 - 740
(2016/12/27)
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- Ratiometric Signaling of Hypochlorite by the Oxidative Cleavage of Sulfonhydrazide-Based Rhodamine-Dansyl Dyad
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(Figure Presented). A reaction-based probe 1 for hypochlorite signaling was designed by the conjugation of two fluorophores, rhodamine and dansyl moieties, by the reaction of rhodamine B base with dansylhydrazine. Probe 1 exhibited pronounced hypochlorite-selective chromogenic and fluorescent signaling behavior over other oxidants used in practical applications, such as hydrogen peroxide, peracetic acid, and ammonium persulfate, as well as commonly encountered metal ions and anions. Signaling was attributed to the hypochlorite-induced oxidative cleavage of the sulfonhydrazide linkage of the probe. In particular, favorable ratiometric fluorescence signaling was possible by utilizing the emissions of the two fluorophores. A detection limit of 1.13 × 10-6 M (0.058 ppm) was estimated for the determination of hypochlorite. A paper-based test strip was prepared and was used as a semiquantitative indicator for the presence of hypochlorite in aqueous solutions. The probe was also successfully applied for the determination of hypochlorite in practical tap water samples.
- Lee, Hyo Jin,Cho, Min Jeoung,Chang, Suk-Kyu
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p. 8644 - 8649
(2015/09/21)
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- Synthesis of rhodamines from fluoresceins using pd-catalyzed c-n cross-coupling
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A unified, convenient, and efficient strategy for the preparation of rhodamines and N,N′-diacylated rhodamines has been developed. Fluorescein ditriflates were found to undergo palladium-catalyzed C-N cross-coupling with amines, amides, carbamates, and other nitrogen nucleophiles to provide direct access to known and novel rhodamine derivatives, including fluorescent dyes, quenchers, and latent fluorophores.
- Grimm, Jonathan B.,Lavis, Luke D.
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p. 6354 - 6357
(2012/02/01)
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- An unprecedented strategy for selective and sensitive fluorescence detection of nitric oxide based on its reaction with a selenide
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A new strategy that utilizes the interaction between NO and a selenide is reported for fluorescence detection of NO, in which rhodamine B selenolactone serves as a model selenide. The Royal Society of Chemistry 2011.
- Sun, Chengdong,Shi, Wen,Song, Yanchao,Chen, Wei,Ma, Huimin
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supporting information; experimental part
p. 8638 - 8640
(2011/10/04)
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- Sulfonyl rhodamine hydrazide: A sensitive and selective chromogenic and fluorescent chemodosimeter for copper ion in aqueous media
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A novel, sulfonyl rhodamine hydrazide chemodosimeter displayed highly selective and sensitive recognition of Cu2+ in aqueous media, via colour change from colorless to pink. The colour change that occurred as a result of complexation with Cu2+ can be attributed to spirolactam ring-opening and hydrolysis of the hydrazide unit to afford C.I. Acid Red 52 (Rhodamine B) in the presence of Cu2+. An analytical method was developed and successfully used for the determination of the copper content in a sample.
- Hu, Zhi-Qiang,Wang, Xiao-Ming,Feng, Yong-Cheng,Ding, Lei,Lu, Hai-Yan
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experimental part
p. 257 - 261
(2011/05/11)
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- A selenolactone-based fluorescent chemodosimeter to monitor mecury/methylmercury species in vitro and in vivo
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A fluorescent probe based on selenolactone displays unique fluorescence enhancement and UV-vis spectral change for mercury/methylmercury species, which were attributed to deselenation reaction. The value of this system was successfully demonstrated by its use in detecting inorganic mercury/methylmercury species in cells and zebrafish.
- Chen, Xiaoqiang,Baek, Kyung-Hwa,Kim, Youngmee,Kim, Sung-Jin,Shin, Injae,Yoon, Juyoung
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scheme or table
p. 4016 - 4021
(2010/07/06)
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- Imaging different interactions of mercury and silver with live cells by a designed fluorescence probe rhodamine b selenolactone
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Rhodamine B selenolactone has been designed, synthesized, and characterized as a new fluorescent probe for imaging both Hg2+ and Ag+ in live cells to better understand their distinct toxicities to organisms. The probe is designed based on the fact that selenium has a strong affinity for mercury and silver, and is constructed by incorporating a Se atom into the spirocyclic structure of rhodamine. It exhibits a rapid and specific spectroscopic off-on response to Hg2+ and Ag+ instead of other species, with detection limits of 23 nM Hg2+ and 52 nM Ag +. Moreover, the probe is membrane-permeable, and can react with Ag+ even in the presence of Cl- because of the higher affinity of Se than Cl- for Ag+, which makes it of potential use for imaging not only Hg2+ but also Ag+ in live cells. This applicability has been demonstrated by imaging Hg2+ and Ag+ in Hela cells. It is observed that the reaction of Ag + with the probe inside the cells occurs much slower than that of Hg2+, which is ascribed to the high concentration of cellular chloride ions inhibiting the formation of sufficient free Ag+. The present finding is helpful to get an insight into the different interaction mechanism of Hg2+ and Ag+ with cells, and more applications of the probe may be expected for studying the behaviors of Hg 2+ and Ag+ in various biosystems.
- Shi, Wen,Sun, Shuna,Li, Xiaohua,Ma, Huimin
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experimental part
p. 1206 - 1210
(2010/04/25)
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- Ionization and Tautomerism of Hydroxyxanthenes and Some Other Dyes in Ethanol
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Protolytic equilibria of hydroxyxanthene dyes, Fluorescein and Eosin, as well as of some related compounds, in ethanol were studied by spectrophotometry. Stepwise ionization and tautomeric equilibrium constants were determined.
- Mchedlov-Petrosyan
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p. 267 - 274
(2007/10/03)
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- Pressure Effects on Equilibrium between Lactone and Zwitterion Forms of Rhodamine B in Primary Alcohols
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The equilibrium between lactone and zwitterion forms of Rhodamine B was studied in primary alcohols and at high pressures.The effects of solvent polarity and pressure on the equilibrium constant were examined by using a Kirkwood-type equation.
- Sueishi, Yoshimi,Sugiyama, Yukie,Yamamoto, Shunzo,Nishimura, Norio
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p. 572 - 574
(2007/10/02)
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- Erythromycin A as a Supramolecular Catalyst: Effect on Rhodamine B Lactonization
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The intramolecular lactonization reaction of rhodamine B base in chloroform solution is remarkably accelerated by the antibiotic erythromycin A.The rate increases by a factor of ca. 1010, a value significantly higher than typical enzymatic factors.This effect is ascribed to the formation of a host-guest complex between the dye and the antibiotic, a process that induces a conformational change conducive to the rehybridization of the central carbon atom of the dye.
- Barra, Monica,Cosa, Juan Jose,Rossi, Rita H. de
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p. 5850 - 5853
(2007/10/02)
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- Aspectroscopic/thermodynamic study of the rhodamine B lactone ->/<- zwitterion equilibrium
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Temperature dependences of the visible absorption spectra of rhodamine B (RB) in water and 18 alcohol solvents have been examined and utilized to estimate thermodynamic parameters (ΔG0, ΔH0, ΔS0) for the RB lactone->///3/mol*cm is estimated.The thermodynamic results suggest that the position of the RB L ->/- Z equilibrium is strongly influenced by self-association of the solvent.The position of the equilibrium in aliphatic alcohols can be predicted from the simple features of the solvent molecules.Consequences of the results regarding calculation of the natural radiative lifetime of the fluorescent state from absorption spectrum are discussed.
- Hinckley, Daniel A.,Seybold, Paul G.
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p. 1053 - 1060
(2007/10/02)
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- Solvatochromism and thermochromism of rhodamine solutions
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Electronic absorption spectra of rhodamine B have been examined in 16 protic and 14 aprotic solvents.Rhodamine B exists in solution as a highly colored zwitterion, a colorless lactone and an intensely colored cation.Protic solvents stabilize the zwitterion: the position of the lactone-zwitterion equilibrium depends upon solvent-dye hydrogen bonding and solvent dielectric/polarizability properties.From its temperature dependencene, thermodynamic parameters (ΔG0, ΔH0, ΔS0) for this equilibrium were determined in water, n-propanol and n-octanol.The zwitterion is not stable in aprotic solvents, in which the cation or lactone is favored according to the acidity or basicity of the medium.Absorption spectra of rhodamine 6G, an esterfied dye which does not exhibit the above equilibria, are only modestly altered by most variations of solvent and temperature.
- Hinckley, Daniel A.,Seybold, Paul G.,Borris, David P.
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p. 747 - 754
(2007/10/02)
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