A "Turn-on" Fluorescent Hg2+ Chemosensor Based on Ferrier Carbocyclization
TL;DR: A "turn-on" fluorescent chemosensor with excellent selectivity and satisfactory sensitivity on Hg(2+) detection in 100% water media has been established employing a carbohydrate based Ferrier carbocyclization reaction.
About: This article is published in Organic Letters.The article was published on 2012-01-20. It has received 62 citations till now. The article focuses on the topics: Ferrier carbocyclization.
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1,497 citations
TL;DR: This tutorial review highlights the representative examples of small-molecule based fluorescent probes for bioimaging, which are operated via the protection-deprotection of key functional groups such as aldehyde, hydroxyl, and amino functional groups reported from 2010 to 2014.
Abstract: Recently, the strategy of protection–deprotection of functional groups has been widely employed to design fluorescent probes, as the protection–deprotection of functional groups often induces a marked change in electronic properties. Significant advances have been made in the development of analyte-responsive fluorescent probes based on the protection–deprotection strategy. In this tutorial review, we highlight the representative examples of small-molecule based fluorescent probes for bioimaging, which are operated via the protection–deprotection of key functional groups such as aldehyde, hydroxyl, and amino functional groups reported from 2010 to 2014. The discussion includes the general protection–deprotection methods for aldehyde, hydroxyl, or amino groups, as well as the design strategies, sensing mechanisms, and deprotection modes of the representative fluorescent imaging probes applied to bio-imaging.
333 citations
TL;DR: A new design of reaction-based fluorescent probe for discrimination of thiophenols over aliphaticthiols through intramolecular charge transfer pathways using N-butyl-4-amino-1,8-naphthalimide as a fluorophore and 2,3-dihydroimidazo-[1,2-a] pyridine moiety as a linker is described.
Abstract: The development of highly sensitive and selective detection techniques for the discrimination of relevant toxic benzenethiols and biologically active aliphatic thiols is of considerable importance in the fields of chemical, biological, and environmental sciences. In this article, we describe a new design of reaction-based fluorescent probe for discrimination of thiophenols over aliphaticthiols through intramolecular charge transfer pathways using N-butyl-4-amino-1,8-naphthalimide as a fluorophore, the strongly electron-withdrawing 2,4-dinitrobenzenesulfonamide group as a recognition unit, and 2,3-dihydroimidazo-[1,2-a] pyridine moiety as a linker. This rational design not only affords finely tunable spectroscopic properties by adding 2,3-dihydroimidazo-[1,2-a] pyridine moiety but also provides the chance to regulate the selectivity and sensitivity of the probe due to the formation of a new type of potentially reversible sulfonamide bond through 4-dimethylaminopyridine-like resonance. The developed probe d...
109 citations
TL;DR: A highly sensitive and selective fluorescent probe for inorganic and organic mercury species displays colorimetric and ratiometric response in a buffer solution via mercury promoted cleavage reaction.
94 citations
TL;DR: Graphene quantum dots (GQDs) have successfully been utilized as efficient nano-sized fluorescence chemosensor to detect selectively Hg 2+ in 100% aqueous solution (pH 7) by employing a number of spectroscopic techniques as mentioned in this paper.
89 citations
References
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TL;DR: While the number of grave cases with acute M. d.
Abstract: Minamata disease (M. d.) is methylmercury (MeHg) poisoning that occurred in humans who ingested fish and shellfish contaminated by MeHg discharged in waste water from a chemical plant (Chisso Co. L...
1,792 citations
1,131 citations
727 citations
TL;DR: A selective and sensitive fluorescent chemosensor for Hg2+, which was composed of two aminonaphthalimide fluorophores and a receptor of 2,6-bis(aminomethyl)pyridine, showed an about 17-fold increase in fluorescence quantum yield upon addition of 1 equiv of HG2+ in neutral buffer aqueous solution.
Abstract: A selective and sensitive fluorescent chemosensor for Hg2+, which was composed of two aminonaphthalimide fluorophores and a receptor of 2,6-bis(aminomethyl)pyridine, was synthesized through the reaction of 2,6-bis(chloromethyl)pyridine and N-[2-(2-hydroxyethoxy)ethyl]-4-piperazino-1,8-naphthalimide. The chemosensor showed an about 17-fold increase in fluorescence quantum yield upon addition of 1 equiv of Hg2+ in neutral buffer aqueous solution, and the other common metal ions did not notably disturb the detection of Hg2+.
555 citations
TL;DR: An irreversible rhodamine chemosensor-based, real-time monitoring system to detect mercury ions in living cells and, in particular, vertebrate organisms and shows that the mercury chemos sensor is cell and organism permeable and that it responds selectively to mercury ions over other metal ions.
Abstract: Exposure to mercury causes severe damage to various tissues and organs in humans. Concern over mercury toxicity has encouraged the development of efficient, sensitive, and selective methods for the in vivo detection of mercury. Although a variety of chemosensors have been exploited for this purpose, no in vivo monitoring systems have been described to date. In this report, we describe an irreversible rhodamine chemosensor-based, real-time monitoring system to detect mercury ions in living cells and, in particular, vertebrate organisms. The chemosensor responds rapidly, irreversibly, and stoichiometrically to mercury ions in aqueous media at room temperature. The results of experiments with mammalian cells and zebrafish show that the mercury chemosensor is cell and organism permeable and that it responds selectively to mercury ions over other metal ions. In addition, real-time monitoring of mercury-ion uptake by cells and zebrafish using this chemosensor shows that saturation of mercury-ion uptake occurs within 20-30 min in cells and organisms. Finally, accumulation of mercury ions in zebrafish tissue and organs is readily detected by using this rhodamine-based chemosensor.
492 citations