Novel Alkali Cation Chemosensors Based on <i>N</i>-9-Anthrylaza-crown Ethers

Witulski, B.; Weber, Michael; Bergsträßer, Uwe; Desvergne, Jean‐Pierre; Bassani, Dario M.; Bouas‐Laurent, Henri

doi:10.1021/ol015778j

Cited by 53 publications

(43 citation statements)

References 20 publications

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“…In addition, Witulski et al prepared an alkali metal chemosensor by an amination to form a 10-cyano-9-N-anthryl-azacrown ether. The nitrogen donor and cyano acceptor create a material showing intramolecular charge transfer that allows spectroscopic detection of metal ions [245]. Concurrently, Zhang and Buchwald employed dialkyl biphenylylphosphines in the synthesis of N-aryl azacrowns.…”

Section: Synthesis Of Small Molecules For Materials Applicationsmentioning

confidence: 99%

Palladium‐Catalyzed Amination of Aryl Halides and Sulfonates

Hartwig

2002

Modern Arene Chemistry

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The transition metal catalyzed synthesis of arylamines by the reaction of aryl halides or triflates with primary or secondary amines has become a valuable synthetic tool for many applications. This process forms monoalkyl or dialkyl anilines, mixed diarylamines or mixed triarylamines, as well as N-arylimines, carbamates, hydrazones, amides, and tosylamides. The mechanism of the process involves several new organometallic reactions. For example, the CaN bond is formed by reductive elimination of amine, and the metal amido complexes that undergo reductive elimination are formed in the catalytic cycle in some cases by NaH activation. Side products are formed by b-hydrogen elimination from amides, examples of which have recently been observed directly. An overview that covers the development of synthetic methods to form arylamines by this palladium-catalyzed chemistry is presented. In addition to the synthetic information, a description of the pertinent mechanistic data on the overall catalytic cycle, on each elementary reaction that comprises the catalytic cycle, and on competing side reactions is presented. The review covers manuscripts that appeared in press before June 1, 2001. This chapter is based on a review covering the literature up to September 1, 1999. However, roughly one-hundred papers on this topic have appeared since that time, requiring an updated review.

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Section: Synthesis Of Small Molecules For Materials Applicationsmentioning

confidence: 99%

Palladium‐Catalyzed Amination of Aryl Halides and Sulfonates

Hartwig

2002

Modern Arene Chemistry

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“…27 In addition, the substituent effects in donor-acceptor-substituted anthracene derivatives may be affected by the analyte, leading to a change of the internal charge transfer (ICT) upon excitation and to a shift of the emission maximum (Scheme 1c). 28 It is certainly beneficial for these studies that the synthesis of the long-known anthracene unit as well as the substituent effects on the photochemical and photophysical properties are well established and in most cases highly predictable. Unfortunately, anthracene and most of its derivatives are hardly soluble in water, which constitutes a major drawback for the application of this fluorophore in biologically or physiologically relevant media.…”

Section: Introductionmentioning

confidence: 99%

The benzo[b]quinolizinium ion as a water-soluble platform for the fluorimetric detection of biologically relevant analytes

Granzhan¹,

Ihmels²,

Tian³

2015

Arkivoc

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In this Account our efforts are described to establish the benzo[b]quinolizinium ion, also known as acridizinium or 4a-azoniaanthracene, as a water-soluble surrogate of anthracene for the development of selective fluorescent probes. It is demonstrated with selected examples that especially the 9-aminobenzo[b]quinolizinium is a donor-acceptor dye with favorable absorption and emission properties and may be used as a versatile building block for fluorescent light-up probes and ratiometric probes.

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“…The other is the facile modulation at the upper and lower rims of calix[n] arenes, which leads to attractive features in calix[n]arene derivatives [9] . Up to now, the fluorescent chemsensors for sodium ion based on the framework of calix [4]arene have been frequently reported [10−16] . Shinkai and coworkers have designed a calix [4]arene having two pyrene moieties on the lower rim as fluorescent chemsensor for sodium ion based on the ratio of the monomer vs. excimer emission [10] .…”

Section: Introductionmentioning

confidence: 99%

“…Up to now, the fluorescent chemsensors for sodium ion based on the framework of calix [4]arene have been frequently reported [10−16] . Shinkai and coworkers have designed a calix [4]arene having two pyrene moieties on the lower rim as fluorescent chemsensor for sodium ion based on the ratio of the monomer vs. excimer emission [10] . In a similar system, a calix [4] arene bearing pyrene (as a fluorophore) and nitrobenzene (as a quencher) was synthesized, which was response to the sodium ion by the intramolecular photoinduced electron transfer process [11] .…”

Section: Introductionmentioning

confidence: 99%

Highly selective fluorescent chemosensor for Na+ based on pyrene-modified calix[4]arene derivative

Wang

Guo

Jiang

et al. 2009

Sci. China Ser. B-Chem.

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A novel calix[4]arene derivative with pyrene fluorophores at the upper rim and tetraester ionophores at the lower rim was synthesized in six steps, and its structure was proved by NMR and ESI-MS spectroscopies. Furthermore, the chemosensing behavior of the host compound for alkali and alkaline earth metal ions was investigated by fluorescence spectroscopy. The obtained results show that the calixarene host can selectively bind sodium ion with the complexation stability constant of 2190 mol −1 ·L. The complexation with sodium ion can pronouncedly induce the excimer emission to decrease and the monomer emission to increase, whereas the addition of the other alkali and alkaline earth metal ions does not cause appreciable changes in the fluorescence spectrum of the host compound. The present calix[4]arene derivative displays potential application as fluorescent chemosensor for sodium ion. calix[4]arene, pyrene, sodium ion, fluorescent chemosensor

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Novel Alkali Cation Chemosensors Based on N-9-Anthrylaza-crown Ethers

Abstract: [structure: see text] A novel alkali cation selective probe is described which exhibits unique ICT and binding properties, allowing the ratiometric titration of sodium cations in the presence of other alkali metal ions.

Cited by 53 publications

References 20 publications

Palladium‐Catalyzed Amination of Aryl Halides and Sulfonates

Palladium‐Catalyzed Amination of Aryl Halides and Sulfonates

The benzo[b]quinolizinium ion as a water-soluble platform for the fluorimetric detection of biologically relevant analytes

Highly selective fluorescent chemosensor for Na+ based on pyrene-modified calix[4]arene derivative

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