Improved synthetic methods to mixed-donor thiacrown ethers

Glenny, Mark W.; Water, Leon G. A. van de; Vere, Joanna M.; Blake, Alexander J.; Wilson, Claire; Driessen, Willem L.; Reedijk, Jan; Schröder, Martin

doi:10.1016/j.poly.2005.11.006

Cited by 34 publications

(15 citation statements)

References 42 publications

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“…2-chloro-N-8-quinolinylacetamide, [52] 1,4,7-triazacyclononane, [53] 1,4,7-triazacyclononane-1,4-dicarboxylic acid di-tert-butyl ester [54] and 1-aza-4,7,10-trithiacyclododecane [55] were prepared by published methods.…”

Section: Methodsmentioning

confidence: 99%

Aza‐ and Mixed Thia/Aza‐Macrocyclic Receptors with Quinoline‐Bearing Pendant Arms for Optical Discrimination of Zinc(II) or Cadmium(II) Ions

et al. 2020

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The synthesis and coordination properties of two fluorescent chemosensors, featuring [9]aneN3 (1,4,7‐triazacyclononane; L1) and [12]aneNS3 (1‐aza‐4,7,10‐trithiacyclododecane; L2) as receptor units, and a quinoline pendant arm with an amide group as a functional group spacer are described. The optical responses of L1 and L2 in the presence of several metal ions were analysed in MeCN/H2O (1 : 4 v/v) solutions. A selective chelation enhancement of fluorescence (CHEF) effect was observed in the presence of Zn2+ in the case of L1, and in the presence of Cd2+ in the case of L2, following the formation of a 1 : 1 and a 1 : 2 metal/ligand complex, respectively, which was also confirmed by potentiometric measurements. 1H and 13C NMR measurements in CD3CN/CDCl3 in combination with molecular mechanics calculations show that for both complexes of L1 and L2 with Zn2+ and Cd2+, respectively, the coordination of the carbonyl group from the pendant arm could be the origin of the observed optical selectivity.

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Section: Methodsmentioning

confidence: 99%

Aza‐ and Mixed Thia/Aza‐Macrocyclic Receptors with Quinoline‐Bearing Pendant Arms for Optical Discrimination of Zinc(II) or Cadmium(II) Ions

et al. 2020

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“…PEO can be chemically modified and reacted with, or adsorbed onto, other molecules and surfaces . Furthermore, polyethylendithiols are often used as precursor in the synthesis of various ligands such as bis‐phenathrolines, thiacrown ethers , and the preparation of thermoplastic polyurethanes derivatives .…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Bis{(S‐methyl)azolespoly(ethylene oxide)} from 3,6‐dioxa‐1,8‐octanedithiol

Akremi

Beji

Baklouti

2014

Journal of Heterocyclic Chem

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Bis(1,3,4‐oxadiazoles) 4, 5 and bis(1,2,4‐triazoles) 6a, 6b have been prepared from 3,6‐dioxa‐1,8‐octanedithiol 1 through a multistep reaction sequence. Compound 4 reacted with the appropriate alkyl halide in the presence of potassium carbonate in refluxing acetone to give the corresponding bis(S‐alkylated‐1,3,4‐oxadiazoles) 7a, 7b. The title compound 8 was prepared by condensing 4 with benzoyl bromide in the presence of triethylamine. Further, 6,9‐dioxa‐3,12‐dithiotetradecanedihydrazide 3 was converted to bis{N′‐(phenylaminocarbonyl) hydrazides} and bis{N′‐(phenylaminocarbonothioyl)hydrazides} 9a, 9b using phenylisocyanate and phenylthioisocyanate, respectively, which underwent cyclization in alkaline medium to produce 6,9‐dioxa‐3,12‐dithiotetradecane bis(4‐phenyl‐2,4‐dihydro‐3H‐1,2,4‐triazol‐3‐one) and their 3‐thio analogs 10a, 10b. The new compounds 4, 5, 6, 7, 8, 9, 10 were characterized by their IR, 1H‐NMR, 13C‐NMR, MS, and elemental analyses.

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“…Synthesis: 6-Acyl-2-[N-methyl-N-(carboxymethyl)amino]naphthalene [27] (acedane, A) and 2,2'-(4-nitrophenylazanediyl)bis(ethane-2,1-diyl)bis(4-methylbenzenesulfonate) [28] (1) were prepared according to literature methods. The synthesis of other compounds is described below.…”

Section: Methodsmentioning

confidence: 99%

Detection of Nickel in Fish Organs with a Two‐Photon Fluorescent Probe

Kang

Lim

Kim

et al. 2012

Chemistry A European J

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Molecular imaging by two-photon microscopy (TPM) has become indispensable to the study of biology/medicine owing to its capability of imaging deep inside intact tissues. To make TPM a more-versatile tool, a large variety of two-photon probes are needed. Herein, we report a new two-photon fluorescent probe (ANi2) that can be excited by 750 nm femtosecond pulses and detect Ni(2+) ions in fresh fish organs at 90-175 μm depth without interference from the pH value or from other biologically relevant species through the use of TPM. TPM images of fish organs labeled with ANi2 revealed that Ni(2+) ions accumulate in fish organs in the order: kidney > heart > gill ≥ liver. Moreover, a linear relationship was found between the two-photon-excited fluorescence (TPEF) and the inductively coupled plasma mass spectrometry intensities (ICP-MS), thereby allowing the quantitative measurement of Ni(2+) ions in live tissue.

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Improved synthetic methods to mixed-donor thiacrown ethers

Cited by 34 publications

References 42 publications

Aza‐ and Mixed Thia/Aza‐Macrocyclic Receptors with Quinoline‐Bearing Pendant Arms for Optical Discrimination of Zinc(II) or Cadmium(II) Ions

Aza‐ and Mixed Thia/Aza‐Macrocyclic Receptors with Quinoline‐Bearing Pendant Arms for Optical Discrimination of Zinc(II) or Cadmium(II) Ions

Synthesis of Bis{(S‐methyl)azolespoly(ethylene oxide)} from 3,6‐dioxa‐1,8‐octanedithiol

Detection of Nickel in Fish Organs with a Two‐Photon Fluorescent Probe

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