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Preparation and Reactions of Sulfides02:26

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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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DNA probes are fragments of DNA labeled with a reporter tag to enable their detection or purification. The resulting labeled DNA probes can then hybridize to target nucleic acid sequences through complementary base-pairing, and may be used to recover or identify these regions.
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Sulfoxides as response elements for fluorescent chemosensors.

Rahul S Kathayat1, Nathaniel S Finney

  • 1Institute of Organic Chemistry, University of Zurich, Winterthurerstrasse 190, 8057 Zurich, Switzerland.

Journal of the American Chemical Society
|August 10, 2013
PubMed
Summary
This summary is machine-generated.

Sulfoxides can be used in fluorescent chemosensors. Metal coordination enhances fluorescence by suppressing sulfoxide inversion, enabling new sensors for metal ions in water.

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Area of Science:

  • Supramolecular Chemistry
  • Analytical Chemistry
  • Organic Chemistry

Background:

  • Fluorescent chemosensors are crucial for detecting metal ions.
  • Existing sensors often rely on nitrogen coordination, limiting their scope.
  • Sulfoxides present an alternative signaling mechanism.

Purpose of the Study:

  • To explore sulfoxides as a novel reporting group for fluorescent chemosensors.
  • To develop metal ion sensors independent of nitrogen coordination.
  • To investigate the mechanism of fluorescence enhancement via metal-sulfoxide interaction.

Main Methods:

  • Synthesis of sulfoxide-appended fluorophores.
  • Metal ion titration experiments.
  • Fluorescence spectroscopy to monitor emission changes.
  • Computational studies to understand the mechanism.

Main Results:

  • Sulfoxide-appended fluorophores exhibit fluorescence enhancement upon metal coordination.
  • The mechanism involves suppression of excited-state pyramidal inversion of the sulfoxide.
  • The developed sensors show selectivity for oxophilic metal ions.
  • The sensors are functional in aqueous media.

Conclusions:

  • Sulfoxides are effective reporting groups for fluorescent chemosensor design.
  • This approach offers a new strategy for metal ion sensing, avoiding nitrogen coordination.
  • The developed sensors are versatile and applicable in aqueous environments.