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Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

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Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
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Gold dithiolene complexes: easy access to 2-alkylthio-thiazoledithiolate complexes.

Agathe Filatre-Furcate1, Pascale Auban-Senzier, Marc Fourmigué

  • 1Institut des Sciences Chimiques de Rennes, UMR 6226 CNRS-Université de Rennes 1, Campus de Beaulieu, Bât 10A, 35042 Rennes cedex, France. Dominique.lorcy@univ-rennes1.fr.

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|August 8, 2015
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Summary

New gold complexes transform into semi-conducting radical species. These novel gold dithiolene complexes, [Au(RS-tzdt)2]˙, exhibit unique solid-state dimerization, paving the way for advanced materials.

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Area of Science:

  • Inorganic chemistry
  • Materials science
  • Coordination chemistry

Background:

  • N-tert-butyl-1,3-thiazoline-2-thione derivatives are precursors in organometallic synthesis.
  • Gold complexes with dithiolene ligands are of interest for their electronic properties.

Purpose of the Study:

  • To synthesize and characterize novel gold(III) dithiolene complexes.
  • To investigate the transformation of thiazoline-2-thione derivatives into pro-ligands.
  • To explore the redox properties and solid-state behavior of the resulting gold complexes.

Main Methods:

  • Reaction of N-tert-butyl-1,3-thiazoline-2-thione derivatives with methyl iodide (MeI) or ethyl iodide (EtI).
  • Synthesis of gold(III) dithiolene complexes [Au(RS-tzdt)2](-) (R = Me, Et).
  • Oxidation of gold complexes to neutral radical species.
  • Solid-state characterization of the radical species.

Main Results:

  • Transformation of N-tert-butyl-1,3-thiazoline-2-thione derivatives to 2-alkylthio-thiazoledithiolate pro-ligands with loss of the tert-butyl group.
  • Formation of Au(III) dithiolene complexes [Au(RS-tzdt)2](-) (R = Me, Et).
  • Readily oxidation to neutral radical species, e.g., semi-conducting [Au(EtS-tzdt)2]˙.
  • Solid-state organization of the radical species into dimers.

Conclusions:

  • A novel synthetic route to 2-alkylthio-thiazoledithiolate ligands and their gold complexes has been established.
  • The synthesized gold(III) dithiolene complexes can be oxidized to neutral radical species with potential semiconducting properties.
  • The radical species exhibit interesting solid-state self-assembly behavior, forming dimers.