Synthesis, structure, and electrochemistry of N-(3-thenoyl)fluorosulfonimide and bis(2-thenoic)imide. Preparation of polymers containing the fluorosulfonimide group

  • MacNeill C
  • Dai J
  • Day C
 et al. 
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Abstract

N-(3-Thenoyl)fluorosulfonimide, (1), C4H3SC(O)N(H)SO2F, was prepared by the reaction of 3-thenoic acid with fluorosulfuryl isocyanate in acetonitrile solution. The new compound is a moderately strong nitrogen acid having a pKaof 2.4. Single-crystal X-ray structural analysis of (1) shows a pattern of strong intermolecular hydrogen-bonding, resulting in the formation of linear chains. (1) is electroinactive over a range of 2 V but undergoes hydrogen reduction (Ep / 2c= - 0.28 V). The salt of (1) with TBA+, 2, has been prepared and its crystal structure determined. The new dithienyl compound, bis(2-thienyl)imide, 3, has been prepared and crystallographically characterized. The polymers of 1, 3, and a polymer containing the fluorosulfonimide group formed from a copolymer of 3-methylthiophene/3-thiophene carboxylic acid are also reported. © 2009 Elsevier B.V. All rights reserved.

Author-supplied keywords

  • Crystal structure
  • Cyclic voltammetry
  • Polythiophene
  • Proton conductor
  • Sulfonimide
  • Sulfur heterocycle
  • Thiopheneimide

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Authors

  • Christopher M. MacNeill

  • Jian Dai

  • Cynthia S. Day

  • Stephen P. Lazar

  • S. Jarrett Howell

  • Ronald E. Noftle

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