Structural, electrochemical and theoretical study of a new chalcone derivative containing 3-thiophene rings

Ricardo Baggio, Francisco Brovelli, Yanko Moreno, Marcela Pinto, Jorge Soto-Delgado

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

The title chalcone, 1,3-di(thiophene-3-yl)prop-2-en-1-one (C11H8OS2) is an essentially planar molecular with its terminal thiophene rings subtending an angle of 8.9°. The crystal structure consists in the π··π stacking of molecules defining columns along [010], further linked along c by non conventional C-H O bonds, thus determining broad planar arrays parallel to (100). In addition, there are weak S S contacts connecting these weakly interacting 2D substructures. The experimental results obtained from single crystal X-ray diffraction data and the theoretical geometry calculated by molecular mechanics are in good agreement. Electrochemical records reveal an anodic profile with an unsymmetrical irreversible peak at 1.77 V and a shoulder at 1.62 V vs SCE, a behavior interpretable as due to the oxidation of reactive sites present in the molecule. On the other hand, the electrochemical reduction shows a narrow peak at -1.58 V vs SCE, a fact attributable to the carbonyl group. Finally, the values for the energy involved in the departure/arrival of electrons from border orbitals, as calculated using DFT, is compared with experimental data from cyclic voltammetry.

Original languageEnglish
Pages (from-to)1-7
Number of pages7
JournalJournal of Molecular Structure
Volume1123
DOIs
Publication statusPublished - 5 Nov 2016

Keywords

  • 3 di-thienyl-3yl-propenone
  • Chalcone
  • Crystal structure
  • Cyclic voltammetry
  • DFT calculations

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy
  • Organic Chemistry
  • Inorganic Chemistry

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