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Imidazolium-fulleride ionic liquids - a DFT prediction.

Sebastian Anila1,2, Cherumuttathu H Suresh1,2

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Researchers created novel large X-fulleride anions by adding anionic moieties to C60. These new anions show potential for designing ionic liquids (ILs) with tunable properties, like low melting points and high viscosity.

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Area of Science:

  • Computational Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Ionic liquids (ILs) possess tunable physicochemical properties influenced by ion selection.
  • Ion size is critical for regulating IL properties such as melting temperature and viscosity.
  • Fullerene derivatives offer unique structural and electronic characteristics for novel materials.

Purpose of the Study:

  • To investigate the thermodynamic viability of forming large X-fulleride anions (C60X)− via exohedral addition to C60.
  • To explore the potential of these X-fullerides as components for designing new ionic liquids.
  • To characterize the bonding, electronic properties, and ion-pair interactions of the synthesized fulleride anions.

Main Methods:

  • Density functional theory (DFT) calculations using the M06L functional with the 6-311++G(d,p) and 6-31G(d,p) basis sets.
  • Transition state location and free energy calculations for the reaction between C60 and 1,3-dimethyl-2X-imidazole (IMX).
  • Quantum Theory of Atoms in Molecules (QTAIM) and Molecular Electrostatic Potential (MESP) analyses.

Main Results:

  • Thermodynamically viable formation of X-fulleride anions (C60X)− for X = H, F, OH, CN, NH2, and NO2.
  • Low activation free energy barriers indicate the feasibility of the reactions.
  • X-fullerides exhibit covalent C-X bonding and behave as large, spherical anions due to electron delocalization.
  • Ion-pair interactions (Eion-pair) are significantly lower than in typical imidazolium-based ILs.
  • Formation of X-fullerides was not observed for X = Cl and Br.

Conclusions:

  • The exohedral addition of anionic moieties to C60 is a feasible route to novel X-fulleride anions.
  • The unique properties of X-fullerides, including their large size and spherical nature, suggest their potential for creating low-melting point, highly viscous ionic liquids.
  • These findings open new avenues for designing advanced ionic liquids with tailored properties based on fullerene chemistry.