Fullerene–1,4-dioxane adducts: a DFT study of the structural features and molecular properties

Abstract

Using the PBE/3ζ density functional theory method, we have computationally studied fullerene–1,4-dioxane adducts, which were recently synthesized in sonochemical reaction of C₆₀/C₇₀ with ethylene glycol in the presence of NaOH. We have found the preference of the boat conformations of C₆₀ and C₇₀ adducts with 1,4-dioxane over the chair ones. Fullerene–dioxane adducts have the dipole moments of 2.5–3.0 D and band gaps narrower as compared with original C₆₀/C₇₀. Adducts ab-, cc₁-, and cc₂-C₇₂H₄O₂ are revealed higher stability than their regioisomers. Herewith, cc-adducts have the lower mean polarizabilities that corresponds to the experimental observation of the cc-functionalization of the C₇₀ fullerene core. All adducts have the nonzero anisotropies of polarizability higher than the values of starting C₆₀ and C₇₀. The lowest anisotropy corresponds to cc₁-C₇₂H₄O₂ that makes this compound promising for organic solar cells.

Keywords:

• Fullerene adducts
• Conformations
• Regioisomers
• Polarizability
• Density functional theory methods

Acknowledgment

The work has been performed under the theme ‘Novel theoretical approaches and software for modeling complex chemical processes and compounds with tunable physicochemical properties’ (registration number AAAA-A19-119022290011-6).

Additional information

Funding

This work is partly supported by Russian Foundation for Basic Research (project number 19-03-00716).