ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

DFT study on [4+2] and [2+2] cycloadditions to [60] fullerene

Ali Ahmadi Peyghan and Maziar Noei

Chemistry Department, Central Tehran Branch, Islamic Azad University, Tehran, Iran

E-mail: ahmadi.iau@gmail.com

Abstract: The functionalisation of C₆₀ fullerene with 2,3-dimethylene-1,4-dioxane (I) and 2,5-dioxabicyclo [4.2.0]octa-1(8),6-diene (II) was investigated by the use of density functional theory calculations in terms of its energetic, structural, field emission, and electronic properties. The functionalisation of C₆₀ with I was previously reported experimentally. The I and II molecules are preferentially attached to a C—C bond shared and located between two hexagons of C₆₀ via [4+2] and [2+2] cycloadditions bearing reaction energies of −15.9 kcal mol⁻¹ and −72.4 kcal mol⁻¹, respectively. The HOMO-LUMO energy gap and work function of C₆₀ are significantly reduced following completion of the reactions. The field electron emission current of the C₆₀ surface will increase after functionalisation of either the I or II molecule.

Keywords: density functional – nanostructure – chemical functionalisation – ab initio – diene

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-013-0448-z

Chemical Papers 68 (3) 409–416 (2014)