Influence of building block aromaticity in the determination of electronic properties of five-membered heterocyclic oligomers

Abstract

This theoretical study investigates the influence of the building block aromaticity in the determination of electronic properties of five-membered heterocyclic oligomers. More specifically, we considered some fundamental energetic and electronic properties such as energy gaps, vertical ionization energies and static polarizability tensors of oligomers (up to octamers) built from five-membered heterocycles such as cyclopentadiene, pyrrole, furan, silole, (planar) phosphole and thiophene. Our computations are based on ab initio quantum mechanical methods including (time-dependent) density functional theory. We have chosen NICS as a quantitative criterion for measuring aromaticity and making a distinction between aromatic and non-aromatic building blocks.