Issue 11, 2015

Theoretical analysis of [5.5.6]cyclacenes: electronic properties, strain energies and substituent effects

Abstract

A novel class of cyclic conjugated molecules, composed of annelated five- and six-membered rings, is proposed and theoretically investigated using density functional theory and multireference methods with regards to their structures, strain energies, aromaticity (NICS values), electronic ground states, band gaps, and the effect of substituents. These [5.5.6]ncyclacenes are predicted to be low band gap materials (below 1 eV) with, depending on their size, closed-shell singlet ground states. The strain energies from n = 4 upwards lie in the range of the synthetically known [n]cycloparaphenylenes. An investigation of the effect of rim-substitution by methyl, alkynyl, thiomethyl or phenyl groups on the electronic ground states showed that thiomethyl-substitution leads to [5.5.6]ncyclacenes with closed-shell singlet ground states for all sizes n investigated.

Graphical abstract: Theoretical analysis of [5.5.6]cyclacenes: electronic properties, strain energies and substituent effects

Supplementary files

Article information

Article type
Paper
Submitted
19 Jan 2015
Accepted
11 Feb 2015
First published
12 Feb 2015
This article is Open Access
Creative Commons BY license

Phys. Chem. Chem. Phys., 2015,17, 7366-7372

Author version available

Theoretical analysis of [5.5.6]cyclacenes: electronic properties, strain energies and substituent effects

B. Esser, Phys. Chem. Chem. Phys., 2015, 17, 7366 DOI: 10.1039/C5CP00341E

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