Comparison between theoretical and experimental properties of thiazolothiazole derivatives

RODRIGUEZ, BERNIK VAN MIERLOO, ADRIAENSESNS, BOTEK, CHAMPAGNE

C¨®rdoba

Congreso; XVII Cong. Arg. de Fisicoquimica; 2011

AAIFQ

Res¨²men Introduction: The organic field-effect transistors (OFETs) could be used for manyapplications as flexible displays, electronic paper or memory/sensors elements. Thereare many p-type semiconductors, but the number of organic n-type is still limited. Thethiazolo-thiazole unit showed excellent properties for using in electronic devices [1].Objetives: The aim of this study was to compare both theoretical calculations andexperimental results of UV-VIS and NMR spectra of four different thiazolo-thiazolederivatives previously synthesized in the Institute for Materials Research, HasseltUniversity (Diepenbeek, Belgium) so as to interpret their physico-chemical properties.Results: Three conformers were built for each compound (1A-1D), with differentangles ¦Á and ¦Â, see Figure 1). These conformers were optimized using B3LYP/6-31G*level of approximation. The most stable structures resulted to be those with 180¡ã-180¡ãangles, at most 7 kJ/mol lower in energy than the other conformations. A Maxwell-Boltzmann (MB) distribution was performed at 298.15 K to obtain the UV-Visible andNMR average results. Both, the UV-Vis and NMR spectra calculations showed a goodagreement with experimental results. We also observed that the electronic transitionswere mostly described by the single-excited HOMO-LUMO configuration for all thecompounds, where HOMO and LUMO were spread over almost the whole molecule.Conclusions: In this study we investigated the chemical properties of the thiazolothiazolederivatives using a joint experimental-computational approach. The theoreticalresults were in good agreement with measurements, which allows further reliablepredictions of physico-chemical properties.