Synthesis, simulation and optical properties of a quinoline-bearing resorcinarene

Abstract

The design and synthesis of conjugated organic macromolecules is interesting in the area of optoelectronic, for the fabrication of optoelectronic devices, such as organic solar cells, perovskite-type solar cells, OLEDS, thin organic field-effect transistors, sensors, etc. In this work we report the molecular simulation by DFT of a quinoline and thiophene bearing resorcinarene, designated as D. The dendrimer was synthesized following the convergent method of coupling the quinoline dendron to the center. Dendrimer D was characterized by 1H-NMR spectroscopy, FT-IR. The study of the optical properties was performed by UV vis and static and dynamic fluorescence spectroscopy, the results indicate that the dendrimer presents a maximum emission at 574 nm which is located in the green region of the electromagnetic spectrum. The calculation of the optical and theoretical band gap was 2.78 and 3.3 eV respectively, which places this material within the organic semiconductors. The theoretical values of the energy levels of the HOMO and LUMO frontier orbitals of 5.52 and 2.18 eV, suggest its possible application as HTL (hole transfer layer) in the fabrication of an organic heterojunction solar cell.