Chemical and thermal stability of novel phenyl-BODIPY symmetric dimer thin films

Abstract

Phenyl-BODIPY-dimers are an increasingly interesting motif whose unique electronic and morphological properties make them excellent candidates for a wide range of applications in materials chemistry, including device design and fabrication. Two dimers based on the meso‑(4-ethynylphenyl)-BODIPY unit were obtained through sequential Sonogashira and Glaser-Hay-type coupling reactions. The synthesized compounds, present a significant advantage in terms of solution stability compared to their monomers. An evaluation of their properties, both in solution and thin films, highlights that these dimers maintain exceptional chemical and structural stability when deposited in films, suggesting their plausible use in coatings and devices. The studied dimers exhibit reduced wettability given their surface roughness, meaning a potential for varied applications. Finally, a tandem analysis that included UV–Vis/fluorescence measurements and quantum chemistry methods was carried out to analyze the optical properties in solution and solid-state helping to gain insight into the optical properties of the synthesized molecules and the effect of π-interacting solvents.