10.1016/S0040-4039(01)01793-2
The research focuses on the novel synthesis of 24-membered macrocycles with chalcone structural moieties and isobutenyl ether linkages in the core, which are significant for molecular recognition and photophysical properties. The purpose of this study is to incorporate chalcone moieties into macrocyclic structures, leveraging their well-exploited photophysical properties for various optical applications. The researchers envisioned that these macrocycles could be useful for molecular recognition studies and as photo-functional materials. The synthesis strategy involved a mixed aldol reaction of bis-arylaldehyde and bis-arylmethyl ketone, expected to yield a macrocycle with two chalcone moieties and two isobutenyl ether linkages. The study successfully demonstrated a novel approach to synthesize these macrocycles, which possess potential for further modifications under thermal conditions, as shown in the conversion of macrocycle 8a to 9a. The chemicals used in the process include t-BuOK as a catalyst, THF as a solvent, and various substituted aryl groups on the aldehyde and ketone compounds, such as chloro, methoxy, and methyl groups. The synthesized macrocycles were fully characterized using IR, NMR, and ESI-MS techniques. The conclusions drawn from the research indicate that the presence of two isobutenyl ether linkages in the macrocycles are useful for modifications of the macrocycle core under thermal conditions, and the photophysical and molecular recognition properties of these macrocycles will be the focus of future studies.