C3-symmetric triphenylenes based designer surfactants: synthesis, aggregation and catalytic properties studies

Abstract

In this MD Thesis the synthesis of C3-symmetric triphenylene derivatives were performed and largely improved, to achieve water-soluble aromatic compounds bearing hydrophilic sulfonated moieties or PEG chains. Such molecules were obtained from hexahydroxytriphenylenes, using less hazardous reagents and conditions compared to previous ones. The products showed amphiphilic behaviour and were employed directly as catalysts in water or combined with transition metal catalysts to perform cross-coupling reactions. While the anionic surfactant showed lower catalytic activities compared to commercial surfactants, the neutral PEG derivative turned out to improve cross-coupling reactions, observing in many cases enhanced yields and easy product isolation, representing a promising new designer surfactant for future developments. 1H NMR and DOSY experiments at different concentrations were employed to investigate the aggregation properties of these amphiphiles in water, and SANS experiments in collaboration with Dr. Mondelli from ILL Grenoble further enabled to ascertain the size and structure of the micelles. The lockdown period was conveniently employed to collect recent literature regarding innovative designer surfactants and their application in organic synthesis processes, leading to the preparation of a mini-review manuscript under the guidance of Proff. Fabris and Scarso on the field of “designer surfactants” that has recently published in Catalysis Science and Technology.