Hybrid Fluorocarbon–Hydrocarbon Surfactants: Synthesis and Colloidal Characterization - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2021

Hybrid Fluorocarbon–Hydrocarbon Surfactants: Synthesis and Colloidal Characterization

Résumé

Four double-tailed hybrid fluorocarbon-hydrocarbon (F-H) surfactants with a poly(ethylene glycol) (PEG) polar headgroup were synthesized. The hydrophobic scaffold consists of an amino acid core, onto which were grafted both fluorocarbon and hydrocarbon chains of different lengths. The PEG polar head was connected to the hydrophobic scaffold through a copper(I)-mediated click reaction. The four derivatives exhibit aqueous solubility >100 g/L and self-assemble into micellar aggregates with micromolar critical micellar concentration (CMC) values, as demonstrated by isothermal titration calorimetry (ITC), surface tension (ST) measurements, and steady-state fluorescence spectroscopy. The CMC value decreased by a factor of ∼6 for each additional pair of CH2 groups, whereas a decrease by a factor of ∼2.5 was observed when the size of the PEG polar head was reduced from 2000 to 750 g/mol. Dynamic light scattering (DLS) showed unimodal micelle populations with hydrodynamic diameters of 10-15 nm, in agreement with results obtained from size-exclusion chromatography (SEC). The aggregation number increased with the hydrocarbon chain length but decreased with increasing PEG chain lengths. The combination in one molecular design of both low CMC and high water solubility makes these new surfactants promising systems for novel drug-delivery systems.

Domaines

Chimie
Fichier non déposé

Dates et versions

hal-04611913 , version 1 (14-06-2024)

Identifiants

Citer

Emilie Grousson, Florian Mahler, Sandro Keller, Christiane Contino-Pépin, Grégory Durand. Hybrid Fluorocarbon–Hydrocarbon Surfactants: Synthesis and Colloidal Characterization. Journal of Organic Chemistry, 2021, 86 (21), pp.14672-14683. ⟨10.1021/acs.joc.1c01493⟩. ⟨hal-04611913⟩
4 Consultations
0 Téléchargements

Altmetric

Partager

Gmail Mastodon Facebook X LinkedIn More