Year: 2025
Type: preprint
Abstract: Unconventional amphiphilic molecules having a rigid hydrophobic central unit and flexible or semiflexible hydrophilic chains on the rim, have proven valuable in several technological applications, for example host-guest chemistry. The further presence of alternating hydrophobic and hydrophilic tails complicates the definition of clear core and shell regions, resulting in complex segregation and frustrated self-assembly. In this study, we investigate symmetric triphenylene-based amphiphilic derivatives with alternating benzyl and alkylsulfonate groups. We characterize their self-assembly in water and different solutions using several experimental techniques — NMR, atomic force microscopy, dynamic light scattering, small-angle X-ray and neutron scattering — alongside extensive molecular dynamics simulations, both atomistic and coarse-grained with metainference. In aqueous solutions, these amphiphiles form stacked assemblies, adopting alternate up-down conformations driven by π-stacking of up to six molecules. The introduction of NaCl salt screens unfavorable electrostatic interactions thus promoting further π-stacking and leads to the formation of larger elongated aggregates.
Source: ChemRxiv
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W4414088613