Nanofiber Networks from Self-Assembling Cardanol Amphiphiles: Toward Renewable Multifunctional Surfactants

This article focuses on the utilization of the supramolecular self-assembly of renewable materials derivatives to obtain functional compounds. Novel bio-based amphiphile molecules (CALAH and PALAH) were synthesized through a tailored process, involving Williamson ether synthesis and amidation reactions, employing renewable amino acid and cashew nut shell liquid (CNSL) derivatives as essential reactants. Their molecular structures were confirmed by nuclear magnetic resonance (NMR), high-resolution mass spectrometry (HRMS), and Fourier-transform infrared spectroscopy (FT-IR). Notably, these compounds self-assemble into nanofibers that organize into a fibrous network, unexpectedly exhibiting two distinct morphologies: curved and rigid nanostructures. These structures were characterized by scanning electron microscopy (SEM), and their formation mechanisms were elucidated through temperature-dependent NMR studies and density functional theory (DFT) calculations. The sodium salts of the compounds (PALA and CALA) exhibited fundamental surfactant properties, exhibiting a hydrophilic lipophilic balance (HLB) value of 13.7 and critical micelle concentration (CMC) values of 1.05 × 10^-5 M and 4.10 × 10^-6 M. They also demonstrated low cytotoxicity, suggesting potential suitability in consumer applications. Furthermore, the compounds exhibited multi-functional performance as effective inhibitors of Staphylococcus aureus and efficient adsorbents for gaseous pollutants.