A Family of Photolabile Nitroveratryl-Based Surfactants That Self-Assemble into Photodegradable Supramolecular Structures.

Abstract

Here we report the synthesis and characterization of a family of photolabile nitroveratryl-based surfactants that form different types of supramolecular structures depending on the alkyl chain lengths ranging from 8 to 12 carbon atoms. By incorporating a photocleavable α-methyl-o-nitroveratryl moiety, the surfactants can be degraded, along with their corresponding supramolecular structures, by light irradiation in a controlled manner. The self-assembly of the amphiphilic surfactants was characterized by conductometry to determine the critical concentration for the formation of the supramolecular structures, transmission electron microscopy to determine the size and shape of the supramolecular structures, and dynamic light scattering (DLS) to determine the hydrodynamic diameter of the structures in aqueous solutions. The photodegradation of the surfactants and the supramolecular structures was confirmed using UV-vis spectroscopy, mass spectrometry, and DLS. This surfactant family could be potentially useful in drug delivery, organic synthesis, and other applications.