Synthesis, Self-Assembly Properties, and Degradation Characterization of a Nonionic Photocleavable Azo-Sulfide Surfactant Family

Abstract

We report the synthesis and characterization of a new family of maltose-derived nonionic surfactants that contain a photocleavable azo-sulfide linker (mAzo). The selfassembly properties of these surfactants were investigated using surface tension measurements to determine the critical micelle concentration (CMC), dynamic light scattering (DLS) to reveal the hydrodynamic radius of their self-assemblies, and transmission electron microscopy (TEM) to elucidate the micelle morphology. Ultraviolet−visible (UV−visible) spectroscopy confirmed the rapid photodegradation of these surfactants, but surface tension measurements of the surfactant solutions before and after degradation showed unusual degradation products. The photodegradation process was further studied using online liquid chromatography coupled with mass spectrometry (LC−MS),which revealed that these surfactants can form another photo-stable surfactant post-degradation. Finally, traditionally challenging proteins from heart tissue were solubilized using the mAzo surfactants to demonstrate their potential in biological applications.

Synthetic approaches of carbohydrate based self-assembling systems

“…Several maltose-based nonionic surfactants 251a–c containing a photocleavable azo-sulfide linker were synthesized and the self-assembling properties of these surfactants were explored (Scheme 36). 122 β- d -Maltose octaacetate 248 was converted to the corresponding thiolglycoside 249 through glycosylation using thiourea followed by reduction. The coupling reaction of the hydrolyzed product 250 with diazonium ions led to the formation of the maltose azo sulfide compounds 251 .…”

Trends in the Diversification of the Detergentome

“…[182] In another case study, a maltose head has been linked to a non-polar tail through an azo-sulfide linker (Figure 16). [183] The azo group either linked to a sulfonate or sulfide can be cleaved via irradiation with ultraviolet light to expel nitrogen gas, which results in complete breakdown of the detergent nanocarrier. Whether they change polarity, are cleavable or dictate the geometry of the molecules and supramolecular aggregates, linkers between polar and nonpolar groups play an important role in the development of tailor-made detergents for individual applications.…”