A novel low molecular weight chiral gelator for apolar organic solvents

The synthesis, molecular structure, and properties of a new chiral gel-forming agent 1 are described. Key structural features in 1 are a gamma-alkoxybutyrolactone tetralin moiety and an angular phenylsulphone unit. The new low molecular weight gelator 1 can reversibly form stable gels in low concentrations (e.g., 1:800 for n-hexane) with isopropanol and a variety of apolar organic solvents, The gels were studied with differential scanning calorimetry and a combination of electron microscopy techniques, which revealed a highly ordered three-dimensional network of entangled fibers. X-ray analysis showed that the aggregation of 1 leads to a helical structure in the solid state. Nonchiral analogues 2 and 3 were unable to initiate gel formation.