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A Novel Low Molecular Weight Chiral Gelator for Apolar Organic Solvents
Author(s) -
Snijder Carina S.,
de Jong Johannes C.,
Meetsma Auke,
van Bolhuis Fré,
Feringa Ben L.
Publication year - 1995
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.19950010905
Subject(s) - moiety , tetralin , hexane , differential scanning calorimetry , chemistry , organic chemistry , polymer chemistry , chemical engineering , solvent , engineering , thermodynamics , physics
The synthesis, molecular structure, and properties of a new chiral gelforming agent 1 are described. Key structural features in 1 are a γ‐alkoxybutyro‐lactone 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.
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