Krishna Damodaran - Supramolecular Synthons in Designing Low Molecular Mass Gelling Agents: L-Amino Acid Methyl Ester Cinnamate Salts and their Anti-Solvent-Induced Instant Gelation

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      Publication Details (including relevant citation   information):

      Chem.   Asian J. 2011,   6, 1038



      Easy access to a class of chiral gelators has been achieved by   exploiting primary ammonium monocarboxylate   (PAM), a supramolecular synthon. A combinatorial   library comprising of 16 salts, derived from 5 l-amino acid methyl esters and 4 cinnamic   acid derivatives, has been prepared and scanned for gelation.   Remarkably, 14 out of 16 salts prepared (87.5 % of the salts)   show moderate to good gelation abilities with various solvents,   including commercial fuels, such as petrol. Anti-solvent induced   instant gelation at room temperature has been achieved in all the   gelator salts, indicating that the gelation process is indeed an   aborted crystallization phenomenon. Rheology, optical and   scanning electron microscopy, small angle neutron scattering, and   X-ray powder diffraction have been used to characterize the gels.   A structure-property correlation has been attempted, based on   these data, in addition to the single-crystal structures of 5   gelator salts. Analysis of the FT-IR and 1H NMR   spectroscopy data reveals that some of these salts can be used as   supramolecular containers for the slow release of certain pest   sex pheromones. The present study clearly demonstrates the merit   of crystal engineering and the supramolecular synthon approach in   designing new materials with multiple properties.

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