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Issue 8, 2010
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Self-sorting chiral organogels from a long chain carbamate of 1-benzyl-pyrrolidine-3,4-diol

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Abstract

(3S,4S)-1-benzylpyrrolidine-3,4-diyl bis(dodecylcarbamate), a pyrrolidine ring bearing two long carbon chains connected by carbamate functionalities, is the origin of stable gels in both polar and apolar solvents. Several experimental and theoretical techniques (cryo-TEM, AFM, DSC, circular dichroism (CD), molecular mechanics calculations and CD simulations) were used to describe the formation and the characteristics of the chiral supramolecular structures and fibers constituting the gel. The chirality at both supramolecular and microscopic level depends on the configuration of the stereogenic centers of the pyrrolidine unit. The gels formed by the two enantiomers of the gelator and their mixtures display enantiomeric discrimination resulting in a self-sorting process. In fact, separate fibers of opposite helicity are obtained, which suggests this class of compounds has strong potential for realizing functionalized chiral architectures.

Graphical abstract: Self-sorting chiral organogels from a long chain carbamate of 1-benzyl-pyrrolidine-3,4-diol

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Publication details

The article was received on 09 Sep 2009, accepted on 22 Dec 2009 and first published on 22 Feb 2010


Article type: Paper
DOI: 10.1039/B918709J
Citation: Soft Matter, 2010,6, 1655-1661
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    Self-sorting chiral organogels from a long chain carbamate of 1-benzyl-pyrrolidine-3,4-diol

    S. Cicchi, G. Ghini, L. Lascialfari, A. Brandi, F. Betti, D. Berti, P. Baglioni, L. Di Bari, G. Pescitelli, M. Mannini and A. Caneschi, Soft Matter, 2010, 6, 1655
    DOI: 10.1039/B918709J

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