The purpose of this study is to compare the gelling behavior of two molecules: a chiral compound and its achiral counterpart. The chiral partner is characterized by a rigid, chiral pyrrolidine nucleus, while the achiral one contains a flexible diethanolamine moiety. The chiral compound is an already known good organogelator, but also the achiral compound shows remarkable gelling properties. Very interestingly, a small fraction of the chiral compound induces chirality and strong CD effects in its aggregates with the achiral one. The observed chirality amplification corresponds to a peculiar sergeant-and-soldier effect. Molecular modelling and CD calculations suggested a model for the supramolecular assembly of hetero-aggregates that fits the experimental data.

Chiral/ring closed vs. achiral/open chain triazine-based organogelators: induction and amplification of supramolecular chirality in organic gels

PESCITELLI, GENNARO;
2014-01-01

Abstract

The purpose of this study is to compare the gelling behavior of two molecules: a chiral compound and its achiral counterpart. The chiral partner is characterized by a rigid, chiral pyrrolidine nucleus, while the achiral one contains a flexible diethanolamine moiety. The chiral compound is an already known good organogelator, but also the achiral compound shows remarkable gelling properties. Very interestingly, a small fraction of the chiral compound induces chirality and strong CD effects in its aggregates with the achiral one. The observed chirality amplification corresponds to a peculiar sergeant-and-soldier effect. Molecular modelling and CD calculations suggested a model for the supramolecular assembly of hetero-aggregates that fits the experimental data.
2014
L., Lascialfari; D., Berti; A., Brandi; S., Cicchi; M., Mannini; Pescitelli, Gennaro; P., Procacci
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/438067
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