Abstract
This feature article gives a general introduction to the phenomenon of supramolecular chirogenesis using the most representative examples of different chirogenic assemblies on the basis of ethane-bridged bis-porphyrinoids. Supramolecular chirogenesis is based upon a smart combination of supramolecular chemistry and chirality sciences and deals with various aspects of asymmetry induction, transfer, amplification, and modulation. These chiral processes are governed by numerous noncovalent supramolecular forces thus allowing a judicious, mechanistic, and dynamic control by applying a variety of internal and external influencing factors. Currently, supramolecular chirogenesis is widely used in different fields of fundamental and applied branches of science and modern technology, touching on such important issues as origin of chirality on the Earth, asymmetry sensing, enantioselective catalysis, nonlinear optics, polymer and materials science, pharmacy and medicine, nanotechnology, molecular and supramolecular devices, chiral memory, absolute configuration determination, etc.
Highlights
Chirality in general is an ability of some objects to exist as a pair of non-superimposable mirror images (Figure 1)
With supramolecular interactions being responsible for such chiral transformation, all the phenomena dealing with various aspects of asymmetry induction, transfer, amplification and modulation come under the heading of supramolecular chirality or supramolecular chirogenesis [2–7]
In the case of (R)-enantiomers, the relative orientation between these two electronic transitions of the neighboring porphyrin moieties is anticlockwise, which according to the exciton chirality method [34] corresponds to negative chirality, whilst for (S)-enantiomers the orientation of these transitions is opposite, resulting in the positive sign of the induced chirality (Figure 5)
Summary
Chirality in general is an ability of some objects to exist as a pair of non-superimposable mirror images (Figure 1). In the case of (R)-enantiomers, the relative orientation between these two electronic transitions of the neighboring porphyrin moieties is anticlockwise, which according to the exciton chirality method [34] corresponds to negative chirality, whilst for (S)-enantiomers the orientation of these transitions is opposite (clockwise), resulting in the positive sign of the induced chirality (Figure 5) This comprehensive rationalization of the host-guest interaction and chirality induction mechanisms allowed the development of a smart and universal chirality sensor, which can be used for straightforward determination of the absolute configuration of various chiral guests, and the detailed investigation of various external and internal factors controlling the chirogenic properties in these supramolecular systems. Over a period of 4 days, exceptionally high optical activity with the anisotropy factor being as great as 0.015 was generated, the sign of which was the same as that observed for the solid state systems on the basis of 1, indicating essentially the same chirogenic mechanism
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