Chiral Auxiliaries and Chirogenesis II

This Reprint Book highlights and overviews the most important and novel aspects of chiral auxiliary and chirogenesis in different natural/physical sciences and in modern technologies. In particular, some newly emerging classes of molecules used for these purposes have been described. Furthermore, some important experimental and theoretical issues associated with the chirality field have been addressed. This book consists of one review article and six research papers and is of interest for general chemistry readership, including graduate and post-graduate students, and for researchers specializing in the fields of chirality and stereochemistr

Proline Enantiomers Discrimination by (L)-Prolinated Porphyrin Derivative Langmuir–Schaefer Films: Proof of Concept for Chiral Sensing Applications

A porphyrin derivative functionalized with the L-enantiomer of proline amino acid was characterized at the air–pure water interface of the Langmuir trough. The porphyrin derivative was dissolved in dichloromethane solution, spread at the air–subphase interface and investigated by acquiring the surface pressure vs. area per molecule Langmuir curves. It is worth observing that the behavior of the molecules of the porphyrin derivative floating film was substantially influenced by the presence of L-proline amino acid dissolved in the subphase (10−5 M); on the contrary, the physical chemical features of the floating molecules were only slightly influenced by the D-proline dissolved in the subphase. Such an interesting chirality-driven selection was preserved when the floating film was transferred onto solid supports by means of the Langmuir–Schaefer method, but it did not emerge when a spin-coating technique was used for the layering of the tetrapyrrolic derivatives. The obtained results represent proof of concept for the realization of active molecular layers for chiral discrimination: porphyrin derivatives, due to their intriguing spectroscopic and supramolecular properties, can be functionalized with the chiral molecule that should be detected. Moreover, the results emphasize the crucial role of the deposition technique on the features of the sensing layers

Proline enantiomers discrimination by (L)-prolinated porphyrin derivative Langmuir-Schaefer films: proof of concept for chiral sensing applications

A porphyrin derivative functionalized with the L-enantiomer of proline amino acid was characterized at the air-pure water interface of the Langmuir trough. The porphyrin derivative was dissolved in dichloromethane solution, spread at the air-subphase interface and investigated by acquiring the surface pressure vs. area per molecule Langmuir curves. It is worth observing that the behavior of the molecules of the porphyrin derivative floating film was substantially influenced by the presence of L-proline amino acid dissolved in the subphase (10(-5) M); on the contrary, the physical chemical features of the floating molecules were only slightly influenced by the D-proline dissolved in the subphase. Such an interesting chirality-driven selection was preserved when the floating film was transferred onto solid supports by means of the Langmuir-Schaefer method, but it did not emerge when a spin-coating technique was used for the layering of the tetrapyrrolic derivatives. The obtained results represent proof of concept for the realization of active molecular layers for chiral discrimination: porphyrin derivatives, due to their intriguing spectroscopic and supramolecular properties, can be functionalized with the chiral molecule that should be detected. Moreover, the results emphasize the crucial role of the deposition technique on the features of the sensing layers

Chiral Auxiliaries and Chirogenesis

This Reprint Book highlights and overviews the most important and novel aspects of chiral auxiliary and chirogenesis in different natural/physical sciences and in modern technologies. In particular, some newly emerging classes of molecules used for these purposes are described. This book consists of four review articles and one research paper and is of interest for general chemistry readership, including graduate and postgraduate students, and for researchers specializing in the fields of chirality and stereochemistr