Abstract
Chirality is a powerful tool for the generation of order, directionality, and, as such, of function, in assembled nanoscale chemical devices. Axially chiral binaphthyls have been widely used in organic synthesis; the stability of the enantiomers enables their use as robust chirality inducers and catalysts in asymmetric reactions, and they are nowadays industrially applied in a variety of organic transformations. Applications of these compounds in the field of nanosciences are more recent, and not yet fully explored. The integration of such a robust class of chiral compounds, capable of efficient transfer of stereochemical information, into functional aggregates and nanoarchitectures is of great current interest. We will discuss preeminent examples of applications of these synthons in several fields of nanoscience, such as reticular chemistry, non-linear optical materials and imaging, and liquid crystals.
Highlights
Chirality is a fascinating property of molecular compounds
Substituted 1,10-binaphthyl derivatives are a versatile class of compounds which have found applications in many different areas of chemistry.[2]
Two previous comprehensive reviews have illustrated applications of 1,10-binaphthyl derivatives in general,2a and BINOL,2d and illustrated the synthetic procedures for the preparation of these compounds. The scope of this Feature Article is to highlight recent examples related to the use of axially chiral binaphthyl molecular skeletons in a context where nanoscale structuring translates into bulk materials properties; we decided to exclude aspects related to a “classical” supramolecular approach,[4,5] such as the use of axially chiral binaphthyl compounds in mechanically interlocked molecules and macromolecules,[6] and in chiral chromatographic separations.[7]
Summary
Chirality is a fascinating property of molecular compounds. The translation of molecular chirality into supramolecular and nanoscale chirality has been the subject of intense research activity in recent years.[1]. Pasini for the award of the PhD in Chemistry (January 2011) He developed supramolecular and nanoscale materials using binaphthyl-based macrocycles. Two previous comprehensive reviews have illustrated applications of 1,10-binaphthyl derivatives in general,2a and BINOL,2d and illustrated the synthetic procedures for the preparation of these compounds The scope of this Feature Article is to highlight recent examples related to the use of axially chiral binaphthyl molecular skeletons in a context where nanoscale structuring translates into bulk materials properties; we decided to exclude aspects related to a “classical” supramolecular approach,[4,5] such as the use of axially chiral binaphthyl compounds in mechanically interlocked molecules and macromolecules,[6] and in chiral chromatographic separations.[7]
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