RSC Publishing


Publishing

 

Cover image for Chemical Communications, select for current issue

Chemical Communications

Urgent high quality communications from across the chemical sciences.



Subscribers

Non-subscribers

Free access



Feature Article

Chem. Commun., 2009, 5958 - 5980, DOI: 10.1039/b909582a

Probing molecular chirality by CD-sensitive dimeric metalloporphyrin hosts

Nina Berova, Gennaro Pescitelli, Ana G. Petrovic and Gloria Proni

This feature article reviews dimeric metalloporphyrin hosts employed as chirality probes in chiral recognition processes involving synthetic compounds and natural products. Upon formation of a chiral host–guest supramolecular complex between an achiral bis-metalloporphyrin derivative and a chiral non-racemic guest, a CD response occurs in the porphyrin spectral region, which is diagnostic of the guests absolute configuration. Several bis-porphyrin hosts used in the stereochemical investigation of organic compounds are described and the scope of their application as chirality probes critically assessed. The review encompasses the description of structural features of the host–guest complexes, the nature of the chirality transfer mechanism and the practical application in solving stereochemical problems. In particular, with reference to the method based on bis-porphyrin tweezers, we describe recent advances based on the use of molecular modeling, which have broadened the applicability of the tweezer methodology and allowed extraction of deeper structural information contained in the experimental CD data.

Graphical abstract image for this article (ID: b909582a)