Issue 40, 2009

Probing molecular chirality by CD-sensitive dimeric metalloporphyrin hosts

Abstract

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 guest’s 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: Probing molecular chirality by CD-sensitive dimeric metalloporphyrin hosts

Article information

Article type
Feature Article
Submitted
18 May 2009
Accepted
03 Aug 2009
First published
16 Sep 2009

Chem. Commun., 2009, 5958-5980

Probing molecular chirality by CD-sensitive dimeric metalloporphyrin hosts

N. Berova, G. Pescitelli, A. G. Petrovic and G. Proni, Chem. Commun., 2009, 5958 DOI: 10.1039/B909582A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements