| Sensitive detection of enantiomeric excess in different acids through chiral induction in an oligo(p-phenylenevinylene) aggregate. | |
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MedLine Citation:
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PMID: 23001258 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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Induction of chirality in achiral aggregates of an oligo(p-phenylenevinylene) has been used to detect the enantiomeric excess in acids used in the resolution of chiral compounds. The chiral acids which induce helicity in the aggregates are present at only 10% of the concentration of the chromophore, whose chiroptical activity can be detected using circular dichroism spectroscopy. An ee of 10% in mixtures of (+) and (-) acids has been clearly evidenced in a series of samples using only 1.5 μg and concentration of approximately 10 μM of the chiral compound. The composition of both carboxylic and phosphoric acid derivatives can be detected, thanks to their binding to the dimerised core ureidotriazine unit attached at one end of the oligo(p-phenylenevinylene) which induces a preferred twist in the aggregated aromatic rod. This chiral arrangement is reflected in the Cotton effects that the assemblies show. The sign of the induced dichroic signal can be affected by the substituents around a stereogenic centre of otherwise identical configuration, and can lead to ambidextrous assemblies as seen in Cotton effects at different positions for different acids. While this technique can be used to detect enantiomeric excess, screening of the pure enantiomers is wise prior to the use of the method to detect scalemic mixtures. This supramolecular approach to evaluation of chiral content in samples could also be applied to other types of aggregates based on achiral molecules which show sensitivity to molecular chiral inducers. |
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Authors:
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François Riobé; Albertus P H J Schenning; David B Amabilino |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2012-9-24 |
Journal Detail:
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Title: Organic & biomolecular chemistry Volume: - ISSN: 1477-0539 ISO Abbreviation: Org. Biomol. Chem. Publication Date: 2012 Sep |
Date Detail:
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Created Date: 2012-9-24 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 101154995 Medline TA: Org Biomol Chem Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
Affiliation:
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Institut de Ciència de Materials de Barcelona (ICMAB-CSIC), Campus Universitari, 08193 Bellaterra, Catalonia, Spain. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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