Chiral Self-Recognition and Self-Discrimination of Strapped Perylene Bisimides by π-Stacking Dimerization

Narcissism of molecules! Configurationally restricted chiral perylene bisimide dyes show a very strong preference for the formation of homochiral dimers (self‐recognition) (red pair) upon π stacking in solution. Minor amounts of heterochiral dimers (red– yellow pair) enable the determination of P/M...

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Bibliographic Details
Published in:Chemistry : a European journal 2010-07, Vol.16 (25), p.7380-7384
Main Authors: Safont-Sempere, Marina M., Osswald, Peter, Radacki, Krzysztof, Würthner, Frank
Format: Article
Language:English
Subjects:
chiral recognition
dyes/pigments
homochirality
pi interactions
self-assembly
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Summary:Narcissism of molecules! Configurationally restricted chiral perylene bisimide dyes show a very strong preference for the formation of homochiral dimers (self‐recognition) (red pair) upon π stacking in solution. Minor amounts of heterochiral dimers (red– yellow pair) enable the determination of P/M enantiomeric ratios by 1H NMR spectroscopy without using any chiral auxiliary.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201001137