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Chiral Self-Discrimination and Guest Recognition in Helicene-Based Coordination Cages
Thorben R Schulte1, Julian J Holstein1, Guido H Clever1
1Faculty of Chemistry and Chemical Biology, TU Dortmund University, Otto-Hahn-Str. 6, 44227, Dortmund, Germany.
Angewandte Chemie (International Ed. in English)
|February 15, 2019
Summary
Researchers developed chiral coordination cages using [6]helicene backbones for enantioselective recognition. These supramolecular structures, formed via self-assembly, exhibit tunable properties for chiral guest binding and discrimination.
Area of Science:
- Supramolecular Chemistry
- Coordination Chemistry
- Chiral Materials
Background:
- Chiral nanosized confinements are crucial for biological enantioselective recognition and reactions.
- Supramolecular self-assembly offers a route to artificial mimics with adjustable sizes and properties.
Purpose of the Study:
- To introduce a novel family of [Pd2L4] coordination cages based on a chiral [6]helicene backbone.
- To investigate the self-assembly behavior of these ligands with Pd(II) cations.
- To explore the chiral recognition and discrimination capabilities of the resulting cages.
Main Methods:
- Supramolecular self-assembly of bis-monodentate pyridyl ligands with Pd(II) cations.
- Synthesis of chiral [6]helicene-based ligands (L1 and L2).
- Chiral recognition studies using optical isomers of chiral guests.
- Characterization using circular dichroism (CD) spectroscopy and ion mobility mass spectrometry.
Main Results:
- A racemic mixture of L1 selectively self-assembles into an achiral meso cage.
- Enantiopure L1 forms homochiral cages.
- A longer derivative L2 forms chiral cages with larger cavities capable of binding chiral guests with differential affinities.
- The cages exhibit distinct chiroptical properties, enabling discrimination of non-chiral guests based on length by modulating cavity size.
Conclusions:
- Novel chiral coordination cages based on [6]helicene were successfully synthesized.
- These cages demonstrate selective binding and discrimination of chiral guests.
- The tunable cavity size and chiroptical properties allow for the differentiation of guests based on length, highlighting their potential in molecular recognition.
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