Chiral 1,1’-binaphthyl-linked diporphyrin ‘tweezers’ (
R)-1/(
S)-1 and the corresponding zinc(II) complexes (
R)-2/(
S)-2 were prepared as chiral host molecules, and their utility for chiral analyses (especially enantiomeric excess (
ee) determinations) were evaluated. Tris(1-
n-dodecyl)porphyrins were used for the first time as the interacting units. Host capabilities of the diporphyrin tweezers were investigated by titrations with (
R,
R)- and (
S,
S)-cyclohexane-1,2-diamine (CHDA). The host molecules could be used as multichannel probes of
ee by using UV-vis, circular dichroism (CD), fluorescence emission and
1H nuclear magnetic resonance (
1H-NMR) methods. Chiral configurations could also be differentiated using CD or
1H-NMR spectroscopy. All three optical techniques give good resolution of
ee with reasonable sensitivity considering the low concentrations used (ca. 10
−6 mol·L
−1). The
ee determination of CHDA enantiomers using NMR spectroscopy is also possible because of the reasonably well separated resonances in the case of (
R,
R)- and (
S,
S)-CHDA. Non-metallated (
R)-1/(
S)-1 hosts could not be used to detect chiral information in a strongly acidic chiral guest. This work demonstrates the utility of 1,1’-binapthyl-linked chiral hosts for chiral analysis of ditopically interacting enantiomers.
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