TY - JOUR
T1 - Synthetic macrocyclic receptors in chiral analysis and separation
AU - Ema, Tadashi
N1 - Funding Information:
carboxylate anion of 37 is hydrogen bonded with the NH groups of 36. The higher affinity of (S)-36 for (S)-37 is probably due to the favorable pi–pi interactions between the naphthyl group in (S)-36 and the phenyl group in (S)-37, while the lower affinity of (S)-36 for (R)-37 is likely to be caused by the unfavorable steric interactions between (S)-36 and the phenyl group in (R)-37. This was supported by density functional theory (DFT) calculations.
Funding Information:
Acknowledgments The author thanks the organizing committee of Association of Research for Host–Guest and Supramolecular Chemistry (Japan) for giving him ‘‘HGCS Japan Award of Excellence 2011’’ and the opportunity of writing this review. The author is grateful to Professors Takashi Sakai and Toshinobu Korenaga (Okayama University) for their valuable suggestions and discussions. The author also thanks all of the collaborators. His works were partly supported by Grant for Research for Promoting Technological Seeds from Japan Science and Technology Agency (JST), Okayama Foundation for Science and Technology, and Daicel Chemical Industries.
Copyright:
Copyright 2012 Elsevier B.V., All rights reserved.
PY - 2012/12
Y1 - 2012/12
N2 - Chiral synthetic macrocyclic receptors that can achieve chiral discrimination by NMR spectroscopy and/or chiral separation by HPLC are overviewed. Synthetic macrocycles introduced here include crown ethers, calixarenes/calixresorcinarenes/calixpyrroles, macrocyclic amides/amines, and porphyrins. These macrocyclic frameworks are advantageous because intermolecular interactions can take place effectively, such as the ion-dipole interactions in crown ethers, the CH/π and π-π interactions in calixarenes, hydrogen bonding and salt formation in macrocyclic amides and amines, and π-π stacking and metal coordination in porphyrins. Additional functional groups on the periphery of the macrocyclic platforms not only make the whole molecule chiral but also act as the interaction sites. Chiral macrocyclic receptors can show a high degree of chiral recognition/discrimination by using the peripheral functional groups as well as the macrocyclic skeletons (preorganization). Both hosts and guests are shown in the figures to quickly overview the molecular recognition scope of synthetic macrocyclic receptors in chiral analysis and separation.
AB - Chiral synthetic macrocyclic receptors that can achieve chiral discrimination by NMR spectroscopy and/or chiral separation by HPLC are overviewed. Synthetic macrocycles introduced here include crown ethers, calixarenes/calixresorcinarenes/calixpyrroles, macrocyclic amides/amines, and porphyrins. These macrocyclic frameworks are advantageous because intermolecular interactions can take place effectively, such as the ion-dipole interactions in crown ethers, the CH/π and π-π interactions in calixarenes, hydrogen bonding and salt formation in macrocyclic amides and amines, and π-π stacking and metal coordination in porphyrins. Additional functional groups on the periphery of the macrocyclic platforms not only make the whole molecule chiral but also act as the interaction sites. Chiral macrocyclic receptors can show a high degree of chiral recognition/discrimination by using the peripheral functional groups as well as the macrocyclic skeletons (preorganization). Both hosts and guests are shown in the figures to quickly overview the molecular recognition scope of synthetic macrocyclic receptors in chiral analysis and separation.
KW - Chiral discrimination
KW - Chiral recognition
KW - Chiral solvating agent
KW - Chiral stationary phase
KW - HPLC
KW - NMR
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U2 - 10.1007/s10847-012-0136-6
DO - 10.1007/s10847-012-0136-6
M3 - Article
AN - SCOPUS:84864458771
VL - 74
SP - 41
EP - 55
JO - Journal of Inclusion Phenomena and Macrocyclic Chemistry
JF - Journal of Inclusion Phenomena and Macrocyclic Chemistry
SN - 1388-3127
IS - 1-4
ER -