1. Planar-Chiral Macrocyclic Host Pillar[5]arene:
No Rotation of Units and Isolation of Enantiomers by Introducing Bulky Substituents
Tomoki Ogoshi,* Kae Masaki, Ryohei Shiga, Keisuke Kitajima, and
Tada-aki Yamagishi
Graduate School of Natural Science and Technology, Kanazawa University,
Kakuma-machi, Kanazawa , Japan
2/25/2011
Received January 10, 2011

2. The composition of pillar[5]arene is almost the same as that of
cyclodextrin
The composition of pillar[5]arene is almost the same as that of
typical calixarenes.
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3. Background of present work…….
First reported in 2008, JACS
Side view upper view
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4. In the present work…….
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5. They synthesized (c) and (d)
Studied Host-guest properties by adding OTMA
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6. Variable-temperature partial 1H NMR spectra of (a)
Cy-C2-Pillar and (b) Cy-C1-Pillar in toluene-d8.
Planar chirality and restricted rotation
Of pillar arene were confirmed by
VT-NMR and Chiral HPLC studies
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7. (a) Chiral HPLC traces of Cy-C1-Pillar and (b) the first
fraction of Cy-C1-Pillar byholding at 40 Cfor 18h.Hexane/EtOH=
97/3 (vol%) was used as eluent. (c) UV-vis and (d) CD spectra of
the first and second fractions (14 μLmol-1cm-1) inhexaneat25C.
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8. Host-guest properties…….
Peaks of Cy-C1-Pillar become broadening
New peaks from complexes and free OTMA
1H NMR spectra of (a) Cy-C1-Pillar, (b) OTMA, and
(c) the 1:1 mixture of Cy-C1-Pillar and OTMA in 10 mM in
CDCl3 at 25 C.
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9. peaks of phenyl proton peak of Cy-C1-Pillar were utilized.
Job plots of the complex between Cy-C1-Pillar and OTMA (1:1 stoichiometry).
The Job plots were conducted by varying the mole fractions of guest OTMA
and host Cy-C1-Pillar. Integration ratios between complexed and uncomplexed
peaks of phenyl proton peak of Cy-C1-Pillar were utilized.
Concentration: [OTMA]+[Cy-C1-Pillar] = 10 mM. Association constant was 830 M-1
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10. Thanking you In conclusion….. Developed a planar chiral host molecule
Enantiomers were separated and characterized
Host-guest properties
Schematic representation of the rotation movements
of bulky percyclohexyl-substituted pillar[5]arenes.
Thanking you
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