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 920-1192, Japan 2/25/2011 Received January 10, 2011

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. 2/25/2011

Background of present work……. First reported in 2008, JACS Side view upper view 2/25/2011

In the present work……. 2/25/2011

They synthesized (c) and (d) Studied Host-guest properties by adding OTMA 2/25/2011

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 2/25/2011

(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. 2/25/2011

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. 2/25/2011

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 2/25/2011

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 2/25/2011