Synthesis,functionalization, and isolation of planar-chiral pillar[5]arenes with bulky substituents using a chiral derivatization agent |
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Authors: | Talal F. Al-Azemi Mickey Vinodh Fatemeh H. Alipour Abdirahman A. Mohamod |
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Affiliation: | Chemistry Department, Kuwait University, P. O. Box 5969, Safat 13060, Kuwait, Fax: +965-2481-6482, +965-2498-554 |
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Abstract: | Bulky perneopentyloxy-pillar[5]arene (Pillar-1) was synthesized and its conformational mobility was investigated using variable-temperature 1H NMR spectroscopy. The host–guest interactions between Pillar-1 and n-octyltrimethylammonium hexafluorophosphate (OMA) were investigated, and the formation of a 1 : 1 complex was revealed via1H NMR. Planar-chiral isomers were synthesized via the reaction of a hydroxy-functionalized pillar[5]arene with chiral derivatization agent (S)-(+)-MTPA-Cl. The (Sp, R)-and (Rp, R)-forms of the pillar[5]arene diastereomers were isolated by HPLC, and their structures were analyzed by 19F NMR. HPLC measurements indicated that racemization did not take place at 40 °C for 72 h.Bulky perneopentyloxy-pillar[5]arene was synthesized. Complexation behavior and conformational mobility were investigated using 1H NMR spectroscopy. Isolation of planar-chiral pillar[5]arenes using a chiral derivatization agent were carried out. |
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