Al-Azemi Talal F, Vinodh Mickey, Alipour Fatemeh H, Mohamod Abdirahman A
Chemistry Department, Kuwait University P. O. Box 5969, Safat 13060 Kuwait
RSC Adv. 2019 Jul 26;9(40):23295-23301. doi: 10.1039/c9ra03135a. eCollection 2019 Jul 23.
Bulky perneopentyloxy-pillar[5]arene (Pillar-1) was synthesized and its conformational mobility was investigated using variable-temperature H NMR spectroscopy. The host-guest interactions between Pillar-1 and -octyltrimethylammonium hexafluorophosphate (OMA) were investigated, and the formation of a 1 : 1 complex was revealed H NMR. Planar-chiral isomers were synthesized the reaction of a hydroxy-functionalized pillar[5]arene with chiral derivatization agent ()-(+)-MTPA-Cl. The (Sp, )-and (Rp, )-forms of the pillar[5]arene diastereomers were isolated by HPLC, and their structures were analyzed by F NMR. HPLC measurements indicated that racemization did not take place at 40 °C for 72 h.
合成了大体积的戊氧基柱[5]芳烃（柱[5]芳烃-1），并使用变温核磁共振氢谱研究了其构象流动性。研究了柱[5]芳烃-1与六氟磷酸辛基三甲基铵（OMA）之间的主客体相互作用，核磁共振氢谱显示形成了1:1的配合物。通过羟基官能化柱[5]芳烃与手性衍生试剂（）-(+)-MTPA-Cl的反应合成了平面手性异构体。通过高效液相色谱法分离了柱[5]芳烃非对映异构体的（Sp，）-和（Rp，）-形式，并通过氟核磁共振对其结构进行了分析。高效液相色谱测量表明，在40℃下72小时内未发生外消旋化。
