Yakimova L S, Shurpik D N, Gilmanova L H, Makhmutova A R, Rakhimbekova A, Stoikov I I
Kazan Federal University, A.M. Butlerov Chemical Institute, 420008, Kremlevskaya Street, 18, Kazan, Russian Federation.
Org Biomol Chem. 2016 May 4;14(18):4233-8. doi: 10.1039/c6ob00539j.
A new water-soluble pillar[5]arene with an amide fragment and triethylammonium groups was synthesized by our original method of aminolysis of the ester groups. Using UV-spectroscopy, it is shown that cationic pillar[5]arenes are able to selectively form 1 : 1 complexes with some hydrophobic anions: the guests with bulky uncharged or negatively charged substituents hindering entry into the macrocycle cavity. Highly selective binding of the most lipophilic guest, methyl orange dye, in the form of organic anion salts by positively charged water-soluble pillar[5]arenes was detected. In the case of the azo dye the appropriate Kass values were 10-100-fold higher than those calculated for the other sulfonic acid derivatives studied. The 2D NMR NOESY (1)H-(1)H spectroscopy confirms the formation of the inclusion complex: negative charge sulfonate head is outside the cavity of pillar[5]arenes and the hydrophobic fragment of the guest is located in the cavity.
通过我们原创的酯基氨解方法合成了一种带有酰胺片段和三乙铵基团的新型水溶性柱[5]芳烃。利用紫外光谱表明，阳离子柱[5]芳烃能够与一些疏水性阴离子选择性地形成1∶1配合物：带有庞大不带电荷或带负电荷取代基的客体阻碍进入大环腔。检测到带正电荷的水溶性柱[5]芳烃以有机阴离子盐的形式对最亲脂性客体甲基橙染料具有高度选择性结合。对于偶氮染料，合适的Kass值比针对所研究的其他磺酸衍生物计算的值高10 - 100倍。二维核磁共振NOESY (1)H-(1)H光谱证实了包合物的形成：带负电荷的磺酸根基头在柱[5]芳烃腔外，客体的疏水片段位于腔内。
