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Phenanthroline-strapped calix[4]pyrroles: anion receptors displaying affinity reversal as a function of solvent polarity
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2020/01/02 , DOI: 10.1039/c9qo01377f Nam Jung Heo 1, 2, 3, 4 , Ju Hyun Oh 1, 2, 3, 4 , Jeong Tae Lee 4, 5, 6, 7 , Qing He 8, 9, 10, 11, 12 , Jonathan L. Sessler 13, 14, 15, 16 , Sung Kuk Kim 1, 2, 3, 4
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2020/01/02 , DOI: 10.1039/c9qo01377f Nam Jung Heo 1, 2, 3, 4 , Ju Hyun Oh 1, 2, 3, 4 , Jeong Tae Lee 4, 5, 6, 7 , Qing He 8, 9, 10, 11, 12 , Jonathan L. Sessler 13, 14, 15, 16 , Sung Kuk Kim 1, 2, 3, 4
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Calix[4]pyrroles 1 and 2, diametrically strapped with a phenanthroline via ester and amide linkages, respectively, have been synthesized as anion receptors. It was revealed by 1H NMR spectroscopic analysis that receptors 1 and 2 possessing both hydrogen bonding donors and acceptors were able to bind the bicarbonate anion (as its tetraethylammonium (TEA+) or sodium salt) in CDCl3, as well as in 15% aqueous DMSO with high affinity and selectivity over other anions. The amide-based receptor 2 contains additional potential hydrogen bonding donors relative to its ester-based congener 1. Nevertheless, in CDCl3 receptor 1 was found to display a higher affinity for all test anions than receptor 2. In contrast, in 15% aqueous DMSO solution the affinities of receptor 2 for anions, in particular chloride, bicarbonate, and dihydrogen phosphate, were enhanced, whereas those of receptor 1 were reduced dramatically with no appreciable interaction being seen in the case of most test anions considered in this study. These reversals in selectivity and affinities underscore the importance of solvent in regulating the recognition features of seemingly similiar anion binding agents.
中文翻译：
邻菲咯啉束缚的杯[4]吡咯：阴离子受体显示亲和力逆转与溶剂极性的关系
分别通过酯和酰胺键与菲咯啉径向键合的杯[4]吡咯1和2已被合成为阴离子受体。通过1 H NMR光谱分析表明，既具有氢键供体又具有受体的受体1和2能够结合CDCl 3中的碳酸氢根阴离子（作为其四乙铵（TEA +）或钠盐），以及15％的碳酸氢根阴离子。DMSO水溶液，对其他阴离子具有高亲和力和选择性。相对于基于酯的同类物1，基于酰胺的受体2还包含其他潜在的氢键供体。然而，在CDCl 3中，发现受体1对所有测试阴离子的亲和力都比受体2高。相比之下，在15％DMSO水溶液中，受体2对阴离子（特别是氯离子，碳酸氢根和磷酸二氢盐）的亲和力增强，而受体1的阴离子亲和力显着降低，在大多数测试中均未观察到明显的相互作用。本研究中考虑的阴离子。选择性和亲和力的这些逆转强调了溶剂在调节看似相似的阴离子结合剂的识别特征方面的重要性。
更新日期：2020-02-13
中文翻译：
邻菲咯啉束缚的杯[4]吡咯：阴离子受体显示亲和力逆转与溶剂极性的关系
分别通过酯和酰胺键与菲咯啉径向键合的杯[4]吡咯1和2已被合成为阴离子受体。通过1 H NMR光谱分析表明，既具有氢键供体又具有受体的受体1和2能够结合CDCl 3中的碳酸氢根阴离子（作为其四乙铵（TEA +）或钠盐），以及15％的碳酸氢根阴离子。DMSO水溶液，对其他阴离子具有高亲和力和选择性。相对于基于酯的同类物1，基于酰胺的受体2还包含其他潜在的氢键供体。然而，在CDCl 3中，发现受体1对所有测试阴离子的亲和力都比受体2高。相比之下，在15％DMSO水溶液中，受体2对阴离子（特别是氯离子，碳酸氢根和磷酸二氢盐）的亲和力增强，而受体1的阴离子亲和力显着降低，在大多数测试中均未观察到明显的相互作用。本研究中考虑的阴离子。选择性和亲和力的这些逆转强调了溶剂在调节看似相似的阴离子结合剂的识别特征方面的重要性。
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