Ferrocene-amino acid macrocycles as hydrazone-based receptors for anions
Ferrocene-amino acid macrocycles as hydrazone-based receptors for anions
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DOI：
10.1039/c1sc00168j
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发表时间：
2011-01-01
期刊：
影响因子：
8.4
通讯作者：
Sanders, Jeremy K. M.
中科院分区：
文献类型：
--
作者：
Beeren, Sophie R.;Sanders, Jeremy K. M.
本文报道了一类新的大环腙类阴离子受体的合成。这些大环化合物是由乙醛和一个螺旋氨基酸双取代的二茂铁二酰肼反应形成的，含有1 - 8个二茂铁部分。四个最小的大环的分离和它们的特征，通过紫外-可见光谱，CD和NMR光谱进行说明。探索的大环化合物的构象，特别是与参考的螺旋分子内氢键结构的形成。使用这些大环作为阴离子受体的调查表明，它们都是有效的主机;较大的大环显示出最高的亲和力的阴离子。使用NMR光谱的研究表明，阴离子识别的结果主要来自阴离子和酰腙的正电性N-H质子之间形成的多个氢键。
We report the synthesis of a family of new macrocyclic hydrazone-based anion receptors. Formed from the reaction between isophthalaldehyde and a helical amino acid-disubstituted ferrocene dihydrazide, these macrocycles contain from one to eight ferrocene moieties. The isolation of the four smallest of the macrocycles and their characterisation by UV-Vis, CD and NMR spectroscopy is described. The conformation of the macrocycles is explored, particularly with reference to the formation of a helical intramolecularly hydrogen-bonded structure. An investigation of the use of these macrocycles as anion-receptors shows that they are all effective hosts; the larger macrocycles show the highest affinities for anions. Studies using NMR spectroscopy suggest that the anion-recognition results primarily from the formation of multiple hydrogen bonds between the anions and the electropositive N-H protons of the acylhydrazones.