Recognition of chiral catechols using oxo-titanium phthalocyanine.
Recognition of chiral catechols using oxo-titanium phthalocyanine.
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DOI：
10.1021/ja039843r
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发表时间：
2004-03
影响因子：
15
通讯作者：
A. Muranaka;M. Okuda;N. Kobayashi;Ken R. F. Somers;A. Ceulemans
中科院分区：
文献类型：
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作者：
A. Muranaka;M. Okuda;N. Kobayashi;Ken R. F. Somers;A. Ceulemans
合成了儿茶素和苏木素(天然邻位二醇型手性化合物)的氧钛酞菁(TiOPc)衍生物，并用光谱和色谱技术对其进行了表征。结果表明，TiOPc单元通过其孤立的Q跃迁是手性识别的良好模板。苏木素与螺旋二聚体形成的络合物在Q带区诱导了很强的CD-活性。将从头算几何优化与Kuhn-Kirkwood耦合振子机制相结合，得到了苏木素的绝对构型。此外，研究还表明，所描述的手势识别方法对轻微的构象变化敏感。
Oxo-titanium phthalocyanine (TiOPc) derivatives of catechin and hematoxylin (natural ortho-diol type chiral compounds) have been prepared and characterized by spectral and chromatographic techniques. It is demonstrated that the TiOPc unit is an excellent template for chiral recognition through its isolated Q-transitions. The formation of a helical dimeric complex with hematoxylin induces strong CD-activity in the Q-band region. Ab initio geometry optimizations were combined with a Kuhn-Kirkwood coupled-oscillator mechanism to obtain the absolute configuration of hematoxylin. In addition, it is shown that the described chiroptical recognition method is sensitive to slight conformational changes.