Abstract
Oxo-titanium phthalocyanine (TiOPc) derivatives of catechin and hematoxylin (natural orthodiol 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.
Original language | English |
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Pages (from-to) | 4596-4604 |
Number of pages | 9 |
Journal | Journal of the American Chemical Society |
Volume | 126 |
Issue number | 14 |
DOIs | |
Publication status | Published - 2004 Apr 14 |
Externally published | Yes |
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry