Oxo−titanium phthalocyanine (TiOPc) derivatives of catechin and hematoxylin (natural ortho-diol type chiral compounds) have been prepared and characterized by spectral and chromatographictechniques. It is demonstrated that the TiOPc unit is an excellent template for chiral recognition through itsisolated 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−Kirkwoodcoupled-oscillator mechanism to obtain the absolute configuration of hematoxylin. In addition, it is shownthat the described chiroptical recognition method is sensitive to slight conformational changes.