Recognition of Chiral Catechols Using Oxo-Titanium Phthalocyanine

Atsuya Muranaka; Masako Okuda; Nagao Kobayashi; Ken Somers; Arnout Ceulemans

doi:10.1021/ja039843r

Recognition of Chiral Catechols Using Oxo-Titanium Phthalocyanine

Atsuya Muranaka, Masako Okuda, Nagao Kobayashi, Ken Somers, Arnout Ceulemans

Research output: Contribution to journal › Article › peer-review

45 Citations (Scopus)

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
Pages (from-to)	4596-4604
Number of pages	9
Journal	Journal of the American Chemical Society
Volume	126
Issue number	14
DOIs	https://doi.org/10.1021/ja039843r
Publication status	Published - 2004 Apr 14
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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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.",

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AU - Muranaka, Atsuya

AU - Okuda, Masako

AU - Kobayashi, Nagao

AU - Somers, Ken

AU - Ceulemans, Arnout

PY - 2004/4/14

Y1 - 2004/4/14

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AB - 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.

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Recognition of Chiral Catechols Using Oxo-Titanium Phthalocyanine

Abstract

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