Recognition of Chiral Catechols Using Oxo-Titanium Phthalocyanine

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

Research output: Contribution to journalArticlepeer-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 languageEnglish
Pages (from-to)4596-4604
Number of pages9
JournalJournal of the American Chemical Society
Volume126
Issue number14
DOIs
Publication statusPublished - 2004 Apr 14
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint

Dive into the research topics of 'Recognition of Chiral Catechols Using Oxo-Titanium Phthalocyanine'. Together they form a unique fingerprint.

Cite this