Recognition of Chiral Catechols Using Oxo−Titanium Phthalocyanine
- 18 March 2004
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 126 (14) , 4596-4604
- https://doi.org/10.1021/ja039843r
Abstract
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.Keywords
This publication has 44 references indexed in Scilit:
- A mutually perpendicular phthalocyanine pentamer obtained by a one-step reactionChemical Communications, 2000
- Study of Substituent Effects on the Photoconductivity of Soluble 2,(3)- and 1,(4)-Substituted Phthalocyaninato- and Naphthalocyaninatotitanium(IV) OxidesJournal of the American Chemical Society, 1998
- Facilitated Catecholamine Transport through Bulk and Polymer-Supported Liquid MembranesJournal of the American Chemical Society, 1996
- Band Deconvolution Analysis of the Absorption and Magnetic Circular Dichroism Spectral Data of ZnPc(-2) Recorded at Cryogenic TemperaturesThe Journal of Physical Chemistry, 1995
- Photochemical Formation of the Anion Radical of Zinc Phthalocyanine and Analysis of the Absorption and Magnetic Circular Dichroism Spectral Data. Assignment of the Optical Spectrum of [ZnPc(-3)]-Journal of the American Chemical Society, 1994
- The First Structural Characterization of a Metal–Enterobactin Complex: [V(enterobactin)]2−Angewandte Chemie International Edition in English, 1992
- Homoisoflavonoids and related compounds. II. Isolation and absolute configurations of 3,4-dihydroxylated homoisoflavans and brazilins from Caesalpinia sappan L.CHEMICAL & PHARMACEUTICAL BULLETIN, 1987
- Circular dichroism of charge transfer and magnetic dipole forbidden d-d transitions. Application to chiral chelate complexesJournal of the American Chemical Society, 1979
- Theoretical Aspects of Optical Activity Part Two: PolymersAdvances in Chemical Physics, 1962
- CII.—Brazilin and hœmatoxylin. Part VII. Synthesis of derivatives of hydrindene closely allied to brazilin and hœmatoxylinJournal of the Chemical Society, Transactions, 1907