1. The 'Helmet Phthalocyanines': Synthetic and Catalytic Studies on a New Class of Chiral Phthalocyaninato-Metal Complexes
Robert W. McGaff, Chemistry Department, University of Wisconsin-La Crosse
The metallophthalocyanines, as a class of compounds, has few matches in terms of variety of chemical and technological applications, ranging from longstanding uses as dyes and pigments to more contemporary applications relating to gas-sensing, nonlinear optics, photosensitizers, and catalysis. Our PRF-supported research over the course of the past sixteen months has involved the exploration of a class of chiral metallophthalocyanine derivatives discovered in our laboratory as potential enantioselective oxidation catalysts. Overall, we seek to:
(1) Demonstrate that 14,28-diiminoisoindolinatophthalocyaninato (diiPc) “helmet” complexes of Co and Fe, and related chiral 14,28-alkoxy-substituted complexes of Ni do in fact catalyze oxidation reactions, as do many known (achiral) metallophthalocyanines
Separate enantiomers of these potential catalysts
Investigate potential enantioselective oxidation catalysis employing enantiopure diiPc and related 14,28-alkoxy-substituted complexes of Ni
Thus far in our project, we have succeeded in goal (1), where the catalyst is a diiPc complex of Co, and one of the two products is a chiral indanol…
…and in goal (2). Specifically, baseline resolution of two fractions has been achieved for a pure racemic mixture of
[14, 28-(CH3O)2Pc]Ni via HPLC employing a carbohydrate-based chiral stationary phase (CSP). Scale-up of this separation and extension to diiPc complexes of Co and Fe comprise the immediate focus of our efforts.