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The 'Helmet Phthalocyanines': Synthetic and Catalytic Studies on a New Class of Chiral Phthalocyanin

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Title: The 'Helmet Phthalocyanines': Synthetic and Catalytic Studies on a New Class of Chiral Phthalocyanin


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-diiminoisoindolinatoph
    thalocyaninato (diiPc) helmet complexes of Co
    and Fe, and related chiral 14,28-alkoxy-substitute
    d 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)2PcNi 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.
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