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Related Experiment Videos

Phthalocyaninodehydroannulenes.

M J Cook1, M J Heeney

  • 1School of Chemical Sciences, University of East Anglia, Norwich, UK. m.cook@uea.ac.uk

Chemistry (Weinheim an Der Bergstrasse, Germany)
|January 11, 2000
PubMed
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Researchers synthesized novel nickel phthalocyanine complexes with ethynyl linkages. These phthalocyanine macrocycles, including dinuclear and annulene structures, exhibit unique optical properties and liquid crystal behavior.

Area of Science:

  • Materials Science
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Phthalocyanines are macrocyclic compounds with diverse applications.
  • Functionalization of phthalocyanines is key to tuning their properties.
  • Developing novel phthalocyanine architectures, such as linked systems and annulenes, is of significant interest.

Purpose of the Study:

  • To synthesize novel brominated and ethynylated nickel phthalocyanine complexes.
  • To investigate the formation of dinuclear and dehydroannulene phthalocyanine structures.
  • To characterize the optical properties, aggregation behavior, and liquid crystalline nature of these new compounds.

Main Methods:

  • Cross tetramerization reactions using brominated phthalonitriles and nickel acetate.

Related Experiment Videos

  • Sonogashira and Stille coupling reactions for ethynyl group introduction.
  • Oxidative coupling for dinuclear and dehydroannulene formation.
  • Spectroscopic techniques (UV-Vis, Mass Spectrometry) for characterization.
  • Differential Scanning Calorimetry (DSC) and Polarized Optical Microscopy (POM) for liquid crystal studies.

    • Main Results:

    • Synthesis of monobromo- and dibromo-dibutoxyhexadecylphthalocyaninato nickel(II) complexes.
    • Formation of ethynyl-linked dinuclear phthalocyanines and phthalocyaninodehydroannulenes via coupling reactions.
    • Identification of diphthalocyaninodehydro[12]annulene as the major product and triphthalocyaninodehydro[18]annulene as a minor product.
    • Observation of significant Q-band splitting in the visible spectra of the dehydroannulenes.
    • Demonstration of discotic liquid crystal behavior in mononuclear precursors and the diphthalocyaninodehydro[12]annulene.

    Conclusions:

    • Novel synthetic routes to functionalized nickel phthalocyanines and their extended architectures were established.
    • The synthesized dehydroannulene phthalocyanines exhibit unique optical properties.
    • The diphthalocyaninodehydro[12]annulene displays thermotropic liquid crystalline behavior but undergoes irreversible oligomerization at elevated temperatures.