Controlled orientation of metalloporphyrins and regioselective epoxidations in thermotropic liquid crystals

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The orientation of a porphyrin molecule in a thermotropic nematic liquid crystal can be controlled by molecular design. Thus, the porphyrin plane of tetraphenylporphyrin (TPP) is aligned parallel to the director of a liquid crystal whereas a porphyrin with orthogonal substitution of mesogenic 4-n-butoxybiphenyl appendages (MesogenP) is oriented in a perpendicular conformation. The alignment was determined by time resolved EPR spectroscopy of the triplet state of the free base porphyrin. Manganese TPP and MesogenP porphyrins then were used as catalysts for the epoxidation of alkenes using iodosobenze as oxidant. Reaction yields and regioselectivity for enlongated substrates such as cis-stilbene and 4-vinylbiphenyl were dependent on the alignment of the alkene and its carbon-carbon double bond relative to the director and metalloporphyrin catalyst.

Original languageEnglish
Pages (from-to)33-37
Number of pages5
JournalMolecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals
Issue number1
Publication statusPublished - Feb 1 1994


ASJC Scopus subject areas

  • Chemistry(all)
  • Materials Science(all)
  • Condensed Matter Physics

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