Synthesis and Chiroptical Properties of aryl-(2-pyridil)-(3-pyridil)-(4-pyridil)methane

DOI

Bibliographic Information

Other Title
  • アリール-(2-ピリジル)-(3-ピリジル)-(4-ピリジル)メタンの合成と光学的性質

Abstract

We have synthesized phenyl-(2-pyridyl)-(3-pyridyl)-(4-pyridyl)methane 1 and the corresponding tris(pyridine N-oxide) 2 as prototypal chiral molecules based on tetraarylmethane framework. Both 1 and 2 are resolved by a chiral HPLC, which is confirmed by the measurement of CD spectra of the separated two fractions. We also determine their absolute configuration by the comparison of the experimental CD spectrum with the calculated CD curve based on time-dependent density functional theory (TDDFT). We assign the relationship of the absolute configuration of 1 and 2 by measurement of CD spectrum of 2 derived from oxidation of the optically active 1. The result is accordance with that obtained by the calculated CD curve based on TDDFT. Furthermore, We have also synthesized the related chiral molecules 3 and 4, in which the phenyl group in 1 is replaced by pyradinyl or 2-pyrimidinyl group, respectively. These chiral molecules are expected to exhibit metal-chelating properties, which would be detected by CD spectroscopy. We already resolved these compounds by a chiral HPLC. We will also report the chiroptical properties, absolute configuration determination, and metal-binding properties of 3 and 4.

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Details 詳細情報について

  • CRID
    1390001205555049472
  • NII Article ID
    130004645207
  • DOI
    10.11494/kisoyuki.2008.0.103.0
  • Text Lang
    ja
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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