Dicondensed indolinobenzospiropyrans as precursors of thermo- and photochromic spiropyrans. Part II: Assignment of (1)H and (13)C NMR spectra

Magn Reson Chem. 2006 Jan;44(1):90-4. doi: 10.1002/mrc.1718.

Abstract

The (1)H and (13)C NMR spectra of dicondensed indolinobenzospiropyrans as precursors of thermo- and photochromic spiropyrans, DC1-DC5, were completely assigned. Especially, the (1)H assignment and coupling characteristics of the diastereotopic protons at the carbon-3 position of the benzopyran rings were achieved by conducting (1)H-(1)H COSY and nOe experiments. The dihedral angles (theta(1), theta(2) and theta(3)) calculated from the experimental values of the vicinal coupling constants ((3)J) of DC5 are in good agreement with the observed values in the solid state. All of the carbons in the DC dye molecules were investigated through a combination of heteronuclear 2D-shift correlation spectroscopy (HETCOR) and DEPT135.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzene Derivatives / chemistry*
  • Benzene Derivatives / metabolism
  • Benzopyrans / chemical synthesis
  • Benzopyrans / chemistry*
  • Benzopyrans / metabolism
  • Carbon Isotopes / chemistry
  • Hot Temperature
  • Hydrogen / chemistry
  • Indoles / chemistry*
  • Indoles / metabolism
  • Luminescence
  • Magnetic Resonance Spectroscopy*
  • Molecular Structure
  • Nitro Compounds
  • Photochemistry
  • Reference Standards

Substances

  • Benzene Derivatives
  • Benzopyrans
  • Carbon Isotopes
  • Indoles
  • Nitro Compounds
  • spiropyran
  • Hydrogen