University of Illinois Urbana-Champaign

Solid-State Chemistry of Quinizarins and Naphthazarins

Hall, Robert Cargill

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Description

Title
Solid-State Chemistry of Quinizarins and Naphthazarins
Author(s)
Hall, Robert Cargill
Issue Date
1986
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Organic
Abstract
  • Crystalline organic materials possessing a polar axis have potential applications in information processing and communications fields.
  • Previous work suggests that crystalline naphthazarin (5,8-
  • The case of 12 is interesting because it undergoes a single crys- tal to single crystal phase change. X-ray diffraction of transformed individual crystals show retained crystallinity.
  • dihydroxy-1,4-naphthoquinone) undergoes a rapid tautomeric exchange between 1a and 1b at room temperature.
  • (DIAGRAM, TABLE OR GRAPHIC OMITTED...PLEASE SEE DAI)
  • Upon cooling below 110(DEGREES)K, one form of naphthazarin undergoes a reversible centrosymmetric to noncentrosymmetric phase transition.
  • This thesis reports the structures and solid state chemistry of several quinizarins.
  • Thermally induced solid state transitions have been identified in quinizarin 2 as well as the 2,3-dichloro and 2,3-dimethyl quinizarins 11 and 12. These transitions have been characterized by differential thermal analysis, X-ray powder diffraction, FTIR spectroscopy, and laser second harmonic generation (SHG). X-ray crystal structures have been determined for two forms of 11 and one form of 12. Other quinizarins, naphthazarins, and naphthazarin esters have also been
  • investigated in the solid state, and in several cases X-ray crystal structures have been determined.
  • The transition of 11 is unusual in that it involves a non-polar to polar phase change upon heating. The transition of 11 was charac- terized by the development of laser frequency doubling while heating a powdered sample. The powder SHG efficiency of the high tempera- ture form of 11 is more than twice that of urea (a common SHG standard).
Graduation Semester
1986
Type of Resource
text
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