Chromoisomers and Polymorphs of 9-Phenylacridinium Hydrogen Sulfate

Pascal H. Toma, Michael P. Kelley, Thomas B. Borchardt, Stephen R. Byrn, Bart Kahr

Research output: Contribution to journalArticlepeer-review

Abstract

The debate about the meaning of the defunct term chromoisomerism is reviewed. The central role of red and green crystals of 9-phenylacridinium hydrogen sulfate (1) in fueling this dialogue is highlighted. Single-crystal structures of a red (1r) and a green (1g) form were determined by X-ray diffraction, 1r: monoclinic, space group P21/c, a = 9.266(1) Å, b = 8.582(1) Å, c = 20.690(3) Å, β = 98.03(1)°, Z = 4. 1g: triclinic, space group PĪ, a = 8.597(1) Å, b = 10.449(1) Å, c = 10.822(1) Å, α = 101.33(1)°, β = 108.73(1)°, γ = 114.65(1)°, Z = 2. Differential scanning calorimetry revealed that the polymorphs 1r and 1g underwent comparable endothermic transitions. The thermal transformations were monitored and characterized by thermal gravimetric infrared spectroscopy and X-ray powder diffraction. Taken together these data failed to reveal a thermal transformation between 1r and 1g. Diffuse reflectance spectra of powders, coupled with INDO/S calculations, did not identify the origin of the color difference. Optical processes in related dye polymorphs are discussed. The short-lived and physically ill-defined term chromoisomerism is illustrative of the introduction, refinement, and abandonment of a concept in organic chemistry.

Original languageEnglish (US)
Pages (from-to)1317-1324
Number of pages8
JournalChemistry of Materials
Volume6
Issue number8
DOIs
StatePublished - Aug 1 1994

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Materials Chemistry

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