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 journalArticle

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 P1, 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
StatePublished - 1994

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Polymorphism
Sulfates
Hydrogen
Fueling
Powders
X ray powder diffraction
Differential scanning calorimetry
Infrared spectroscopy
Coloring Agents
Dyes
Crystal structure
Single crystals
Color
X ray diffraction
Crystals
Hot Temperature

ASJC Scopus subject areas

  • Materials Science(all)
  • Materials Chemistry

Cite this

Toma, P. H., Kelley, M. P., Borchardt, T. B., Byrn, S. R., & Kahr, B. (1994). Chromoisomers and polymorphs of 9-phenylacridinium hydrogen sulfate. Chemistry of Materials, 6(8), 1317-1324.

Chromoisomers and polymorphs of 9-phenylacridinium hydrogen sulfate. / Toma, Pascal H.; Kelley, Michael P.; Borchardt, Thomas B.; Byrn, Stephen R.; Kahr, Bart.

In: Chemistry of Materials, Vol. 6, No. 8, 1994, p. 1317-1324.

Research output: Contribution to journalArticle

Toma, PH, Kelley, MP, Borchardt, TB, Byrn, SR & Kahr, B 1994, 'Chromoisomers and polymorphs of 9-phenylacridinium hydrogen sulfate', Chemistry of Materials, vol. 6, no. 8, pp. 1317-1324.
Toma PH, Kelley MP, Borchardt TB, Byrn SR, Kahr B. Chromoisomers and polymorphs of 9-phenylacridinium hydrogen sulfate. Chemistry of Materials. 1994;6(8):1317-1324.
Toma, Pascal H. ; Kelley, Michael P. ; Borchardt, Thomas B. ; Byrn, Stephen R. ; Kahr, Bart. / Chromoisomers and polymorphs of 9-phenylacridinium hydrogen sulfate. In: Chemistry of Materials. 1994 ; Vol. 6, No. 8. pp. 1317-1324.
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