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Issue 19, 2016
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Polymorphism of the azobenzene dye compound methyl yellow

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Abstract

The crystal structure and polymorphism of the well-known aminoazobenzene, N,N-dimethyl-4-aminoazobenzene (DAB) are studied; a second polymorph of DAB reported and the relationship between the two polymorphs studied using differential scanning calorimetry and by evaluating their lattice energies and absorption spectra. Without significantly strong intermolecular interactions present in the two forms of DAB, a balance between conformational strain and a cumulative π-orbital overlapping effect results in the existence of the enantiotropically related polymorphs and their alternative packing arrangements. The UV/vis spectra of the two polymorphs are different, thus illustrating the significance of small structural changes on the colour of a material, which could behave differently under particular sensing conditions. DAB has been used primarily as an acid/base indicator solution and a dye molecule and the implications of the polymorphic relationships established here are discussed with respect to the range of applications this molecule finds as a sensor and for its incorporation into various functional films and devices.

Graphical abstract: Polymorphism of the azobenzene dye compound methyl yellow

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Publication details

The article was received on 16 Feb 2016, accepted on 19 Apr 2016 and first published on 20 Apr 2016


Article type: Paper
DOI: 10.1039/C6CE00387G
CrystEngComm, 2016,18, 3456-3461
  • Open access: Creative Commons BY-NC license
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    Polymorphism of the azobenzene dye compound methyl yellow

    D. L. Cruickshank, C. H. Hendon, M. J. R. Verbeek, A. Walsh and C. C. Wilson, CrystEngComm, 2016, 18, 3456
    DOI: 10.1039/C6CE00387G

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