Polymorphism of the azobenzene dye compound methyl yellow

Dyanne L. Cruickshank, Christopher H. Hendon, Matthew J R Verbeek, Aron Walsh, Chick C. Wilson

Research output: Contribution to journalArticle

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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.

LanguageEnglish
Pages3456-3461
Number of pages6
JournalCrystEngComm
Volume18
Issue number19
DOIs
StatusPublished - 21 May 2016

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p-Dimethylaminoazobenzene
methyl compounds
Azobenzene
polymorphism
Polymorphism
Coloring Agents
Dyes
dyes
lattice energy
molecules
energy spectra
heat measurement
absorption spectra
color
orbitals
acids
crystal structure
scanning
sensors
Molecules

Cite this

Cruickshank, D. L., Hendon, C. H., Verbeek, M. J. R., Walsh, A., & Wilson, C. C. (2016). Polymorphism of the azobenzene dye compound methyl yellow. CrystEngComm, 18(19), 3456-3461. https://doi.org/10.1039/c6ce00387g

Polymorphism of the azobenzene dye compound methyl yellow. / Cruickshank, Dyanne L.; Hendon, Christopher H.; Verbeek, Matthew J R; Walsh, Aron; Wilson, Chick C.

In: CrystEngComm, Vol. 18, No. 19, 21.05.2016, p. 3456-3461.

Research output: Contribution to journalArticle

Cruickshank, DL, Hendon, CH, Verbeek, MJR, Walsh, A & Wilson, CC 2016, 'Polymorphism of the azobenzene dye compound methyl yellow' CrystEngComm, vol. 18, no. 19, pp. 3456-3461. https://doi.org/10.1039/c6ce00387g
Cruickshank DL, Hendon CH, Verbeek MJR, Walsh A, Wilson CC. Polymorphism of the azobenzene dye compound methyl yellow. CrystEngComm. 2016 May 21;18(19):3456-3461. https://doi.org/10.1039/c6ce00387g
Cruickshank, Dyanne L. ; Hendon, Christopher H. ; Verbeek, Matthew J R ; Walsh, Aron ; Wilson, Chick C. / Polymorphism of the azobenzene dye compound methyl yellow. In: CrystEngComm. 2016 ; Vol. 18, No. 19. pp. 3456-3461.
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