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6,6'-Dibromoindigo

6,6′-Dibromoindigo is an organic compound with the formula (BrC6H3C(O)CNH)2. A deep purple solid, the compound is also known as Tyrian purple, a dye of historic significance. Presently, it is only a curiosity, although the related derivative indigo is of industrial significance. It is produced by snails of the family Muricidae.

The pure compound has semiconductor properties in the thin film phase, which is potentially useful for wearable electronics, and has better performance than the parent indigo in this context.

Biosynthesis

Biosynthesis of the molecule is intermediated by tyrindoxyl sulphate. The molecule consists of a pair of monobrominated indolin-3-one rings linked by a carbon–carbon double bond.

Dibromoindigo can also be produced enzymatically in vitro from the amino acid tryptophan. The sequence begins with bromination of the benzo ring followed by conversion to 6-bromoindole. Flavin-containing monooxygenase then couples two of these indole units to give the dye.

Chemical synthesis

The main chemical constituent of the Tyrian dye was discovered by Paul Friedländer in 1909 to be 6,6′-dibromoindigo, derivative of indigo dye, which had been synthesized in 1903. Although the first chemical synthesis was reported in 1914, unlike indigo, it has never been synthesized at commercial level. An efficient protocol for laboratory synthesis of dibromoindigo was developed by Wolk and Frimer in 2010.

References

References

  1. (1990). "Royal Purple dye: The chemical reconstruction of the ancient Mediterranean industry". Accounts of Chemical Research.
  2. (13 August 2020). "In Search of Surface-Induced Crystal Structures: The Case of Tyrian Purple". The Journal of Physical Chemistry C.
  3. "Tyrian purple: The lost ancient pigment that was more valuable than gold".
  4. (2016). "Extraction and Quantification of Bioactive Tyrian Purple Precursors: A Comparative and Validation Study from the Hypobranchial Gland of a Muricid ''Dicathais orbita''". Molecules.
  5. Friedlaender, P.. (1909). "Zur Kenntnis des Farbstoffes des antiken Purpurs aus ''Murex brandaris''". Monatshefte für Chemie.
  6. (1903). "Über ''p''-Halogen-''o''-nitrobenzaldehyde". Berichte der Deutschen Chemischen Gesellschaft.
  7. (1981). "Indigo". Encyclopædia Britannica, Inc.
  8. Cooksey, C.J.. (2001). "Tyrian purple: 6,6′-dibromoindigo and related compounds". Molecules.
  9. (August 2010). "A simple, safe and efficient synthesis of Tyrian purple (6,6′-dibromoindigo)". Molecules.
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indigo-structure-dyes bromoarenes organic-semiconductors
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