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Bis(2,4,5-trichlorophenyl-6-carbopentoxyphenyl)oxalate: Wikis

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Bis(2,4,5-trichlorophenyl-6-carbopentoxyphenyl)oxalate
Bis(2,4,5-trichlorophenyl-6-carbopentoxyphenyl)oxalate.png
IUPAC name
Other names CPPO
Identifiers
CAS number 30431-54-0
PubChem 93137
SMILES
InChI
InChI key TZZLVFUOAYMTHA-UHFFFAOYAP
ChemSpider ID 84082
Properties
Molecular formula C26H24Cl6O8
Molar mass 677.18 g mol−1
Melting point

188–192 °C

Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Bis(2,4,5-trichlorophenyl-6-carbopentoxyphenyl)oxalate (CPPO) is a solid ester whose oxidation products are responsible for the chemiluminescence in a glowstick. It can be synthesized by reacting 2-carbopentoxy-3,5,6-trichlorophenol with oxalyl chloride.

When mixed with hydrogen peroxide in an organic solvent in the presence of a fluorescent dye CPPO causes the emission of light, as per the following scheme:

Cyalume-reactions.svg
(Note that many side-groups of the aromatic rings are not shown.)

The reaction rate is pH dependent, and slightly alkaline conditions achieved by adding a weak base, e.g. sodium salicylate, will produce brighter light. Developed by American Cyanamid in the 1960s, the formulation containing CPPO, a fluorescor, and a glass capsule containing hydrogen peroxide and a base catalyst, all in dialkyl phthalate solvents, was marketed as Cyalume.

The following colors can be produced by using different dyes:

Color Compound
Blue 9,10-Diphenylanthracene
Green 9,10-Bis(phenylethynyl)anthracene
Yellow-green Tetracene
Yellow 1-Chloro-9,10-bis(phenylethynyl)anthracene
Orange 5,12-Bis(phenylethynyl)naphthacene, Rubrene, Rhodamine 6G
Red 2,4-Di-tert-butylphenyl 1,4,5,8-tetracarboxynaphthalene diamide, Rhodamine 101

References

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