Bis(2,4,5-trichlorophenyl-6-carbopentoxyphenyl)oxalate
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| Bis(2,4,5-trichlorophenyl-6-carbopentoxyphenyl)oxalate | |
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oxalate.png) |
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Bis(2,4,5-trichlorophenyl-6- carbopentoxyphenyl)oxalate |
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Other names
CPPO |
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| Identifiers | |
| CAS number | 30431-54-0 |
| PubChem | 93137 |
| ChemSpider | 84082  |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C26H24Cl6O8 |
| Molar mass | 677.18 g mol−1 |
| Melting point |
188–192 °C |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| 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:
- (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 |
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| 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, Rhodamine B |
