Bis(2,4,5-trichloro-6-(pentyloxycarbonyl)phenyl)oxalate

Bis[2,4,5-trichloro-6-(pentyloxycarbonyl)phenyl]oxalate (also known as bis(2,4,5-trichloro-6-carbopentoxyphenyl) oxalate or 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.

Bis[2,4,5-trichloro-6-(pentyl­oxycarbonyl)phenyl]oxalate
Skeletal formula
Space-filling model of the CPPO molecule
Names
Preferred IUPAC name
Bis{3,4,6-trichloro-2-[(pentyloxy)carbonyl]phenyl} oxalate
Other names
CPPO
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.045.618
  • InChI=1S/C26H24Cl6O8/c1-3-5-7-9-37-23(33)17-19(31)13(27)11-15(29)21(17)39-25(35)26(36)40-22-16(30)12-14(28)20(32)18(22)24(34)38-10-8-6-4-2/h11-12H,3-10H2,1-2H3 checkY
    Key: TZZLVFUOAYMTHA-UHFFFAOYSA-N checkY
  • InChI=1/C26H24Cl6O8/c1-3-5-7-9-37-23(33)17-19(31)13(27)11-15(29)21(17)39-25(35)26(36)40-22-16(30)12-14(28)20(32)18(22)24(34)38-10-8-6-4-2/h11-12H,3-10H2,1-2H3
    Key: TZZLVFUOAYMTHA-UHFFFAOYAP
  • Clc2c(C(=O)OCCCCC)c(OC(=O)C(=O)Oc1c(C(=O)OCCCCC)c(Cl)c(Cl)cc1Cl)c(Cl)cc2Cl
Properties
C26H24Cl6O8
Molar mass 677.17 g·mol−1
Melting point 188 to 192 °C (370 to 378 °F; 461 to 465 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
"CPPO" redirects here. For dcpos with a minimal element, see complete partial order.

When mixed with hydrogen peroxide in an organic solvent (diethyl phthalate, ethyl acetate, etc...) in the presence of a fluorescent dye CPPO causes the emission of light, as per the following scheme involving 1,2-dioxetanedione (note that many side-groups of the aromatic rings are not shown.):[1]

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 fluorescer, 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, Rhodamine B

References
  1. Yoshinaga, Tetsutaro; Tanaka, Yasuo; Ichimura, Teijiro; Hiratsuka, Hiroshi; Hasegawa, Miki; Kobayashi, Michio; Hoshi, Toshihiko (2001). "Solid Surface Enhancement Effects on Chemiluminescence. III. Diaryloxalate as Chemiluminescence Reagent and Inorganic Materials as Media Solids". Bulletin of the Chemical Society of Japan. 74 (8): 1507–1516. doi:10.1246/bcsj.74.1507.
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