Week 10: Synthesis of Chemiluminescent Esters

1) Source(s) This lab was developed by a team of students from a recent JCE article: Synthesis of Chemiluminescent Esters: A Combinatorial Synthesis Experiment for Organic Chemistry Students,” Duarte, Robert; Nielsen, Janne T.; Dragojlovic, Veljko. J. Chem. Educ. 2004, 81, 1010. A good resource for this experiment is a website: “Chemiluminescence of Oxalate Esters” http://www.chem.leeds.ac.uk/delights/texts/VV_exp_26.htm

2) Changes to published procedure
We scaled up the procedure and worked without a drying tube on the reaction flask.
We evaporated the acetone with forced air rather than a rotary evaporator.
We limited the choice of phenol to: 2,3,6-trifluorophenol, 2,4,6-trichlorophenol, 4-nitrophenol, and 2,4-nitrophenol.
The fluorescent indicators we used were rubrene, and 9,10-diphenylanthracene.
We performed a UV scan of the products.

3) Positive
+ Chemiluminscence is a cool phenomenon. A nice break from the syntheses of white powders and clear liquids.

4) Neutral
± This was the most expensive lab to prepare for us.
± The chemiluminescence does not last long: mix the peroxide into the mixture while in a darkened room.

5) Negative
– Most of the combinations (phenol and indicator) proposed in the article don’t chemiluminesce. It seems like a good idea for each student to synthesize at least one product that gives off light.

6) Inquiry & Extension ideas.
● “Let’s make glowsticks,” one student said.

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  1. […] of Chemiluminescent Esters” experiment that was performed by a handful of students in Spring 2008. This time the experiment was performed by 65 sophomore organic chemistry students. We followed the […]

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